Notes to self, Valentine’s Edition

(Originally published on Medium on February 14, 2018)

In a post in July, I wrote about my tradition around birthdays — writing myself a birthday card for the following year and opening the card from the previous year (addressed to me, one year in the future). That way, no matter what, I’m bound to receive a lovingly-written card, even if it’s just from me.

I’d been doing the birthday “notes to self” since 2010, and in 2014, for reasons I can no longer remember, I started doing the same for Valentine’s Day. Thanks to that stroke of inspiration in 2014, this morning, I was able to open cards from someone other than my mother and grandmother: I get to open cards from versions of me one, two, three, and four years in the past.

Here’s some snippets of context and favorite lines from each of them:

2014 for 2015: I gave my notice for the kitchen lease for my food startup because the owner was a complete nightmare. The card was short and my handwriting gigantic and my state of mind very “woo woo” since my spiritual life at the time was rather strong. Because I was writing the card on the day I had chosen to end a toxic business relationship, the content of my love letter to self was about continuing to be fearless.

I love you. Don’t stop believing. Don’t quit before the miracle happens.

2015 for 2016: I was on a dating spree on Tinder at the time and found myself torn between two or three people — one of whom was distant but intriguing and mysterious, another of whom was charming and outgoing but in front of whom I’d deeply embarrassed myself when things got physical. I felt doomed to romantic failure. I didn’t realize at the time that I’d end up dating the first guy for the next two years (almost).

I know that Februaries are tough for you. You almost always fall into something new right after Valentine’s Day and it ends before the next one happens. The good thing? You are constant. These people, these situations are temporary. So take in the joy and savor it even when it breaks your heart to let it go…I know none of it feels like it will ever work out, but it does and it will.

2016 for 2017: I was months away from the end of graduate school, feeling proud of how far I’d come (getting a job, starting a podcast) and hopeful of what could come next (a new career in tech, boyfriend and I moving in together into a beautiful apartment). The only thing that was really getting me down was my relationship with my body and with food. Half of the card discussed my wishes for myself that in 2017, I’d find a form of exercise I genuinely enjoyed and not using food as a drug of choice. (The exercise part came would come true in 2017 — just not by Valentine’s Day. The food part is ongoing).

Above all, I want for your relationship with food and your body to be healed. I want you to have ended your war against yourself when you sit down for a meal or try on a dress in your closet. I want you to have achieved all you need to be physically confident and let nothing hold you back and no one hold you down.

2017 for 2018: All the things I had hoped for myself in my card the previous year were up in flames when I wrote this card. Though I had some great coworkers, I was overworked at my job and had no boundaries between the office and my personal life. I had been dumped by the boyfriend and was living in (and paying for) our beautiful apartment on my own. Worst of all, I was eating my feelings about all of the above.

Despite all that was going on, the 2017 card was a positive one. In many ways, it was a synthesis of things I wrote in previous years, celebrating my friendships and professional trajectory, and encouraging me to be resilient in tough times and live my best, boldest life. Also, in a weirdly specific moment in the card, I talk about how I was anxious about ordering sushi for my team at work. DoorDash would screw up my order and leave my team hungry and sushi-less the following day, so that anxiety was genuinely warranted.

You are a strong woman making plans for yourself, determined to not let the embers of a heartbreak burn you…I wish you levity, joy, adventure, and the courage to live even more bravely and boldly.

2018 for 2019: As I write my card to myself for next year, this is the context. I’m thinking about my grandmother, whose birthday is also today. She reminds me that this holiday doesn’t have to be about the roses or chocolate. She reminds me, single once again, that I never have to worry about being loved, even when I’m not in a relationship.

Aside from a writing career of renown and a little more travel in my life, I have a life that I love right now— great friends, a steady and interesting job with good people, and after all these years, a form of exercise that I enjoy and keeps me grounded. What’s inside that card will have to wait to be read next year, but when I open it, I hope that that all these things remain true and that there’s someone else to share the them with me.

If you like Valentine’s Day, I wish you a happy Valentine’s Day. If you don’t, I wish you a Happy February 15th Eve. Tomorrow, all the chocolate and flowers will be 50% off. Regardless, you are loved, too.


Technically Speaking

(Originally posted on Medium on January 29, 2018)

Before going to college, it seemed as if everything about my future was going to be on the technical side. My favorite subjects were Chemistry and Calculus, my quant scores vastly eclipsed my verbal scores on every standardized test I’d ever taken, and my college admissions essay was about the joy of soldering circuit boards and building a metal detector.

Then I got to college, and after one unpleasant semester of core engineering curriculum, I left the program. Eventually, I decided to study Chinese and become a Comparative Literature major — both challenging in their own ways, but neither particularly technical.

Unfortunately, it’s far easier to market yourself if you’re coming from a technical than a liberal arts major in the job market. So after two years writing case studies and teaching notes at HBS, I headed to business school in hopes of building up some technical chops at arguably the most technical Top 10 MBA program in the country, MIT.

While in business school, as I witnessed classmates gravitating towards performing quantitative analyses in Excel and creating colorful charts in PowerPoint, I was reminded that my “Microsoft Office Spirit Animal,” as an old boss of mine called it, is definitely Word.

Luckily, for the purposes of getting hired, the technical reputation of MIT rubbed off on me and my resume. Still, it’s something of an illusion — I would not say I’m technical. I understand enough of the technical to get by on the job and occasionally spout a few organic phrases of technical jargon, but that’s as close as I get. I can only manage the basics in Excel. I’ve gotten by without learning R and SQL (so far, but who knows for how long). I’ve done some light coding before and don’t enjoy it, because staring at a screen all day troubleshooting bugs makes me want to cry.

In interviews, I get most insecure when asked about my “hard skills,” because the truth is I don’t have many relevant hard skills. Whatever “hard skills” I have for my job in Product come from learning the more approachable pieces of tech stack on the job. If a company is looking for a technical PM, I’m not the girl and probably never will be. The only thing that’s technical about me is my jiu-jitsu (and that’s because it has to be — trying to match the strength of men twice my size isn’t going to work).

That’s okay though. I’m not great with machines. I’m better with people. My proudest (non-writing) accomplishments aren’t about technical skill so much as people management and communication: launching a food business and a podcast; in business school, turning The Yarn, a casual monthly storytelling night, into a widely-attended, can’t-miss community event; launching a new website at Wayfair against all odds (an aggressive deadline, a skeleton crew, tons of work to complete, and countless people across the organization to coordinate).

Being open to feedback, really listening, developing relationships, finding common ground between people — that’s what I’m building my career on in tech, in part because being technical isn’t my strength, but also because no matter how good you are at talking to machines, nothing gets coded and no product gets launched without talking to people. I have to believe that if I’m still working in product, I’m more than decent at getting technical and nontechnical people to work together to make things happen. That’s not to say I’ll never have to run some numbers or query a database, but it’s more likely I’ll hire for the more technical skills that I lack.

And that’s technically a skill, too, right?


2017, in conclusion

(Originally posted on Medium on December 31, 2017)

New Year’s Eve, though often overpriced and overhyped, has held some good memories for me (seafood tower, resolution-making with friends, Veuve Clicquot champagne) as well as some bad ones (big fights, drunken assault, a spinach cocktail).

This year, though, I was determined to have a good, “significant,” New Year’s Eve, which meant spending it doing the thing I enjoy the most: writing. (No contest here between writing and jiu-jitsu, because my gym is closed until January 2).

Type A as I am, I can’t begin the next year without putting some sort of structured reflection into the previous year, and I tend to spend the tail end of December ruminating and spin-cycling words and memories of the previous year.

Despite my post earlier this year, I still have perfectionist tendencies, which meant I sat down this morning, on the last day of the month, intending to write my December blog post and make it my best piece of the year. Somewhere in the middle of the day though, my perspective changed from “It’s the last day of the year and there’s something significant about that! Write something awesome!” to “Girl, get real. It’s just another day, and an unpleasantly cold day at that: 9 degrees Fahrenheit that feels like negative 7. Write what you can, but don’t worry about how it comes out. Just do it. And don’t go outside without a hat.”

So after days of putting it off and then trying to write it all out this morning, instead of spending most of New Year’s Eve hashing out the sentences, I gave up and decided to draw out a representation of this year as I remember it instead. After all, a picture is worth a thousand words, and since I can’t draw very well, most of my pictures include words anyway.

If I had to draw a picture of this year, this is what it would look like: neatly synthesized, orderly, and ready to be put to bed. If had to represent what’s in store for next year and the chaotic cluster of intentions and activities lined up for it, here’s what that would look like, too: shapeless, explosive, bubbling, and filled with anticipation. 2017 is a mediocre PowerPoint slide-style collection of major events, things I was feeling, and overall body/mindset. 2018 is…a creative, freeform plop with some resolutions scattered about. See the below:


In an update email to friends, family, and other “life stakeholders” that I sent out this morning, I described my personal life the last six months as being full of “fighting and writing.” There will be more fighting and writing next year. That’s the only thing I promise to myself and anyone reading this. Aside from fighting some real people (in tournament settings, not streets — I hope), I intend to fight the inner critic that’s prevented me from putting out real, published work, and give the real critics a chance to tear me apart.

2017 for me was a dark year, but there were more than a few bright stars that sparkled and defied the vast swath of darkness. 2018? We’ll see. At the very least, I’m determined to fight to make it a better one.

But for now, I’m spending the final hours of 2017 drinking red wine, watching my significant other make me gluten-free pasta, watching Sherlock, and going to bed early. I hope you spend it celebrating in a way that makes you happy, too.

All best wishes —


Acceptance Criteria: from MBA to product manager

(Originally published on Medium on November 30, 2017)

TL;DR: I got here mostly by accident, but you don’t have to. Read top to bottom for the narrative backstory. To cut to the actionable advice, scroll to the end.

Over the last year and especially over the last week getting involved as a host for a MIT Sloan January internship program in product management, I’ve had a number of MBA students in the Boston area reach out to me to ask about my career backstory and my post-B-school experience in product.

While I love helping people, I tend toward introversion, hate scheduling and am very frugal when it comes to giving people my time. Luckily, whenever anyone reaches out to me asking to talk about business school and the application process, I offer them links of blog posts I wrote when I was a student and tell them, “Read these posts and if you have any further questions, we can set up a call.” I still end up speaking to a few people on the phone, but in most cases, the posts give people what they need — or they’re too scared to ask for the follow-up.

I haven’t had the same point of reference I could offer with regard to Product Management, so I’ve spent many hours talking to people on the phone or in person about how I got to where I am and what I’ve learned being a PM. Instead of continuing to tell people the exact same story and advice, I’m documenting it.

For the next MBA who wants to know about my life in product (so far!), I hope you’ll find starting here helpful. If this proves useful to you, when we speak, we can get to a more nuanced conversation of why you want to be a product manager and where I can help you. For anyone reading this who doesn’t have a MBA, you can do all of this, too and you’re likely saving a lot of money in the process.

Just remember : I’ve only been a full-time PM since July 2016. Take my “one woman’s perspective” as you will and for whatever it’s worth as I write this in November 2017.

How I ended up in business school to begin with

I graduated with a degree in Comparative Literature, which didn’t make me eminently employable, but I got one of the few jobs where my skills in writing and foreign languages could be useful. I clocked in two years a Research Associate at Harvard Business School for a professor whose focus was business in China and spent the time writing case studies for the HBS MBA program and helping my professor run his spring course, ‘Doing Business in China in the 21st Century.’

I’d planned on getting my MBA since I decided on a humanities degree in college, and working at HBS reinforced that I wanted to be the person on the other side of the classroom —the one reading and discussing the cases with her peers, not the one writing them. That said, I didn’t have a real reason for wanting to earn the degree until, a year into working at HBS, I started an allergy-free food business in Cambridge. I decided to apply to MBA programs that cared about entrepreneurship and hoped to learn the skills that would help me turn my little, crowdfunding-backed baking startup into a health and wellness empire. Somehow, I convinced MIT that I was a horse worth betting on and got into Sloan.

My internship recruiting scramble

I applied to Sloan with the pitch of growing my business, but by the time I got to school, I moved a little bit away from the startup hustle: I decided that in order to really understand how to build a brand and scale in the food and broader consumer goods industry, the best use of my time would be to seek out a summer internship at a food giant and soak up best practices from one of the big guys instead of learning strictly on the fly (and stumbling a lot). Unlike Kellogg, Sloan isn’t exactly known as a recruiting hub for retail or CPG (consumer packed goods), so my search for internships in Brand Management was a struggle. Companies have their feeder schools for interns and the odds are low of getting to be the one intern who comes from a non-feeder school. After hundreds of companies refused to give me the time of day, I managed to get into talks with Pepsi, far along into interviews with Nestle, L’Oreal, and Ocean Spray, and eventually received an offer for Brand Management with Dr. Pepper Snapple Group (DPSG).

Since I’m writing this in Boston, not Plano, it’s clear I didn’t end up at selling soda or Snapple. The day I flew down to Texas do final-round interviews at DPSG, I also got an offer from Sephora out in California. The Sephora offer surprised many of my classmates — I’m not especially appearance-conscious, I don’t wear much makeup, I’m generally closeted about my love of the beauty industry. As much as it surprised them, it surprised me even more: How did I end up in a tech job?

The fortuitous fall into Product

That summer, Sephora had 8 open roles for a MBA internship program that no longer exists. The job I got at Sephora was not for Brand Management or International Strategy, the roles to which I’d initially applied, but for Product Management, which a girl from Sloan had done the previous summer. I have to believe she paved the way for me to get my foot in the door — I had a passion for beauty, and a willingness to work hard, for sure, but no applicable experience. I was relying on MIT’s brand to lend me any credibility in technology. Something worked.

Even with the good karma, I still don’t know how I got this job — I made a huge gaffe as I began my interview with my would-be manager talking about a completely different position than the one I was actually interviewing for. “I thought this was the Product interview for Payments?” “No, this is the one for Store Digital.” “Oh, okay. I’m sorry about that. Can you tell me more about this role?” If I were in her shoes, I’m not sure I’d have been as forgiving to me as Andrea was, but at this point, I don’t question it anymore. I had a lot of fun working on her team that summer.

So that was how I first got into Product: because I wanted to be a brand manager but didn’t want to sell soda, because someone from my school paved the way for me by doing a good job the previous summer at a company I liked, and because my manager else took a chance on me.

When I asked my manager at Sephora about it later, she said she believed that I might actually like Product or at least be smart enough to figure it out. She also said that she didn’t like anyone else she talked to on her applicant list and her two top picks signed offers at other companies. (If I had to guess, those other company were willing to pay their interns a better salary. My Sephora summer paycheck went nowhere in San Francisco. To make things work, I lived in a bunkbed for three months in an Airbnb “Hacker House”: in reality, a condo loft meant for two people that I was sharing with five other people).

Finding the full-time product job

I came out of my summer at Sephora with a new focus: after graduation, I wanted to do a job in e-commerce product management at a retailer or a brand. (In the span of one year, I’ve gone from wanting to graduate from b-school as a food business founder, as a consumer goods brand manager, and now as a tech product manager).

Unfortunately, my ten weeks in product at Sephora wasn’t enough for any companies to take a second look at my resume. I considered going back to Sephora, but would have had to wait until the spring before I’d be able to apply to an open positions (unless I wanted to apply in September and drop out of school to start working in October). I also considered working at a startup, but knowing they tend to hire ad hoc, I’d have had to wait until April or May to start applying and interviewing.

Business school makes you forget that the real world of job hunting does not obey an academic calendar and spoil you with luxuries like on-campus recruiting where jobs literally come to you. Business school also makes waiting until the spring to find work — as all your friends sign full-time offers with fat bonuses with the companies they worked for over the summer —inordinately stressful. It’s hard to tune out the noise and feel at ease about your employment situation when you’re surrounded by hordes of people who have their near-term post-graduation s*** together (even if some crazy high percentage of MBAs leave their post-graduation jobs after just one year). I wish I could say I had the courage and conviction to hold out and not take the first thing that fell in my lap, but the truth is I took the first thing that fell in my lap, even though I knew it was probably wrong for me on a number of counts.

That first thing that fell in my lap was a job at Wayfair that I gleaned through the on-campus recruiting cycle in Fall 2015. It was the only company that came on campus for Product that humored me into a final round. Amazon memorably side-eyed me out of the room.

I got the offer from Wayfair in November and it would expire in January. Nothing about the salary or benefits were competitive, especially for product and especially for me, since they brought me in at a lower level, salary, and title than every other MBA who received an offer from my school (which was immensely frustrating during my time at Wayfair).

With the holiday season approaching, it was impossible for me to drum up another offer from a company that was more interesting to me — or even just to counter — before January. I wanted the security of having an offer in my pocket and knowing what I was doing when I threw my cap up in the air at Commencement in June.

I had connected with my future manager at a recruiting event and he was also my last interviewer in my on-site final rounds. He promised me I’d learn everything I said I wanted to learn on the job, and he said it was okay if I hated furniture.

In the end, no other company had given me the time of day, so the promise of learning, and the comfort of staying in Boston a little longer made the offer appealing enough for me to take it. Believing that no one else would want to take a chance on me, I figured this offer was the best I could do for now. At the time, it probably was.

Taking what I got— and making it work

Wayfair was rough in a lot of ways that I can’t write about but am happy to talk about offline. My year at Wayfair also coincided with a lot of rough stuff in my personal life, which didn’t make work feel any more manageable. I’m still thankful for getting the project of a lifetime in Perigold and for the friends I made while working there.

While it was exceptionally demanding and left me no room for having a personal life, Wayfair’s aggressive pace meant I worked on years’ worth of projects in 11 months, arming me with enough experiences to “talk the talk” and “walk the walk” when it comes to product.

I learned how to do the “meat and potatoes” pieces of Product: writing stories, planning a sprint, running a retrospective. I learned the “soft skills” pieces of the job: talking to tons of stakeholders, figuring out what they care about, and aligning them toward a common goal. I began to understand all the jokes about designers and engineers and product managers and why they don’t always get along.

In terms of having a complete Product skill set, I could be better-rounded: I’m not a data analysis junkie and I don’t have much experience doing customer interviews. Becoming more technical is a constant quest — working in software, a lot of the architecture discussions go over my head. I don’t know how you get better at product “visioning.” I’d like to improve at everything I just mentioned, but for now, I’m confident in my abilities of execution, which is arguably the most important thing a product manager can do — actually GSD. The rest will come with more experience in more companies.

Even though I only ended up interviewing at Hybris, where I work now, had I gone through a more comprehensive job search, if given an interview, I have to believe that I could convince companies who wouldn’t ever consider me a year ago that I can now do this job in product.

Grains of wisdom: things I wish I’d known then and what I know now

  1. The responsibilities and scope of work for a product manager differ from company to company and can even change month to month as a company grows and scales (this was definitely true for me at Wayfair). From a development perspective, as well, there’s no single approach: whether you’re in hardware or software, agile or waterfall, B2B or B2C, the demands of the PM role change. When looking at product jobs, it’s critical to understand what Product Management means at the company and where PMs fit into the development process and the overall business.
  2. Any MBAs who go into product thinking they’re going to be doing something sexy and were marketed the line of “As a Product Manager, you get to be the CEO of the Product!” has a lot of unsexiness ahead — and more meetings on their calendars than anyone should ever have to attend.
  3. If your background is unconventional but you really want to be in product (or any other career for that matter), first figure out a way to spin up your background and story so that it sounds more “product-y.” Did you plan a 6-month strategy for something in your previous role? Call it a “roadmap” on your resume. Work a lot with customers? Speak to your experiences understanding their wants and prioritizing their needs.
  4. Once you’ve got your Product story straight, your best bet is increasing your odds of finding someone who will take a chance on you. It could be through a networking event in real life or cold on Linkedin (incidentally, how my current manager recruited me). Tech communities — no surprise — are heavily connected and even if you talk to someone who can’t help you, they might know someone who can and would be willing to make an introduction for you.
  5. School isn’t always the answer — There’s no question my degree made me look good, but in the end, I’d say the MIT part of my graduate degree ended up being more marketable than the Sloan or MBA part. No one looks at me the way they did when I was interviewing for jobs after college and I said my degree was in Comparative Literature. That was always the plan — to get out from the shadow of being the literature student who still needed credibility to handle the business stuff. But you don’t need your MBA or other remedial courses to become a product manager. They can help you skip a few steps here and there, but nothing helps you become a product manager like getting your foot in the door and getting that first job in product.

Newsletters and Resources I find useful (somewhat Boston-centric)

  1. AmericanInno: I subscribe to the Boston edition of this Newsletter, BostInno, and get their daily updates of what’s going on in the local tech community.
  2. Silicon Valley Product Group (SPVG): Marty Cagan is the man, and the blog has some of the best free advice on the internet.
  3. Entering StartupLand: this was written by Jeff Bussgang, a VC at Flybridge Capital Partners. I know Jeff because he teaches second year MBAs during the spring at HBS. I cross-registered for his course “Launching Tech Ventures” in 2016 and being the odd kid out as a Sloanie in a swarm of Harvard MBAs in his class was worth it. This book effectively breaks down the key roles at a technology startup and helps you understand what you’re getting yourself into, whether you’ve signed on in product management, business development, or something else
  4. VentureFizz — similar to AmericanInno, run by Keith Cline, this site features stories on what’s happening in tech in the Boston metro area, interviews of local tech leaders, and a robust job board with solid company profiles and office tours of established as well as up-and-coming tech companies in Boston.
  5. Tech Ladies — obviously targeted towards those who identify as female, this is also more of a job board for engineering, UX, and Product, but a good way of scoping out opportunities in tech hubs like NYC, Boston, and SF.

Like reading this? Clap or comment below, follow me here on Medium, or subscribe for updates.

Haunt you every day

It's Halloween, and with it, the cold weather, an abundance of candy, selfies of friends in costume, and talk of ghosts.

At some point or another in our lives, we find ourselves haunted, whether it's by something we saw, something we did, or someone we used to know.

Haunting doesn't have to be an inherently spooky thing—I think fondly of my first dog, who loved chasing tennis balls, whenever I see a fuzzy neon Wilson on the floor of my parents' house. When I roll the the ball and it moves a little farther than I would expect the laws of physics to carry it, I joke and think it's the ghost of Ziggy.

Preparing for the holidays that follow Halloween, though, I am haunted by something less innocent than my childhood pup: the ghost of boyfriend past. I'm in a great relationship now, and I wouldn't trade it for what I had. But I'd be lying if I said I wasn't still haunted by the one that came before.

The breakup happened suddenly the Sunday night after Thanksgiving. He moved out of the apartment we were living in together two days later. I lived in that apartment for another three and a half months alone before I moved. I switched floors but still live in the same building.

One night lately, when I was really out of it, I hit the button to my old floor. Another time, on my current floor, I put my key in the door of a unit on the other side of the hallway, where my old unit was.

Walking one way to my new boyfriend's apartment, I pass by a restaurant and the hotel bar we visited on the last night before he ended things in November.

When I walk to my gym after work, I pass by the venue where we ran into each other at a startup event. It was the night after we'd broken our lease in March, a night that came as close to what I imagine a divorce would feel like.

Walking another way to my new boyfriend's apartment, I pass by the hotel where he, drunk and uninvited, crashed an event I was attending there with some girl I had never seen before. It was barely a day after he had woken up in my bed and we had discussed couples counseling and all the ways we would "make things right" this time around.

For both the startup event and the hotel event—I didn't know he would be there. I don't know if he knew I would be there. He later called it the universe bringing us together. I called it my angels warning me to stay away.

En route to the gym, I also pass by a bar where we met up in February when we were trying to work things out the first time—he mentioned something about how cute our kids would be, I said something about wanting to have a clean slate and discussed dates I had gone on during our hiatus (in hindsight, didn't owe him any of that).

I walk through the North End during lunch sometimes and pass by the fountain where I chewed him out for the rent money he owed me for months. I got my first third of what I demanded that night as I climbed the 3 flights up to my improv class on Hanover Street.

He always wore suits, or at least a pressed collared shirt. I now work in the Financial District, where almost all the men I see who aren't tourists dress this way. Whenever I see a man with dark, straight hair in a suit of a similarly slim build, with a similarly slicked-back side part hairstyle, I experience a moment of panic. Even though the chances of seeing him during my workday are slim to none (he lives and works in Brighton and his client base is heavily suburban), I have a mild heart attack. After all, it stands to reason that one day he could be in the neighborhood to meet his little brother, who interned for a company in my building, for lunch.

Today, Facebook showed me a picture of myself in costume as Audrey Hepburn. I can't see myself in that costume without thinking of him and how he did my hair and how pretty he told me I looked. Humorously, though, I still haven't seen Breakfast at Tiffany's (though I have read it).

I haven't seen him since a dinner in August, which I believed would give me closure and allow me to move on. But the I have moved on, but I haven't forgotten that pain, especially as I hit its anniversary this November. Perhaps, with the passage of Thanksgiving, it will go away and lose its power. I hope so—otherwise, more time would seem to be the only way to break the spell and ward away this ghost. 

I can only hope that I, too, haunt him everyday.

Me, too

(Originally published on Medium on October 16, 2017)

This isn’t the first time I’ve thought about writing this. The timing is unfortunately impeccable.

It’s nearly 14 years to the date and this was the first time I found myself in a sexual situation that was nonconsensual. I wish it were the only time something like this ever happened to me — not one of five.

I’ll add that those are only the five that immediately come to mind. No doubt there are many others buried in my memory but have felt so commonplace, so embedded in the experience of being female, that I have cast them off as “normal.”

In a sentence, for anyone who wishes to cut to the chase before (or without) reading further: this is the story of how I was manipulated and coerced into oral sex for recovering a friendship when I was thirteen. Needless to say, the friendship didn’t recover; instead I spiraled secretly into a depression until I wrote my way out.

The first time I ever wrote something personal for others to read was because of this incident. I wouldn’t be who I am, writing what I write, believing what I do about men and women without it. Writing set me free when my mind had me in chains and I had no courage to speak aloud.

I can’t remember exactly when I first met him, but we inevitably spent a fair bit of time together starting in the 6th grade. Outside of school, our parents were friendly because they belonged to the same golf club in my hometown. In school, we were around each other quite often between the shared roster of honors classes and the long bus ride we shared to school. Most of our classmates lived about 5–15 minutes away — we lived between 30 minutes and an hour away, depending on traffic.

Even though we saw each other every day and were connected both inside and outside of the classroom, I wouldn’t say we were really friends — I wanted to be friends with him, but I was the total nerd, friends with a group of culturally-diverse outsiders. He was a popular boy, funny-looking but athletic, charismatic and friends with the uberwealthy, cool kids.

Still, somehow, over time, I think in the tail end of seventh grade, something began to bubble between us. The pinnacle of our intimacy was holding hands while watching Van Wilder or Out Cold at my house and he felt me up. He might have kissed my neck, I can’t remember. It was completely hush, hush, of course, because I wasn’t cool enough to be seen with him in school and I felt embarrassed at the idea of what my friends would say if I told them that I liked him.

I recall taking that physical movement as a sign of net forward motion, in addition to frequent conversations on AOL Instant Messenger (I can’t believe that product is being deprecated, but good riddance. I can’t think of the product without thinking of this guy, his screen name, and everything that was communicated and not communicated via DM).

It’s all very hazy at this point, but what I do remember is we had been getting closer and friendlier on the down-low and I thought we were making headway toward a real, public relationship until one day he suddenly stopped talking to me. Nothing had changed or happened (that I was aware of) that would change our dynamic.

Anyway, he stopped talking to me and I didn’t know why. I reached out over AIM for an explanation of why he was acting so weirdly. I made no headway. As the conversation continued and I asked what it would take for us to be friends again — more than friends, I hoped in the long term, but at least back to where we were before — and he made a proposition. In exchange, he wanted oral sex.

I was confused, scared, embarrassed, upset, and didn’t know what else I could do. I didn’t feel like there was anyone I could trust or talk to about what was going on. I wanted this person back in my life and I was mindfucked into believing it was worth doing whatever it took to get him. I didn’t want this, but I talked myself into it.

I went over to his house the following Friday, I think. He was completely cold. I walked into his bedroom and remember a sports game playing on his TV, loudly so nothing could be heard over it. The door was locked. The quilt was grey. It was the first time I had ever seen a penis and I remember being disgusted by the sight of that rogue fleshy finger-sized appendage between the legs through the frond of pubic hair. He pressed my head down. Hard. I didn’t have the faintest clue of what I was doing with my lips or teeth, though if I knew then what I know now, I’d have bitten his dick off. I didn’t want to be there. I just wanted to be back to where we were.

I remember him reaching his hands down my pants and appearing disgusted by my ungroomed pubic hair. Again, I didn’t know much about these things. His crowd was a fast crowd — not as fast as the kids I heard about in the New York prep schools, but close to it.

We never kissed on the lips. That should tell you all you need to know. The crude, transactional nature of the whole thing. He never cared about me. If he did, his friends probably made him feel ashamed of it and he’d have rather had been cool than be caught liking someone like me.

I held back tears on the ride home as my mother picked me up. Normally chatty, I was quiet. My innocence and lightness toward the world was gone that night. I was never the same.

When Monday came, I was hopeful that what I had done would have achieved the desired result. Instead, things got worse. He ignored me, treating me with coldness or indifference. I felt like I was crazy.

Did I want this? Was this consensual? Would anyone believe me if I told them what had happened? I was depressed and out of my damned mind. And I would continue to be for the next six months.

We had a field trip sometime at the end of the winter/beginning of sprint to a nearby museum. For English class, we had an assignment to write a story about a piece we saw at the museum — I picked a sculpture by George Segal called “The Parking Garage.” It showed a man, likely a parking attendant, face and body hunched beneath the bright ‘PARK’ sign. It’s primary colors, white, and black, paper cache. It gelt abject and absolute. I don’t know much about George Segal and his work but the deflation of this man struck me hard.

I began the writing assignment talking about my dad’s kids from his first marriage and my trips to New York with my mom and dad to visit them and their children — they were my primary association with parking garages. It transformed into an autobiography of the last 13 years of my life, at least 20 pages long. The middle of it included the story of what happened with him. Harassment. Assault. I still don’t know what to call it to this day.

I tried to edit and cut what I wrote, but decided against it. I submitted it, raw, exposing myself in every line, pseudonyms barely concealing what was really going on. I didn’t care that my teacher, a little bit of a dirty old man, would read it.

When I was done, I gave it to my mom to read — I couldn’t use the words, so I let her read it. She cried with me on my bed, stroking my hair, saying over and over, “I am so, so sorry.”

It took me six months to tell her and to tell my friends. They all supported me unilaterally. I wished I had said something sooner. I wish I had told this story sooner.

Later that year, I won an English award. I think this piece, along with an essay on Fahrenheit 451, were the main reasons for it.

All’s well didn’t end well, though. My academic rival, friends with him, who learned what I had written, wrote a response story from his perspective, trivializing what had happened to me, saying that I had wanted it and it was all my fault. I remember getting a hold of a copy from one of my friends and it made me sick.

This wasn’t the last time a man would take control of a narrative and make a women look insane and obsessive — in my life or the lives of others I know.

Four years later, after I thought all this shit was dead and gone and completely under the bridge, at an intramural sporting fundraiser, a friend of his brought it up to attempt to humiliate me. Four years later, I was still being quietly and insidiously bullied and teased. It felt like there was no justice either when we both got into good schools and there was no consequence, divine or otherwise, for what happened.

It’s one thing when the person who sexually harassed you is a total stranger on the street, someone you never have to see again. It’s another when the person is sharing breathing room with you in the crammed space of a school bus with you for four years after the fact, making you think you’re crazy, forcing you to pretend you’re fine and cool with everything that happened, avoiding eye contact or having to share a seat.

There was never an apology. I doubt there was ever remorse.

Even though I begrudgingly went through with the act, I didn’t want any of this at all. I was thirteen. This wasn’t someone I loved. He manipulated me and it wasn’t my fault.

In hindsight, I don’t even know why I ever found him attractive. Why I was always so nice to him. Why I helped him as often as I did with homework. This was the kind of guy who was smart and didn’t need to cheat but cheated anyway, from what I remember. Needless to say, he went from Wharton to investment banking to venture capital to HBS. We got coffee peaceably in San Francisco when I spent the summer out there. He is in a super-committed relationship now. Our parents remain acquaintances, still at that golf club. My mom knows what happened. My dad does not. His parents know nothing.

He is now in Boston. We crossed paths about a month ago, not acknowledging one another in a bar in Harvard Square. Thank goodness, I was in the company of two girls from my jiu-jitsu gym to celebrate one girl’s birthday. “No one could fuck with us even if they wanted to,” paraphrasing the refrain of Cardi B. The birthday girl, in particular, could put someone to sleep with a guillotine chokehold in a matter of seconds.

I shot him a quick Facebook message later that night acknowledging that I didn’t acknowledge him because I wasn’t sure it was him. This was a lie — I just didn’t want to speak to him and the same seemed true of him. (He never replied to the message). Part of the reason I didn’t want to speak to him was because I had spent 2.5 hours that night grappling and going out to birthday drinks afterwards was a already physical stretch. But mostly, I didn’t want to speak to him was because I didn’t like the fact that he was in my city, the place I called home for the last five years that he would have as his for the next two. I still don’t.

I’m over it and at peace with it, but I’m not past it. I won’t forget.

Writing saved me then. It always has since. Speaking aloud or on paper when my voice was too shaky has gotten me into trouble, but done me far less harm than good.

What an older me would say to the younger me now is this: “This was someone who was far beneath you. He didn’t deserve to touch you. He didn’t deserve the emotional influence he had over you. I wish I could have supported you then to find the courage to say, ‘No, this isn’t right.’ Or to tell him to fuck off. I know you felt like you had no options and you had no one to talk to, and I am so, so sorry. Regardless, It happened. I believe you. You aren’t alone. I wear that shame with you, but your have nothing to be ashamed of. Let’s go back into the light together. “

If you’re reading this, all I want to say is even if you think no one is listening, someone is — someone who needs to hear what you have to say at the very moment that you have to say it.

Speak up. We hear you and we’re here for you. You won’t regret it.

parking garage.jpg

George Segal, The Parking Garage (1968)


Do you remember the [second] night of September?

(Originally published on Medium on September 30, 2017)

I think I always will.

About a year ago, I had been asked by one of my closest friends to be her Maid of Honor in her wedding in San Francisco. Under the condition that one day, she would do me the same honor at my wedding, I accepted her proposal.

I was flattered and excited to be able to do this for her. At the same time, I was terrified because I had absolutely no idea what I was doing. Of all the things I did or didn’t do as Maid of Honor, the three I am proudest of are:

  1. Coordinating a 3-day “destination” Bachelorette party in Miami Beach with an appropriately full but fun schedule.
  2. Carrying a 25–30-pound dress, covered in a thick plastic garment bag, in a record-breaking San Francisco heat wave of 100+ degrees.
  3. Delivering a toast that will be hard to top if someone asks me to do give a speech at his/her wedding in the future

Number 1 can be summarized with “beach, booze, and brunch.” Number 2 speaks for itself. Number 3 deserves more detail.

Sometime after the Bachelorette party, I started thinking about the toast and free-writing down everything I wanted to say about the bride. Reviewing the notes and trying to patch them together into a speech wasn’t working out too well: the sentimental anecdote I had prepared was too sad and more about me than about her, and very little of the drafted content of the speech had anything to do with the groom aside from using his name once. On the whole, the toast felt very generic — like someone could have put it on any or all of the 5 websites I had looked at with blog posts titled “How to write a great Maid of Honor toast!”

How do you encapsulate everything you could possibly want to say about someone you love on one of the most important days of her life? On one hand, there is too much to say. On the other hand, there’s nothing to say, because you’re speechless.

About a month before the wedding, I had an idea that caused me to scrap everything that I had come up with for the toast. I decided I was going to channel my Grandmother — my awesome Grandma Toby who recites a rhyming poem she writes for every special events for friends and family — and do something lyrical.

I have the bride to thank for a lot of obsessions —Tom Ford lipstick, the latest one — but the one most relevant to the speech would be Hamilton: An American Musical. She hooked me on the soundtrack in the spring of our second year of business school and turned my initial skepticism of the show into an addiction. I had become one of those Broadway showtune people that generally drove me crazy, living near Emerson College in downtown Boston with its hordes of theater students.

I resolved that I would take a song from the show, rework the lyrics into a wedding toast. If nothing else, I figured 1. Restricting myself to the length of a song would prevent the toast from getting too long 2. Singing a toast instead of speaking it would be a little unexpected and interesting for the attendees (in a good way), provided I didn’t lose my voice or drink too much.

Then it came down to picking the song. Striking from the list the rap battles, the sadder minor key melodies, and any song that was already overused in Hamilton-inspired wedding toasts on YouTube, I decided on the ballad “Dear Theodosia.” It’s a heartfelt gem tucked in at the end of Act 1, in which Aaron Burr and Alexander Hamilton sing to their newborn children, who fill them with awe and hope for the future of their nation. Even though I was delivering this toast to celebrate a wedding and not the birth of a child, I wanted to evoke a similar mix of awe and hope — awe in the beauty of the bride and of the day and collective hope for hers and the groom’s shared future together.

When it comes to most writing I do, I tend to hold out until the final days before it’s due to give me a real sense of urgency and pressure. For this, I forced myself to start a few weeks in advance of when I had to deliver this toast. I sat in the hippiest cafe in Cambridge, MA, hoping the divine spirits of Life Alive would be my muses and bring me some much-needed inspiration. Between that and a session at my +1’s apartment about a week or so before the wedding, I had the toast 99% under lock.

I was really proud of what I’d written, but the night before the wedding, I started getting nervous. At the cocktail event after the rehearsal dinner, a few old classmates expressed their excitement for my speech the following night at the wedding reception. Over a year out of business school and not having gone onstage to perform or public speak in a creative capacity since then, I forgot that my reputation at school had been “the writer and storyteller”. So aside from meeting my own high standards, there were other people’s standards I was suddenly considering when delivering my speech the next day.

Sitting in bed, making final tweaks for the toast, I told my +1 how much my old schoolmates’ comments were psyching me out and how I was afraid I wouldn’t deliver something that their expectations. He had the perfect, perspective-oriented reply.

+1: “Do you think the bride will like it?” 
Me: “Yes, no question.” 
+1: “Then does anything else really matter?”
Me: “Uh…no.”

I woke up the next day and spent the morning with one of the other bridesmaids — together, we survived the jabs of a hundred bobby pins in our hair and multiple coats of makeup to withstand the freakish heat wave in San Francisco. Fully varnished with hairspray and setting spray, eyelashes coated in waterproof mascara, we met up with the other two bridesmaids in the bride’s suite and, hair and makeup done, set off to the venue for photographs and final preparations.

They walked down the aisle, the bride and groom gave their vows and kissed, everyone cheered, and at last, the reception began, at which point I began counting the minutes until I was supposed to give my speech. I’m glad I cut the sleeves on the bridesmaid’s dress so I didn’t have visible sweat stains from the anxiety. I didn’t want to rush the wedding because I was having a great time, but at the same time, 10PM wasn’t coming soon enough.

10 o’ clock arrived, everyone took their seats, and someone announced me on a microphone, at which point I stumbled through an introduction and proceeded to sing for the next three minutes.

Given that the bride started crying on the spot, collapsing into the white, feathery pile of her dress, later telling me to send her the lyrics because she had totally lost it and couldn’t pay attention anymore, I think it was a winner.

If only I were 10 months sooner — I could have beaten this guy to going viral:

Thank you for the privilege, Cary. As I’ve said before and will say again, I’d do it all over again for you.


Privilege, influence, and action: a reflection

(Originally published on Medium on August 31, 2017)

You can sense America‘s current state based on small talk and lunchtime conversations. Lately, they are no longer as frivolous as “How are you?” or “How was your weekend?”

The last month in my office, alongside light chitchat about the solar eclipse and what we would do if we won the lottery (since a Massachusetts woman won the $7.58MM Powerball), we had some much heavier discussions: “Who is going to the protest tomorrow?” “What we would grab in a natural disaster?” “What we would do today if nuclear war began tomorrow?”

Today’s political and social landscape demands a whole new level of understanding, information, and empathy, and if I am being completely honest, I don’t measure up. Embarrassingly, I know far more about how Amazon’s price changes on Whole Foods will affect my grocery budget than how Trump’s proposed healthcare plan would affect millions of Americans. I could speak more cogently about the love triangles on Bachelor in Paradise than I could about the proposed Trans military ban.

I’m well aware of this ignorance, and while it’s shameful, it’s not so unique. I’d be willing to bet that more Americans have a stronger perspective on the season finale of Game of Thrones or the outcome of Mayweather v. Macgregor than on the latest nuclear threat from North Korea or best ways to help Hurricane Harvey victims.

Many would argue that I and others can afford this ignorance simply because we are privileged — they are right. Speaking for myself on just a few of the ways in which I experience privilege: I am white. I am heterosexual. I grew up in a family of means. I went to college at an Ivy League school. I have a master’s degree. I work in technology. I am in good health. I have money in a savings account. I live in Boston, a super-liberal, educated, expensive, and largely white city. I have American citizenship, which remains desirable despite the horrors of the present administration.

The pieces of my identity that put me most at risk, are that I am female and Jewish. My situation is nowhere near as hard as that of friends who are nonwhite, Muslim, or homosexual, but being a Jewish woman still puts me at some risk. The country has demonstrated fewer and fewer reservations about expressing its tendencies toward sexism, homophobia, racism, xenophobia, religious and cultural intolerance.

Still, because of my amount of privilege, the only time I tend to have a strong perspective is when something directly affects me — when that is the case I obsessively amass a Google’s worth of breadth and depth of knowledge about it. For example, it’s the difference between knowing that there are people who have cancer versus knowing a loved one has cancer. Right now, it’s the difference between knowing people will be deported and knowing your best friend is getting deported.

Martin Niemoller’s poem, “First they came,” comes to mind.

First they came for the Socialists, and I did not speak out — 
Because I was not a Socialist.
Then they came for the Trade Unionists, and I did not speak out — 
Because I was not a Trade Unionist.
Then they came for the Jews, and I did not speak out — 
Because I was not a Jew.
Then they came for me — and there was no one left to speak for me.

If there is anything I have wholly realized in the last few weeks, it is nothing is truly safe or sacred — it is only a matter of time before your privilege is under threat. It’s all the more imperative for individuals in a position of privilege to use it wisely, responsibly, and for the greater good. The bigger the platform, the bigger the responsibility, the greater the need to represent the people whose voices are muted, and, most importantly, helping them be heard, instead of speaking on their behalf.

On that note of privilege and influence, I’d like to give Tina Fey the benefit of the doubt in her Weekend Update segment, in which she plows her way through a sheet cake while ripping through the failures of the administration post-Charlottesville. She concludes with the call to action to “let the white supremacist groups shout angrily into the empty air.” I share the perspective of a few articles like this one, that Tina Fey’s segment was satirical. Others hold different opinions, but most prominently, I saw her satirizing white feminists in that and the only action they are taking in light of recent events is staying home and eating their feelings. But I also share the concern of numerous people who think her closing lines were supporting inaction. I worry that some took the segment as validation from a celebrity comedienne to shut the door, say “What a pity!” “How horrible!” and binge on sweets as if nothing happened.

We cannot ignore voices of hatred and bigotry because they aren’t falling on deaf ears — they’re continuing to find audiences. “Letting people shout angrily into the empty air” is not a solution — just because we are ignoring them doesn’t mean people who would listen don’t exist. We thought by ignoring one presidential candidate’s ludicrous statements and treating him like a joke would destroy his credibility in the electoral race. That candidate is now our Commander-in-Chief by the hand of those people we didn’t realize existed.

Compared to someone like Tina Fey, I’m in no position of influence, but by writing this instead of remaining quiet, giving more support to causes in need, and gaining perspective beyond a white, liberal elite lens, I am trying to use the privilege I have and what little platform I have to heal a little piece of the world. There is more I can do — and I welcome the suggestions — but it’s a start. From where I stand, taking action is not just a right — it’s a civic duty.

I like to believe that people in my piece of the world already do this, but the reminder is worth it: no matter your political views, I encourage you to support and stand up for those who do not enjoy the same level of privilege as you do — and empower those people to be heard and speak for themselves. Educate yourself on as many perspectives as you can so you better understand the beliefs of people who see the world differently from you. Donate your money or time to organizations doing good work to make society safer, happier, and more equitable.

Arguably, being able to do something but choosing to not do anything is also a right. It comes with freedom, but it is a dangerous luxury of privilege. At best, by choosing to act, you are truly helping others. At worst, you are purely self-interested and saving yourself so the day will never come when your privilege, and potentially your freedom, is gone.


Notes to self, birthday edition

I often take time to reflect—at least once a month in the writing of blog posts—but I reflect the most around December/January and June/July: I use the end of the year to take stock of the previous year, envision possibilities for the new year, and set resolutions. I use the middle of the year not only to reevaluate the ideas and goals I had for myself back in January but also to make birthday wishes: I think of where I want to be in my life—physically, emotionally, spiritually—and wish for what it’ll take for me to get there by next year, when I’m a year older.

I document these wishes by way of an annual practice: writing myself birthday cards each year. I read the card I wrote to myself last year and write myself a new card to read next year. I do this for Valentine’s Day, too. In both cases, I am guaranteed to have a card on these occasions from someone other than direct family that makes me feel loved*

Last July’s card had me wishing for two things—professional success at Wayfair and personal fulfillment in my relationship.**

Some excerpts:

“I hope you’ve gone from feeling shaky, confused, and insecure to confident, at ease, and killing it on the job…and that your success with Joss and Main propels you to renown around the company, even to the C-suite”

“I wish you continued happiness, love, and adventure in your relationship…Did you make it back to Miami? To Hong Kong and Shanghai?”

The former happened, more or less—I made some amazing friends during my time working on Storefront Product, and my work got some measure of C-suite renown largely coming from getting to build and launch Wayfair’s newest site, Perigold with my team. Amusingly, by the time I read the card, I had left Wayfair and was days away from staring an awesome new opportunity at SAP.

The latter also happened, but with a catch. We both found some combination of happiness, love, and adventure—or at least I did, through dear friends, a jiujitsu gym, and trips to LA, SF, Chicago, and around New England. I eventually made it to Miami and he got to Hong Kong and Shanghai. We just weren’t together when any of it happened. 

Here’s where things get even more interesting.

Back in December, I was convinced I had lost the birthday card I had written myselfin July 2016 for July 2017, so I wrote myself a new birthday card in December 2016 for July 2017. In the end, I found the first card, so I ended up with two cards for myself this birthday.

Because of where I was emotionally in December, the card had nothing to do with wishes for work. It was purely about the state of my heart. The shining piece was this:

“I want to remind you that no matter your relationship status that you are loved…You have so many people who love and believe in you and downright adore you. You deserve a man in your life who treats you and your golden heart with that level of care. Let’s be honest here. You’ve dated men who think you are beautiful. You’ve dated men who think you are intelligent. You’ve dated men who respect you and even love you. But you’ve never dated someone who truly adored you, and that is something you deserve.”

Wholly unexpectedly, I have reason to believe that this happened, too. And instead of finding reasons to doubt it, question it, challenge it, undermine it, and self-sabotage it, I’m allowing myself more than my usual flicker of joy. I’m pleased to report—much to my own surprise and despite the rampant global chaos—that I am netting out at a state of happiness. I can only hope that by the time I reflect this time next year that I will have lived up to the last line of that December 2016 card—and not just by watching GoT or doing the whole bit with the Seven Kingdoms:

“The power and crown are yours, Queen. Now go into your next year on the globe and take the throne.”

*I should note that I love my mother, grandmother, and aunt, for keeping Hallmark in business and making me feel loved by way of snail mail, among many other reasons.

**I also wrote in the card, “Remember never to waste a good mistake.” On Facebook, per a challenge I ended up documenting two-and-a-half months of mistakes. With the exception of a lame status or two, those mistakes didn’t completely go to waste. I also made plenty of mistakes offline, most notably the execution of my job switch and countless things involving men last year.

The Victory Lap

(Originally published on Medium on June 30, 2017/July 1, 2017)

In late 2016, I was sitting on the worn wooden floor of a small house in Bloomfield New Jersey with a coach I’d been working with for most of the year. A true Digital Nomad, she had been merely a virtual presence for our sessions until this final one — both of us being from New Jersey, she offered to do one in-person intensive super-session. The timing was convenient: days away from the new year, I wanted to reflect on my last year and my goals for the next.

Much of our conversation revolved around the themes of embracing imperfection and creative expression — after a year of working with me, my coach was well aware of my overthinking, perfectionistic tendencies and how often they got in my way of doing more writing and undertaking more creative work.

We brainstormed ideas for how I could improve at both of these and somewhere in there was the nugget that would become my first 75 days of the year, where I’d highlight a #dailymistake from my day.

This was the first post:

My friend, Christine, challenged me to live more vulnerably and expressively in 2017. Here it goes —
Social media is a place for the ‘highlight reels,’ the filtered, best-of-the-best, wittiest, most golden thoughts and moments. Rarely is it a place where personal failure, undone-ness, and other inconvenient feelings make their way to the surface (except in political and social justice op-eds)
Every day, I am challenging myself to share something about mistake I’ve made that day to balance out the more careful, overly-deliberate persona I have on social media. Some mistakes will be boring. Some will be next-level ridiculous. Some will be sad. Many will be relatable, and, I hope, offset the potential that the my daily posting becomes insufferable.
I hope to come out of 2017 taking myself a little less seriously and being more comfortable being unabashedly myself in public — internet included. If you’re reading these, I hope you’ll be entertained and maybe a little bit inspired to share some mistakes of your own with the world…

Over the next few months, the mistakes ranged from totally mundane to completely absurd, the more personal to the more professional.

Some from the archives that were a little more serious:

February 20: allowing myself to live in fear of a number on the scale.
March 9: feeling afraid, ashamed, or otherwise unable to ask for help when I know I need it.”
January 10: having to shut down a project one of my engineers had in the pipeline for 2 months because of important questions from other teams that surfaced too late in the game. Had I engaged my cross-functional partners sooner or more often in the building process, we could have addressed the other teams’ concerns early on and saved the work. Still so much to learn in #productmanagement

And others that were a little funnier:

January 13: Walking into Sephora on payday. My checking account never stood a chance. If you can’t dress like a million bucks, put your best face forward?
January 30: spent all day crafting and editing an important email to about 100 people. Noticed after sending that I began the email with “Happy Tuesday” when it is definitely not Tuesday yet.
January 26: #tbt to that night shaving my legs in the bathroom of a bar earlier in this month. Lesson: shaving your legs — no matter your romantic prospects the rest of the evening — is never that urgent. If anything, in the confines of a bar bathroom, it can be dangerous.

About 2.5 months in, though, I went for a switch from mistakes to victories. My execution was clumsy and lacked a decent explanation:

March 15: ignoring the feedback the first few times that it was time for a more positive rebrand of this daily practice.
March 16: becoming ready and willing to acknowledge that feedback and to make a change in a more positive direction.

The truth of it is, more than getting random crap from people for the mistakes, the real reason I ended up switching was because I was feeling sad. I ended up overly-focused on the mistake I made that day instead of the thing I learned from the mistake. Instead of coming to the end of the day to think of something positive that happened, identifying mistakes every day just stoked the flame of my inner critic. Even though, at the end of it, it’s just a matter of terms (I could have called this experiment a #dailylesson or #whatilearnedtoday or some other hashtag) but the reality was I was in a dark mental space at the time. I wasn’t in a position to see many of the things happening in my life as much growth opportunities so much as ways in which I was “not enough” and a “f***-up.”

I spent the next 3.5 months writing about little wins from my day to day instead. Even though most days the reality is getting through the day was my #littlevictory, I came up with some more creative ones:

March 30: the political climate in America may be dark and stormy, but it can’t put a damper on the rainbows and light in the Castro.
April 5: saying something that turned a dear friend’s day around, making her laugh so hard she forgot why she had been sad.
May 15: Saturday me, knowing Monday me was going to have a rough day, ordering gifts off my Amazon wish list to come home to on Monday night. I’ve never been so happy to see two books of poetry, five new sports bras, and a new pair of shoes.
June 16: conversation with a peer tonight at the gym, with me approaching a 3-month anniversary with jiujitsu: “You’ve gotten a whole lot better since you first stepped on the mat.” 🙌

And possibly my favorites:

June 19: actually being able to wear a bridesmaid’s dress again for an occasion other than the wedding for which it was purchased and tailored. I’m convinced this rarely — if ever — happens.
June 27: becoming the proud owner of a Le Creuset Dutch Oven, or “losing yet another reason to get married because I just acquired the thing I’d have wanted most off a registry.” Stephen and Daniel — props to you both and Nick for the rewards bucks that made this purchase happen.

There were multiple posts about jiujitsu and Keytar Bear and cooking — if I’m being truly honest, I don’t do much with my life in Boston anymore aside from roll, seek out the Bear, and cook things. And maybe go on a few ridiculous dating adventures from time to time. That’s about as interesting as I get.

Why stop the #littlevictory train? Because if I’m being true to myself, I’ve reached a point in this experiment where it’s feeling more forced than fun to come up with things that are a win for the day.

So in that spirit, the final #littlevictory here is knowing when a good thing has come to an end and it’s time to move on. But not without reflecting on it a little bit — hence this blog post.

Here’s what I learned from this experience.

  1. You never know what will resonate with people. You also don’t know who and what people will read. There were posts that I expected to strike a chord that fell completely flat and others that exploded with likes that made me ask, “Really? That one?” There were days where I had people I rarely speak to reach out with a direct message to say something kind — or in the case of one person, to call me a bitch. I promptly blocked that person.
  2. Achieving and sustaining any measure of internet influence is difficult. I’m convinced that the only way I’ll be able to start a real movement on social media is by getting cast on a reality television show and endosing slimming teas and tooth whiteners. That said, perhaps I hadn’t been giving enough credit to the Twitter pundits and Instagram influencers who do this kind of content creation work for a living: coming up with something fresh, on brand, relevant, and authentic on social media with meaningful consistency is a challenge.
  3. I became absurdly addicted to Facebook ‘likes’ and reactions — more than I thought I would be. It became easy to treat these as a reflection of how many people care, instead of as the product of an algorithm into which friends’ behavior have only so much input. I noticed myself becoming competitive with myself regarding the posts, feeling withdrawal when I came off a day with lots of likes and was met by very few the following day. It was problematic, because it was this kind of thinking that threatened to undermine the spirit of ingenuity and whimsy on which the #dailymistake and #littlevictory were based.

Social media is exhausting — both contributing to it and consuming it. So now I’ll be going back to posting when I feel like I really have something to say. Maybe daily, maybe rarely. Social media is just another tool for documenting and sharing. Sometimes it brings us together, sometimes it distances us. I still don’t know the right balance of including it in my day to day.

All I know for sure is that we don’t need posts or pictures to affirm to ourselves or prove to others that we’re “winning” or losing at life. It’s not a game, but a journey, right?

To the Fabulous Miss Flanagan

(Originally published on Medium on May 29, 2017)

(To my first friend in the city the occasion of your law school graduation and departure from Boston)

Dear Katie,

I have tried writing you this essay five times over, and now, at 8:15PM on a Sunday, an unconventional two glasses of wine deep, I am finally unfiltered enough to write you this.

This makes sense, since much of this friendship was cemented by way of some heavier drinking, but, much to my contentment, had a foundation much stronger than stiff liquor.

Even though it was determined from the very first day we met, I cannot believe that you have graduated law school and will be leaving Boston. You’ve defined my last five years in more ways that you will ever know, and the attempt to summarize them in a blog post or a card for your graduation is feeble. But because I promised you that I would write something — something I hoped would be worthy of you, our friendship, and the internet — and because, if nothing else, I am a woman of my word and a woman of words, here we are. The next two times I do this, it will be for a roast at your wedding one day and writing about you in the memoir. Needless to say, you’ve earned more than just this post.

I can’t say I knew our friendship was going to be something legendary, given that it began in earnest over $3 Mystery Shots at Tavern in the Square and Monday Karaoke nights at the now-closed Fire+Ice in Harvard Square, featuring that guy who sang “My Neck, My Back” without a hint of irony. All that was certain to me at that point was that being around you would guarantee adventure, witty banter, and a lot of Pinot Grigio, all of which I needed moving to a new city, knowing few people, still incredulous that I had gotten a job offer a week before I was due to start.

Nothing gives me a greater pang of nostalgia than thinking of the patio outside of Morgan Hall at HBS, where you’d be working on your laptop and I’d be napping on a bench, flanked by the rabbits that made their home in the bushes around the campus. (We will never have jobs that easy again, will we?) On the rare occasions I find myself over by HBS, past that patio, I smile. No matter how many years pass, no matter what else people call it, it will always be “The Katie Patio” to me.

I have you to thank for helping make this city into a home for me, as you welcomed me into your fold of fellow Ephs from Williams and whoever else made their way to your crazy parties, with the free flowing “Jungle Juice” and vodka lemonade concoctions, the playlists replete with dirty hip hop music, and the notorious “Makeout Chair” (which, alas, I am too late to occupy and make out with someone in). After being in an all-female a cappella group in undergrad, hanging out with you is the closest I ever got to feeling like I was in a sorority.

Even though I know that this is not the end of our friendship — far from it if I have anything to do with it — the thought of you leaving feels like a breakup. I’ll bike through Cambridge, passing the Phoenix Landing and Hancock Street and think of your latest nights out dancing or barbecuing and playing corn hole. I’ll go to Ruka and feel compelled to order a caipirinha and start drawing a portrait on a citrus fruit at the bar, or, feeling bold, juggle a pair of limes. One day, I’ll move out of this apartment of mine and think of the day you helped me move in, eating your Potbelly sandwich and surfing on the hotel dolly.

I’ll never forget the night that we met up. a few months ago and you told me about yet another old judge whom you’d charmed during a clerkship interview. He complimented you by saying you had a sunny disposition. His observation was spot on. Because of it, the way that I now describe you to others is, “She is sunshine.” From the first day I met you, golden-haired and smiling and charmingly midwestern, you were always sunshine. I thought we’d never be friends because I’m a little more of a raincloud. But being around you meant I could never be dark and stormy for too long. I will never forget the times you came to my defense and showered me with love when I needed it most, especially in the last six months. In your final days in the city, our friendship has gone through a brilliant renaissance rivaling that of our first days here.

You party like a demon — at Storyville of all places — and excel in your law school courses. You drink like a fish and still have visible abs. You have impeccable memory for song lyrics, a phenomenal squash game, and pretty great pitch. You are going to be a fantastic lawyer and you are show-stoppingly beautiful. (How is this fair?)

Five years of friendship later, only three question remain —

  1. “u a hurricane, katrina?”
  2. “u wanna text?”
  3. How do you not have any cellulite?

These will remain as much a mystery as the shots that forged our friendship.

You are magnetic and brilliant and bold. Keep spreading your sunshine — I’ll be in withdrawal of it here in Boston, with no other choice but to chase it all the way to Chicago.

All my love and wishes for more life and more success,


Finding myself in “Fight Club.”

Over the course of the last two weeks, a handful of people have caught glimpses of my arms, heavily bruised from a new practice of Brazilian Jiu-Jitsu. These were the responses I received:

“Jeez…that’s disgusting.” — One friend

“Did someone take a baseball bat to your arm?” — Another friend

“I still don’t understand this new hobby of yours, but if it helps, all the more power to you.” — Mom

“I always thought of you as a fighter. This actually makes perfect sense.” — An ex-boyfriend.

My relationship with jiu-jitsu officially started on March 22, 2017, but the story of how I found myself in the basement on Broadway goes back a little farther than that.

The interest in martial arts and fighting isn’t terribly new. I took karate as a kid until age 13, when I was two belts away from being a black belt, but, choosing to focus my spare time and energy on academics, didn’t pick up any fight sports again for another 10 years.

When I returned to fighting, it was six months after I moved to Boston. Joining the club of folks who make fitness resolutions in the new year, I started boxing in January 2013. Based on what I wrote about it at the time, I liked it a lot and felt like a total badass doing it, but once the Groupon expired, the gym became very expensive, and I never found enough of a sense of camaraderie at the gym to keep me coming back. The experience was very individual. People came to class and left. Boxing was a part of their workout routine — not so much a meaningful part of their lifestyle. By the end of March, I, along with all the others who hopefully take up new athletic hobbies on January 1, left the gym.

After that stint in fighting in 2013, I tried yoga, spinning, and pilates by way of free classes around Boston and services like ClassPass for the next four years. Still, I found the same thing to be true: no matter how frequently I went — or how much I paid — the studios never felt like home. Despite my regular attendance, no one knew my name or seemed to care whether I was there or not. There was no sense of continuity or community. At their worst, the environments made me feel like I had to put on an act and be someone other than myself. No matter what I did or how hard I attempted to embody athleisure, I always left class feeling like the biggest, sweatiest, most brutish girl in the room with the least fashionable clothing and the gnarliest hair.

If you have read anything else I’ve written in the last year, you’ll already know 2016 was a year of transition: out of graduate school and into the workforce, into a new industry and role, and out of a major relationship. The adjustment to all of these changes was extremely slow-going, and I finally “bottomed out” in March 2017, right around the end of a major work project.

With the project launch complete, I was finally able find my footing and listen to the advice from caring friends who saw me struggling over the course of the previous months:

“You should get more time outside of that office and do something that gives you a sense of purpose. You’re too wrapped up in your work.”

“You should try new physical activities that are fun and don’t make you feel so self-conscious.”

“You should do something completely badass that will help you get your swagger back.”

In early March, all these pieces of advice together when I went out to dinner with with a business school friend. Continuing to add to reasons why he’s probably the most interesting person I know, he told me he had recently added Brazilian Jiu-Jitsu to his repertoire of fight sports, including Krav Maga and Muay Thai. If you ever met him, from a few minutes of conversation, you could easily tell this he could “rip you a new one” with words, but from the boyish face, you might not guess that he could seriously mess you up. (I think it’s pretty awesome).

Somewhere in our conversation, he encouraged me to come to a jiu-jitsu class. While I’m sure he makes the offer to many friends, I’m not sure how many of them take him up on it. After thinking it over, and after a particularly rough week after we met up, I told him I was in for next Wednesday.

By the time Wednesday arrived, I was having second thoughts and contemplating ways to get out of the commitment, but by noon, he had shot me a text on when to arrive and what to expect. I couldn’t flake now.

I left work at 5PM, sharp (a rarity), and headed to the gym in South Boston. Arriving at the building, I laughed. The last time I was there, it was December 31, 2013 for a “New Year’s Flow and Meditation” class in the yoga studio upstairs. “How things have changed,” I reflected, and instead of heading upstairs to the more familiar place, I descended into the sweaty, mixed-martial arts cage-bowels of the building and entered another world. As I signed my waiver, I watched in awe of the men and (scarce) women in blue, black, and white gis as they rolled around, grabbing and attempting to immobilize their partners in different holds. My friend welcomed me, showed me how to do a basic hip escape move, and told me where to stand in the lineup (at the very end, as the newbiest of newbs).

“Welcome to ‘Southie Fight Club’,” I thought, as I bowed to the instructor and class began. One hour and many cross-collar chokes from my partner later, my ego had also been choked out. As I’ve written before, in most of my life, I am biased toward selecting activities that I am likely to be good at over trying something new. Even when I try something new, I tend to pick things up quickly and get decent at them without trying too hard. BJJ was clearly something I would not be good at for a long time and not without a lot of practice, patience, and effort.

When I got dinner with my friend after class, I don’t think he expected me to come back. Frankly, I’m not sure I expected to come back, but I was determined to give it an honest try of 3 classes before shooting it down. I showed up to a class on Friday and returned for a class on Monday.

Even though it was only my third class, the teachers and students I worked with already remembered my name. They were kind, encouraging, and humble, teaching me moves with tireless patience as I continued to screw them up in new ways each time. I noticed how they came early and stayed late after class, smiling and chatting and helping each other practice different holds. I thought, “These are the kinds of new friends I want to have. This is the kind of community I want to be a part of.”

After those 90 minutes flailing, falling, and frustrated, I was physically fulfilled; my brain, typically overwhelmed by all things work, was free of its usual chatter. I couldn’t believe it. I got so tired from getting beaten up that I didn’t have the energy to beat myself up. I was forced to be in the present and fight back at the person in front of me instead of fighting myself and the things in my head. Even as I was getting completely destroyed by my partner, the whole experience was was liberating and addictive.

As I packed up to leave, it occurred to me that this gym was the first place where I had truly checked the rest of my life at the door. As I asked other students what they did when they weren’t at the gym (students, bartenders, waiters, and more), it occurred to me that my professional credentials, personal identity, and all the things for which the outside world valued me, were inconsequential and — refreshingly, delightfully — unimpressive in this context.

I resolved to keep coming. I recalculated my budget and signed the papers for a six-month membership. Six months of getting up more often than I fall down. Six months of bruises changing the color of my arms. Six months of being chest to chest, head to crotch, and otherwise physically close to strangers in ways I would otherwise never fathom until a sixth date. (Needless to say, choking people makes for an interesting foundation for friendships, but that’s pretty much how it’s all likely to shake out.) Six months of something I will likely not be good at for at least six years. At the very least, after six months, I hope to have some clue for what to do with my hands in guard, a healthy amount of core strength, and a kinder attitude toward myself.

While I am far from free of my tendencies to obsess over the past and worry about the future, I now have 5–10 hours of dependable relief from that (largely self-imposed) psychological burden. Many aches, bumps, and bruises later, I’m noticing the physical resilience is making way for mental resilience.

I find it ironic that after years of trying to “be kind to myself” in yoga class, I’ve gotten closer to that mantra by getting my ass kicked in a jiu-jitsu class. For whatever reason, I have faith that something about this will pay off — I believe there’s more magic there on those mats in the months to come.

So begins the journey to quietly becoming the most lethal person I know.

(Originally posted on Medium on April 9, 2017)

March 2017: “The Perfect Trap”

I have heard all the truisms. Perfect is boring. Perfect is impossible. Perfect is dangerous. Still, none of those lines stopped me over the years from wanting to be perfect and trying to be perfect.

If you looked inside my brain, this is the dysfunctional chain of thinking you’d find: first, wanting to be perfect. Next, because I cannot be perfect, wanting to be the best at something compared to anyone else around me. Then, if I cannot be the best at something compared to anyone else around me, wanting to be good at something — but when I say, “I want to be good at something,” what I really mean is “I want to be good at something the minute that I try doing it.” Not only am I perfectionist, but also I am extremely impatient.

The worst part about it? Becoming good at things does not end up making me happy enough to justify the self abuse along the way: I am hard on myself when trying to become good at the thing, I tell myself I can only be happy once I have become good at the thing, and even if I eventually become good at the thing, I feel like I don’t deserve to be happy because I am still “not good enough” at the thing.

This is kind of a ridiculous way to think and live, isn’t it? There’s more to life than being good at things and enjoying life does not require being good at things. I would argue that enjoying life demands moments of being stupid and being thoughtless and getting in trouble and embarrassing yourself and adventuring without knowing what’s around the bend. In other words, a life well lived is a messy, imperfect one.

Why have I held myself to absurd standards and logic? The short answer is they served me well enough that it was worth putting up with them.

I have a decent history with perfectionist thinking and behavior— the most vivid memories come from when I was learning to play tennis as a kid. You’d think my dog had died if you saw how upset I got at myself for hitting a ball into the net or getting a fault on a serve. The behavior continued all through school, when I’d destroy myself for scoring anything outside of the A-range on a test or paper. Unhealthy as it was, grinding myself into a perfectionist pulp worked for a while — at least as far as getting me into college and graduate school.

Now, in my last 8 months of attempting perfection as a product manager and in my personal life outside of work, the cost is no longer worth my mental and physical health. I’d hardly compare my level of stress to that of Obama or Bush, but looking at these pictures of aged Presidents, I’m a case in point of the same phenomenon. Never has one experience aged me so much in such a short period of time as my current job.

Even though everyone I know has told me at some point to cut myself a break and be nicer to myself, I could never envision what life would look like for me if I were less hard on myself. This month, I think I started to see the light as I started taking improv and doing jiujistu.

I intend to write more about both of these experiences, but in a few sentences, what I like about them is that there is no way I can be perfect at either of them. My next line or move depends on the person matched up with me, and there is only so much I can anticipate or prepare for.

All I can do in improv is say “Yes, and,” and continue the exchange on the stage. All I can do in jiujitsu is try to extricate myself with what little technique I possess. I am inelegant and completely graceless, lacking the luxury of time to think through a next move and lacking the intuition that comes with experience in both improv-ing and fighting. I have to roll with the outcome — in the scene and on the mat.

The irony of all this is that one of the activities helping me learn to be less hard on myself is an activity that is physically hard on me.

Regardless, this is as close as I’ve come to escaping “The Perfect Trap.” Not by working harder or writing more, but by doing more things that forbid me from thinking.

Isn’t that a perfectly poetic solution to the perfect problem?


(Originally posted March 26 on Medium)

February 2017: “A Little Bit Sad”

Dear whoever is reading this,

I won’t lie to you. February has taken its toll on me and it’s no secret to people close to me that there were moments this month when it’s felt like this was the lowest I’ve ever been (and it very well might have been). What cemented this idea was something while having drinks with a coworker outside the office one day: “I like chatting with you and hanging out with you, but you always seem a little bit sad.” Even though he was fairly drunk at this point in the conversation, I couldn’t help but take his comment to heart. I tend to write off comments from people who don’t know me extremely well, but in this case, it almost meant more to me that someone who barely knows me but works with me has the impression that I’m “a little bit sad.”

It is true. In the last year, I have been “a little bit sad.” For what it’s worth, the last year has had an above-average amount of upheaval. I graduated from business school, moved into a new apartment, started a new job, and had a trying first 90 days adjusting to it. The pieces of my personal life I relied on most and relied on for their stability were suddenly in flux. With all that life change, the strength and confidence on which I pride myself took a huge hit.

I’m reassured looking back at my 5-year journal, where I started doing a daily log of my days on January 1, 2016. Looking at the entries from last February on top of the ones from this February, I was anxious and depressed pretty much the entire month last year, too. I didn’t come out of the funk until March 5. This gives me hope for the same this year — that the feelings are at least partially influenced by the winter season and that the storm clouds will lift as the daylight extends. I can’t afford to think of an alternative that’s anything but positive.

When I finally get off the waitlist for a therapist, the first thing I will say to him or her is, “I’m afraid I’ll always be ‘a little bit sad.’ I don’t want to be known — in work or outside of it — as the person who is ‘a little bit sad.’”

Because I am still at least 5 weeks away from getting matched with a therapist, I am trying to find things in my life to look forward to next month. Because my life lately has revolved around work, the thing I am most looking forward to involves work:

Just as my personal life hit the fan three months ago, I was conveniently given a project that would consume my entire life and distract me from any thoughts about anything but work. Barring any “Ides of March” hiccups, the launch goes live to the public on March 15.

When job-hunting in business school, I asked myself often, “What kind of projects do you want to be doing in your job after your MBA?” My answer was something to the effect of, “High profile, extremely cross-functional projects with superhero-level impact. I want to be doing things that are unlike anyone in the company has done before.” I got exactly what I wished for: It’s a stay-at-the-office-late, test-your-resolve, nearly-break-your-team kind of project. I know the scale of it is huge when my company, despite being notoriously frugal when it comes to swag and spending on food, signed off on letting us get have a party with catered food and team T-shirts.

I hope that by the time we are celebrating this launch, I will be closer to being a little less sad. If nothing else, I’ll be just two weeks away from a 5-day trip to California, and I am optimistic that getting to a different state will help put me in a different state.



January 2017: Back to the Blogging Basics

Dear whoever is reading this — hopefully more than just my mother (but because I know my mother will be reading this, I’ll just say it: “Hi, Mom. I love you”),

I hope you’re doing well since I last wrote, about a month ago. It’s a strange new year and if your January was anything like mine, it was a rough one. Wherever you are, I hope you are finding and practicing kindness, both with yourself and with whoever you know in this world is in need of it.

It seems that 2017 will be a roller coaster, and it’s tempting to for me to shut down with the fury toward this new “president” and the endemic imbalance of work and personal life. But writing has been my only form of accountability, and in addition to sharing a #dailymistake every day on social media, I am honoring my plan to write something publicly that’s more than a Facebook post’s length at least once a month. 

Cheers to checking the box on “January.” It’s the little things.

My blog, first “A Summer Crossing,” then “Boston Uncommons,” was started in 2012 on the premise of writing “the open letter” to anyone who wanted to know what was going on in my life. This year, I am taking my blogging back in that direction for the sake of fulfilling my writing dream of becoming publicly known as a writer. 

Over the last four-and-a-half years since I began blogging in earnest, my style changed from a weekly story of something that happened in my (then-new) life in Boston to a longer-form style, generally aimed at sharing something on the theme of personal growth and development. I very much like the direction my writing has taken and am quite proud of it. The more I nurture the writing, the more love and support I unlock from family and friends and sometimes strangers. However I generally can’t submit essays that have been previously published — even on personal blogs — to publications, unless I rework them to the point of being very different.

So I am working in the shadows on these longer-form pieces, not sharing them here unless they get categorically rejected and they can’t find a home somewhere other than But if you ever what to know what I’m writing about outside of these update letters, just ping me. I can always use the brainstorming help. One piece I’m working on is about adopting an agile product management approach to life design, another on the role of cartoons — especially some anime — in my childhood, and the rest are largely about romance. There are plenty of product managers and anime-watchers in this world who would probably relate to the two former pieces, but my stories on dating and relationships tend to be the most entertaining and most relatable. I’m betting on those. If nothing else, it’ll be fun to have them documented for my grandchildren — or my friends’ grandchildren, since my more stable friends have decided to live vicariously through me — to read and enjoy one day.

While my memory is quite good, I’d be foolish to trust it with all the hilarious details even five years from now. My best okcupid stories from 2012 and Tinder stories from early 2015 have become crippled in time, reduced from their fifteen-minute scope to a witty tweet’s worth of content.

For example, my story about the yoga teacher who wasn’t a yoga teacher was epically told back when it happened in November 2014. Now, it’s encapsulated in a single scene: in a Downtown Crossing apartment on Temple Street, awkwardly cuddling after flaccid-then-failed coitus on a winter night. Turning on “Suits” of all things, and pulling me in closer with a compact-but-toned bicep (which was not the only compact thing about him since I had “intimidated him” into a flaccid state), he said, in accented English that had sadly ceased to be sexy, “Just pretend to be my girlfriend. Just for a little while.” Thankfully it was a Sunday night and I could use the excuse of work the next day to GET THE F — — OUT OF THERE. And I did. I BOOKED IT back to my old apartment in Boston’s hospital-land, the non-neighborhood of the West End.

Point being: who doesn’t love a good love story?

Anyway, because of this decision to reserve the more polished think pieces for other outlets, I will use this platform to be a little less groomed than I typically am when writing publicly. I won’t be so unpolished that a reader couldn’t follow, but turning off my tendency to self-edit will lead to me writing more frequently and vulnerably in the moment, instead of over-analyzing and reworking the writing about my emotional state until it’s “perfect” (it never is and never will be). It is this kind of self-editing that prevented me from writing something in the moment when all the events I describe in “Dear World” happened. Especially the election.

I’ll probably do a kindle book of these epistolary posts in the future if they turn out to be any good. It’s likely the things that come up in these letter-style posts will inspire what I write next for a long-form essay. But anyway, there’s a lot of joy in experimentation here, and after reading “Big Magic,” I grudgingly agree with the insufferable-but-sometimes-inspiring Elizabeth Gilbert, that this creative process must be a one of joy and light and mess and community — not darkness and isolation. Here’s to embracing it.

Wishing you strength and stamina for February,


2016 End-of-Year Update: "The Year of The Thicker Skin"

If you want to get on the mailing list for posts and updates like these, here’s a link to subscribe. And if you have any ideas how I can make my creative dreams come true in 2017 (to become a published and more publicly-known writer and speaker) let me hear them. 


Happy Chanukah, Merry Christmas, Happy New Year—whatever you celebrate! As you read this, I hope you’re in the company of people you love in the coming days, especially since the last two months in America—and outside of it—have been full of fear and violence and vitriol. 

As I write, I’m chugging along on the faithful Northeast Regional Amtrak train, en route to visit family in New Jersey for the holidays. With the holiday hustle at Wayfair over and half the office out of town on vacation or working from home for the next week, there’s finally some time for me to think and reflect about something other than Q1-Q2 planning. 

Professionally, my update is a net positive one. It took the full 90 days before I really felt like I was getting the hang of big company life, tech life, and product management life. Since I hit that threshold, Wayfair has really started to feel like home. I got tapped to lead a challenging, cross-functional, and high-visibility project, the kind I was hoping for after graduation: if all goes well, it will launch in March to significant PR. My coworkers, especially the other female product managers, are genuinely good people, and I enjoy spending time with them off the clock as much as many of my peers from business school. My engineers have become a little tribe after the first three months of instability with people leaving the company or being added to the team. My most memorable moment was in November, when we had a karaoke outing with our pod, when the quietest, most polite engineer on my team, out of nowhere and to everyone’s surprise, took the mic and did a jaw-dropping rendition of Eminem’s ‘Lose Yourself.’ 

I’m still trying to figure out how to collaborate with my very tricky tech lead, who had been the greatest source of frustration in my first months on the job. Then again—no one ever said management was easy. I should have expected how our dynamic would be less than ideal when, in our first lunch together in July, he expressed his skepticism and distaste for business and MBAs. His behavior and attitude toward me demonstrates his lack of trust in my judgment, and he has repeatedly undermined me in front of the team to the point that one of my engineers flagged her concern to me at how “openly disrespectful” it was. The win here is that I’ve learned how to appropriately escalate this situation to supervisors instead of trying to handle everything on my own (as I tend to do), and my skin has gotten thicker—I don’t spend my weekends and spare time in agony at the prospect of having to talk to and work with him. The next time I walk into an interview and am asked, “Tell us about a time when you worked with someone difficult,” I will be able to paint a very vivid picture of what I did and how I got through it: 1. By making him feel empowered and accountable with as many facts as I have to share from the business side 2. By getting a gut check from his very equal-minded manager when my intuition tells me that he’s saying something weird, misleading, or straight up inaccurate. 

Personally, my update is more mixed. First, for the sadder stuff. My relationship of nearly two years with the boyfriend I would have thought I’d be married to in the next five years is on the rocks and may be over. 

I was blindsided when he asked for “space" the Sunday of Thanksgiving weekend and promptly moved out of our apartment on the following Wednesday—it escalated exceptionally quickly and for reasons that came from out of nowhere, that I still don’t understand, and that may not be true. “I feel like I’m holding you back.” “I feel like I haven’t been able to give you 100%.” “I feel like I have no control and no ownership.” He is 26, and I’m writing this off, in part, to a quarter-life crisis. He doesn’t feel like he’s successful enough yet or has the lifestyle he wants yet, but who is or does in their twenties? Is there ever an “enough”?

Reflecting on my piece in this break, in the stress of my adjustment to post-MBA life, I realize I was more focused on myself and, in my own obsession about my future and success, was likely blind to what was going on with him. Even though I suspect that this breakup has less to do about me and more to do with him, my analysis of my role in the circumstances has gotten me this far: I spoke my mind unapologetically. I was rigorously honest. I didn’t pretend that things were all right when they weren’t, which meant I had days of being impossibly euphoric and days of being inconsolably sad in the last six months. I worry that my style of communication, which is super direct, overwhelmed him, came off as abrasive, and made him feel unsafe to express himself, as if there was no room for his feelings in our tiny apartment. But I can’t blame myself for his failure to open up in the moment, when he needed to—not months later—and I can’t blame myself for his lack of emotional maturity in these situations.

He is back in Hong Kong with his family for the holidays and we will talk again when he returns in January. He claims he still loves me, but I find it hard to believe anyone who loves me would do this to me. I am nauseated by his cowardice, both in how he broke up with me and how he has opted to eliminate our relationship instead of finding the courage to end the relationship that really seems to not be serving him—the one with his cofounder, who is a poisonous, emotionally-manipulative human being. I hope my likely-ex realizes that “hitting [their] number" in the next few months is nowhere isn’t as valuable to his life as the loving relationship we had. I’ve always believed success is nothing without people to share it with you, and at this point, he has cut out pretty much everyone in his life in dogged pursuit of that number. I wonder, if he hits that number and if we are out of each others’ lives, if there will be anyone left to celebrate it with him. 

I don’t know what comes next, but whatever happens next month when we communicate again and he is back in the United States, the break has reminded me how many people I have in my corner, and that I have many other people in this world who love me who would never hurt me like this. For what it’s worth in this, my skin has gotten thicker in my personal life, as well.

Now for the happier stuff—and there’s a lot of it. I have four cousins and all of them had babies this year, the last one born just a few days ago. My 75-year-old father is transitioning into retirement from his law practice, which has relieved a ton of stress at home, especially for my mother, who has worked for him since they got married. Tomorrow, they celebrate their 35th anniversary, which gives me a reason to elevate the Jewish tradition on Christmas of Chinese food and a movie with a little bit of champagne. I’m still blogging once a month, with the highlights in the tail end of the year being a post about meeting Bruce Springsteena post about Halloween costumes and self-expression  and a reflection on 2016 on Medium, which I’m using as an a bonus blogging platform to my personal website—the tracking is better, posts are easier to share, and the design is superior to what I’m capable to riffing up on my Squarespace site (that said, I’m hoping to spruce up the personal site with the help of my coworkers. I’m lucky to now have a slew of creative tech folks I can consult to help me make my online identity sing). 

A not-so-secret secret I have is that this creative work is something for which I want to be known in a big way one day. And not just writing—public speaking, too (the podcast I started last year was a small step in that direction). For now, and for lack of better ideas, I’m planning to refine and edit posts I’ve written on my blog the last 4.5 years and turn them into an e-book of personal essays. If the goal is to give my work more public exposure outside of my personal network, there’s nothing like the universe of Amazon. It’ll also be good to get a little bit of criticism and rejection from total strangers, at least in the cases where it makes me a better, more thoughtful writer (and help me develop a thicker skin against internet trolls). For 2013, one of my new year’s resolutions was to submit a piece to the New York Times’ Modern Love column, and four years later, I have yet to find the courage to submit anything. Maybe now is the perfect time, in the embers of a heartbreak and with the dawn of a new year, for me to write that piece. 

In all seriousness, if you have any ideas to help me make the writing and speaking dreams come true, please share them. I’m currently in the midst of evaluating what I write, where I write and speak about it (online/offline, certain media outlets, etc.), and how I can get my voice out there in the world to the people who would benefit from hearing it.  

With that, I wish you and yours warmth, light, and joy this holiday season and in the new year. Whether you’re near or far, please be in touch—I’d love to hear how you’re doing, even if it’s just a quick “Hi” back. Thank you for caring about me and reminding me that the world, for all the pain of the last year, is still a place worth cherishing and saving. 

All best wishes,


Dear World,

The holiday season makes my soul crackle with warmth and light. I walk around rapt by the magic of icicle lights and pine garlands snaking around city lampposts. I dream of parties with balsam fir-scented candles burning, crystal bowls filled with eggnog. I’m wearing a dark velvet dress with black stockings and red lipstick, embracing a friend with one arm, holding a glass of champagne with the other. I feel warmth. I feel at peace with my sense of self and truly believe in joy as carols quiver in the wintry air of the east coast in December. 

Even if all this vision comes true for me this holiday season (that I magically fit into that velvet dress and that the red lipstick does not make my skin look sickly pale, but “Russian novel protagonist alabaster”) my body and spirit will be heavy — and not just with the weight of Thanksgiving indulgence or gluten-free fruitcake. World, you have taken some serious hits this year. There are not enough gifts I can give, letters I can write, or kisses I can blow to make those hits better for you, for myself, or for those around me. I’ve shed my tears for the violence in the Middle East and Europe, for the rising toll of BLM and police deaths. I’ve mourned the collective heartbreak of liberal, Muslim, LGBTQ, and ovaried America with the election of the notorious DJT, whose fledgling administration gives me pause, as just a year ago, I was in Yad Vashem, staring at the shoes of Jews who were gassed and incinerated during the Holocaust, thinking, “The world would never let this happen again, right?”

For all the horror, fear, and pain, I must remember that this was not a lost year:

I delivered my “grad school baby.” My cousins delivered real babies. 

I recommitted to Boston for at least two more years (or until something worth breaking my lease for comes along). 

I watched Bruce Springsteen in concert and met him in the flesh eight months later— the stuff of adolescent dreams, fulfilled. 

I led events where student peers and faculty opened their hearts onstage, sharing stories about themselves at their most vulnerable in front of the rest of the community. I still have no idea how I did this in the context of a MBA program, which is all poise and pretense and polish. 

I discovered Austin, Texas, and survived SXSW. I rediscovered Miami’s Coconut Grove. 

I served as [wo]Man of Honor at a close friend’s wedding in Middle of Nowhere, Missouri. I was asked to serve as Maid of Honor at a close friend’s wedding in Beautiful Somewhere, San Francisco. 

With the help of the latter friend, I discovered (and then revered) the music of ‘Hamilton.’ 

I learned what a sideboard was and what an endpoint was and what a Product Manager wasn’t.

I nurtured new relationships and cemented the older ones. I almost healed the one with my father. I partly healed the one with my body, as I finally wriggled back into the most-cherished item in my closet.

I lost some of my identity. I found some of my voice.

There are countless reasons for me and for others to cry about the broken state of you, to wring our hands in despair or bury our faces in them. But as the year ends and the snow begins to fall, I thank you, World, for reminding me that I still have reasons to smile through the holidays this year, to remain enlivened by the spirit of connection, compassion, kindness, and cookies.

Dum spiro, spero. While I breathe, I hope.

And I hope, World, for all the people who would wish you dead or have you end, that you smile and spin on. 


Inspired in part by the “The How Life Unfolds: Letters of Peace” campaign

Beyond the Tricks and Treats: Finding Truth on Halloween

Today is Sunday, October 30, 2016. Even though Halloween is still one day away, by tomorrow, I have already celebrated it 5 times over.

  • Wednesday, I celebrated Halloween by watching a bit of the office’s children’s Halloween parade. I’m biased, but my boss’ angelic one-year-old girl as a bumblebee was certainly the most adorable tot in the lineup.
  • Thursday, I humored the “grown up” Halloween festivities at the office, where more than half of the 3,000 people in the building ended up dressing up, myself included, as a tiger. In an office full of engineers (and therefore a ton of Star Wars, Pokemon, and Game of Thrones costumes) I’ll remember the engineer who defied convention in his costume by walking around with a Union Jack shirt and an Exit sign around his neck. Get it? #brexit
  • Friday, I endured Halloween on my Lyft home from dinner, as my driver plowed through side streets teeming with costumed masses waiting to get into trashy Theater District clubs. Were I not completely cold and exhausted, I would have loved get in line to talk to the guy dressed up like a box of Crayola crayons. I’ve just never seen that costume before. 
  • Saturday, I went to an actual Halloween party, where the best costume were a pair of friends dressed like the Boston subway stops Alewife and Brainstree (as in one was a wife bearing ale and a tree with an exposed brain. I'll never think about the Red Line the same way ever again).
  • This morning, I watched hungover college student-zombies fill their baskets at CVS with Gatorade and Tylenol, as I bought the store out of its clearance Halloween candy to use for Christmas baking. 

For all the Halloween fatigue I’m experiencing, I’m generally a fan of costumed holidays. My favorite holiday—bar none— is the Jewish holiday, Purim. Most people don’t what it is, but many have implicitly “celebrated” it by eating a Hamentaschen cookie (which looks like this) at some point in their lives. Similar to Halloween, it’s a day for children to dress up and eat sweets, and for adults to sometimes dress up, and definitely drink up. Unlike Halloween, Purim has a pretty sophisticated story behind it, and the holiday places as much emphasis on merriment and self-indulgence as on charity and giving to others. Still, barely 2% of the U.S. population is Jewish and even in a city like Boston, which has strong pockets of Jewish people, it looks pretty weird to see people out in costume in March, when Purim tends to fall. 

The thing I like the most about Purim and Halloween and that I have thought about much in the last few days is how holidays like these give us a judgment-free pass to be somebody else for the day (or longer, depending on how long you and your friends celebrate). Whatever we choose to wear on an ordinary day showcases our personality in some way, but on Halloween, we can take that self-expression to an extreme. Take away the alcohol—Halloween as a holiday is a social lubricant. We can feel safe enough to show pieces of ourselves that, for whatever reason, we don’t feel comfortable showcasing on every other night of the year. I’d argue that the people who dress up in costume are more themselves than the people who go to a party and say “This year, I’m being myself.”* 

I always think of the line from the movie ‘Mean Girls’: “Halloween is the one night a year when a girl can dress like a total slut and no other girls can say anything about it.” I have to say that girls who do that should be able to dress and express themselves however they wish: I don’t like when girls dress a certain way for the attention of men when it’s coming from a place of feeling inadequate and craving validation but am fully in favor of women dressing a certain way if it’s coming from a place of confidence and empowerment. Are you a woman who feels like her sexuality has no outlet to express itself or is otherwise under lock and key? By all means, channel your Dita von Teese or Pamela Anderson, and be yourself on this night for the first time, when it’s safe to be “somebody else.” 

Last year, I was Holly Golightly and Carmen Sandiego—the classically glamorous silver-screen socialite and the sexy, sleuthing, mysterious globetrotter. In previous years, I was Wonder Woman and Katniss Everdeen from the Hunger Games—two powerful, headstrong heroines, leading and fighting for justice in their respective stories and on an American media stage historically dominated by male heroes. This year, at the office, I was a tiger—not my most inspired costume, but it was tremendously joyful day holding team meetings that included a panda, a cow, a sloth, a chipmunk, and a giraffe, and going out for lunch at one of Boston’s highest-traffic malls in an animal onesie. But even choosing to be a tiger served another purpose beyond being part of a team costume and getting to use that costume again for a college reunion. They’re smart, beautiful, regal, a little fearsome, and “solitary-but-social” animals. What I think about these costumes inevitably says something about me. Wearing them is a way that I express how I think about myself, what I aspire to be, and how I want other people to think about me. 

It’s a holiday that makes me wonder about all the ways in which I hide in plain sight from people about how I really am. Last weekend, I got into an argument with my dad about politics, and I never felt more myself and in a state of flow than when exchanging blows. He’s an aggressive lawyer with forty-plus years of court under his belt, and I have spent much of my life simultaneously arguing against him and trying to please him and have him be proud of me. Anyway, when we debated, I was confident and full of conviction when speaking to him and explaining my beliefs, even if exposing those beliefs put me at risk of making him angry to the point of him kicking me out of the house. In the company of friends and coworkers, I wish my I could express my voice so strongly on other topics about which I feel passionate. I generally have a strong perspective on many things but hesitate to share it for fear being disliked, ruffling feathers, losing friends. Sometimes this voice comes out in writing, and I’m doing better to have it come out more in writing and outside of it. That strength of voice and opinion is something that deeply defines who I am and what I value and like about myself, but it’s not something that people really see much from me or that I allow to come out. I believe this is true for many others as it is for me.

So this year, if you’re going out (again), I encourage you to pay attention to what you wear and what your friends are wearing and what typically-hidden thing people around you are choosing to show about themselves for the night. If you decide to get psychoanalytical about it, there’s a lot you can learn about people by observing what people chose to be. Even the person dressed up like a hot dog because it was the only thing that they could borrow at short notice or get in time for Halloween with Prime shipping. 

I hope you’ll take advantage of the night to fully express yourself and find the courage to show a little more of your costumed self on the other days of the year.

Happy Halloween!

*Unless the person doing that is a new-age-y friend who’s stoned or tripping on something else. Then it’s more likely they’re being themselves. 

The Remarkable Mr. Springsteen

I have spent the last month and a half waiting for this Tuesday. I have plenty of books on my bookshelf, but I’ve saved a top-shelf space for the occasion. A new book is joining my library and it is Bruce Springsteen’s memoir. 

I have never bought Vanity Fair, but as soon as I read Bruce Springsteen's interview in it online and learned from it that he was coming out with a memoir, I bought the magazine when it hit newsstands so I could own the issue in glorious print. I might cover it in plastic, as comic book collectors do their precious issues. I don’t want to let a mite of dust fade the Annie Liebowitz portraits or a careless spill of water to log the pages of the interview. 

I didn’t always love “The Boss,” even though I probably should have had his music in my bones as soon as I left the womb. I was born in Long Branch, New Jersey at the same hospital where he was born, and my mom’s side of the family has a long history with Asbury Park, where he and the E Street Band got their start at the beachside rock bar, The Stone Pony. 

Growing up, my tolerance of Bruce Springsteen was low, because it was circumscribed to “Born in the USA” on the Fourth of July in New Jersey, and what other pieces of his music I heard were in my dad’s car, where my dad, half-deaf, played the music so loud you couldn’t decipher the words. "Bruce Springsteen" was what I called the raucous, growling sounds of family car rides down to weekends at the Shore to visit my grandma and cousins. 

Around 10th grade, my first boyfriend changed my perspective on “The Boss.” 10th grade was the year I had to memorize Shakespearean sonnets for English class and write cuentos inspired by the master of magical realism, Gabriel Garcia Marquez for Spanish class. It was my year of imagination. 

We were sitting on the floor of his room one afternoon, and while talking about our favorite musical artists, he started searching through his CDs. I asked what he was looking for, and when he said a Bruce Springsteen album, I immediately groaned. He finally found the CD he was looking for, and as he raised it into the sunlight to blow off the dust from it, it created rainbows across the room. I know that CDs do this all the time, but something about those rainbows in that moment made me believe that something special was about to happen. He pressed play, and this time, at 60 decibels instead of what felt like 600, I could actually make out the words of the songs, and they struck their first chords with me. 

Weirdly enough, my “gateway songs” for Bruce weren't the classics like, “Thunder Road,” or “Hungry Heart," but Bruce's folk rock take on the spiritual “O Mary Don’t You Weep” and “Outlaw Pete,” a sprawling but catchy 8-minute cowboy epic. “Outlaw Pete” was released my freshman fall of college, about a month after that boyfriend and I went to see Bruce Springsteen in Madison Square Garden for his birthday. It was my first Bruce Springsteen concert and it was characteristically overwhelming experience, but I remember a few things: 1. How bowled over I was by the man’s vigor. 2. How little of his music I actually knew at the time. 3. How confused I was when I saw Elvis Costello join the band onstage to conclude the show with “Your Love is Lifting Me Higher.” 

There were only two stable things in my life as a college freshman: my boyfriend—the rock, and Bruce Springsteen—the rock and roll. Both got me through physics and linear algebra that fall and then out of my engineering major by the end of the year. 

By the time my relationship with that boyfriend had ended, halfway through college, and after nearly 6 years, I had developed my own relationship with Bruce Springsteen. Luckily, Bruce Springsteen didn’t have to choose a side in this breakup, and we were both able to keep a piece of him with us. But if only one of us could have him, I’d have fought like hell to beat the boy for “The Boss.”

No longer having to compare or benchmark my understanding and passion for the music against my ex’s, my love for Bruce Springsteen’s songs grew. I spent the last two years of my time in my college a cappella group trying to get the group to agree to arrange “Born to Run.” My next boyfriend and I talked about him learning the piano melody and me learning the lyrics of "Thunder Road” to perform it somewhere. As an upperclassman, I was finally able to have a car on campus, and whenever I got out of the suburban side roads and hit the New Jersey highway to head home to the Shore, that was my cue to put on “The Essential Bruce Springsteen.” “Atlantic City” for the more contemplative nighttime drives, ”Cover Me” for the more energetic daytime ones, or to cheer me up in bumper-to-bumper traffic on the Turnpike. 

The Boss left my life for a while when I moved away to Boston. My connection and sense of identity associated with New Jersey disappeared for about a year. Then I went through the exercise of self-reflection and reconnection that was applying to business school and Bruce broke his way back into my life, my muse in full musical force. One of my essays was even themed around a few Springsteen songs, but because it was an application to Berkeley, I’m guessing it sent the opposite message I was intending to send to the admissions committee. I have no doubt by the time they finished reading it that while this "Jersey Girl” was a decent writer, she would never get in a “Pink Cadillac” and move across the country to California for school. Because I’d managed to get into MIT, they were right on that count.

Springsteen fell off of my playlists again as I dove into statistics and strategy, barely returning to the surface until my last year of business school. My dad has boasted for years of his “connections,” which had yet to come through for me in my professional or personal endeavors save for this: two tickets to this year’s “The River Tour”  at Boston’s TD Garden. It was a hectic last first week back at school, but February 4, 2016 would be worth every bit of exhaustion on February 5.

It was my second Bruce Springsteen concert, and very unlike the first, which I’d seen about 8 years before. I was with the first person who put a roof over my head when I moved here: a dear family friend who I consider my "Boston big sister," who also grew up at the Jersey Shore. I was weary of school and anxious to start the next phase of my life in Boston, with graduation four months away. I was impressed by Bruce Springsteen's vigor after all these years on stage, putting an 80s workout star to shame. I was delighted to discover new favorites ("Independence Day" and "Point Blank") as Bruce and the band played through the entire “The River” album plus 12 more songs to bring the concert to a whopping four hours. I marveled at all the things that had and had not changed in my life the last ten years of conversion to the gospel of Bruce Springsteen. 

The night opened with a line I’ll never forget: "Are you ready to be entertained? Are you ready to be transformed?”

I was entertained. I was transformed. I can’t wait to be both entertained and transformed again, this time by the book on my shelf. I haven’t decided if I’m going to devour the book or try to savor every single page because I won’t want it to end once I begin. Even though I know a little bit about of what to expect from the memoir from reading all the advance press and parsing the lyrics of his songs, I'm certain the book will find its ways to surprise me in its 510 pages. I’m excited to see how much of his life went written and unwritten in his songs.

It’s as true now as it was when I was a college freshman: the two most stable things in my life right now still are my boyfriend (a different one)—the rock, and Bruce Springsteen—the rock and roll. Bruce Springsteen always shows up when I need him most, and this book has come at just the right time on this new-ish job.  I’m two-and-a-half months into work, haven’t hit my stride yet, and feeling frustrated at feeling unsettled. Enter Bruce to help me get my life back on track: to bring me back to a state of purpose and confidence; to put back the song in my heart and help me find the courage to sing it in an environment where my voice is still shaking; to help me be my most creative while off the clock, as I muster the spare focus and energy to keep my writing dreams alive.

The man lives his truth every time he steps onto a stage. He gives his whole self to each performance, jumping around, leathery, muscled and vital as ever at 67. I pray that at 67, I’ll look just as good as Bruce Springsteen does and will have had a lifetime of doing the work I was born to do. If I’m lucky, I’ll have more than a few fans screaming my name by then, too. 


Until then, in pursuit of that sense of purpose,, working hard at becoming a boss at my job, I’ll be counting the days to my first day off in October, when I'll meet the "The Boss," the man, myth, and legend, and have him sign my copy of his book. 

10 Weeks a Graduate: A Post-MBA Update Email

Views expressed are solely my own and do not express the views or opinions of my employer.

Twice a year, I write update email to my old professors and bosses, keeping them posted on what I've been up to in the half-year since we last connected. Below is what I wrote in the most recent update. I found it fitting to post this letter as this month's piece since this blog began four years ago as "the open letter" to anyone who cared about me and wanted to know what I was doing in my life.


I’ve had a hard time writing since June. Or, more accurately, I’ve made a lot of excuses to not write over the last two months. “Post-MBA life is so busy,” was the main one, and, “I’m afraid of having nothing to say,” was the second. At any rate, this weekend, four weeks into a new apartment, new job, and fully-formed new life after graduate school, I decided to put both these thoughts aside and put fingers to keyboard.

Here’s how I’ve spent the last few months:

Since graduating on June 3rd, I spent the next month decompressing from business school (as I wrote in the last post) and taking a few trips—Chicago for a long weekend of food, drink, and improv shows, and twice back to NJ/NY to see family and celebrate friends’  weddings, which are suddenly becoming frequent commitments. The travels weren’t as exotic as some of the global adventures my peers took after graduation, but I never really bought into the “extravagant trips” part of the MBA experience, and I’m relieved that that part of my life is now over. I saved most of my spare money and energy this summer for moving into a new apartment with my boyfriend in Chinatown. It’s a 20-minute walk to my new office, and while it’s summer in Boston, it’s nice to be outside and take in the sight of Boston Common and Copley Square in my morning commute before they’re teeming with Pokemon Go players. 

Speaking of the job, I started at Wayfair in Boston four weeks ago as a Product Manager for the largest of its four Lifestyle Brands, Joss and Main. After 2 years at MIT, I had hoped I’d have a better answer to the question of “What does a Product Manager do?” The best I can say to friends and family these days is, “It differs by company, and even differs within my company, but in my specific role, anything that involves the look, feel, and functionality of Joss and Main’s website on a laptop and phone is my responsibility." Most of my time is spent identifying problems to fix on the website (totally real example: your shipping address doesn’t show up when checking out) or brainstorming new things to build and getting senior management to buy into them (totally fictional example: if there were a multi-million dollar opportunity in making a filter feature to better help animal-loving customers find wall art exclusively with pictures of dogs, I would be the one making the case for building the filter and then leading my team to make it happen). 

Despite graduating with a master’s degree from a school of management, I’m far from good at the management part of my job yet. This makes sense because I’ve never actually managed people before—and when it comes to managing people, managing engineers has its particular challenges. Then there’s the added challenge of communicating with and managing the expectations of my business stakeholders in marketing and merchandising. They’re mostly ex-"Big 3" Consultants who are hardcore data junkies. So to the engineers, I need to speak in code, and to the stakeholders, I need to speak in numbers. 

In that regard, my life seems like it hasn’t changed at all since my life as a Comparative Literature major in college—today I’m still learning new languages and practicing them simultaneously. In the effort to be patient with myself in this transition, I’ve even likened this job to my experience learning Chinese: in the first two months, I could barely say two words without one of them being a mistake, but by the time I was nine weeks in, things were starting to click and I could say a sentence with confidence. Tomorrow starts my fifth week, so I’m hoping in another month, I’ll feel like I’m getting closer to “proficient” in all things Wayfair, and maybe, six months in, approaching “fluent."

Especially with the Olympics on, I've had an interesting time to reflect on how my sense of identity has changed pretty much every year for the last five years. Five years ago, I was in Beijing and Rio doing thesis research on the Olympics, and people in college knew me as “the language person.” When I started my job at HBS and wrote case studies on Chinese companies for the MBA program, I was “the China expert.” Next year, starting up the baking business in Boston, I was  “the food entrepreneur.” My last two years, I was “the MBA blogger/storyteller/podcaster” and “the girl who was interested in the food industry but interned at Sephora.” I want to be known for more than being a product manager at Wayfair, but it means actively considering the questions of who I am and what I care about outside of the office. But for now, I’m just trying to find some solid ground in a time of major transition. Or, to continue the Olympics talk, trying to “stick my landing” like all these very inspiring gymnasts.

I hope you’ve been well and would love to hear what you’ve been up to the last few months. And needless to say, if you’re in the market for home furnishings and decor, let me know. I’m a little biased, but Joss and Main has a fabulous selection and you’ve got someone inside with a great corporate discount :)