LinkedIn at 1:45 p.m.

What does ambition look like when it no longer fits on a business card?

I open LinkedIn and see the usual updates. A few people in my network have joined OpenAI, Anthropic, FAANG, or the newest unicorn startup. Others have been promoted, graduated with an Ivy League MBA, or started companies of their own. I’m happy for them but the next second I feel conflicted. I sometimes wonder where my career would have taken me if I weren’t here in Japan. But I don’t have much time to wonder about it. It’s 1:45 p.m., so I close my laptop. I need to pick up my daughter from school.

One of the most common questions I get since moving to Tokyo (besides how long we’ll stay and if I speak Japanese) is whether I’ll go back to work full-time. I never know the answer because I’m still trying to figure it out myself.

Part of the reason is practical: I’ve accepted that I’m unlikely to find a similar role, or even a more junior one, in Japan without business-level Japanese and a company willing to sponsor a work visa without it. Even companies that once advertised English-speaking roles now want bilingual candidates, even with referrals. Every recruiter who reaches out to me eventually highlights the same requirement: business Japanese, spoken and written. I’m still learning Japanese, but my language learning journey has been slower than I anticipated. Kids growing up here spend over a decade learning kanji starting in elementary school, so I’m trying to give myself grace. Anyone who has attempted to learn a language as an adult knows how humbling it is and how much time the grind asks of you.

The other reason is harder: I’m no longer sure what I’ll be returning to. For most of my adult life, my career followed a relatively straightforward path. I started in healthcare, worked at one of the largest healthcare companies, went to graduate school, moved into technology at a FAANGMULA, and eventually got a leadership role at a startup. Success was easy to measure by the next title, the next promotion, a company people recognized, and it mattered a lot, especially when you’re living in San Francisco.

Then life started introducing forks in the road.

A few years ago, I was in the final round at Slack while it was being acquired by Salesforce. Around the same time, I was given an offer by a health tech startup. I dropped out of the Slack process and took the startup offer. At the time, it felt like the more exciting bet - faster pace, more ownership, the ability to manage my own team, the chance to build something from scratch. It was all of that. I loved the people, the culture, and the mission.

But a year later, the startup went through a three-way merger, and so much of what drew me there changed drastically. Around the same time, my husband and I unexpectedly found out we were expecting a baby, and we moved from the city to the LA suburbs to be closer to family. When I came back from maternity leave, I was on my third boss post-merger, and everything felt different again.

Having my daughter changed everything. Whatever framework I used to evaluate my career decisions just didn’t seem to apply anymore. There was someone else besides myself I needed to consider at every waking moment.

Around that time, my husband’s work started pointing us toward Japan. Taking a break after a difficult postpartum season and years of working so hard didn’t feel like quitting. It felt like stepping off the traditional path, betting on myself, and seeing what life had in store across the other side of the world. I was excited.

When we first moved here, it seemed like a dream. So much of everyday life was easier. I could walk to the grocery store and the train station. I had restaurants and parks just outside my apartment. I felt safe walking at night when I had a craving for a treat at the konbini.

Super ball scooping (スーパーボールすくい) - a summer matsuri staple ☀️🎆

I also feel like I’m giving my daughter a great childhood - we get smoothies at the 7-Eleven on the way home, she plays with her friends at the park after school, fishes for crawfish in the river near our apartment in the summers, goes to Japanese festivals, and is learning a new culture and language. She sees kids walk home from school by themselves, something that would never happen in the States. Most days, I think we’re giving her a better childhood than we could have given her there.

All of this is true. But also, it hasn’t been the easiest decision for my career. When someone used to ask, “What do you do for work?” and I said I worked at a well-known tech company or was a Senior Director at a Series B startup, there was weight to that answer. I felt like it legitimized me, that I was a capable person making an impact on the world. Now, when people ask what I do, I hesitate before responding. I advise and I write (on top of being a mother, which is a full-time job itself), but the startups are smaller and don’t carry a name people recognize. It’s also difficult to measure success as a writer (I appreciate all 22 of my subscribers, thank you thank you 🥹). These days, I feel like I am not making the same impression as I used to. When I see their eyes flicker for a brief moment after I answer (Japan has taught me a lot about reading the air), I know I’m being filed away mostly as a mom.

I still think about the other timelines sometimes: the Salesforce job, the RSUs, the version of me who stayed. I don’t know if I would have been happier though.

A different kind of work 🇯🇵 📚

But ambition looks different than it used to. A few years ago, it meant a title, a compensation package, and a company name people recognized. These days, it looks more like advisory work I enjoy, learning Japanese, rebuilding community, figuring out who I am outside of full-time corporate work, and writing again. Two weeks ago, I went to an alumni event for my graduate school chapter in Tokyo. It was my first time going and I was nervous partly because I didn’t know anyone and partly because I didn’t want to say I don’t have a full-time corporate job here. But the conversations didn’t go as I had feared. Some of us were foreigners, some Japanese, all of us somewhere in between. We talked about our stories, raising kids across cultures, what we missed at home but what we loved about building a life here. By the end of the night, I had added six of them on LINE. I had walked in afraid of how I’d be filed away. But I had walked out with real connections, built over shared experiences, and none of them came from a company name.

I realized I haven’t stopped being ambitious. My ambition just looks different now, and I’ve been trying to stop using a job title as such a huge part of my identity.

Maybe the fork in the road wasn’t choosing one career over another. Maybe it was realizing there are more ways to build a life than the one I thought I knew before.

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P.S. I had this in my drafts for a few weeks, but it never felt quite finished. Then I read Natalie Docherty’s post, “Choose the Life You Already Have,” and it moved something in me. It helped me flesh this draft out until it finally felt ready to publish. I highly recommend reading her post as well if this essay resonated with you.