It’s ‘one of the best career decisions’

My commute might look pretty unusual to most people: I usually catch a 7 a.m. flight from Los Angeles to San Francisco every Wednesday and fly home every Friday night — traveling about five hours door-to-door each way.

I never planned on becoming a supercommuter. But an unexpected conversation turned into a job offer, and I found myself splitting my life between two cities.

I live in Los Angeles, but I lead sales and marketing as Head of GTM (go-to-market) at the AI startup daydream. In addition to two flights, my weekly commute also consists of too many Ubers and more 4:30 a.m. alarms than I care to count.

A year into my supercommute, though, I can say that what started out as exhausting — and honestly a little unhinged — turned into one of the best career decisions I’ve made.

Here’s why I chose this path, and what I’ve learned from it.

I needed to be in the room

The biggest driver behind my decision was access. San Francisco’s AI scene has a concentration of builders, thinkers, and off-the-record conversations that Los Angeles just could not match.

It’s easy to underestimate the power of proximity these days, but being in the room changes everything. You meet someone at a panel, grab coffee after, and suddenly, you’re part of the conversation.

That’s how I landed this role. I connected with someone in San Francisco over a shared interest in search engine optimization (SEO), which is the process of adapting your website to reach more users through search. A few chats later, they said, “Is it crazy if we brought you on?” I had no sales background, but I said yes and figured it out as I went.

These kinds of doors don’t usually open over Zoom. The last three roles I’ve landed all came from face-to-face interactions.

I didn’t want to give up what either city had to offer, so I chose both.

Being in the room helped me get my bearings and succeed as I pivoted to a new industry and a new job function. It meant I could solve problems shoulder-to-shoulder with colleagues, bounce ideas around in real-time, build trust with clients, and boost team morale. That’s hard to replicate from a screen.

I wasn’t willing to choose between ambition and roots

San Francisco offered a chance to step into a bigger role. At daydream, I lead all our go-to-market efforts. It’s high-stakes, fast-paced work that pushes me to learn constantly.

But Los Angeles is home. My family is here. So are my closest friends, some since the 2nd grade. It’s where I reset and feel like myself again, whether that’s through dance classes, quiet walks, or simply being around people who know me beyond my job title.

Supercommuting means weekly flights, leaving San Francisco early Wednesday mornings and flying back to Los Angeles on Friday nights.

Courtesy of Janet Lee

It’s also where I run my personal finance coaching business, Doing Well, in the evenings and on weekends. I started it after building a money management system to overcome my own financial anxiety, and now we help others do the same.

Juggling a business and a full-time job is exhausting, and being in Los Angeles — near my support system and many of my earliest clients — helps me stay grounded and motivated to keep my side hustle going.

I didn’t want to give up what either city had to offer, so I chose both, even though it meant living out of a suitcase.

I weathered short-term discomfort for long-term growth

Despite the wins you might see now, the first few months were hard. I left a stable job. I’ve cried in Ubers and eaten solo dinners at the office. And I bounced between short-term rentals, often in sketchy neighborhoods, to save money.

Typically, daydream encourages people to relocate. Since I made the choice to supercommute, the travel costs are on me. So I pay for every flight and hotel out of pocket, averaging around $450 per week.

At first, I didn’t feel grounded in either city. I work remotely from Los Angeles on Mondays and Tuesdays, then in San Francisco Wednesday through Friday. In the early months, I hadn’t built community in San Francisco yet. And even though I had deep roots in Los Angeles, the constant travel made it hard to be fully present.

I still pack bags, hop flights, and juggle multiple projects, but now it feels like momentum, not chaos.

I started doing affirmations and reminding myself every morning why I was doing this: to level up my career and take on bigger responsibilities that push me to grow. Discomfort wasn’t a sign to quit. It was part of the process. Eventually, it became proof that I was building my skills, expanding my network, gaining confidence, and opening new doors for myself.

A year into this commute, things are finally clicking. I still pack bags, hop flights, and juggle multiple projects, but now it feels like momentum, not chaos. I’ve built deeper relationships, shined in my new role, and stayed connected to the life I love in Los Angeles.

Some opportunities are earned that way — by showing up again and again, even if it means flying five hours to do it.

Janet Lee is the Head of GTM at daydream, an AI startup that helps companies grow by building and managing their end-to-end organic growth engine, from SEO to generative engine optimization (GEO). She also founded Doing Well, a personal finance company that offers monthly coaching and bookkeeping to help people manage their money, build better habits, and make informed financial decisions. She regularly shares personal finance and career insights on her socials @startdoingwell. Find her on Linkedin.

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