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.
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.
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.
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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