LOS ANGELES, june 15, 2025
My weekly commute looks anything but ordinary: I fly from Los Angeles to San Francisco every Wednesday morning and head back home on Friday nights, a five-hour journey each way. It wasn’t a life I planned,but one unexpected conversation led to a job offer that split my life between two cities.
Supercommuting, while exhausting, turned into a career decision that paid off.
- Access to San FranciscoS AI scene was a major driver.
- Supercommuting allowed a balance between ambition and personal roots.
- Short-term discomfort led to long-term career growth.
What does it mean to be a supercommuter? For Janet Lee, the Head of GTM (go-to-market) at the AI startup daydream, it means weekly flights between Los Angeles and San Francisco. the demanding schedule includes too many early alarms and a constant flow of Ubers. But despite the initial challenges, this supercommuting arrangement has proven to be one of the best career decisions she’s made.
The Power of Being “In the Room”
The draw to San Francisco was about access. The city’s AI scene is a hub for innovative thinkers and off-the-record discussions that simply aren’t as accessible in Los angeles.
Being physically present makes a huge difference.Chance meetings at panels or casual coffee chats can open doors. These in-person connections led to her current role, starting with a shared interest in search engine optimization (SEO). Despite lacking a sales background, she took a leap of faith, learned on the job, and hasn’t looked back.
Did you know?-SEO, or search engine optimization, is the process of improving a website’s visibility on search engines like Google. It involves various techniques to help a website rank higher in search results, driving more organic traffic.
These kinds of opportunities rarely come through virtual interactions. Her last three roles were all a direct result of face-to-face connections.
I didn’t want to give up what either city had to offer, so I chose both.
Being there in person helped her navigate a career transition, and she was able to collaborate with colleagues, brainstorm ideas in real-time, build client trust, and strengthen team morale – aspects that are arduous to replicate virtually.
Balancing Ambition and Roots
San Francisco offered the chance to step into a larger role. At daydream, she leads all go-to-market initiatives, a fast-paced, high-stakes job. It pushes her to learn and grow constantly.
Reader question:-If you were offered a dream job that required a meaningful commute, what factors would you consider before accepting the position?
Yet, Los Angeles is home. It’s where her family and lifelong friends are. It’s her place to reset and feel grounded, whether through dance classes, quiet walks, or simply being around the people who know her best.
Supercommuting means weekly flights, leaving San Francisco early Wednesday mornings and flying back to Los Angeles on Friday nights.
courtesy of Janet Lee
Additionally, she runs her personal finance coaching business, Doing Well, in the evenings and on weekends. She started the business after creating a money management system to manage her own financial anxiety, and now helps others do the same.
Juggling a business and a full-time job is a challenge,and being in Los Angeles-close to her support system and early clients-helps her stay focused and motivated to keep her side hustle going. She didn’t want to sacrifice either city,so she chose both,even if it meant living out of a suitcase.
Embracing Short-Term Discomfort
The initial months were tough. she left a secure job and experienced moments of difficulty, from tears in Ubers to solo dinners at the office. Saving money meant staying in short-term rentals, sometimes in less-than-ideal neighborhoods.
Since she chose to supercommute, she pays for every flight and hotel, averaging around $450 per week. At first, feeling grounded in either city was difficult. She worked remotely from Los Angeles on Mondays and tuesdays, then in San Francisco Wednesday through Friday. Building a community in San Francisco took time,and the constant travel made it hard to be fully present,even in Los Angeles.
I still pack bags, hop flights, and juggle multiple projects, but now it feels like momentum, not chaos.
Affirmations and reminders helped her stay focused on her goals: to advance her career and take on more obligation. Discomfort became a sign of progress, as she built skills, expanded her network, and gained confidence.
A year into this commute, things have changed. She still packs her bags, boards flights, and juggles multiple projects, but now, it feels like progress. She’s built deeper relationships, excelled in her role, and maintained connections with her life in Los Angeles.
Sometimes, opportunities are earned through consistent effort, even if it means flying five hours to make it happen.
The Supercommuting lifestyle: Beyond the Flights
The life of a supercommuter, as Janet Lee exemplifies, extends far beyond the hours spent in the air. It’s a balancing act that requires careful planning and resourcefulness,a lifestyle choice at the intersection of professional ambition and personal fulfillment. While the initial appeal might potentially be the career opportunities, the real test lies in the daily execution and long-term sustainability of this demanding routine.
For Lee, supercommuting is a core component of her career success. But it is also a lifestyle that provides some versatility, allowing her to balance both her career and personal life. Lee balances her demanding role as Head of GTM at a San Francisco AI startup with running her personal finance coaching business in Los Angeles.
One of the less-discussed aspects of supercommuting is the financial toll. Beyond the weekly flight and hotel costs, there are the everyday expenses. Meals, transportation within each city, and the need for duplicate essentials-clothing, toiletries, and office supplies-all add up. Lee’s dedication means that weekly expenses average roughly $450, and that’s just one part of the equation.
Financial planning is essential.Budgeting, a skill Lee honed, becomes critical for long-term sustainability.
To manage these expenses, Lee leans on her personal finance expertise. She has developed a budget that accounts for all expenses, tracking everything to the penny. “It’s not just about the big costs,” she explains. “It’s about being mindful of every dollar spent to make sure it aligns with my overall financial goals.” This attention to detail is not just about scrimping; it’s about making informed choices that maximize her budget and keep her on track toward her financial objectives.
Practical Tips for Supercommuting
- budget ruthlessly: Track every expense and allocate funds to categories related to travel,lodging,meals,and incidentals. Use budgeting apps.
- Leverage travel rewards: Accumulate points and miles through credit cards and airline programs. This helps offset flight and hotel costs.
- Pack strategically: Reduce checked bag fees by packing light. Invest in versatile clothing items that can be mixed and matched. A capsule wardrobe is ideal.
- Utilize co-living spaces: Explore options in both cities if you are a frequent commuter.this can reduce lodging expenses and offers chances to build community.
- Streamline logistics: Use ride-sharing services or public transportation when feasible. Set up automatic bill payments to avoid late fees when on the go.
Beyond the financial aspect, the emotional toll of supercommuting must be managed. How do supercommuters maintain a sense of presence in both of thier lives? Lee recommends regular check-ins with yourself. Acknowledging the challenges, celebrating small wins, and engaging in self-care activities helps.
A simple daily journaling practice can help to improve well-being, she explained. Prioritizing mental health through mindfulness, meditation, or therapy, she says, is a must, too. This way, she continues to find that she is “building momentum, not experiencing chaos” as she continues her enterprising schedule.
Supercommuting: Myths vs. Facts
Myth: Supercommuting is only for high-earning executives.
Fact: While it can be a significant investment, careful financial planning is key. Supercommuting is attainable for those in various roles, from tech to creative fields, who value the opportunities it offers.
Myth: It’s unachievable to maintain a healthy social life while supercommuting.
Fact: Building a social network takes effort; it takes time. The key is prioritizing time with friends and family, being present when you are with them, and embracing opportunities for connection in both cities.
myth: Supercommuting always leads to burnout.
Fact: Burnout is a risk, but it can be mitigated through self-care, clear boundaries, and seeking support when needed. Lee’s experience shows how supercommuting, while challenging, can be a rewarding experience.
The choice to supercommute is not just about the job; it’s a thorough lifestyle decision. It requires discipline, resilience, and a clear understanding of what matters most. As Lee continues her journey,she serves as a reminder that with thoughtful planning,a supercommuting life can lead to a rewarding career and a richer personal experience.
Frequently Asked Questions
What is the most challenging aspect of supercommuting?
The biggest challenges are frequently enough the time constraints and logistical complexities. The need to manage two completely separate households is a significant undertaking that needs a large dose of dedication. Travel, as a notable exmaple, requires a considerable amount of preparation and time, wich can cut into work and leisure activities.
How can someone considering supercommuting prepare for the financial impact?
Create a detailed budget that includes all travel, lodging, transportation, and living expenses in both cities. Optimize expenses and utilize travel reward programs. Consider setting up a separate bank account or budget specifically for covering those travel necessities.
Can supercommuting positively impact mental health?
It depends.it can be incredibly rewarding to maintain a career and a fulfilling home life.Though, it is indeed also significant to create solid boundaries between personal and professional life. Prioritize adequate rest, self-care, and seek support to avoid burnout.
What are the long-term benefits of supercommuting?
Long-term benefits can include career advancement, increased earning potential, broader professional networks, and the chance to experience diverse cultural and social environments. It fosters adaptability and resilience and encourages a focus on what matters most.
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