Episode 6: Thriving in San Francisco as an Introvert — Rest, Reflection, and Redefining Success
In this episode of Fresh Out and Figuring It Out, Connor Callahan, a 20-something computer engineering grad living in San Francisco, talks about what really happens after college and how he moved past negative thought spirals, learnedto value rest, and found his people in a city obsessed with status, startups, and questions about “what you do”.
Connor opens up about moving to a big city, being an introvert in an extrovertedworld, building websites that unexpectedly took off online, and deciding to join his family’s cheese and yogurt business, Bellwether Farms. He shareshonestly about imposter syndrome, “doom loops” of negative thinking, learning to ask for help, building community when you don’t naturally love socializing, and what it actually means to be a man with purpose and values today.
It’s a grounded, thoughtful conversation for anyone who thought life would feel “figured out” by now—and is realizing that this in-between stage is where the real growth happens.
What You’ll Hear:
- The story behind his viral writing tool website “Lose theVery” and other creative side projects
- What it’s really like to move to a new city aftercollege as an introvert
- How imposter syndrome shows up in everyday choices—socially, professionally, and personally
- The concept of the “doom loop” and how gratitude andperspective helps break it
- Why long walks, solo runs, and technology-free time became essential for his mental health
- How a first serious relationship forced him to grow, make hard decisions, and take agency over his life
- Practical ways he’s building community now—run clubs, coffee meetups, tennis, poker nights, and more
Key Takeaways:
- Life after college is the first time you design your ownstructure. Freedom is amazing—but you have to be intentional about how you spend your time and where you put your energy.
- Introverted doesn’t mean antisocial. You might prefer depth over crowds, but you still need people—and it’s okay to build community at your own pace.
- Your mind can trap you in “doom loops.” When your thoughts spiral into “I don’t belong” or “I’m behind,” you start seeing proof everywhere. Gratitude, old letters, and real rest can reset that pattern.
- Rest is not laziness—it’s growth. Long walks withoutpodcasts, runs without music, and quiet time away from your phone help you actually hear your own thoughts and values.
- Experiment early and often. Try different jobs, cities, androles. Optimize for learning, experience, and people you can grow from—not just titles and short-term prestige.
- Decisions are part of adulthood. Not choosing is still achoice. Whether it’s a relationship, a job, or a city, you won’t get guaranteed “right” answers—but you will learn who you are.
Who This Episode Is For:
- New grads trying to figure out life after college,especially in big cities
- Introverts who want community but feel drained by typical “networking” culture Parents & caregivers who want to better understand what their sons are actually navigating right now
- Early-career professionals questioning if the path they’re on is really theirs—or just what they thought they “should” do
- Anyone in their 20s or 30s who feels behind, stuck incomparison, or caught in their own doom loops and wants a more grounded way forward
I would love to hear your thoughts and comments and share this podcast with your friends so that we can figure it out together! Follow me so we can stay connected!
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