"What If This Was Fun?"
A Thank You For the Biggest Year Yet
“What if this was fun?!”
…said Dave Möschler, a conductor I have worked with for over a decade.
We were in the middle of a final rehearsal before a musical’s opening night, and something was off with the mics.
As the tech crew finagled with the cables at our feet, Dave continued: “Bailey always says this to me when I’m in the middle of a stressful situation…”
“‘What if this was fun?!’”
(Bailey is Dave’s fiancée.)
“And…it is simultaneously the most (and least) helpful thing she could say.”
The whole orchestra laughed.
❤️ Thank You For A Huge Year
So, as I write to you from the passenger seat of my Subaru Crosstrek — the sight of tumbleweed blowing furiously back and fro on the I-5 (connecting Northern and Southern California by the most monotonous stretch of open road) — I want to take a moment to celebrate two wonderful plot twists that resulted from my asking myself this exact question (“What if this was fun?”):
In 2023, while slowly burning out from my corporate job as an epidemiologist at a government consulting firm, I started interviewing small-business owners, artists, and creatives in my neighborhood on lunch breaks and after work. It gave me incredible relief from my long days, and sparked both my curiosity and creativity. Without realizing it at the time, I asked myself: How could I re-inject energy and lively connection back into my daily life? How could I make life… fun, again?
Fast forward to 2025: government funding for public health projects shrank and I was laid off from my 9-to-5 job. Although losing a stable income comes with financial uncertainty, it was truly a blessing in disguise. With extra time (and energy) on my hands, I turned my full-time attention to growing Tomatokind and — again — asked myself: What if this was fun?!
The result? 2025 was Tomatokind’s BIGGEST year yet — and I thank you from the bottom of my heart for being part of this very special chapter.
This year, I:
Was invited to speak at the 2nd Annual Pay Yourself Summit — reaching thousands of entrepreneurs with my story of starting Tomatokind.
Doubled the size of our Substack community and launched the paid subscription — reaching like-minded creatives across 27 U.S. States and 23 countries.
Committed to collaborating with Bay Area-based creatives — from photographers including Patrick Perkins and Gretchen Robards to entrepreneurs like Sapna Tandel and Magali Mathieu, and fine-artists including Jackie Sarah Brown and Sophia Sattar.
Spotlighted the journeys of 11 creative entrepreneurs across women’s health, indie music, hospitality, arts and disability, journalism, and radio from the U.S. and abroad.
Launched Possibilities Club (and Field Trips) — a workshop series that gathers adventurous souls to improvise, dream, and dare their future creative selves into existence.
Learned from over 2,000 storytellers, artists, and creative entrepreneurs at the 2025 Alt Summit (a magical community of women entrepreneurs) and the American Institute of Graphic Artists Design Conference 2025 (a gathering of multi-disciplined visual strategists and builders).
Journeyed through The Artist’s Way — twice (plus added numerous creative recommendations to our Creative Journey Library).
Worked with a business coach for the first time (shoutout Diana Davis!) to progress Tomatokind from a passion project into a sustainable dream.
Showed up bravely on Tomatokind’s Instagram and LinkedIn in a way that I would never dream of in a previous life (yet simply human).
Creative Wins Aside…
2025 was big in other ways:
I married the love of my life in the beautiful backwaters of Kerala, India;
I traveled solo to four new countries (Mexico, Peru, Indonesia, Costa Rica) — and brought you along with me;
I started my Spanish-learning journey;
I said yes to a role at a startup called Tribe to help build a future I deeply believe in; and,
I celebrated myself through deep ritual on and around my 30th birthday (more details in our prior 2 posts).
So, dear reader, whether you’ve been with me from the beginning or just stumbled on this corner of the internet today, I am so happy you are here — and I cannot wait for what is in store for us together in the coming months and years.
For now, I leave you with a small (but potentially big) question:
“What if this [fill in the blank] was fun?”
With zealousness and gratitude for this creative life,
Vanessa
P.S. Speaking of fun, you may or may not be heading to a holiday gathering today. If so, check out this hilarious Dysfunctional Family Bingo game you can play with your friends to make your next dysfunctional family gathering a little more...(dare I say)…fun? It was introduced to me recently, and it perfectly captures the spirit of adding a bit of whimsy to a potentially stressful situation. 🤪
Vanessa! Thank you (& HBD on a Milestone Bday and year!) for your Energy, Verve, Joy, Openness to Creative Women across the Bay and beyond! Your willingness to show up, reach out and give an enthusiastic voice to interesting, creative women across the spectrum is magical and infectious and needed. And I personally thank you for running after me as I was running out the door (post-reading); a wise person once told me: you don't need everyone to hear your story to heal and make things better, you just need one... and I couldn't be more grateful that you were "that one" for me. Have a glorious end to 2025 and ever forward into a more Fun and always interesting 2026; keep going... 🍅💎🌟