10 beautiful strangers gathered around picnic blankets in a beautiful park, laughing at Lisa Frank stickers, clipping images of their dream lives from lifestyle and travel magazines, passionately bonding over their tastes in music, sharing anecdotes of life transitions and milestones, and inadvertently witnessing each other in the journey back to themselves.

“I’m in a season of getting back into my body,” one of the attendees shared. And, that was literally the theme of the evening.

As we flowed into the gathering and reflected on our visions for the rest of the year, the tactile practice of layering glue and block-font and gemstones unlocked the stories between us. People shared about their health journeys, return to (and departures) from career paths, passion projects (that they were trying to be more brave about sharing), and the complex emotions behind the question “what’s next?”.

Throughout the evening, we noticed that returning to the activities we loved to do as children was a big part of our collective return to ourselves.

As the sun set and evening chill started to creep in, folks lingered to exchange numbers and even make plans to connect more over a meal.

One individual stopped me mid-clean-up to share that the night had reminded her of a ritual she used to do: at the end of each day (after a day's worth of accounting work), she would come home and paint or sketch. It was a routine that she cherished and felt alive doing. But, as many of us can relate, work began to take over her life and she forgot about it.

“Now, when I start to pick up something creative to do, it feels weird,” she said. “But, I want to get back into it.”

So, I ask you, dear reader: what is a routine, habit, or activity that you’ve lost touch with but want to bring back?

I hosted this gathering to help folks reflect on the year so-far, tap into their intuition, pause from their claustrophobic social and work calendars, and visualize their life priorities going forward.

But, even if you were not able to join us (from wherever in the world you are), I want to share some questions to reflect on before the summer ends. Many of these I credit to fellow creative entrepreneurs Naomi Peña of That Art Party and of The Unlock Your Vitality Community & podcast.

Questions to reflect on the year so far

1. What do I want to celebrate from 2026 so far?

2. When have I felt most myself this year? Most energized, creative, and light?

3. What no longer feels aligned, or draining?

4. What are the top 3 lessons I’ve learned (from both wins and challenges)?

5. Have my priorities changed from the beginning of the year until now? How so?

Questions to manifest the rest of 2026

1. Who am I becoming (or want to become), and am I supporting that vision of myself?

2. What would I do differently if I lived more consciously in the next 5 months?

3. What do I want the second half of this year to feel like?

4. If I only had 1 month left in 2026, what would suddenly feel important?

5. Think about the habits that are currently working for you. What new habits do you want to cultivate, and how can you leverage the learnings from how you’ve built good habits in the past?

Ok, you know what you need to do, right?

Find an open and expansive chunk of time this week or weekend and sit down with these questions, a pen, and a piece of paper. Maybe, suggest these reflection prompts as a group activity with loved ones (friends? a romantic partner? your grandma?), and share your answers with each other after you’ve had solo time to reflect.

Reflecting on your honest answers to these might just be the mid-year life audit you needed.

With zeal and gratitude for this creative life,

Vanessa

I’m writing to you (all 300+ of you!) today from a corner of my local library. I rotate between a few branches, and this is the smallest one (but never ceases to be what I need).

In my peripheral vision, twenty-some knitters and crocheters are gathered around a communal table for their bi-weekly meetup. A new member just joined, and one of the veteran crafters are giving them a lay of the land (note to self: pick up a flier to share with my mom).

To my left side, two preschool-aged children are playing who-can-spin-in-this-chair-faster while their parents exchange numbers. And, across from me, a fellow millennial types away at their computer.

More often than, this is the beautiful community-centered setting where I compose most of my newsletters.

Welcome to our dream-board, a weekly column that was born from an IG story and this little thread in our community chat!

Straight to your inbox every week: I round up creative part-time/ full-time opportunities, fellowships, workshops, brick and mortar offerings, and other creative voices and resources to help you pursue a life of creative abundance!

Initially, all subscribers will get access to this weekly board. Eventually, we’ll be limiting this column to paid subscribers only. So, dig in now (and tell us what you want to hear more of)!

Weekly Dream-Board

• Are you an early-to-mid career animation filmmaker? Maybe, you’ve been pining away at a creative vision on the side. If so, you have a few days left to submit your work to this Short Animation Fellowship co-sponsored by Titmouse Foundation and Warrior Art Camp.

• Do you have a passion for working with artists, and thrive in a fast-paced touring environment? The NYC-based Paul Taylor Dance Company is looking for a full-time Stage Manager.

• If you’re passionate about food and providing culinary education to empower youth in their communities, SF-based Culinary Artistas is looking for both a Culinary Apprentice and Youth Culinary Educator.

• Are you a papermaker and community arts educator? The Morgan Conservatory, which is the largest arts center in the U.S. dedicated to every facet of paper-making, book arts and letterpress printing, is looking for their next Paper Studio Manager.

Other cool stuff

• Currently navigating a career pivot? Follow SJ on IG for permission to explore something totally different! After getting laid off from her corporate job, SJ started interviewing people about their career pivots and jobs (from surf instructor to wine bar owner). So fun and 1000% our jam.

• Looking for an aligned arts residency? Res Artis is a 32-year-old worldwide network of arts residencies that contribute to the thriving global arts ecology. Check out current open calls here.

• Have a podcast, but need a community of other hosts and potential guests? Check out The Podcast Collaborative, a supportive network and directory to help grow your podcast vision.

Volunteer opportunities

And, in case you missed them, here’s a compilation of creative volunteer opportunities we’ve highlighted from the past month!

• Art Heals Arizona (formerly Free Arts) creates moments of connection and creativity for children who have experienced trauma. Through their Art + Mentors = Resilience model, they help youth build resilience through connecting them with caring adult mentors and intentional arts activities. You don’t need to be an artist to be a volunteer.

• Textile Center in the Twin Cities of Minnesota is a national center for fiber arts. Volunteers can help out at The Stashery (which provides accessible, donated materials for artists), support harvesting and education at their natural dye garden, and help run other creative workshops.

• Esalen is a holistic and educational retreat space in Big Sur, California dedicated to providing workshops and experiences in the healing and somatic arts. Volunteer opportunities to help support the community and its grounds (cabins, kitchen, farm & garden) are available daily.

• Are you an SF-based creative whose passionate about exploring a career in events? Volunteer with That Art Party!

• Crews for a Cause is a nonprofit production group that connects video and media professionals with causes they truly care about (and that are in need of impactful storytelling). Check out the crew!

• Creative Growth is the oldest and largest nonprofit art studio for artists with intellectual and developmental disabilities, and is looking for remote/in-person volunteers to help run the studio and organize exhibits!

• NextGen Pallete is a vibrant, inclusive marketplace built to empower young, underrepresented artists from around the globe. Currently, they’re seeking volunteers to serve as International Arts Community Leads (remote, online).

• If you are passionate about working with community youth and have a background in dance based in IL, Restoring Our Youth is looking for a volunteer head dance coach.

• Crescent Hospice supports the healthcare needs of residents and caregivers in Orangeburg, SC, and are looking for music therapy volunteers to share the healing power of music with patients and their loved ones.

With zeal and gratitude for this creative life,

Vanessa

I’m really struggling. I’m really struggling. I’m really struggling. This it how I felt for over a month as I procrastinated on executing the raw footage for this first episode. And now, I was hearing these same words from the professional I had hired to help me bring this vision to life.

"This is not a format I’ve ever done before,” she said. “I think it will be absolutely beautiful in the end. But, I am just really struggling right now to figure out the process and get it to the finish line.”

And, I felt for her. We had spent over 2 months chatting about a fieldnotes podcast concept, and I had spent another month coordinating my guest’s and my own audio segments. And, now, my producer was experiencing all the novelty and disruptions of executing this concept on the backend. So, we brainstormed together: ways to tweak the process, tools to streamline communications and edits, and considerations for the show’s sustainability…(more on the show later)

I share this behind-the-scenes tidbit because, oftentimes, this is the reality of pursuing our creative endeavors. It is sticky, messy, tests our patience, and a true labor of love.

And, these feelings are exactly what our last Community Coffee Chat was about, where I invited fellow creative entrepreneurs Gretchen Robards and Nicole Rangel to share candidly about how they: overcome the fear of being seen, invite more joy into the hard work of building their dreams, and grapple with the complex realities of financially investing in themselves.

Gretchen Robards is a multi-disciplinary creative working across photography, creative direction, and design, with movement, music, and writing woven into everything she does. Nicole Rangel is a holistic educator and papermaker who handcrafts (and teaches others to handcraft) plantable paper goods that are designed to be shared and planted to grow organic flowers, herbs, and food-bearing plants. And, this conversation spoke directly to my heart.

5 Takeaways from Our Conversation

If you’re a paid subscriber, feel free to go straight to our full conversation by clicking the video above. Or, you can browse below for the topics that stayed with me the most.

1. Curiosity is a compass.

Some people call it “distraction”, but curiosity is often the map to where we’re going next. At times, it can show up in delightfully unserious ways. In others, it can feel quite existential.

Read more

“Making new core memories with my parents” was not on my 2026 vision board. It wasn’t part of my big, bold, beautiful plans for starting my 31st trip around the sun.

But, what an oversight that was.

This year, I’ve spent more hours holding my parents’ hands, asking them about their life story, giving them shoulder massages, leading them down literal memory lanes, and sharing in their favorite pastime (gardening) than the past 5 years combined.

A prior version of me would have predicted: “at 30, you’re probably still taking your parents for granted, stalemating over past wounds, and cancelling weekend plans because ‘something came up.’” But, I’m not. I’m ditching “fun plans” to be with them. Because, I can’t think of anything more fun than spending hours laughing over (way too much) home-cooked food, watching them tease each other over habits they’ve solidified over the course of their long marriage, recounting stories that have been told a thousand times (and, some, for the first time), and creating mundane yet momentous memories that will stay with me for the rest of my life.

And, this alternative reality feels profound. It feels urgent, even. And, it feels like home.

So, here’s a little reminder: if you’re surprising a past version of yourself by acting differently or making different choices, it probably means you’ve grown and evolved somewhere along the way.

Hopefully, you can set aside self-judgement for both the past and present you and lean into the reality of how all your life experiences and learnings have shaped you.

Welcome to our dream-board, a weekly column that was born from an IG story and this little thread in our community chat!

Straight to your inbox every week: I’ll be rounding up creative opportunities, fellowships, workshops, brick and mortar offerings, and other creative voices and resources to help you pursue a life of creative abundance!

Initially, all subscribers will get access to this weekly board. Eventually, we’ll be limiting this column to paid subscribers only. So, dig in now (and tell us what you want to hear more of)!

Weekly Dream-Board

• Looking for an opportunity to position public art as a catalyst for community identity, civic pride, economic vitality, and cultural expression? The Greater Columbus Arts Council is hiring its Art in Public Places (AiPP) Director.

• Are you a storyteller with a vision that reflects the spirit of Los Angeles and its diverse cultural mosaic? As LA prepares to host its historic third Olympic & Paralympic Games in 2028, PBS SoCal invites local storytellers to help capture the city’s legacy and transformation through their Community Storyteller Initiative.

• Do you enjoy overseeing creative production as well as managing creative vendor partnerships? The San Francisco Ballet is looking for their next Brand Strategy & Communications Lead.

• Are you an arts educator with experience developing teams and organizational direction? Flint School of Performing Arts, one of the largest community schools of the arts in the country, is hiring their next director.

• Do you have experience mixing large-scale musical productions and live orchestra? Cumberland County Playhouse is looking for a new lead sound engineer.

Volunteer opportunities

• NextGen Pallete is a vibrant, inclusive marketplace built to empower young, underrepresented artists from around the globe. Currently, they’re seeking volunteers to serve as International Arts Community Leads (remote, online).

• If you are passionate about working with community youth and have a background in dance based in IL, Restoring Our Youth is looking for a volunteer head dance coach.

• Crescent Hospice supports the healthcare needs of residents and caregivers in Orangeburg, SC, and are looking for music therapy volunteers to share the healing power of music with patients and their loved ones.

With zeal and gratitude for this creative life,

Vanessa

Sophie Davies is the founder of Cuppa Culture, a community bringing women together through local culture, conversation, and storytelling in support of local businesses. She curates Bay Area–based openings, events, and pop culture in CUPPA on Substack, and facilitates monthly Substackers gatherings where women explore their editorial voice, share ideas, and learn from one another. She co-hosts a speaker series called Sips & Stories with The Spoonlist that spotlights creatives and business owners who contribute to the fabric of Marin County’s neighborhoods.

Drawing on a career in public relations, marketing, and events in the U.K. and U.S. in the fashion, lifestyle, and publishing industries, Sophie believes the best conversations don’t just happen online—they continue around neighborhood tables, and between people, preferably over a warm cuppa!

Follow Sophie on her Instagram

Today, I have the absolute pleasure of featuring Sophie as a guest contributor! So, I’ll pass it off to her…

Hi Tomatokind readers,

When Vanessa asked me to write a personal essay for TomatoKind magazine, I said yes immediately. I started it, stopped, started, stopped, and avoided writing it for days. Not because I didn’t have anything to say, but because writing about myself feels very different from my usual writing about other people…especially about a vulnerable topic like visibility.

The universe has been whispering to me through different people and scenarios that it’s time to widen my comfort zone and take bolder action to be more visible and share more of myself.

Somewhere during the process of writing this essay, I realized Vanessa hadn’t just asked me to write a guest post. She had unknowingly given me a challenge and another opportunity to become more visible. I started taking steps to put myself out there more, taking up more space, and raising my hand to be on bigger stages. The first draft was theory. The second draft was taking action. And the third draft became a chance to look back and realize how much had changed in just a few weeks.

Looking back, I realized this wasn’t a new challenge. My career has continued to push me out of my comfort zone since I was a shy 21-year-old graduate who went straight into a decade-long public relations career in the fashion industry. My days were spent pitching stories, building relationships with journalists, running events, leading teams, and helping brands tell their stories. It was an exciting career that took me into rooms I never imagined I’d be in!

But I was the PR dressed in black with a headset—the woman you see just behind the celebrities on the red carpet. My job was to make sure the brand, or the face of the brand, was the star of the show. I wasn’t supposed to be visible. My career has always revolved around helping other people become visible.

When I co-founded a branding and marketing agency in my thirties, I was navigating entrepreneurship for the first time while raising two children under the age of five. I was tired, but a level of visibility as a founder was required to build a reputation from the ground up, which meant running workshops and speaking at conferences. We were marketing our clients, and used our company blog, newsletter, and social media to sell our expertise and services. I admittedly preferred to do it through photos rather than video, and in person through sales and networking.

Even today, through my Substack , I spend my time introducing people to local businesses, curating recommendations, and bringing communities together. I’ve always loved holding the spotlight for other people.

What I’ve been slower to learn is how to stand in it myself.

Why This Feels So Hard

As a British Gen X business owner, I struggle with the performative nature of marketing yourself on social media to stay top of mind and relevant. I have been both reluctant and defiant about appearing in front of a video camera. I suspect the messy reality of midlife has a lot to do with this. I noticed a significant change that happened in my early to mid-40s that affected my self-trust, confidence, and belief in myself—perimenopause, which generally has a huge impact on women’s visibility for countless reasons I won’t go into in this essay.

So I started to ask women my age who show up online in videos how they do it.

I was speaking to an amazing content creator who produces the most joyful videos about cooking. Check out Marin Mama Cooks! She makes it look so effortless that when I said it probably sounds silly how hard I find it to be in front of a video camera, she responded with something that has stayed with me:

“Making recordings of yourself helps you fall in love with yourself more because you become more familiar with the person you see.”

That idea stopped me in my tracks. As a British person who struggles with the concept of self-love or being your own best friend, it’s a challenging concept to grasp. I often criticize how I look, sound, and what I say, and that has a lot to do with my formative years. Growing up in an Irish family in London, standing out wasn’t encouraged. Modesty was. Sharing your opinions too loudly wasn’t something we celebrated; it was “getting too big for your boots.”

Life Had Other Plans

Speaking of family, at the beginning of 2025, I was navigating my father’s cancer diagnosis and flew to London to celebrate his 80th birthday (we share a birthday) before he went into surgery. It was the first time we celebrated our birthdays together in 18 years, since I moved to the Bay Area.

At the time, I was professionally in a bit of a creative funk. I had just decided to walk away from the corporate job that required me to shapeshift in order to produce finance programming and events for C-suite executives.

It was a reminder that life is short, and spending my days in constant Zoom meetings discussing topics that don’t match my interests and natural curiosities was wasting my potential.

Around the same time, my co-working space of 11 years, The Hivery (where I co-ran my marketing agency), was reopening. I needed to creatively express myself again so I made myself a simple promise: I was going to show up for my writing again.

Finding My Way Back

I wanted to start a Substack to find my way back to creativity and joy again. Of course, the path from wanting to do something and actually doing the thing took a minute… It took a few months to pluck up the courage to get started, as it required being… yes, you guessed it… visible.

I craved a way to share the types of things I was naturally curious about in long form writing again. The Substack platform was enabling me to reconnect with the thoughts of magazine editors I hadn’t heard from in nearly 20 years, since I served them as a fashion PR director. I saw how these editors were able to reconnect with readers, in a more accessible way, after their magazines folded years ago. One of the things I appreciate about Substack is that it’s a place where people who still appreciate long-form writing hang out. Not everyone can be summed up in a quick caption on Instagram, and nor should they be. The human experience is more nuanced than that.

I saw it as a sign to start blogging again.

I started getting excited about the prospect of sharing my writing again. Back in 2009, I started blogging as a therapeutic way to navigate the culture shock of moving to America from England as a new parent, creating posts about places and activities moms could take their kids to and meet other parents. Then local businesses started reaching out to me to be featured, so my PR skills came in handy, and I started using social media to market the content, which progressed into social media marketing job roles for a couple of years before co-founding a marketing agency.

The Visibility Practice

To some women, I probably already appear visible through the community gatherings I facilitate. I run a Substackers group where women explore their editorial voice, share ideas, and learn from one another in community. I often recap these in-person moments on Substack and Instagram, but I find it easier to share a photo rather than a video for the reasons I’ve mentioned.

The online world requires me to produce videos that will probably do a better job of capturing the energy and what it feels like to be in the room. As soon as someone points a camera at me, I go from being present to becoming too self-conscious. It’s something I’m still working on. But on the days I’m hard on myself, I trust that people don’t connect with perfection—they connect with people.

On the subject of connection, it’s the supportive people in my life that help me increase my visibility. The ones who want me to do well, give me helpful feedback, push me out of my comfort zone, and open doors. the owner of my community space, The Hivery, is one of those people. She has supported me through professional changes over the last 12 years and continues to make space for me to thrive in a kind, curious, and joyful community.

Grace is an expander—someone who is a few steps ahead of where you want to be. We all need expanders in our lives to light the way!

is another expander in my life. She is a podcaster and community leader of Liberty Road—a community for women in midlife based in Los Angeles.

Last summer, when I was just a few weeks into writing my Substack, I was invited to speak on a panel moderated by Nada Jones. I shared my experience of plucking up the courage to start something new, and how it was going so far. It was a visible moment that I was grateful for.

It led me to co-hosting an ongoing speaker series called Sips & Stories with Megan Stewart of The Spoonlist that spotlights creatives and business owners who contribute to the fabric of Marin County’s neighborhoods.

Fast forward to now, during the process of writing this essay, Nada and I were messaging each other about the events I’m doing, and she mentioned “let’s find a way to get you down here too” (in LA). In the spirit of being more visible, I proposed doing a Substackers breakout session at her annual summit, Liberty Road Live, on October 1st. I pitched the concept and outcome, and I will be included on the lineup being announced soon. I am so grateful for the opportunity, and it is another example of the big steps I have taken while writing this essay.

What I’ve Learnt

The funny thing is, I thought writing this essay would simply be an opportunity to tell my story about my creativity through writing on Substack.

Instead, it quietly changed my attitude towards visibility.

Over my career, I’ve realized confidence has never arrived before a new chapter in my life. It has always arrived because I stepped into one.

I’m still much more comfortable shining a light on someone else’s business than talking about my own, but I will be sharing more of myself in my Substack writing.

I’m still more likely to post a photograph than a video, although I’m trying to get over being self-conscious and do that more.

I’m still practicing becoming visible. But perhaps that’s the point.

Visibility isn’t a destination we suddenly arrive at one morning. It’s a practice. One conversation. One essay. One brave raise of the hand and saying “yes, I can do that” at a time.

Substack reminded me that writing isn’t simply about sharing what we know. Sometimes it’s about sharing who we are becoming.

I’ve spent years creating space for other people’s voices and stories, and now, gently and imperfectly, I’m learning to trust my own.

My community gatherings and my content in are about highlighting culture and local businesses. But they’re also about helping people feel seen.

This essay—and everything it asked of me while writing it—helped me learn to extend that same generosity to myself.

So perhaps this essay isn’t the conclusion after all.

Maybe it’s simply another small act of becoming more visible.

Note from Vanessa: I’m so grateful to you for sharing a piece of your heart and your story with our readers. And, for starting and stopping so many times. I feel many points of connection, and I am certainly taking a piece of your vulnerable spirit with me into the rest of my week as I battle more fear-based, creative blockers of my own. Because, this self-discovery journey is hard. Really hard. And, you sharing openly about the messiness of it is neccessary, and moving, and real. Thank you.

Dear readers, to immerse into Sophie’s beautiful community (and to read her many more candid writings to come), visit .

With that, have a beautiful and creative rest of your month, friends!

Welcome to our dream-board, a weekly column that was born from an IG story and this little thread in our community chat!

Straight to your inbox every week: I’ll be rounding up creative opportunities, fellowships, workshops, brick and mortar offerings, and other creative voices and resources to help you pursue a life of creative abundance!

Initially, all subscribers will get access to this weekly board. Eventually, we’ll be limiting this column to paid subscribers only. So, dig in now (and tell us what you want to hear more of)!

Weekly Dream-Board

• Are you an appreciator of 18-century music with a knack for producing events and launching fundraising campaigns? Music of the Baroque is a dynamic Chicago-based orchestra and chorus looking for a talented and passionate Development and Special Events Manager.

• Do you believe art is a tool for change across our government bodies, the business sector, local communities, and society at large? CA for the Arts is California’s statewide arts advocacy organization and they’re hiring multiple roles.

• Calling art history grads who are interested in fine and decorative art valuation! O’Toole-Ewald Art Associates is hiring for a paid apprenticeship.

• Do you thrive in multi-disciplined, collaborative environments? San Diego International Airport is looking for their newest Art Program Manager to lead the planning and integration of public art projects into the airport’s architecture. You’ll work with artists, designers, space planners, and engineers from concept through installation.

Other cool stuff

• Located in the beautiful Marin Headlands in Marin County, CA, the Headlands Center for the Arts offers artist programs that nurture creativity across all disciplines, from the visual arts to performance, music, writing, and film and video, both independently and through collaboration. Check out their current happenings, including a monthly supper series, open house, and summer 2026 artist residency!

• The Arts Research Center at UC Berkeley is a multidisciplinary arts think tank which is a community hub and research/ gathering space that offers an Indigenous Performing Arts Residency and space for public programming.

• Recently, I’ve had multiple folks express to me their interest in travel writing. So, if writing about your latest adventure interests you, check out this deeply human piece by about what it’s like to be a travel writer in 2026. Plus, go peek into ’s world!

Volunteer opportunities

In case you missed them, here’s a compilation of volunteer opportunities highlighted from our last 2 newsletters!

• Art Heals Arizona (formerly Free Arts) creates moments of connection and creativity for children who have experienced trauma. Through their Art + Mentors = Resilience model, they help youth build resilience through connecting them with caring adult mentors and intentional arts activities. You don’t need to be an artist to be a volunteer.

• Textile Center in the Twin Cities of Minnesota is a national center for fiber arts. Volunteers can help out at The Stashery (which provides accessible, donated materials for artists), support harvesting and education at their natural dye garden, and help run other creative workshops.

• Esalen is a holistic and educational retreat space in Big Sur, California dedicated to providing workshops and experiences in the healing and somatic arts. Volunteer opportunities to help support the community and its grounds (cabins, kitchen, farm & garden) are available daily.

• Crews for a Cause is a nonprofit production group that connects video and media professionals with causes they truly care about (and that are in need of impactful storytelling). Check out the crew!

• Are you an SF-based creative whose passionate about exploring a career in events? Volunteer with That Art Party!

• Creative Growth is the oldest and largest nonprofit art studio for artists with intellectual and developmental disabilities, and is looking for remote/in-person volunteers to help run the studio and organize exhibits!

With zeal and gratitude for this creative life,

Vanessa

Meet and , co-creators of a boutique consulting agency called The Sparklit Group that helps individuals and organizations ask better questions, tell their stories, and build better futures.

This conversation really touched me because the three of us met in a very different world: a 10,000-person company in a highly-regulated industry with lots of standard operating procedures, well-defined pipelines, and bureaucracy. In 2025, though, around the same time, we all left to build our own things (I went full-time on Tomatokind, and Dan and Lynne launched The Sparklit Group).

So, in this conversation, we get honest about what it really felt like to give up a direct deposit (and a community we genuinely cherished) to embark on an ever-evolving business and personal journey.

5 Takeaways from Our Conversation

If you’re a paid subscriber, feel free to go straight to our full conversation by clicking the video above. Or, you can browse below for the topics that stayed with me the most.

Read more

Welcome to our second dream-board, a weekly column that was born from an IG story and this little thread in our community chat!

Straight to your inbox every week: I’ll be rounding up creative opportunities, fellowships, workshops, brick and mortar offerings, and other creative voices and resources to help you pursue a life of creative abundance!

Initially, all subscribers will get access to this weekly board. Eventually, we’ll be limiting this column to paid subscribers only. So, dig in now (and tell us what you want to hear more of)!

Weekly Dream-Board

• Are you a poet with a passion for literary arts education? Chapter 510 is seeking an experienced Poet Teaching Artist to be the lead teacher in residence for their Young Oakland Poets Expedition, a poetry writing and publishing program for 4th graders across Oakland Unified School District.

• Interested in shaping conversations at the intersection of arts, culture, and civic life in San Francisco? The Asian Art Museum is looking for their new Director of External Affairs and Strategic Communications.

• Are you a strategic visionary with a deep care for the creative arts and social impact philanthropy? The Snap Foundation, an advocacy and education organization committed to developing pathways to the creative economy for underrepresented youth in Los Angeles, is searching for a new CEO.

• Are you a NYC visual/cinematic artist with a pulse on pop-culture? New York Theater Workshop is looking for a Marketing Content Creator.

• Are you a woodworker with teaching and coordination experience? The Crucible, an industrial arts school in Oakland, is looking for a Woodworking Department Head.

• Are you an experienced wardrobe professional? Ballet Hispánico, the nation’s largest Latino cultural organization and one of America’s premier dance companies, is looking for a Wardrobe Director.

Volunteer opportunities

• Art Heals Arizona (formerly Free Arts) creates moments of connection and creativity for children who have experienced trauma. Through their Art + Mentors = Resilience model, they help youth build resilience through connecting them with caring adult mentors and intentional arts activities. You don’t need to be an artist to be a volunteer.

• Textile Center in the Twin Cities of Minnesota is a national center for fiber arts. Volunteers can help out at The Stashery (which provides accessible, donated materials for artists), support harvesting and education at their natural dye garden, and help run other creative workshops.

• Esalen is a holistic and educational retreat space in Big Sur, California dedicated to providing workshops and experiences in the healing and somatic arts. Volunteer opportunities to help support the community and its grounds (cabins, kitchen, farm & garden) are available daily.

With zeal and gratitude for this creative life,

Vanessa

is an engineer, a juggler, and a punk... and was Time Magazine’s Person of the Year twice (2003 and 2006, look it up). He served for more than 20 years in the US Air Force, testified before the Senate Armed Services Committee and the British House of Commons, and authored four book. He’s a co-founder of The SparkLit Group, a small consulting firm that helps people ask bolder questions and build better futures.

Today, we have the absolute pleasure of featuring Dan as a guest contributor! So, I’ll pass it off to Dan…

I worked my way through high school and college as a performing magician, doing shows at birthday parties, libraries, and hospitals. While my friends were flipping burgers or waiting tables, I spent my weekends spreading happiness and wonder. Not a bad way to make a buck.

My shows involved making things appear, vanish, and float through the air, but I always opened with a magic-adjacent routine: juggling. I juggled balls, of course, but also clubs, knives, and – for my outdoors performances – flaming torches.

These days I do fewer card tricks and more juggling, although seldom for an audience. I keep several sets of juggling props in my office, and regularly take short juggle breaks throughout the day. It’s a playful, meditative way to do a little reset, mentally and physically, and it never fails to brighten my mood and unlock my creativity.

If you don’t already know how to juggle, I highly recommend giving it a try. There’s even a technique called functional juggling that makes the hobby accessible to people with a variety of physical and mental abilities. Juggling really is for everyone.

When I learned to juggle in the summer of 1986 (wow, 40 years ago!), I struggled at first. Not because juggling is hard, although yes, juggling is hard. My core struggle came from a misperception about how juggling works. I was focused on the wrong thing.

The struggle got easier and the breakthrough happened when I decided to accept the following advice:

Read more

July 2: What I Learned When I Learned to Juggle by Dan Ward

Tomorrow, we’re inviting Dan Ward (who spent much of his youth performing magic shows at birthday parties, libraries, and hospitals) to share a piece of advice from learning (and teaching others) to juggle. And, it might just be the life metaphor you didn’t know you needed!

In addition to being a juggler, Dan Ward is an engineer, a punk... and was Time Magazine's Person of the Year twice (2003 and 2006, look it up!). He served for more than 20 years in the US Air Force, testified before the Senate Armed Services Committee and the British House of Commons, and authored four books (Punk, Lift, The Simplicity Cycle, and F.I.R.E). He's a co-founder of The SparkLit Group, a small consulting firm that helps people ask bolder questions and build better futures.

This piece will be available to paid subscribers only.

Subscribe now

July 8: Community Coffee Chat with Gretchen Robards and Nicole Rangel (12pm PST)

As part of our monthly Community Coffee Chat series, where we invite creatives from the Tomatokind community to share candidly about the messy middle of their creative journeys, we’ll be chatting with Gretchen Robards and Nicole Rangel.

Gretchen Robards is a multi-disciplinary creative working across photography, creative direction, and design, with movement, music, and writing woven into everything she does. Equal parts artist and community-builder, she uses each medium as a doorway to genuine connection, turning collaborations into safe spaces and creative work into shared experiences. Whether behind a camera, on stage, or designing for a brand, her through-line is the same: create with intention, connect without pretense.

Nicole Rangel, Ph.D., is a holistic educator, papermaker, and daughter of Colombian immigrants, proud to come from a long lineage of green thumbs. She handcrafts (and teaches others to handcraft) plantable paper goods that are designed to be shared and planted to grow organic flowers, herbs, and food-bearing plants. Her work is an invitation to slow down, play, give with intention, and practice a more regenerative relationship with the land that sustains us.

Together, we’ll be sharing our honest feelings across topics including: how to overcome the fear of being seen, inviting more joy into our work, and the complexities of financially investing in ourselves.

This Substack live is open to all, so feel free to share this newsletter with a friend!

I'd love to tune in!

July 10: Making this Podcast is Hard by Vanessa Li

For the past 6 months, I’ve been working on a podcast that is really more of an audio-documentary than a traditional podcast. Each episode will introduce you to a creative person somewhere in the world and you’ll step into a week in their life through an immersive audio diary experience. But, it’s been a long production process of figuring out the technology, timeline, creative partners, and…honestly…just prioritizing and making time for the project. It’s the longest-form content that I’ve ever made, and I have been dreams for it. But it’s taking forever, so I’d love to bring you along for the ride.

This piece will be available to paid subscribers only.

July 22: Live Conversation with Nicole Garfunkel (11am PST)

When I first met Nicole many months ago in a creative community we both were a part of, I was struck by her story and the mission behind her work in fashion. So, I am beyond excited to invite her to the community to share the story behind her work.

Nicole Garfunkel is a personal stylist who helps people use fashion as a tool for showing up fully in their lives in eating disorder recovery. Her approach goes beyond aesthetics. It's about aligning your personal style in a way that feels authentic, empowering, effortless, and fun, and without changing your body for the sake of “looking stylish.”

This Substack live is open to all, so feel free to share this newsletter with a friend!

I'd love to tune in!

July 24: Creative Lunch Club Picnic (12pm PST in Berkeley, CA)

In collaboration with Creative Lunch Club, a worldwide community of creatives meeting up in-person every single month, we’ll be hosting a picnic at Strawberry Creek Park in Berkeley, CA. Bring a blanket, some food and drinks, and join us for a relaxed afternoon. Meet other multi-passionate creatives, and maybe walk away with a new friend.

This meetup is open to all. RSVP below!

A Summer Picnic?? Say less!

July 27: On Writing & Creativity by Sophie Davies

You may recognize Sophie from our Substackers Meetup last month!

Sophie Davies is a culture-obsessed British woman living in Marin County (between San Francisco and Napa Valley) who is fueled by tea, culture, and community. A lover of film, books, magazines, and most things secondhand, she was born and bred in South London and came of age in the 90’s, an exciting time for creatives who broke through the British class system to make something of themselves in the exciting worlds of music, fashion, art, and design (that were exploding at the time).

Sophie is also the founder of Cuppa Culture, a Marin County, CA-based community for women that hosts networking events, speaker series, and editorial partnerships supporting female-owned businesses in the SF Bay Area.

In this guest piece, she’ll share a bit about her writing practice (something she doesn’t share too often in her work), and how it has helped her unlock a new chapter of creativity.

This piece is available to paid subscribers only.

July 29: Summer Vision-boarding (6pm PST, Berkeley, CA)

Oh, Summer: the season for road trips, reading romance novels in your sunnies, outdoor concerts, delicious grilled veggies...and, dare we say....vision-boarding??

For me and fellow-creative Sasha Purdy (founder of Manifest Creative Club), summer feels like the perfect time for an expansive, reflective, and hopeful intention-setting ritual: a chance to pause and tap back into our visions for this one big beautiful life. So, we will be hosting a summer vision-boarding session that will feel like an afternoon community sleepover. Imagine: a creative meditation with art supplies galore and friendly faces all gathered round.

I'm in!

July 31: Possibilities Club (3pm PST, Zoom)

Join us for our monthly Possibilities Club workshop: a playful, expansive workshop for anyone pursuing a dream.

In this interactive and reflective hour, you’ll:

• gain clarity in your squishy ambitions

• step into an expansive version of you

• have a heart-to-heart with your future-self

• and, give/ receive support from fellow multi-passionate creatives

This month’s theme is: ALIGN

So, ask yourself: What currently feels off in your life or creative practice? What parts of your life feel most like you right now, and which feel like a facade? What are you ready to realign, release, or recommit to?

This workshop is available to paid subscribers only.

I'm a paid sub, & I'm in!

In addition to these July events, we’ll also be in your inboxes every Monday with our new Dream-Board column! If you haven’t seen this week’s, check it out here!

Alrighty, creative friends…hope to see you soon!

With zeal and gratitude for this creative life,

Vanessa Li

P.S. Here are some reminders on how to make the most of this community!

• Join our subscribers-only community chat - Think of it as a friendly group chat to hang out with fellow multi-passionate creatives and converse about all things worth dreaming about. The chat has been live since January and folks have connected through sharing creative rituals, advice on business/life dilemmas, book recs, physical and digital resources, and also cat pics. 😺 New in the chat: Possibilities Pings! To keep things light and breezy this summer, we’ll be sending you a short-and-sweet “Possibility Ping” with an inspo from our world or other corner of the internet.

• Check out our Creative Journey Library - People are always coming to us for book recs on how to design their life (a.k.a., how to do more art, ignite their creative joys, start a dream project, tap into their inspiration, live more fully), so…we’ve compiled a list! If you decide to dig into one of our recs, or have titles to add, we’d love to hear about it!

• Follow us on Instagram (@tomatokindmagazine) and LinkedIn (Tomatokind) - We share daily creative and life tid-bits there, plus offerings and announcements. Plus: fun things like giveaways!

• Browse our Creative Spaces Map - This is our dynamic, open-source map of creative spaces, studios, and hideaways across North America. It is curated from our editorial adventures as well as reader submissions, and designed for you to get into the community and make stuff, co-work, and experience creative adventures! We have a ton of listings in our backlog waiting to be added to the map, but please send us more (it might just be the kick in the booty we need to update the map!).

Welcome to our very first dream-board, a weekly column that was born from an IG story and this little thread in our community chat!

Straight to your inbox every week: I’ll be rounding up creative opportunities, fellowships, workshops, brick and mortar offerings, and other creative voices and resources to help you pursue a life of creative abundance!

Initially, all subscribers will get access to this weekly board. Eventually, we’ll be limiting this column to paid subscribers only. So, dig in now (and tell us what you want to hear more of)!

Weekly Dream-Board

• Are you a creative events producer or cultural curator? Check out SF-based creative hub Brave New Spaces and their Founding Studio Residency.

• Do you have experience as a barista or baker, and love chai and cozy community spaces? Check out roles at the beloved Berkeley & SF-based chai cafe elaichi co.

• Are you a bilingual teaching artist (English/ Spanish) based in Colorado? Children’s Museum of Denver is looking for a storyteller and play champion to craft imaginative educational adventures and immersive activations.

• Looking for a creative conference to attend this year? There’s still time! Here’s a fantastic global list courtesy of the Creative Lunch Club. Maybe join us at Create & Cultivate in LA from Sept 19-20?

• Are you a foodie creative in LA with a restaurant dream? This kitchen in Old Pasadena is looking for a new tenant.

• Calling all Seattle creatives! Connect with each other at one of Creative People Doing’s many summer gatherings.

• Are you a freelance creative with pitch paralysis? Here’s a Creative Mornings FieldTrip just for you.

Volunteer opportunities

• Crews for a Cause is a nonprofit production group that connects video and media professionals with causes they truly care about (and that are in need of impactful storytelling). Check out the crew!

• Are you an SF-based creative whose passionate about exploring a career in events? Volunteer with That Art Party!

• Creative Growth is the oldest and largest nonprofit art studio for artists with intellectual and developmental disabilities, and is looking for remote/in-person volunteers to help run the studio and organize exhibits!

With zeal and gratitude for this creative life,

Vanessa

Community Coffee Chats are monthly candid conversations with entrepreneurs, creatives, and small-business owners in our community.

Join our next one on Tuesday, 6/30 at 11am PST!

This month, we’re chatting about working with a creative business partner, leaving corporate, navigating interpersonal friction, embracing “the suck” at times, and the endless surprises of entrepreneurship.

How do we adapt to a new sense of community and financial instability?

Learn to communicate effectively with a co-founder?

And, pivot our businesses…a lot?

Join me, and of for a “messy middle” conversation on all the above!

I'm interested!

About my Coffee Chat Guests:

Lynne recently left a 25-year career in health care to launch The SparkLit Group. Before health care, she spent a hot minute as a journalist. Now she puts her passion (and history) for asking thoughtful questions and listening carefully to the answers to work as a leadership coach and facilitator of growth and discovery. An ironman triathlete, she knows that FORWARD is the pace that gets you across the finish line, a discipline she is now putting into practice as an entrepreneur.

Dan is an engineer, a juggler, and a punk... and was Time Magazine's Person of the Year twice (2003 and 2006, look it up). He served for more than 20 years in the US Air Force, testified before the Senate Armed Services Committee and the British House of Commons, and authored four books. He's a co-founder of , a small consulting firm that helps people ask bolder questions and build better futures.

Event Details:

📅 June 30 | 11am PST

📍 Your Substack app or web browser

🎟️ Add the event to your calendar!

Alrighty, creative friends…hope to see y’all next week!

With zeal and gratitude for this creative life,

Vanessa Li

P.S. Here are some reminders on how to make the most of this community!

• Join our subscribers-only community chat - Think of it as a friendly group chat to hang out with fellow multi-passionate creatives and converse about all things worth dreaming about. The chat has been live since January and folks have connected through sharing creative rituals, advice on business/life dilemmas, book recs, physical and digital resources, and also cat pics. 😺 New in the chat: Possibilities Pings! To keep things light and breezy this summer, we’ll be sending you a short-and-sweet “Possibility Ping” with an inspo from our world or other corner of the internet. Our first one dropped yesterday!

• Check out our Creative Journey Library - People are always coming to us for book recs on how to design their life (a.k.a., how to do more art, ignite their creative joys, start a dream project, tap into their inspiration, live more fully), so…we’ve compiled a list! If you decide to dig into one of our recs, or have titles to add, we’d love to hear about it!

• Follow us on Instagram (@tomatokindmagazine) and LinkedIn (Tomatokind) - We share daily creative and life tid-bits there, plus offerings and announcements. Plus: fun things like giveaways!

• Browse our Creative Spaces Map - This is our dynamic, open-source map of creative spaces, studios, and hideaways across North America. It is curated from our editorial adventures as well as reader submissions, and designed for you to get into the community and make stuff, co-work, and experience creative adventures! We have a ton of listings in our backlog waiting to be added to the map, but please send us more (it might just be the kick in the booty we need to update the map!).

It was a full-circle moment because I first met Krystal at one of my early Possibilities Club workshops, which I co-hosted with local illustrator in Berkeley, CA. At the time, Krystal was in a major life and career transition, and had just settled into her new home and art studio in San Francisco.

Krystal: “That Possibilities Club workshop really meant a lot to me. It was one of those critical, epiphany moments in my creative journey.”

Ever since then, we’ve had a front row seat in each other’s worlds, and I’ve witnessed Krystal build Pissed Off Moms from the ground up: an art collective and gathering series for women reclaiming their creative authority. Part exhibition, part ritual, part rallying cry; a space where mothers and makers come to remember who they are.

5 Takeaways from Our Conversation

If you’re a paid subscriber, feel free to go straight to our full conversation by clicking the video above. Or, you can read below for the topics that stayed with me the most.

1. When it’s not about discovery, but reclamation

Krystal didn’t become an artist overnight, when she sunsetted her creative agency and stopped bending to the visions or her corporate clients.

Read more

Tomorrow, I’ll be gathering a group of writers and creatives at my favorite third-space, Local Economy, to chat about what it’s like to express ourselves, build businesses, and story-tell here on Substack. If you’re in the SF Bay Area, you can join us here :)

Anyways, co-hosting this meetup with fellow substacker () got me thinking about my own journey on this platform, which goes something like this:

Year 1.

3 years ago, I started with a “Humans of New York” vision.

I have always been that person who lingers in brick-and-mortar establishments to hear the origin stories of shopkeepers: their personal stories, visions, creative processes, business decisions, and life circumstances. I would also often come home from walking my dog or grocery shopping with the phone number of a strangers’ in my pocket, following a random conversation about life.

So, it just felt natural for me to revisit my childhood love for writing by sharing these stories about my community. Plus, I was working a 9-5 job that offered me very little creative leeway, so I was craving that spark.

That first year, I published 1-2 features a month, interviewing and uplifting the journeys of local documentary filmmakers, music directors, winemakers, vintage clothing curators, artists, boutique gym founders, and chefs.

I felt: inspired, connected, and re-energized

I learned that: the marriage of “writing for my own creative expression” and “writing to celebrate and share the beautiful, ordinary lives of my community” gave me an immense sense of purpose and joy

But, I worried that: people wouldn’t want to read about my own creative journey and was here only for those I wrote about

Year 2.

This is when I became more aware of my creative process, as well as my likes and dislikes.

I loved escaping my day-to-day routine to meet up with my guests for an interview at a local coffeeshop or park bench. I was obsessed with facilitating these conversations, learning about their passions and interests, and getting curious about the intricacies of their life and career journeys. These conversations would always be the highlight of my weeks, and helped me power through everything else in life.

I still remember Sierra Antroniese Young (owner of a mango smoothie cart in Oakland, CA) saying to me: “This is the first time I’ve paused to even think about how I got here and started my food truck. I’ve just been hustling this whole time. So, thank you for giving me a chance to reflect and share my story.”

I also deeply loved the writing process: weekend mornings sitting in my sunroom and crafting a story from beginning to end. I would also call up my guests’ friends, family members, and colleagues and ask them to share meaningful anecdotes about the person I was featuring. One story would often take weeks, but it satisfied my soul.

What I didn’t love, though, was the busy work of transcribing my notes and the lack of dedicated time to write. And, facing the inevitable question: “But, is anyone even reading this? Who is this for?”

In that second year, I published about 1 feature a month, and experimented with sharing other pieces like fiction, poetry, and pieces about my personal grappling with creativity.

I felt: a mix of flow and stuckness, but a deep sense of purpose

I learned that: it was difficult to channel the high, initial energy of my interviews with guests to the finish line of publishing each piece. I would inevitably lose momentum over the multiple weeks I was spending writing.

And, I worried that: I might not be able to sustain this project, and that readers were not getting as much value from it as I was (on a personal level).

Year 3.

Aka, the year of massive experimentation and growth.

I finally started understanding the inner workings of Substack. I saw that my opportunity to create on the platform went beyond writing. I could build a community of multi-passionate creatives here.

So, I finally got clear on my vision to do this: to not just spotlight inspiring people, but also to share honestly about my own creative journey, and create a space for others to connect and share from their own experiences.

I started paying more attention to creating experiences and to curation. I wrote a lot more from the heart, and shared things that were more personal (like this article on 30 jobs I worked before turning 30, and this one on my relationship with classical music). I experimented with shorter features (which took less time) and showcased more of my guests’ practice and art. I created my signature workshop series Possibilities Club, shared experiences from my travels, and started curating events roundups.

In year 3, I published 4-5 articles a month, and shared over a dozen in-person and online experiences including Substack live interviews, in-person workshops, meetups, a weekly community chat for subscribers, guest contributions, and more.

I feel: expansive, optimistic, and like I’m a tree growing a million new branches

I’m learning that: Trying new things is the biggest gift I can give myself. And, leaning into change and doing it with others are a close second and third.

Though, I still worry that: I’m not seeing the bigger picture - that I’m thinking too small, and not optimizing my energy and time. There’s so much I want to do, and I still struggle to choose which direction to take a step in right now.

So, that’s a little bit of what my Substack journey has been like.

What about you?

Are you active on Substack?

Are you a writer, or mostly a reader?

Maybe, you’re thinking about starting a publication, or making some significant changes about how you show up here?

Reply to let me know, and come join me and other Substack writers tomorrow in Oakland to chat about everything we’re loving/ uncertain/ curious about writing on this platform!

Count me in!

In this conversation, Mary shares stories from her youth and young adulthood, moments of finding creative expression in unexpected places, how she pivoted between many careers including social work and film production (all of which involved being close to the stories of ordinary people), the journey to reversing traditional metrics of success, the serendipitous gift of curating a community that celebrates the multitudes of grief (often in a humorous way), and exciting new projects (spoiler alert: Mary’s writing a book!).

In fact, the second I logged off the event, messages immediately poured in about how inspiring it was to hear Mary’s life story and the beginnings of Tips from Dead People.

5 Takeaways from Our Conversation

If you’re a paid subscriber, feel free to go straight to our full conversation by clicking the video above. Or, you can browse below for the topics that stayed with me the most.

1. Ordinary lives are worth documenting.

Many of us fall into the trap of thinking that someone’s life (or our own) needs to be impressive, visibly eventful, grand, or otherwise traditionally accomplished to matter (or to be recognized).

Read more

Morgan’s passion is helping women find joy and light in life. With over a decade of experience in small businesses, non-profits, and at Microsoft, she drew on her background, including being an athlete and parent, to create the Light 56 framework. This approach creates personalized habits that stick, unlocks motivation, and adds fun through unique challenges.

A top speaker at Microsoft Inspire, Morgan now shares her insights at events and on podcasts, covering topics like Redefining Success, Living Lightly, and Ditching Perfectionism. She also founded Light 56 Circle, a community for women who tackle hard things in a light and feminine way! Light 56 aside, you can find Morgan wakesurfing behind a boat, creating something with her son, or in the mountains with her husband training for her next endurance hike.

Today, we have the absolute pleasure of featuring Morgan as a guest contributor! So, I’ll pass it off to her…

Hi Tomatokind readers!

For a long time I thought the goal in life was to be happy and successful, and the way to get there was through self-discipline and doing more to prove my worth. After struggling with secondary infertility, studying how high performers approach rest, and diving into positive psychology, I kept arriving at the same question: what if there’s a lighter way? A way that prioritized my favorite things, focused on progress not perfection and could work for the hardest things as well as the most joyful ones.

Since 2017, I’ve been obsessed with feeling lighter in my life. Not lighter in my body or minimalist in my home but feeling light. Similar to when you take the weighted vest off after a long walk or open a beautiful hotel room on vacation. I wanted to feel more of that!

Can you describe when life feels light for you?

If not, you’re not alone! 💛

It’s unique to each person and often shifts with the season. In winter I’m all about feeling cozy, being steady, feeling wise and rested versus in the summer when I want to feel sparkly, playful, connected and fully alive.

What it means to feel “light”

Many of us don’t have the words to articulate it yet. But “light” is becoming a new kind of goal, moving away from happy or perfect toward something that helps you feel more like your favorite self and something that feels possible even when things are tough, dark or out of our control.

The word “light” is showing up more and more in conversations, captions, and communities because it’s still possible, even when everything else feels heavy.

To help you find the words, I created the Feeling Light Wheel. It has six categories that capture what feeling light most commonly looks and feels like.

Based on years of conversations with women, research in positive psychology, spending time with kids who instinctively know their favorite things and getting curious about the words people use when they talk about what lights them up, I found 6 main categories to describe feeling light: joy, gratitude, progress, confidence, calm or anchored and feeling bright or fully alive.

I believe knowing what feeling light means to you can become your Why.

Read more

One of the most difficult things about being a creative business owner is all the decisions I have to make every single day: what to start, stop, continue, tweak, spend time on, don’t spend time on…

I get overwhelmed because I feel the pressure to both ask the right questions and have the correct answer.

Previously, in my corporate job, I always felt there was someone to consult for a second opinion: a boss, a teammate, a mentor. But, on my own, it feels different and much harder.

Earlier today, I tuned in to a conversation with and . They talked about what it’s like to share unfinished/ unpublished excerpts of their book manuscripts with their communities: the emotions that come with it, but also the benefits of listening to what resonates (and what doesn’t).

Their conversation made me remember that, for a while now, I’ve been wanting to get your feedback on this publication, community, and the experiences I’ve been hosting:

• What’s been awesome?

• What could be more awesome?

I started a lot of new things this year, from the community chat (come join this week’s thread!) to substack live interviews, monthly community coffee chats, guest articles, and going virtual with our Possibilities Club workshop.

So, I’d love to hear what you think!

If you’ve resonated with anything I’ve created (or if you’re new and want to help shape this space), please take 60 seconds to share your thoughts in the brief survey below. It would truly mean a lot. 🙏

TK Spring Check-In!

Now, to catch you up on the latest…

Recent Happenings

First, I’m feeling really grateful that a lot of new humans have joined this community in the past month. Maybe we met at the panel I spoke at Adobe. Or, perhaps we chatted at a Creative Mornings event, a virtual meetup, a Local Economy gathering, or somewhere else in the wild.

Wherever we may have connected, here’s a little summary of how to plug in!

Our Weekly Community Thread

Every Wednesday, I post a thread on our Tomatokind subscriber chat that invites candid shares about your creative multitudes, projects you’re working on, daily rituals, book/podcast/ small business recommendations, creative blockers/ dilemmas, community resources and offerings, and sometimes just something silly.

For those new to Substack, community chats are exclusive conversation spaces for subscribers of a specific Substack publication. For ours, think of it as a casual chatroom where you can hang out with other multi-passionate creatives.

This week (as it is a new month), I’m asking everyone to re-introduce themselves. So, come say hi and let the community know who you are!

Join the chat!

Possibilities Club

Possibilities Club is our signature workshop, combining improv and visioning exercises to invite your most limitless self to the table to pursue those creative projects and life dreams that have been collecting dust in your notes app.

We’ve run Possibilities Club both in-person and virtual, and each format comes with its own magic! Our next one is virtual and its on June 24th from 5:30-6:30 PST. Open to paid subscribers only!

Subscribe now

Live Interviews

If you’ve been here since the beginning, you’ve probably thought at some point: “Is Vanessa still interviewing small-business owners, artisans, storytellers, and brick-and-mortar shopowners?”

The answer is: yes.

Previously, we featured editorial interviews with creatives around the world every single month, but have been pausing to re-imagine what type of conversations to reserve for our podcast (launching later this year) versus here on Substack.

Just another one of those creative decisions that don’t mean much to you, but that I’ve spent endless hours racking my brain about…

Good news…starting this month, interviews are coming to you as live events on Substack! Because, as much as I love sharing stories of others’ journeys in my editorial voice, there’s just nothing like hearing about someone’s experiences in their own words.

June 12: Live Conversation with Mary McGreevy (12pm PST)

Mary McGreevy (creator of the viral account Tips from Dead People) will be joining us for a live conversation (June 12, 12-1pm PST). Mary will share the stories and people that make up who she is, the unexpected journey of how sharing her lifelong fascination with obituaries with the internet nearly broke it, and her latest endeavor: writing a book.

I want to attend!

June 16: Live Conversation with Krystal Lauk (12pm PST)

Next, we’ll be chatting with Krystal Lauk, a creative leader, curator, and artist based in San Francisco. In 2025, Krystal founded Pissed Off Moms (POM), an art collective and gathering series for women reclaiming their creative authority. POM is part exhibition, part ritual, part rallying cry; a space where mothers and makers to come to remember who they are.

I want to attend!

IRL Events

I hear you. We need to be in-person!

Last week, I was invited to speak on a creative panel at Adobe’s SF office. And, the energy in the room was amazing. If we met there, you know. So, as summer arrives in the San Francisco Bay Area, you bet we’ll have some fun gatherings to attend! Stay tuned.

For now, mark your calendars for a Substackers Meetup I’m hosting with Sophie Davies, founder of CUPPA Culture, at one of my favorite community spaces: Local Economy (Oakland, CA) on June 20th from 2-4pm.

I want to attend!

Guest Contributors

While I’ve called Tomatokind a digital “magazine” since the beginning, it actually took me a while to invite guest writers. But, we are finally at that point!

Last month, fellow creative (composer, collaborative pianist, creative coach) guest-published a piece for us that was a huge hit!

This month, we’re having another gem of a guest writer: Morgan Jackson, founder of Light 56®, a community and accountability practice that supports women struggling to make time for themselves and feel lighter in their body, mind, space, and spirit. This feature will be open to paid subscribers only.

Subscribe now

Monthly Community Coffees

Community Coffee Chats are also a newer addition to our ecosystem. These are monthly candid Substack live conversations with members of the community.

In May, we invited Emery Tran and Prerana Gurubasavaraj to chat about how they navigate high-stress 9-5 jobs (as a designer and regulatory affairs manager, respectively) while simultaneously pursuing their creative dreams as storytellers, podcast hosts, and content creators.

In April, we had Melissa Rivera (of Nonprofit Curious), a coach for non-profit startups and social enterprises, and Keriann Bellamy, a copywriter and marketing strategist for wellness-focused practitioners and small-business owners. We chatted about all things creative entrepreneurship!

As for this month, we’re lining up two special guests and will be announcing a date and time for that conversation soon! Stay tuned.

And, with that, thank you so much for being here!

Please share some feedback to help me grow. It would mean the world.

TK Spring Check-In!

Ok, I’ll be in your inbox again soon :)

With gratitude and zeal for this creative life,

Vanessa

We talked about corporate career pivots and creative ones, noticing and healing from burnout, time management, facing the fear of being seen (by family, coworkers, and the internet), and what it looks like to redefine success for ourselves (as creatives who are also navigating 9-5 jobs).

5 Takeaways from Our Conversation

Community Coffee Chats is a casual conversation series with entrepreneurs, creatives, storytellers, and small-business owners in the Tomatokind community.

Here are our takeaways from our sit-down with Emery Tran, full-time designer and part-time podcast host, and Prerana Gurubasavaraj, full-time regulatory affairs manager and part-time content creator (Paid subscribers can go straight to the full conversation by clicking the video above):

1. Don’t be afraid to reinvent yourself.

Because, life is meant to change you. Iteration is the process of becoming who you are today, and who you become tomorrow. You are allowed to evolve, and that includes: how you make money, how you share your talents, who you choose to spend time with, art you choose to create, and so forth.

You are meant to change, so don’t resist it. Your creative pursuits and 9-5 jobs are no different. Instead of beating yourself up about that recent pivot, consider welcoming what’s next!

2. There’s no such thing as “enough time” or “perfect routine”.

Yes, consistency is important, but listening to our intuition is even more important. While some part-time creatives have very regimented production schedules (filming short-form content on Tuesdays from 9-11pm) to navigate the constraints of their full-time jobs, that doesn’t work for everyone. Sometimes, it’s just what works this week, and that is perfectly fine. Remember, you’re pursuing your creative dreams because you want to, not because you have to. It’s supposed to be fun!

3. It’s your choice who and when to share your creativity with.

Because, creative expression is scary. Many of us wait years to share our creative sides with our family, 9-5 coworkers, or even friends. Because, our creative work is not just work. It is our identity, our world views, and our inner universe. The good part, though, is that we get to choose when and who we want to be brave with. Some of us have parents who are the staunchest supporters of our creative work. Others of us prefer to keep our creative expression far from our families. There’s no one right answer.

4. Chasing external success metrics will burn you out.

So, try shifting to measures that are more sustainable and authentic to you. For example, in lieu of focusing on “likes” on social media, ask yourself: “Am I proud of what I created?”, “Did this feel good to make?”, or “Did it resonate with even one person?”

The juggling act of pursuing multiple life-callings is hard enough. So, let’s not impose external metrics that are misaligned with our values. Instead, take a moment to reflect on your goals with each endeavor and redefine your own markers of accomplishment.

5. First and foremost, create the thing for you.

Here’s a challenge: create it for you first. Be selfish. Ignore “the market", and just let your creative expression guide your pen (or paintbrush or key strokes). It may be helpful to consider: “What if your creative work exists to satisfy you and only you? And, it just so happens to help or inspire others? What if your job was not to serve and provide?”

If the above was true, would you create differently?

You can now listen to our full conversation by clicking the video above. And…

With zeal and gratitude for this creative life,

Vanessa Li

About Emery & Prerana:

Emery is a UX designer, community builder, and creator behind From Remey: A Voice Journal, a podcast and blog documenting her evolving career, creative pursuits, and life in transition. She began her career in the art world, working with internationally renowned artists including Betye Saar, as well as curators from institutions like LACMA and MoMA, before transitioning into design. Outside of her full-time work, she helps foster creative community in San Francisco through events, collaborations, and conversations that bring people together.

Prerana is a regulatory affairs manager who guides digital health products, including software and AI-powered tools to-market, safely and responsibly. She’s worked in the space since 2018 and sees it shaping the future of healthcare. Outside her 9-5, she’s the creator and storyteller behind @dessertdigestplus, a space documenting recipes, cultural traditions, beauty, and the everyday rhythms of life in Orange County. “It’s a creative outlet that’s grown alongside my career.” Prerana also works in real estate, guiding family and friends through one of the biggest decisions of their lives: buying or selling a home.

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For context, my partner and I use dry-cleaning services once in a blue moon, so we end up trying a new spot every time. Thus, we know very little about dry-cleaning business norms.

Anyways, as I entered the shop earlier and apologized for being late (by 2 weeks) to pick up our items, I asked the staff, sheepishly: “So, how long do you typically keep items until? Do you…get rid of them after it’s been a while?”

I thought maybe I was so tardy to pick-up our items that they were at risk of being thrown out. So, I wanted to know what “deadline” to keep in mind next time.

“Oh, we keep items forever,” she replied. “Just last week, someone came to pick up a pair of socks from 2023.”

FROM 2023?? My mouth hung open, and stayed like that for a while.

WAIT, WHAT?! How is that even possible? How did they forget for that long? Then, manage to remember all this time later?

It was such a funny tidbit to me. So, I asked more questions, and soon, the woman pointed out a duvet cover that has been waiting to be picked up since 2021 and another one since her mother used to work there.

As I left the store, it got me thinking about all the things I’ve procrastinated on over the past days, months, and maybe even years. It may or may not be dry-cleaning, but I guess we all lose track of things we need (or just want) to do in life…one way or another.

Have you ever forgotten about something for a long time, then came back to it?

June Happenings

In the spirit of now, I want to share all the happenings we have lined up for you this month (before my procrastination takes over). In-person meetups, guest contributors, interviews, live events! 🌸🌼🌷

June 3: Community Coffee Chat with Emery Tran & Prerana Gurubasavaraj (Replay)

Last week, we invited fellow creatives Emery Tran and Prerana Gurubasavaraj to chat about how they navigate high-stress 9-5 jobs (as a designer and regulatory affairs manager, respectively) while simultaneously pursuing their creative dreams as storytellers and content creators.

We talked about corporate career pivots and creative ones, noticing and healing from burnout, time management and “doing it all”, facing the fear of being seen (by family, coworkers, and the internet), and what it looks like to redefine success for ourselves.

This replay is open to paid subscribers only.

June 9: ABC Framework with Morgan Jackson

We’re welcoming guest contributor Morgan Jackson to our Tiny Experiments column! Morgan a.k.a. one of my favorite people to hop on an impromptu FaceTime with has a certain glitter and zest for life that is oh-so-contagious.

Morgan is the founder of Light 56®, a community and accountability practice that supports women struggling to make time for themselves and feel lighter in their body, mind, space, and spirit. Influenced by Brene Brown, Dr. Michael Gervais, Dr. Daniel Siegel and other experts on mental health, positive parenting, and habit building, Morgan developed the ABC Framework (which is easy and kind) to help you make steady progress towards achieving your goals (big or small).

This feature is open to paid subscribers only.

Subscribe now

June 12: Live Conversation with Mary McGreevy (12pm PST)

It’s finally happening! (creator of the viral account Tips from Dead People) will be joining us for a live conversation (June 12, 12-1pm PST). Mary will share the stories and people that make up who she is, the unexpected journey of how sharing her lifelong fascination with obituaries with the internet nearly broke it, and her latest endeavor: writing a book.

Mary and I met at Altitude Summit 2025, and have been hoping on video calls every couple months since (plus: we’re co-hosting something special in Oakland this fall 🤫). We’ve shared tender moments about family, questioning spirals about life and career pivots, and just generally have the best time together. So, I can’t wait for you to tune in!

This Substack live event is open to the public. Paid subscribers will be invited to submit questions beforehand.

I want to attend!

June 16: Live Conversation with Krystal Lauk (12pm PST)

Next, we’ll be chatting with !

Krystal is a creative leader, curator, and artist based in San Francisco. I first met Krystal at one of my earliest Possibilities Club workshops in Berkeley, CA, and our parallel dream-building journeys have been blossoming aside each other ever since!

In 2025, Krystal founded Pissed Off Moms (POM), an art collective and gathering series for women reclaiming their creative authority. POM is part exhibition, part ritual, part rallying cry; a space where mothers and makers to come to remember who they are. I am beyond excited for Krystal to share her journey building POM with this community!

This Substack live event is open to the public. Paid subscribers will be invited to submit questions beforehand.

I want to attend!

June 20: Substackers Meetup with Co-host Sophie Davies (2-4pm PST in Oakland)

This one’s for the Bay Area writers who want to swap ideas, chat about all things “behind-the-scenes” of writing and growing a Substack, and be in community with others who are at all stages of the journey.

I’ll be co-hosting this event at Local Economy with Sophie Davies, founder of CUPPA Culture, a community-marketing consultancy helping female business-owners tell their stories and connect with their audiences through community events and editorial partnerships.

Whether you’re still developing your editorial voice, or actively growing a community on Substack, come join us for an informal supportive conversation! Don’t have a Substack yet? Come hear about others’ journeys and get your newbie questions answered :)

This in-person event is open to the public.

I want to attend!

June 24: Possibilities Club Workshop (5:30-6:30pm PST)

We’re back, baby (iykyk)! Join us for our monthly Possibilities Club workshop: a playful, expansive workshop for anyone pursuing a dream.

In this interactive and reflective hour, you'll:

• gain clarity in your squishy ambitions

• step into an expansive version of you

• have a heart-to-heart with your future-self

• and, give/ receive support from fellow multi-passionate creatives

This month's theme is: DARE!

So, ask yourself: What have you been avoiding? What feels scary but necessary for growth? Maybe you want to commit more boldly to something, and need to speak it into existence? Bring what's on your heart and mind, and let's explore what's possible!

This workshop is open to paid subscribers only.

Subscribe now

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How is your month going? May-hem 🤪, or blooming vibes 🌸?

For me, I’ve been feeling a bit all over the place (like I’m balancing on one leg most of the time), but with grand pauses of gratitude for the abundance around me. Mostly, I’m just figuring things out!

Aren’t we all?

2 Events for my Creative 9-5-ers!

This month in the SF Bay Area has been so sunny: blue skies, searingly-hot concrete, blooming wildflowers, and beach days. In parallel, we’ve enjoyed bringing sunshine into this community in our own way.

May Possibilities Club (5/12) was a blast (take it from attendees Dan and Nicole)!

We’ve also been collaborating with fellow creatives, including pianist, composer, and creative coach , who shared her wisdom on “How to Come Back to Your Creative Self” in our publication last week. Her 8 questions for creative self-reflection were a huge hit. Check out the piece here!

The fun doesn’t end there, though. We have 2 more events in May, so come find us!

May 28: “Futures of Creativity” (Adobe SF)

Join for “Futures of Creativity,” a candid, evening panel exploring how multi-hyphenate creatives have navigated multi-passionate career paths, and how you might think differently about your own creative trajectory. Expect a chat about: pivots, entrepreneurship, non-linear career paths, design, creativity, and stories of personal identity and evolution.

This event is hosted by Service Design Network, Women in Innovation, & Adobe, and moderated by Emery Tran. And, my kick-ass co-panelists are: Kathy Wang, Tina Yip, and Gayatri Gaekwad!

Details:
📅 May 28 | 5:30–7:30pm PST
📍 Adobe San Francisco (601 Townsend Street, San Francisco, CA 94103)
🎟️ RSVP here!

May 29: “Community Coffee Chat with Emery Tran and Prerana Gurubasavaraj” (Substack Live)

Come hang at our monthly Community Coffee Chat (casual conversations featuring members of this community)! This month, we are yapping about how to navigate a high-stress 9-5 job while simultaneously pursuing your creative dreams. How do we manage our time, define success on our own terms, avoid burnout, and find joy in it all?

Join me, Emery Tran, and Prerana Gurubasavaraj for a “messy middle” lunch-time conversation on how we navigate our 9-5 careers and our creative endeavors, especially when we love them both!

About my coffee chat guests:

Emery is a UX designer, community builder, and creator behind From Remey: A Voice Journal, a podcast and blog documenting her evolving career, creative pursuits, and life in transition. She began her career in the art world, working with internationally renowned artists including Betye Saar, as well as curators from institutions like LACMA and MoMA, before transitioning into design. Outside of her full-time work, she helps foster creative community in San Francisco through events, collaborations, and conversations that bring people together.

Prerana is a regulatory affairs manager who guides digital health products, including software and AI-powered tools to-market, safely and responsibly. She's worked in the space since 2018 and sees it shaping the future of healthcare. Outside her 9-5, she's the creator and storyteller behind @dessertdigestplus, a space documenting recipes, cultural traditions, beauty, and the everyday rhythms of life in Orange County. “It’s a creative outlet that's grown alongside my career.” Prerana also works in real estate, guiding family and friends through one of the biggest decisions of their lives: buying or selling a home.

Details:
📅 May 29 | 12:30–1pm PST
📍 Your Substack app or web browser
🎟️ Add the event to your calendar!

Alrighty, creative friends…hope to see y’all next week!

With zeal and gratitude for this creative life,

Vanessa Li

P.S. Here are some reminders on how to make the most of this community!

• Join our subscribers-only community chat - Think of it as a friendly group chat to hang out with fellow multi-passionate creatives and converse about all things worth dreaming about. The chat has been live since January and folks have connected through sharing creative rituals, advice on business/life dilemmas, book recs, physical and digital resources, and also cat pics. 😺

• Check out our Creative Journey Library - People are always coming to us for book recs on how to design their life (a.k.a., how to do more art, ignite their creative joys, start a dream project, tap into their inspiration, live more fully), so…we’ve compiled a list! If you decide to dig into one of our recs, or have titles to add, we’d love to hear about it!

• Follow us on Instagram and LinkedIn - We share daily creative and life tid-bits there, plus business musings. And, fun things like giveaways!

• Browse our Creative Spaces Map - This is our dynamic, open-source map of creative spaces, studios, and hideaways across North America. It is curated from our editorial adventures as well as reader submissions, and designed for you to get into the community and co-work, make stuff, and experience creative adventures! We have a ton of spaces in our backlog waiting to be added to the map, but please send us more (it might just be the kick in the booty we need!).