Why I started a Substack, and how it’s going

Plus: join me in Oakland tomorrow!

Local Economy (Oakland, CA)

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 (CUPPA with Sophie Davies) 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.

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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!