Welcome (back) to Thought Dumpling

To new beginnings.

Long before Jon Stewart became a household name with a nationally televised talk show, he was a struggling young comedian whose sole focus was to get “good enough” at stand-up that he could earn a few dollars. While comedians like Seinfeld and Rosanne had been plucked from obscurity and launched into the national spotlight with TV sitcoms, Stewart was still sharing a room as an adult, and asking the chef at the bar he worked at for free meals that he could pack in a tin and take home with him. What allowed him to endure all these “indignities,” as he called them, was his ability to focus on the milestones immediately in front of him.

“I didn’t think they’re going to discover me like they discovered Seinfeld and Rosanne,” Stewart said. “It was: ‘I hope I get good enough to pass the club.’ You think, ‘How am I going to get good enough at this so that they let me work here for the $15 I might be able to get?’ … Good enough that they’ll let me work on the weekend?”

I don’t share much in common with Stewart, but when I heard him tell this story on a podcast over the summer, it resonated with me. I started Thought Dumpling back in May 2020, with the same mentality as Stewart: I wanted to get better at writing. I wanted to get “good enough” that maybe one day it could lead to something (but I never defined what that could be). So on a weekend during the pandemic, I told my wife that I was starting a newsletter. I asked her to help me come up with a name (of which she deserves all the credit), and a few days later, I was publishing my first post. I had no idea what Thought Dumpling was meant to be, but I thought if I kept writing, I’d figure that out later. I published a post every two weeks for two and a half years, until one day in August 2023, I stopped.

After 60+ posts, I realized that later had arrived, and I still didn’t know what my newsletter was about. To me, Thought Dumpling was just a feed of pithy anecdotes and throwaway stories, which, while fun to write (and hopefully entertaining to read), were mostly pointless. So I stopped writing and started thinking about what the point of it could be.

Or more aptly, I started overthinking. I convinced myself I needed to nail down a good topic or theme for the newsletter, something that’s clever, original, interesting, and also uniquely me. Without that, there was no point in writing. I spent hours mind-mapping and brainstorming new ideas based on my interests and experiences in search of a niche. I developed a new logo and branding because maybe that would spark something. I tinkered endlessly with my About section and bio to find the right summary. I started and stopped dozens of drafts that never saw the light of day, copying other people’s writing styles as I tried to develop mine. I analyzed what others were doing, subscribing to over 30 newsletters, just to see if there were any structures or themes I could borrow and apply to my own. I even started a new newsletter focused on marketing because I thought a fresh start might be the answer. Nothing helped me, and I spiralled further into this state of despair and self-doubt, which was entirely self-imposed and completely ridiculous.

That’s what I’ve been doing for the past two years. Of course, in hindsight, it’s easy to see I was avoiding the only work that would’ve helped me move forward: writing and publishing.

Which brings us to now.

I’ve spent enough time sharpening the pencil. It’s time to take it to the page. Let it be known, there are still lingering questions, and I still haven’t figured it all out. But I am happy to write that Thought Dumpling returns to your inbox starting Monday with a new focus:

Every week, I’ll share something that’s helped me be more creative, work smarter, or live happier.

Like how important it is to get out of your own head and focus on the milestones immediately in front of you.

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I hope you stick around and join me for the new Thought Dumpling. If you do, I encourage you to leave your thoughts and feedback in the comments about the stories and ideas that resonate with you. And if you’re looking for ways to support my work, the best way to do it is by sharing it with others.

See you next Monday.