What I’ve Learned After Two Months on Substack

On going viral, real relationships, and trying not to chase the algorithm

I’m two months into Substack, and I’m so grateful for every single person who has subscribed, read an essay, left a comment, or shared something I wrote! Part of why this has meant so much to me is where I’m writing from. I live in Japan, where the cultural barrier makes small talk hard and the language barrier can make deeper conversations even harder. So I get a bit of both on here :)

After a long day of not always being able to communicate exactly how I want to, it’s been really refreshing to come here to write and talk to people all over the world.

To celebrate two months, I thought I’d do a mini retrospective on what I’ve learned so far.

When I first started writing on Substack, I was incredibly intimidated. I had never encountered so many amazing writers on one platform, and I wasn’t sure if I even belonged here. I started wondering: why write when there’s already so much talent here?

But people always say the best way to get lucky is to increase your surface area for luck. Publishing online gives you more chances for unexpected people and opportunities to find you. This has especially felt meaningful for me when my real life world has become smaller.

I’m still very new to all of this but I wanted to share a few things I’ve learned.

1. Going viral is exciting and immediately messes with your brain

A couple weeks after joining Substack, I wrote a Note that initially got four likes. I remember this very clearly because my brother-in-law was the only person who commented lol.

Then, about three weeks-ish later, it suddenly started spreading. The Note eventually reached thousands of people, and I went from 54 subscribers to over 100 almost overnight. Many of my current subscribers came from that one Note.

It was pretty incredible to watch something I wrote travel beyond my immediate circle. People commented, shared it, and told me stories from their own lives.

But when things go high, they also go low. Once that Note took off, every Note I posted afterward suddenly seemed disappointing by comparison. My next essay got an even smaller response and I caught myself wondering whether it was bad, too niche, or simply not worth reading.

It’s strange how quickly creative work you genuinely enjoy can turn into a numbers game. One viral post can completely reset your expectations. A perfectly normal response starts to feel like a failure just because something else briefly took off. I was never able to replicate the success of that note since.

There’s also a lot of talk about “Notesmaxxing” on here. Notes are clearly an important way for new readers to find you, but I’m still trying to figure out the balance. I like Notes, and they’ve obviously been the biggest driver in helping people discover my work, but long-form essays are the reason why I came to write on Substack in the first place.

I don’t want to spend so much time chasing the algorithm that I stop enjoying the writing itself. But I also refresh my notifications constantly, so clearly I haven’t achieved peace just yet 😅

2. Writing online can lead to real relationships

I’ve met so many people here who are navigating the same things I am: career changes, nonlinear paths, identity shifts, motherhood, life abroad, and writing again.

One of my former colleagues, Matt Yao found me through one of my Notes. We reconnected and caught up on everything that had happened since we last worked together, and he invited me to join his Free Agents group - a community for ambitious, multidimensional people who are taking career breaks, rethinking work, and rebuilding careers outside of traditional employment. It felt like such an unexpected full-circle moment. I started publishing because I wanted to write and somehow it also reconnected me with someone from my old life in San Francisco and introduced me to a group of people asking many of the same questions I’ve been thinking through.

I’ve also met people I probably never would have crossed paths with otherwise. Katie writes Multiple Lives Theory. She stepped away from the traditional corporate tech path and is moving to Japan to write this year. Our journeys have so much in common and it still amazes me that we found each other on here.

I’ve also been deeply touched by all the women who messaged me privately after LinkedIn at 1:45 p.m. Some shared their experiences of turning down opportunities, leaving conventional career paths, or making choices other people didn’t understand. One woman told me she had turned down an opportunity that could have been life-changing for her career, because she needed more stability for her kids.

Those messages made me feel like something I wrote helped someone feel a little less alone. That has meant more to me than any subscriber milestone.

3. People actually write back

Substack feels different from other social platforms because people don’t just react or scroll past what you say - people often write back, often thoughtfully. Even writers with thousands of subscribers will respond when you leave a thoughtful comment on their essays or Notes.

Other platforms can feel like everyone is broadcasting, building a brand, or trying to sell you something. Some of that exists here too, obviously. But Substack still feels more like an actual conversation.

People here are vulnerable. They’re incredible at storytelling. They ask questions and reflect back. They remember things you wrote about weeks ago. A comment can turn into a much deeper conversation than you expected.

That’s probably what I appreciate most about being here.

4. Generosity works better than self-promotion

Because Substack feels more conversational, self-promotion can feel even more obvious here.

I didn’t know this when I first joined, and I definitely broke one of the cardinal rules of Substack: don’t drop a link to your own essay or Substack in someone else’s comments or Notes unless they ask for it. Sorry to anyone I did this to during my first few weeks!

The best way I’ve found to grow here is to stop entering every conversation wondering how it might lead people back to your own Substack. Read someone because you’re genuinely interested in what they have to say. Leave a thoughtful comment. Restack something because it moved you or taught you something.

Mention your own writing when someone asks, or when it actually adds something to the conversation. Ironically, that seems to create more connection than promoting yourself ever could. The algorithm also seems to reward being generous with others. Even if it didn’t, the community would still be better for it.

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Two months in and I still feel like I’m only getting started. I’m not a Substack expert and I’m still figuring out what I want this publication to become.

But two months has been long enough to know that this is a pretty special place. During a chapter when my offline world has felt a bit smaller and quieter, writing here has opened it up again. Thank you to everyone who has read, responded, and shared your own stories. I came here because I wanted to write. I didn’t expect to find so many people on the other side of it.