How I Got 1,000 Substack Subscribers by Learning to Be Bad at Something New

I’m not very good at being bad at things.

And I don’t mean I’m good at everything. I mean that when I am bad at something, I turn into a full-on meltdown in progress — think: a kid who got last year’s Labubu for Christmas.

I’m working on it.

The Patagonia Wake-Up Call

This side of myself came to a head last year when I hiked the mountains of Chile and Argentina in Patagonia — challenging, stunning, and absolutely humbling.

Every hike followed the same pattern. We’d start out beautifully — flat trails, lush valleys, ice-blue glaciers in the distance. Then we’d hit the first steep ascent, and my mind would go completely dark.

I can’t do this. This is too hard. Why did we come here? This isn’t a vacation. I hate hiking.

And then, every single time, I’d make it to the top and think: Why did I make this so miserable for myself?

To be fair, my grief was still very fresh. I’d lost my mom less than two years before that trip. And almost everything on that trip was brand new to me: ice climbing a glacier, kayaking 28 miles down a glacier river, hauling myself up mud-caked rocks with my bare hands. I’d never even gone to the bathroom in the woods. (I’m from Philly. We eat hoagies and throw batteries at Santa, lol)

Here’s the thing: I’m actually really good at trying new things. I traveled to China alone at 16. I’ve stood in below-zero temps at Lambeau Field to watch the Packers beat the Bears. I’ve competed in HYROX after brain surgery.

I’m adventurous. I love new experiences.

I just wasn’t good at being bad at them.

What Patagonia Taught Me About Growth

Something about that trip shook something loose in me. I didn’t like the version of myself who shut down the moment things got uncomfortable. That’s not who I am — and it’s not who I want to be.

Real growth doesn’t happen on the flat, easy parts of the trail. It happens on the climb, when everything in you wants to turn back.

That realization didn’t just change how I hike. It changed how I approach my work.

Starting a Substack Nobody Read (and Doing It Anyway)

Last August, I started a personal Substack.

I’m writing there about building a life that exists more offline than online, the truth behind running a business you actually love, and how I’m rebuilding myself after the hardest season of my life.

It was uncomfortable from the start.

I’ve spent years writing content that performed — posts with clear calls to action, listicles with tips people could use, content designed to convert. If a post didn’t “go somewhere,” I didn’t write it.

Suddenly I was writing about how a trip to Disney World felt like a metaphor for grief. About what happened when Amazon stopped being my default. About things that were personal, slow, and uncertain.

And almost no one read it.

In the beginning, I’d get one or two likes — usually from a friend. That was it.

I posted anyway. Every week.

How I Grew to 1,000 Substack Subscribers (Without Poaching My Email List)

Here’s what I want to be clear about: I didn’t drag anyone over from my 62,000-subscriber email list on Kit to inflate those Substack numbers. Every one of those 1,000 subscribers found me organically on the platform.

The thing I’m most proud of isn’t the number itself. It’s that I kept showing up when things felt clunky and uncomfortable. When I didn’t know how the platform worked. When no one was engaging with what I wrote. When it would have been so easy to retreat to the platforms where I already know how to “perform.”

What I’m writing on Substack might not be my best work. It might not even be useful to anyone else — at least not yet. And honestly? Part of my motivation is completely selfish: I want to practice writing so I get better at it. So my next book is even better than my first.

But here’s what’s cool about that: I’m writing before I’m good at it. While I’m getting good at it. Regardless of whether I’m good at it.

That’s the whole game.

Is Substack Right for You?

Substack isn’t a replacement for your email list. I’m still very much building and nurturing my list over on Kit — and I explain exactly why in my latest podcast episode.

But if you’re looking for a social media alternative with better discoverability than Instagram, or you don’t have a website yet but want to write long-form content, Substack is genuinely worth considering.

I just released a full episode of my podcast, On Your Terms®, walking through exactly how I got my first 1,000 Substack subscribers — the plan I’d follow if you’re starting from scratch over there.

The Takeaway

So as I write to you between hikes in Peru (HI FROM PERU, by the way!!) — I’m practicing enjoying the journey. Letting myself be uncomfortable. Maybe even bad at it.

Have thoughts on Substack? Are you already on it, or thinking about starting? Comment below and let me know — I’d love to hear where you’re at.

 Links You’ll Love

Gillian Perkins is hosting a free live workshop called “From Zero Content to Paying Members: A Realistic Membership Content Plan” for anyone who wants to create a membership that brings in consistent income! Sign up→ ($0)​

Get an annual pass to Liz Wilcox’s Email Marketing Membership, plus access to everything she’s ever created. Get the annual pass here→ (affiliate link)

My friend, Linda, curated a roundup of 90+ free business-building resources from handpicked experts to help you get the support you need to clarify your business strategy, sell more of your services, and become more visible this year- all for F-R-E-E!

​Access the Online Biz Owner’s Pot of Gold​→ ($0)

A lot’s changing in the online business space. That’s why I just updated my free legal workshop: 5 Steps to Legally Protect & Grow Your Online Business to add everything you need to know about ADA lawsuits, privacy concerns, and more. In it, you’ll also learn exactly how to start an online business the right way — fluff-free. Watch it here→​

Get my book When I Start My Business, I’ll Be Happy on sale for $17 here→. (affiliate link)

In it, I teach you how I built my 62k subscriber email list, how I plan and run my $500k 4-day launches, and how to create evergreen content that builds your business in your sleep.

This isn’t a legal book (there’s ZERO legal advice!) — if you’ve wanted to learn more of “how I do it,” my book is the only place I teach you. (affiliate link)

The Ultimate Bundle®

The go-to legal program for online business owners to get protected—10 DIY Legal Contract templates, ongoing access to the training and support, including all future program updates.

Get The Ultimate Bundle®