How I Learned to Take My Own Advice

Reflections on the first anniversary of this newsletter.

Emil Jakob Schindler’s Woodland Path via Artvee.

Many years ago, I interviewed author and Buddhist teacher Susan Piver for a story on how to make a big decision. Her advice: Take the next step.

If you’re thinking about moving to Spain, look at real estate listings. Then take the step after that, and the one after that, and so on.

Piver’s advice has helped me navigate many uncertain periods in my life, and it was particularly helpful a year ago when I decided to quit my marketing job to return to full-time freelancing and start this newsletter.

Before I gave notice, I took a lot of next steps—contacting editors I’d worked with in the past, connecting with a friend who ran several very successful newsletters. I researched, wrote drafts, set up my page, and so on.

I also gave myself clear guidelines for how I’d define success. On the freelance writing side, this was a pretty simple equation: How much would I need to earn per month to pay the bills?

On the newsletter-writing side, it was trickier. I needed to give myself time to figure out what worked, and I knew I couldn't expect to be earning much money or bringing in thousands of subscribers right away. Still, I also knew I couldn’t let myself get too hypnotized by the thrill of publishing my own work and the accompanying likes and subscribes. I wasn’t looking for a fun hobby; I was looking for a way to maintain my writing career. There have been many conversations about the demise of my profession, and I won’t rehash them here. I’ll just say that I had seen other writers do well on Substack, and it seemed worth a shot.

It has been both a lot harder and a lot more fun than I expected.

I’ve loved delving into an issue that has obsessed me for many years—how individuals navigate systemic problems—and challenging myself to do the research and thinking required to create this newsletter.

I also like the intimacy of newsletter writing, the way it feels like a conversation between writer and readers. Writing can be a lonely marathon; writing a newsletter is a marathon where people cheer from the side of the road and hand you cups of Gatorade.

Still, when I look at the hard numbers, it’s clear I have a long way to go. A year ago, I imported about 1,900 subscribers from my Mailchimp list—I lost some during the transition but most stayed. My goal was to bring that number to 5,000. If I could add 3,000 or so subscribers, that would tell me the project was on track to one day become self-sustaining. Instead, I gained about 730 subscribers.

On a personal level, this feels amazing—730 people! But I also know how an agent or book editor would view those numbers.

Maybe it just takes more time. Maybe this was a year of planting seeds, and my slow-and-steady line graph of progress will make a dramatic sweep upward this coming year. Maybe the Substack model is saturated, and I’m the equivalent of a multi-level marketing distributor trying to hawk essential oils in a tapped-out market. Maybe the audience for this newsletter is small and always will be. When you’re posting stuff about climate change and failure, you can’t set your expectations too high.

In other words, I’m confronting the very issue that I’m trying to tackle in this newsletter. Is it me? How much of the success of this project is in my control, and how much isn’t?

I’m American enough to believe that I can bootstrap this problem. I just need to work harder—post more pieces, do more self-promotion and networking, etc. I need to be more patient and believe in myself—I’m doing what I love, so the money will follow. Right? Right!?

But I’ve also done enough research to know it’s more complicated than that, and that anyone attempting to succeed in the platform economy must wrestle with invisible forces like algorithms and platform saturation.

Am I taking charge of my career and forging a path to professional independence? Or am I falling for the platform economy’s big con, the “always deferred promise of exposure”? 

I don’t know. And yet, I’ve never doubted what I’m going to do. I’m taking the next step, and the one after that, and the one after that.

The collapse of the journalism profession is systemic. The vicissitudes of the platform economy are out of my control. At the same time, I’ve never had so much control over what I write and publish.

Here’s another Buddhist idea that has helped me: The middle path. I don’t have to be a cheerleader for Substack. It’s a great tool that has enabled me to find a wonderful community; it’s also a for-profit tech company owned by very wealthy men with questionable gatekeeping skills.

I don’t have to be a complete cynic about it, either. I can recognize the way that the platform and its advocates are trying to manipulate me, and I can acknowledge that creating this newsletter broke my two-year-long writer's block (for writing anything other than marketing copy, that is).

At first glance, this chart looks amazing, but look at the bottom. It starts at 1,800. I have not gained 2,604 subscribers this year; I’ve gained about 730.

So I’m continuing down this wooded and winding path, while staying alert to my surroundings and keeping my eyes out for snakes. And I’m pushing myself to do something that is a bit hard for me; I’m asking for help.

If you like this work, there are some no-cost ways that you can hand me a virtual cup of Gatorade. If you read my pieces on Facebook or another platform, consider becoming a free subscriber. If you enjoy a post, please hit the heart at the bottom of the page. It’s great to see likes on Facebook, but the heart and restack buttons in the email or on the Substack page are what tell the almighty algorithm that my stuff is popular and should be pushed out. (Insert heavy sigh about the state of the culture.)

It's always great when readers become paying subscribers—HUGE thanks to the 40-some people who have done so. I understand, however, that there is another systemic issue that readers are confronting: too many subscriptions. If it’s between me and HBO you should pick HBO (or Max—ugh, whatever), especially since a new season of Hacks just dropped.

Finally, as always, I would love to read your comments. Was this piece useful? How do you make big decisions? How do you find your middle path?