(2021-09-01) Owens The Gritty Reality For Substack's Middle Class

Simon Owens: The gritty reality for Substack’s middle class. In November 2019, I turned down a six-figure job so I could continue working on this newsletter.

I left them with a single question: If I took the job, could I keep my newsletter and podcast?

I held firm to my demand, but not without a fair amount of agonizing self-doubt. After all, neither the podcast nor the newsletter were producing any direct revenue

The second major job opportunity I turned down came in January 2021.

It’s incredibly difficult to set benchmarks for success

It’s easy for large media organizations to A/B test different strategies

This kind of user testing is extremely difficult for solo creators

This problem is especially bad during the early days of running a newsletter. In the first few months after launching my paid edition, I’d have weeks where I considered myself lucky if I got one new paying subscriber.

The good news is that this is the perfect time to collect qualitative feedback. Starting in July of last year, I started making it a priority to schedule phone calls with my subscribers

It’s not all bad

While the 2010s birthed a generation of social media megastars, the 2020s will see the emergence of a creator middle class

I’m not bragging that I’m one of those crazy people who work 80 hours per week. I’m a person who likes to have dinner with my wife each night and watch TV with her before bed. I try to exercise every day and am even training for a half marathon right now. But in order to focus on these non-work priorities, I had to get better at saying “no” to anything that didn’t lend itself to content production during my designated work hours.

embarking on a newsletter career requires a leap of faith — a departure from full-time work so you can increase your content output, even though you’re not yet generating enough income to replace your salary. In other words: you need some sort of financial cushion.

You need some sort of financial cushion

While we’d all like to say that content quality is the biggest driver of growth, the truth is that publishing consistency often plays a much bigger role.

For instance, weekday socializing has gone pretty much out the window for me.

Most don’t reach their first 1,000 paid subscribers within their first week. Hell, most don’t reach that threshold within the first six months.

There’s usually no “tipping point” moment for them; instead, they just put in the work, week after week, until they build a sustainable business. I’ve interviewed dozens of them for my newsletter and podcast, and most told me it took them upward of several years before they reached what they considered a “comfortable” income.

You have to learn to say “no” a lot

Let’s jump into the lessons I’ve learned:

Because of this burden, you really have to minimize time spent on anything other than content creation

By this point I had been running the paid version of my newsletter for about eight months

I was only generating about a thousand dollars a month, which really meant that I was hemorrhaging money when you accounted for all of my business and life expenses

And yet pass on it I did. Perhaps I was merely succumbing to the sunk cost fallacy, but I was in too deep

Why am I telling you all this? Because I belong to a group of Substack writers who don’t get written about much in the media — let’s call them Substack’s “middle class” — and I want you to understand the sacrifices we have to make while building our newsletter businesses.

As a creator’s profile rises, they also start getting a lot of emails from random people on the internet who want to talk on the phone. I get pitched by a lot of people who are in the process of building products that they want to demo for me over Zoom.

Slack off on the free content, and your lead generation crumbles. Slack off on the paid content, and people start unsubscribing in droves.