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What I like and dislike about being a self-employed creator

On August 1, I hit my 10-year anniversary of self-employment. For the first six of those years I was a freelance content marketing consultant, which mostly consisted of ghost-writing articles for executives who then published those articles on their blogs and other verticals. And then for the past four years I’ve been operating my newsletter and podcast pretty much full time.

I posted about this anniversary on social media, writing, “I've reached a point where I genuinely enjoy almost every aspect of my work. “ This prompted Neal Ungerleider to ask: 

Congrats Simon - and I love the *almost*. What are the not-great parts if I may ask?

So let’s break it down into the pros and cons of being a self-employed creator:

Pros

No workplace politics: I have a lot of friends and family who spend a considerable amount of time complaining to me about the people they work with. A coworker can be unpleasant to be around or unwilling to pull their weight. The worst is the toxic boss who has more power than anyone to just make your life miserable. I remember having entire days ruined because of one single person. But now, the most any one of my subscribers pays me is $100 a year, which means there’s nobody with the leverage to impact my day-to-day mood.

Creative freedom: I can honestly say that I’m genuinely interested in just about everything I work on these days. Back when I was a marketer, I said yes to every client who had the money to pay me, which means I was rarely very interested in the subject matter for the content I was creating. Even in my journalism days, my output was shaped by those above me, and I often found the editing process to be extremely unpleasant.

Building my own brand: One of the things that frustrated me as a marketer was that, no matter how much I enjoyed creating content for a client, it only served to enhance their brand, not mine. I received no longterm value from that content beyond the fee I was paid to write it. Now, I have a huge archive of content — in text, podcast, and video form — that will continue to serve audiences for years to come. This means that even if I take time off, my brand is still growing. I’m no longer on a hamster wheel that stops spinning the moment I step away.

Schedule flexibility: I have 100% control over my schedule and I love it. Not only do I no longer have to waste time on a commute, but I can optimize my workday so that I always hit my non-work goals. For instance, I rarely ever miss a workout because it’s fairly easy to build it into my schedule, especially when nobody can demand I join a last minute meeting or project. Lately, I’ve been on a pretty strict low-carb diet, and it’s relatively easy to maintain given that my kitchen is three feet away.

Cons

I’m niche trapped: Because of how internet economics work, a solo content creator pretty much has to stick to a single niche in order to succeed. For better or worse, the niche I chose was the business of content. I’ve been more-or-less writing about this subject since 2006, and so it made sense to focus on it when I transitioned to a full-time creator. And to be clear, I do genuinely find this stuff interesting, but do I want to be covering it for the rest of my life? Not really. I’d love to explore other topics and also return to longform feature reporting. But that would require either selling the current business, hiring out a team to run it, or just shutting it down completely. 

Financial instability: You eat what you kill in the creator economy, and to extend this metaphor a little further, you’re competing with millions of other hunters. The last four years have been the most financially unstable in my career, and I still don’t feel like I’m on a firm footing. 

Metrics obsession: I was listening to an interview with YouTuber Johnny Harris recently, and he talked about his obsessive refreshing of the YouTube metrics dashboard in the hours after he posts a new video and how mentally unhealthy that made him feel. As creators, we’re almost entirely beholden to huge tech platforms that just don’t give a fuck about us on an individual level. Last week, a simple Apple Mail security glitch caused open rates for all newsletters to plummet, but it took several days for Substack to identify the problem and issue a statement. I can honestly say that hardly a waking hour went by during that time period when I didn’t feel at least a little anxiety about what a 10% open rate decline meant for my business. 

No workplace camaraderie: Social scientists have found that an adult’s ability to make a friend relies heavily on the number of times that you naturally run into that person, hence why many of the friends we make in life come from either school or work — environments where you’re literally forced to interact with the same people every day. I live in a transient city, which means that a huge number of my close friends have moved away over the years, and since leaving my last job I’ve found it to be especially difficult to make new ones. I do have some exciting news though: I recently made two new guy friends, so there’s hope for me yet. 

How Android Intelligence built a thriving paid membership

When JR Raphael launched his Android Intelligence newsletter in 2018, it was mainly a roundup of news meant to complement his Computerworld column of the same name. But as the newsletter amassed an audience, it began to take on a life of its own, so much so that JR eventually built a thriving paid membership that now provides the bulk of his income.

In a recent interview, JR walked through every aspect of his membership strategy, including why he lets in new members only a few times a year, how he built a thriving community forum where members interact with each other, how he reduces churn, and why he decided to launch two new newsletters focused on Windows and internet tools:

Part of what makes the whole paid community thing work is the fact that it is a small, tight-knit group. And it does exist without us. I mean, I can be away for the weekend and the community keeps going, which is awesome. But there's no denying a lot of the appeal comes down to the voice of the writer being there. And so having it be a little more limited in size helps make sure that we can maintain that more intimate, interactive environment. If we suddenly had hundreds of thousands of people signing up, that'd be delightful. I would invite that problem. But it would really change the nature of the community if hordes and hordes of people were coming in every week and it lost that sort of intimate connection. Because that's what makes it special. The interaction and the access is what makes it more than just what any other place could offer.

Quick hits

My biggest takeaway from this story is that Meta shares so little revenue with creators that the only way to make a decent living from it is to live in a low-income country and specialize in AI-generated content slop that costs nothing to produce. [404Media]

This is a great history of how legacy publications used to split up their web and print staffs — sometimes keeping them in completely different buildings. This actually offered the web staffs a lot of creative freedom, allowing them to experiment without meddling from higher-level executives. [CJR]

The great thing about video podcasts is they provide an opportunity for lean-back consumption. Most audio versions of podcasts are consumed when people are doing something else — like commuting to work, exercising, or cleaning. Video podcasts are consumed when people are sitting at their desks or — even better — watching TV from their couches. Podcasters need to stop thinking of video as an opportunity to generate more listeners; instead, they should view it as a way to reach an entirely different audience that might not even regularly listen to podcasts. [WashPo]

CNET's valuations over the years: $1.8 billion in 2008, $500 million in 2020, and $100 million today. [NYT] Definitely a strange trend considering it operates in such a consumer-friendly niche where online purchases are common.

Two months ago, the theatrical movie release was practically declared dead, but it turns out those disappointing May releases had very little to do with the state of the industry. [Puck]

Max only recently got around to showing a personalized home page based on prior viewing experience. And you wonder why Netflix is so far ahead of the rest of Hollywood? [The Verge]

An Atlanta-based realtor is receiving over 10 million views a month for her social media videos, which generate at least 30% of her client referrals. [Creator Spotlight]

I’m looking for more media entrepreneurs to feature on my newsletter and podcast

One of the things I really pride myself on is that I don’t just focus this newsletter on covering the handful of mainstream media companies that every other industry outlet features. Instead, I go the extra mile to find and interview media entrepreneurs who have been quietly killing it behind the scenes. In most cases, the operators I feature have completely bootstrapped their outlets.

In that vein, I’m looking for even more entrepreneurs to feature. Specifically, I’m looking for people succeeding in these areas:

• Niche news sites

• Video channels like YouTube, TikTok, and Instagram Reels

• Podcasts

• Newsletters

• Affiliate/ecommerce

Interested in speaking to me? You can find my contact info over here. (please don’t simply hit reply to this newsletter because that’ll go to a different email address. )

More quick hits

The PGA is the latest major sports league to incorporate popular creators into its programming. Except unlike most other leagues — which simply invite creators to their events — the PGA is actually letting creators compete in its sport. [Publish Press]

Back in 2018, YouTube shut off advertising for most gun-related content. This caused gun YouTubers to focus on diversifying their revenue through direct sponsorships and merchandise. [Bloomberg] FROM THE ARTICLE: "Today, a gun review video on a major channel will usually have several sponsors."

The AP is slowly transitioning from a newswire model to monetizing its content directly. To aid this transition, it's focused on optimizing its website to drive more traffic. [Adweek]

The Ringer was arguably one of Spotify's best acquisitions because it perfected the chat format that's come to dominate podcasting. What's even more remarkable is that Bill Simmons managed to negotiate the sale so that almost all Ringer shows continued publishing to non-Spotify platforms. He also made sure its website — which publishes a lot of non-audio content — remained an ongoing concern. If he leaves Spotify, then it'll be a huge loss for the company. [New York Post]

In the 2000s, music labels treated piracy as an existential threat, but it paved the way for music streaming, which many artists consider a better form of distribution for their work. [NYT]

Major sports leagues and broadcasters are increasingly partnering with creators so they can reach younger consumers who have mostly checked out of traditional broadcast channels. [FT]

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