It’s So Hard to Sell Out

“`I could tell you my adventures — beginning from this morning,’ said Alice a little timidly: `but it’s no use going back to yesterday, because I was a different person then’.” ― Lewis Carroll, Alice in Wonderland

Two years ago, I wrote the first post that would appear on my blog, I’m Making All This Up. It’s a decent little article. You can see that it’s trying to be good. And if you’re an intermediate improviser confused about the iO-UCB “game of the scene” debate, then you might even learn something.

The reason I still like the post has little to do with the content itself. It’s really just one line that stands out. A line that’s easy to overlook on the first skim.

“I’ve developed my own way of reconciling the two viewpoints, one that will hopefully be helpful to someone besides myself.

That one sentence offers a window into who I was two years ago — my mental state when I started this blog.

I was just a guy who wanted to share his point of view. A guy who had no idea if anyone would ever read his writing. A guy who, more than anything else, just wanted to be helpful.

At first, a few friends reached out to congratulate me on starting a blog. They enjoyed my first few articles and shared them with a their friends and the larger improv community (I was too faux-humble to do that myself). And then, as I kept producing content each week, my following and popularity grew.

I was lucky enough to see some early attention from Jimmy Carrane, a big-name Chicago improviser. I learned about email lists and quickly hit my first 100 subscribers. I used my experience to write a book and my audience to sell over 200 copies of that book. I made a little money off the back of my hard work and creativity. That felt nice.

I share all this not to brag. I share all this as a cautionary tale.

After blogging for a year and publishing a moderately successful book , I realized that maybe “making money with my blog” wasn’t just a pipe dream.

At the time, I hated my job. And I thought that if I could just double down on what I’d learned over the last year, then I could quit my job and live TheDream™.

The blogger from 300 words ago — whose only hope was that someone would find his perspective helpful — was dead.

I stopped writing about improv — it’s a niche topic. I jumped completely into the trendy (but oversaturated) creativity/productivity space. And while I am proud of a number of articles I’ve written on those topics, there are just as many where I did nothing more than reiterate the conventional wisdom in the hopes of attracting new fans.

If my articles were helping people, it was a happy side effect of my new goal — selling out. I wanted a piece of that six-figure passive income. I wanted to be a stay-at-home-doggy-dad who wrote creativity books for a living.

So I did the things I thought I was supposed to do. I wrote breezy listacles. I wrote headlines with the word “f**king” in them. I created an online course. I even started to write a book about creativity.

And then, I couldn’t do it anymore. I buried the book in my Google Drive two months ago and wrote an article (maybe my best) where I said a lot of the same stuff I’m saying today — no more listacles. No more advice that everyone else is already giving. No more life coaching from the guy whose biggest claim to fame is a decent blog and a book that’s still $1,000 away from profitability.

But as much as I wanted to stop doing those things, I couldn’t. Because stopping would mean that I’d have to give up on selling out. And selling out, according to every writer ever on the Internet, was supposed to be easy.

They told me that if I just wrote optimized headlines, 5 quick tips articles, and threw in an email capture form, I too could live TheDream™.

I thought I was so close. That TheDream™ was just on the other side of the hill if I only I kept “hustling.”

And then, I heard a story about Abel Tesfaye (the guy behind the mega-popular band, The Weeknd) and this little quip in The Rolling Stone about success.

“Some people are like, ‘Oh, yeah, just sell out and do pop music.’ So you fucking do it, then! It’s not easy.” — The Weeknd

Then, everything clicked.

Selling out is hard. Like, super hard. And not even “hard” in the fun or challenging way. If you’re going to wake up early, stay up late, or sit at your computer while your friends are out partying, you should at least spend that time working on the things you enjoy, the things that you hope will bring value to other people.

I started I’m Making All This Up in 2014 because I wanted to share my perspectives on improv. The name, which I’m pretty proud of, had a dual meaning. It was a clever, self-deprecating joke that played off my own experience with improvisation, and hit on the idea that everything in improv is made up on the spot. But when I chose the name, I didn’t realize it would take on a third (and ultimately, more important) meaning.

Life is about making it all up.

At some point, I got a bit lost. I forgot about making it up. Instead, I tried to walk the proscribed path to success. But I need to make things up. I need to walk my own path. We all do. And this monomaniacal desire to sell out has been preventing me from exploring, experimenting with, and creating the things I really want to make.

So I give up. I’m done selling out. I am letting go of TheDream™. (For real this time…I hope).

I’m going back to making stuff that “hopefully helps people,” without worrying about the potential to make six figures or earn my first 5000 email subscribers. And if our dog has to stay at home without me for a little while longer…well, she’ll live.

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