Revisiting Perennial Seller

Untangling one of the roots of my perfectionism

For the past eight years, I've been striving to create work that stands the test of time. Work that will be just as relevant in ten years as the day it was published.

I suspect this attitude is a remnant, or a scar perhaps, of my years writing for Unnamed Filmmaking Blog. The vast majority of our content was centered around the hottest new cameras and gadgets, or the latest big blockbuster movie. After a few years of sprinting on the mimetic treadmill of current events coverage, not only was I burned out, but I felt like I hadn't actually accomplished anything, in spite of all the energy I'd poured into writing. I felt a deep yearning to create and consume things that would be relevant for more than two weeks. I wanted depth, perspective, nourishment. I wanted to slow down.

So in 2015 I struck out on my own, and in the years since, I've tried to make thoughtfulness and depth my guiding ethos. In my work at Filmmaker Freedom, and now with Ungated, I've ignored the trends, the hype, the easy attention-grab of piggybacking off current events. Instead, I've taken my time and published a bunch of writing that, while imperfect, still stands in stark contrast to the shallow, rushed content around it. And I'm pretty proud of that.

When Ryan Holiday's book Perennial Seller came out a few years into my independent journey, it felt like validation for this deeper impulse. It felt like I was given permission to take this idea even further than I already was. So I doubled down on the idea of timeless work. I wove it into the essence of my creative identity.

In some ways, I think this has become one of my strengths as a writer. It's hard to argue with the quality of some of what I've published in years past. When it comes to writing fiery manifestos and long-form essays, I think this is a worthwhile frame to play with. A little extra work can yield disproportionate returns when it comes to media assets that will represent your business for years to come.

However, viewing all of my writing through the "will it stand the test of time" frame has not been particularly healthy for my intellectual and emotional development, and has been one of my most reliable sources of perfectionism and overthinking.

I've long wanted to be more prolific, but there's this voice in my head saying everything I write has to be definitive, comprehensive, unique, timeless. I can't tell you how many times I've sat down to write a quick lil post, only for it to expand into a 5,000 word behemoth. Many of those behemoths died behind the scenes, too, never to see the light of day. That's such a frustrating place to be, because one part of me knows the ideas are worthwhile and would resonate, even if I expressed them imperfectly. Yet the inner voice makes me believe I can't do that. They must be High Quality Perennial Sellers because this is who I am as a writer.

If you couldn't tell, I'm trying to break this emotional pattern during my 100 day writing marathon. Partly, I want to share many of the ideas that have been building up over the last two years. There’s still a lot of good stuff buried in those behemoth essays I never shipped. But also, I'm writing to develop myself and become the creative and the thinker I want to be. I'm pushing into uncomfortable territory because I know it will help rewire my relationship with the inner voice.

This is also why I'm starting to think of all my work an ongoing conversation, and why I'm starting to update older pieces of writing with new thinking. It takes so much pressure off knowing I don’t have to Get It Right on the first try.

My hunch, going into week three of this challenge is that the more work I ship, however imperfect, the more quickly I’ll learn. The more quickly I learn, the more I'll able to update my thinking and create things that are closer to being timeless. That's the ironic thing here. Doing more imperfect work more frequently is more likely to result in perennial sellers than just trying to write perennial sellers lol. It's like that old story about the two groups of pottery students—one group told to make one perfect pot during the semester, and the other told to focus on making as many pots as possible. The best pots in the class came from the second group.

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Rob’s Daily Invitation

The best thing I’ve ever done to quiet down my perfectionistic inner voice is becoming an avid experimenter. I love running lil low stakes experiments in my business and life because they aren’t Big Structural Changes, but instead invitations to try something new, think differently, and fuck around and find out.

If you wanna become a fellow Experimentalist, I would def recommend grabbing a copy of this Notion template. It’s the same one I use to keep track of all my crazy nonsense.