Taylor Pearson, CEO of The Mutiny Fund, entrepreneur, and author of The End of Jobs: Money, Meaning and Freedom without the 9-5, joins Stew Fortier to discuss writing as a form of optionality, employing narrative design, and establishing your Twitter community.
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When Taylor Pearson first started writing with professional regularity a decade ago, his intentions were very pragmatic. With a background in b2b digital marketing, Pearson’s first published pieces featured marketing case studies and functioned primarily to drive client acquisition. “It was a very practical thing,” he said. “I wanted someone to be able to send these articles that I had written to potential clients so that they would realize that I’m reasonably intelligent and understand what I’m doing.” After fully establishing his business, Pearson felt he could finally branch out and spend more time exploring and writing about the topics that interested him.
Even with this self-determined, broadened scope, Pearson acknowledges that it’s still difficult to decide what to write about. “I’ve been doing this for awhile, and I still find it really hard. I probably have twenty things I'd like to write about right now. Realistically, I'll actually have time to sit down and write about two to four of those.” When he’s selecting his topics, Taylor focuses on “optimizing for interesting,” an idea supported by the theories of computer scientist Jurgen Schmidhuber about what makes something interesting to humans. “Basically his idea was that the emotion of finding something interesting evolved to indicate to people that this is an area where they have the ability to make intellectual progress. Because of this, whatever I’m most interested in is the leading factor in deciding what topics I choose.”
The second factor that drives the direction of Pearson’s content is whether he has a great story to share. “Stories really matter,” he said. “I do have underlying business objectives. I want this article to generate consulting leads, generally speaking. Great stories tend to do well.” In the early stages of his writing career, Pearson spent his time concentrated on the rationality and logic flow of his ideas without thinking much about the narrative arc he was creating. “If you look at myths across many different religions and cultures, there is this universal story structure known as the ‘hero’s journey.’ It resonates with everyone. So when I can, I like to fit my piece into that sort of structure.” Over time, Pearson codified his writing with this device and the style of opening each article with a story to illustrate his underlying concepts because he found that it was reliably successful. “I think structure is really, really important. You should try to pick a stock structure and fit the piece into that structure consistently.”
When asked how he stays motivated to write every week, Pearson replied, “It’s just deadlines. I think committing to some sort of sustainable publishing schedule makes a big difference ” Pearson’s self-imposed deadlines have varied over the years depending on the type of pieces he was publishing at the time. With longer-form blog posts he would frequently publish every 2-4 weeks, while his newsletter, The Interesting Times, which he founded in 2019, requires a weekly cadence. “With my newsletter, sometimes it's just a really short 300 word thing, and sometimes it's a 1500 word thing, but having that deadline in place is a really helpful constraint. So my recommendation is to pursue whatever feels like a sustainable publishing schedule for you, whether it’s once a day, it's once a week, or once a month.”
When getting started, Pearson emphasizes the importance of producing and publishing the work, regardless of self-doubt or quality. “There’s a famous Napoleon line: ‘quantity has a quality all its own.’ That’s one of the earliest pieces of advice I received when I started blogging. Step one is to write a million words on the internet. By the time you get done with that step, you’ll know step two. I think that’s pretty great advice. You just need to get a ton of volume.”
Taylor acknowledges that publishing fear is common when you start out, but overcame that fear personally by writing anonymously at first. “If you want to come out and reveal your real name at some point in the future, you can, but you don’t have to. When I first started, I was blogging under the URL frontierliving.com. It was a horrible URL, but for about two years, I blogged anonymously there.”
Some writers specialize in long-form publications, while others stick to shorter, more digestible pieces. Pearson’s approach utilizes the best of both worlds by repurposing his content for a variety of platforms to maximize his reach and relevance. “In an ideal world, I try to get multiple platforms under each piece. Some of what I write goes on Twitter, some of it goes in the newsletter, some of it goes in a longer form essay, and then maybe some of it goes in a book. If I can get and get multiple uses out of one chunk of content, that's ideal,” he says.
While Taylor has certainly had the opportunity to hone his craft over the last ten years, he recognizes the value of working with peers to refine his writing. With longer-form pieces, Pearson sends his drafts to six or eight people, a group that is composed of both subject matter experts and laymen so that he feels confident that his work is both accurate and understandable. “I’ll have three smart subject-matter experts read it and tell me it wasn’t wildly inaccurate, and then I’ll have three or four novices read it and tell me that it made sense to them. At this point, I know it’s decent.”
Taylor has also worked closely with professional editors over the years. “I find that professional editors are really helpful for figuring out how to make your writing better. Most editorial advice is bad. People can tell you that they don’t understand something or that something you wrote sucks, but very few people, except perhaps the most experienced writers, can tell you how to fix your writing, how to make it better.” Taylor has picked up some of his best writing and storytelling techniques from working with professional editors. “A close friend and editor of mine, Jody Edinburg, helped translate the appeal of Michael Lewis’ novels, like The Big Short, so I could learn to incorporate a similar style into my own writing. I learned that starting your article in the middle of a scene that has a lot of descriptive detail makes the reader wonder, ‘how did we get here?’ It can really captivate them and make them want to continue reading your stuff. If you pay attention, most movies do this with their opening scenes.”
Pearson understands that quality and quantity of publications are critical goal posts for writers, but he also underscores the importance of finding and developing your audience. “I spend a lot of time on Twitter. I probably spend the majority of my time there because it's hard to convince someone to read 2000 word blog posts if they don’t know who you are. But if you can get them to think three of your 15-word tweets sound intelligent, the odds of getting them to read the blog post increases.” Twitter is a particularly useful tool in cultivating a community of like-minded writers and content experts who can serve as the springboard for successful writing distribution. “I just have a Twitter list of people I follow that I think their stuff is really interesting and I want to network with them. So every day, I just scroll through that list and try to reply to like two or three people.” Taylor’s newsletter The Interesting Times currently has over 36,000 subscribers and that number continues to grow.
Taylor Pearson’s philosophy on writing is unique. “Writing for me has always been a form of optionality. The idea of options trading is that you're betting on something relatively unlikely, but more likely than people expect. Let's say there's something that pays 100 to one, and you can get 25 to one odds. 25 to one odds aren't good, right? You're only going to win 4% of the time, but if it pays 100 to one, it's still a good bet. I think about writing in those same terms. You can write these articles, and in my experiences, there's probably 10 articles that I’ve written that have generated 80% of the ROI. 10 out of 300 is extremely concentrated. I just happened to hit the right spot at the right moment and the right people read it and shared around. Occasionally interesting things come out of those articles, whether that's a speaking engagement or work for my consulting business or other partnership opportunities. Pretty much all of that has happened through writing in some form or another.”
You can learn about Taylor Pearson and his published works by visiting his website, subscribing to his newsletter, The Interesting Times, or reading his book The End of Jobs: Money, Meaning and Freedom without the 9-5. You can follow him on Twitter here.