Welcome to Infinite Play

So long Monday Medley

For the last six years, I've sent a newsletter every Monday. As far as I know, I've never missed the deadline.

It started as the "Monday Medley," a fairly blatant mimic of Tim Ferriss's "5-Bullet Friday" since 6 years ago my strategy for success was basically "do what Tim does."

I eventually stumbled on Azeem Azhar, whose richer (and well-emoji'd) “Exponential View” newsletter format inspired me to try a little harder. The Medley got longer, I dug deeper for interesting things to share, and I maintained that format for a number of years.

I've written a lot since I started blogging 10 years ago. 352 Medleys, 202 articles on my site, 287 book notes, dozens (hundreds?) of articles on other sites, and a few now-defunct entire blogs on other topics. I'd estimate I've published some 1,000+ pieces of some type in the last decade.

But I’ve always felt pulled between what performs and what feels most interesting or challenging to write about. "How to" and SEO-optimized posts bring me plenty of traffic and social shares, but they just don't feel as good. I feel the best when I'm working on the harder topics, the more challenging writing that's usually aimed at trying to answer some deeper question I've been struggling with.

I started moving the Medley in that direction last August in Edition 273. I can't tell you how good it felt to send that newsletter. To say that I wasn't doing the roundup anymore and was just going to write about whatever I felt like.

Since then the Medley has been more inspiring to work on, and it feels best on the days when I write the more challenging pieces like "Do We Know What We Want," "What You Should Write About," and "Shadow Careers and Unembracing Failure."

It still feels somewhat encumbered by its casual past though. It's too easy to dash off a quick essay. To not take it seriously. But more than anything else, I want to be a serious writer. Which brings us here.

Infinite Play is my attempt to take my writing more seriously. Not seriously from a financial perspective, but from a quality perspective. To push myself to improve, explore challenging topics, and write more of the topics that frighten me.

What will I cover? Happiness, fear, anxiety, love, parenting, death, time, beauty, meaning. You know, light stuff. The title is inspired by two books that have strongly influenced me in this direction: "Infinite Jest," and "Finite and Infinite Games."

I hope you enjoy it. And if you've been on the Medley for some weeks, months, or years, your participation in this adventure means the world to me. I'm excited to share this next journey in my writing with you.

The first official post will go out shortly.

Best,
Nat

P.S. Yes it will still go out every Monday, and you don't have to do anything. I migrated the emails.

P.P.S. The blog will still exist, though I'll probably archive some of it in some way. Same with the Medleys. I don't know what I'll do with the book notes, it would be fun to give those their own home of some sort. TBD.

P.P.P.S. My crypto newsletter will continue in its very practical-focused form. That will be the extent of my "business" writing for now.