A Futureproof Content Strategy for Transitioning Servicemembers

People ask me all the time what I read. This question is especially common after I give talks. I imagine the thinking is something like "Hey that was weird and entertaining. I wonder where he got all those weird and entertaining ideas?"

It's probably more interesting to know what I DON'T read (see also: Twitter; Facebook; Instagram; TikTok), but I promised someone recently I would put together a list of some curated content. I think is worth his time as he prepares to take off the uniform and start the next phase of his life. Maybe it has something for you, too.

This list is tailored toward people who are interested in "futureproofing" themselves by thinking deeply about topics that are (a) easy to misunderstand and (b) valuable in the 21st century. It is also intended for people who are getting out of the military who want to transition to a career in technology.

Foundational Content

Finite & Infinite Games always challenges me. I've reread it now four times. Each time I discover new concepts that push me to think differently about my life. This is especially true as it relates to my sense of self, my own importance, and my role in the world.

Hackers & Painters is a joy to read. There are so many overlaps between creative processes. This book offers a crash course on some of the basic ideas that define a particular counterculture strain that persists in tech from the 70s to today.

The Soul of a New Machine won both the Pulitzer Prize and the American Book Award, and I bet you've never heard of it. This book digs into the genius and eccentricity of the tech world in a way that only a great story can.

The Idea Factory is drier, longer, and worth it. There are some amazing stories tucked in this book. It tells the story of an incredible group of scientists and deep thinkers who invented all of the theory -- much of the infrastructure -- we use for communication.

Homo Deus summarizes the broad arc of human history in a way that makes sense only in place like Silicon Valley. This book is almost a litmus test for whether you drink the Kool-Aid of the tech world.

Daily Content

Daily content is intimidating. Very little is worth tracking at that frequency. One obvious exception is scripture. I read a variety of Bible devotional plans, usually 3-4. I sprinkle them throughout the days so I'm never more than a few hours from an inspired Word.

Most people I know who work in tech like to know who's raising money. I am no exception, and Fortune's Term Sheet newsletter is my choice. I mostly skim the the deals to see if there's anything that interests me personally, and who funded them. Sometimes I'll click through to read about the company and maybe connect with someone from their founding team on LinkedIn.

Weekly Content

I got off social media several years ago. Now I rely on two sources of information for what's happening around the world: conversations with my wife, the incomparable Dara Treseder; and The Week magazine. My wife shares news as it occurs to her. I am a little more structured about "The Week." Every Saturday or Sunday evening I sit down on the couch (usually with a bag of pistachios) and catch up on the latest.

Side note: Despite the lack of Twitter, Facebook, and Instagram I don't miss out on much. And I feel a lot less stressed. You should try it!

The Profile by Polina Pompliano is a great newsletter. I have to be careful about selecting more than one of these per week because they are so long. I'm now in the habit of selecting just one per week to read, but it's hard. She finds many interesting long form pieces.

I gladly read through Benedict Evans' newsletter each week. He offers a variety of content on a rich array of topics. I appreciate the way he breaks out the recommended articles, offering enough of a teaser to allow me to select the ones I want to read. Usually he can help me find 3-5 articles worth my time.

Venkatesh Rao's Breaking Smart newsletter is another staple for me. He is by far the most esoteric of the people I read. His language (jargon?) can be intimidating at first, but each post is worth the effort. He thinks deeply about a lot topics than many of us never truly consider.

Shane Parrish's Farnam Street blog is another go-to resource. I have both volumes of his Great Mental Models series, and have also taken their Re:Think Parenting course. There is always something useful to pack from Farnam Street. More so than any other resource, though, mental models require time to think through their application.

Cal Newport is another weekly regular in my inbox. He offers interesting stories and research promoting "deep work." He believes we would all be a lot better off with fewer distractions. I'm inclined to agree.

Monthly Content

First Round Review offers a steady stream of general purpose content about thriving as an entrepreneur (or an employee) in the 21st century economy. They tackle a lot of different topics, and their top articles list is a great place to start.

The Andreessen Horowitz newsletter(s) are also good. I usually find an article or two worth reading each month. If none of the sub-topics grab you, the general newsletter is a great starting point.