A Short History of My Last Six Years — Wait But Why

June 18, 2016. Obama was president, the Cavs were on their way to beating the Warriors in the NBA finals, Game of Thrones was still good, and I was 34 years old with my whole life ahead of me.

Wait But Why had been around for three years, a stretch during which I wrote about 100 blog posts on dozens of topics. On the afternoon of June 18, 2016, I was sitting on the couch engaging in a familiar ritual: looking through my list of future post ideas, trying to pick my next topic. And then I had a thought.

So many of the post ideas I was scanning through were about the future. Virtual reality. Artificial intelligence. Genetic engineering. Life extension. Multiplanetary expansion. But lately, it felt like there was a cloud hanging over all these topics.

My urge to write about the future comes from an excited optimism that’s fundamental to my personality. I believe at a deep level that the future is going to be an amazing, exhilarating ride, and nothing is more fun than learning about cutting edge developments that can offer clues into what magic might lie down the road.

But on June 18, 2016, I didn’t feel excitedly optimistic. There was a different feel to the world than there had been in my previous blogging years. Something seemed off about the society around me, like there had been a subtle, foreboding shift in the balance between reason and madness. It felt like we were losing our grip on something important.

The fun thing about being a blogger is you can write about whatever the fuck you want. And a good compass for me had always been that if something was incessantly on my mind, it was probably a good post topic. So I decided to write what I call a “mini post.”

Wait But Why articles are long, and they go deep. I bathe in the topic for a little while, dread writing it for a little while, then finally pump it out, draw the drawings, give it a read, and post. A mini-post is much chiller—I just open WordPress and type what’s on my mind, and post it.

So I opened WordPress to write a little post about that cloud I felt hovering over my other post topics. I’d knock out a draft tonight, give it a read tomorrow, and publish it.

But nothing came out. I didn’t know where to start.

There were a bunch of bad trends: Tribalism was flaring up everywhere, mass shaming campaigns were roaring back into fashion, politicians were increasingly clown-like, public discourse had become a battle of one-dimensional narratives. But why was all of this happening now? Was the problem related to social media? To politics or current events? Was it some broader cultural or psychological phenomenon?

I also noticed that I wasn’t feeling the normal confidence I felt when I started a new post. Something about this topic felt scary. I never felt scared to write about anything before. This fear of writing about this topic seemed like it was an important part of the topic.

Nope. Not a mini-post. I needed the full week for this one.

But a funny thing happened that week. I didn’t write anything. Instead, I started jotting down notes and ideas in a Text Edit document called “society” that quickly became long and messy. I abandoned that document and opened up “society 2” to give myself a fresh start. Soon there was a Society folder with seven note documents.

I could have just stopped there. Too big a topic, too out of my wheelhouse, too icky, too scary. An outline for a virtual reality post was sitting right there in my Future Posts folder waiting for me.

But I’m really, really bad with the sunk cost fallacy. I had already put so much time and thought in, and I couldn’t handle all of it being for nothing.

And so began the next six years of my life.

I wish I could say that I actively decided to put everything else aside and write a giant opus on the problems with my society. But it didn’t happen like that. If you asked me at any point over the past six years when I was gonna be done with my society post—and plenty of people did—the answer was always, “I’m finally getting close.” And I believed it every time. I fully believed, every time, that this thing was almost done. The delusion of a madman.

And the problem with this particular delusion is that it’s a perfect way to ruin your life. If I believed I was working on a six-year project, I’d have worked the project into my normal life. I’d get into a rhythm that would allow for a work-life balance. But when you think you’re at most a couple months from finishing a big project, it makes sense to put everything else on hold for just a little bit more until the project is done. I wasn’t someone who never made fun plans or who worked on every vacation or who took a lot of Vyvanse—I was someone who did those things just for right now, because I’m in crunch time on a big project. For six years.

In May of 2017, I asked my girlfriend to marry me. We had been dating since 2011. She had seen the whole Wait But Why journey up close and had now been living with “I’m almost done with this big project” Tim for a year. We set our wedding date for October of 2018. Thank god by then I’d be out of this pit and working on all kinds of other fun projects.

But instead of the project wrapping up, it just got bigger.

The topic had led me down dozens of totally different rabbit holes, and everything I read seemed relevant to it. I don’t like telling a partial story. Like I had in other posts, I was determined to tell the full, full story. If I noticed something in my reading or on social media or in the news that seemed like an important piece of the puzzle, it had to be incorporated. If that fucked up the current outline, then the outline would have to adapt.

The problem is that the outlines became ridiculous. I couldn’t keep it all in my head at once, so I made sub-outlines, and sub-sub-outlines. The Society folder now looked like this:

As 2017 became 2018, I decided that the wedding would be the hard deadline that I needed. My girlfriend had spent way too much time with an “I’m almost done with this massive post on society” boyfriend. She would have a much more pleasant husband.

I’m still not sure how I turned into a crazy person. The way to proceed was obvious. I should pick a piece of this albatross, throw the rest away, and focus in on it. Do what I had done for years—suck it up, get serious, knock something out, and move on with my life.

But I’m a nightmare of a perfectionist and knew that the ultimate prize was to figure out how to not focus in but capture it all in a single, overarching story. It all was one big story, and I wanted to tell it.

Wedding day came and went.

People in my life were worried about me. They tried encouraging me, shaming me, setting deadlines for me, reminding me that one post really shouldn’t take multiple years. Nothing seemed to help.

Finally, in mid-2019, I hatched a plan that would once and for all end this thing. Rather than post a gargantuan blog post, I’d make it a series. This would break it into parts, which is less daunting. Plus, I had learned that the adrenaline of knowing that my readers were only days away from seeing what I was working on was a huge motivator that I had been sorely missing.

I called it The Story of Us and in August of 2019, the first chapter went up. The whole thing would be 12 chapters, I decided, and even though the chapters got longer as they went, and the time between them expanded, it was finally happening—I was publishing the damn thing. The end was near.

Then came Chapter 11. The first 10 chapters had introduced the core framework of the series and talked broadly about the big picture of what I thought our problem was. In Chapter 11, I was going to dip into more controversial territory, looking at the past few years of news stories through the lens of the framework we had developed.

It turns out I had a lot more to say about what was going on around me than I had anticipated. Soon, my draft of Chapter 11 was longer than the first ten chapters combined. I have problems.

Now it was the middle of 2020. Covid was in full swing. Thousands of people were marching by my apartment in protest. It was a seismic year for American society. Everything I was writing about was happening, and rapidly evolving, literally outside my window. What I had written months earlier suddenly seemed stale. Also, Chapter 11 was over 100,000 words. Death.

It started to dawn on me that I really needed to just turn this into a book. Between the mountains of feedback I had gotten from readers and friends on The Story of Us and the mountains of new thoughts I had about all the recent developments in the world, I knew that there was one way to really bring the project from hell home: open a blank Microsoft Word document and write a newer, better, complete story, and do it in a book format that people could read more easily than a web page. Somewhere, a fairy died.

So I started writing the book. I’d call it the name it should have always been called: What’s Our Problem? I knew what I wanted to say. I just had to write it.

I finished V1 in December of 2021 and triumphantly tweeted about it.

Done! In a sense! It was 250,000 words, which is about 150,000 words too long. And missing most of the drawings. And I had a giant “ADD IN” document full of news stories which had happened in the year and a half since I started writing the book that would need to be incorporated.

It’s hard to cut writing. Perfectionism, sunk costs, etc. Procrastination abound. I would try to cut a section down, polish it off, and move on, but kept finding myself rewriting the section entirely. I was moving at a snail’s pace.

Then one day in June of 2022, my wife woke me up by handing me a positive pregnancy stick. It was a surreal, joyful moment. I’ve never been anyone’s dad before but always wanted to be. Then the thought hit me.

NOPE. 100% no. It could not happen. This baby could not enter a world where this project was still going on. Suddenly, an old friend entered the room.

The baby was due on March 7, 2023, so this book would be completely done by mid-February, period end of story.

V2 got finished (July 2022). Then V3 (September). Then V4 (December). Editors and fact-checkers and copy editors and ebook designers and audiobook engineers were hired. Alicia (Wait But Why’s Manager of Lots of Things, who had already put in thousands of hours helping with every element of the process), went into crazy crunch time mode. I sat in a booth for 45 hours reading the audiobook (January). The ebook was designed (February). The launch date was set.

It took 2,440 days, but my mini-post on society is done and coming out on Tuesday. Fuckin shit.

Here are the pages:

Some stats:

  • 121,000 words
  • 303 drawings
  • 11,081 documents in my Society folder
  • I’m 41
  • A condensed and re-written Story of Us makes up 25% of the book. The rest is all new.

This book is my best crack at explaining what I think is an existential risk to liberal societies and what I think we need to do to get to that awesome future I used to be so excited about. There are dozens of concepts in the book that serve as a kind of toolbox for understanding our societies, our group dynamics, and our own minds. I’m very proud of the final product and never want to have an experience like this again.

If you would like to take my last six years and put it into your brain, here are the different options (all available on Tuesday Feb 21):

Ebook: Available on most major platforms (you can also buy the EPUB directly). It looks best on color e-readers and tablets (especially on vertical scroll mode), but also fine on phones and black-and-white e-readers. The best ebook experience we’ve seen is Apple Books > iPad > sepia > vertical scroll. Available for preorder on Apple and Kindle – the rest are available on launch day, Feb 21.

Wait But Why: Without the limitations of the other formats, this is where the drawings can be displayed full-size, where footnotes can be interactive, etc. The downside here is that you can only read it on a tablet or phone, not an e-reader, and there’s no dark mode at the moment (we’re working on that for later in 2023). Available here.

Click here to see how the book looks in different formats

Audiobook: Available on most major platforms (or you can buy the mp3 directly). Read painstakingly by me. I personally do most of my reading via audiobook, so I tried to make it the best possible experience. The obvious downside is that the book has 300+ visuals, so we made a webpage (and pdf) for audiobook listeners with the 46 most important drawings, numbered. When I get to that point in the reading, I say something like, “Go look at drawing number 24.” Available for preorder on Kobo and on other platforms (Audible, Apple, Spotify, and more) on launch day.

If you can’t afford it: I really want everyone who wants to read this book to be able to do so, so if you can’t afford to buy the book, email us at [email protected] and we’ll give you a code that lets you read it on WBW for free.

Print: There is not a print version, which I know will disappoint some people. There are a few reasons for this, but the biggest one is that printing this big full-color book would have delayed launch by many, many months, and fuck that.

Also, Idea Labs: A major theme in this book is how we can do better at having productive discussions about tough topics. So we’re planning to create virtual book clubs for anyone who is interested in discussing the book with other WBW readers. More on this soon, but if you’re interested in being part of a book club, enter your email address here.

So that’s the story with this book. Can’t wait to hear your thoughts. If you want to be notified on launch day and keep up with whatever else we work on in the future, make sure you’re on our email list.

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Another time I did something hard: Doing a TED Talk: The Full Story

The number of years this book took me: From 1,000,000 to Graham’s Number

If the news is making you scared about A) UFOs or B) AI

If you’d like to support Wait But Why, here’s our Patreon.



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