Thanks for checking in. No, I didn’t fall into a coma or go to jail. I especially didn’t spend the last 18 months jerking off and watching reruns of The Sopranos. I don’t even have HBO!

So why no posts?

The simple answer is that I lost all enthusiasm to write or share stuff in public. I’m not entirely sure why, but a few best guesses:

• The book was finished, and out in the world. It was a lot of work, and I’d said what I wanted to say.
• I got sick of the sound of my own voice. There’s way too much content in the world already. Most people should shut the fuck up; probably that includes me.
• I felt pressure to write things that blog subscribers and book readers would enjoy, rather than follow my own interests.

My initial impulse was to delete the blog, de-list the book, and generally disappear quietly into the ether. Then, after sleeping on it a while, I figured I could just mothball Deep Dish, and start a new, pseudonymous blog elsewhere with no audience, zero expectations, and a clean slate.

…finally, I decided to stop being a drama queen and start posting again right here, unabashedly rejoining my fellow mentally disturbed people who insist upon Having Opinions in public.

who the fuck is scraeming “LOG OFF” at my house. show yourself, coward. i will never log off

— wint (@dril) September 16, 2012

So that’s what I’m gonna do (with a few small changes).

No More Mister Relatable Content

My highly-advanced productivity strategy involves jumping on whatever happens to catch my interest at any given point in time, rather than forcing myself to do things which are not intrinsically motivating. This has worked out surprisingly great, but is not without its downsides, e.g., you occasionally fall off the grid at the exact moment you ought to be marketing the book you just spent several years of your life working on.

I re-read Optionality this week (I’m making a few final tweaks to go with a new cover design) and damn, it’s actually pretty good. I’m proud of it. You should totally buy a copy!

The book is designed to have broad appeal: getting more money, opening up better choices in life, ‘life hacks’, and so on. Same with most of the stuff I’ve written about here on the blog. I’m still sitting on a bunch more material and drafts in that vein, but the truth is I’m finding it hard to get excited about. It seems like it’s best to write about things while you’re in the process of figuring them out, because they start to feel stale by the time you’re looking back in hindsight.

In short, my interests have diverged somewhat from previous blog material.

On the assumption that something is better than nothing, I’m hereby giving myself permission to write about whatever random crapola I want, even if only three of you read it. I also want to knock out posts with less effort than before, which means they won’t be as polished, fewer pretty pictures, maybe some spicier takes.

Most of you did not sign up for this. Liberate yourself from yet another newsletter cluttering up your inbox! There should be a link to unsubscribe in any email I send you.

More happily: what to write about now?

Current Areas of Interest

The main life update is that I permanently moved back to New Zealand, bought a house, and said goodbye to the nomad life. On the work front, I’ve been building up a better understanding of crypto, selling options contracts, learning the associated tools of risk management, a bit of statistics, and very basic programming. I’m also playing a lot of tennis, reading a lot of fiction, especially short stories (hit me with recs), and organising the Auckland chapter of the Effective Altruism community.

So some of that will probably come through in future posts, along with the following:

• Crypto/web3. Now that it’s totally shat the bed, I feel like we have a nice quiet year or two to look at the industry dispassionately. I’ve gone pretty deep down the rabbithole, and want to write a series of posts looking at it through the lens of optionality, the Matthew effect, social contagion, finance hackery, public goods, etc.
• Random lifestyle research, e.g. ‘here’s an infodump on this little-known amino acid I spent 10 hours looking into’
• Higher-level investing concepts, e.g. finding genuine sources of edge, risk management, volatility drag, position sizing
• Book reviews and recommendations
• Possibly some short fiction

What I Want From You

It’s still fine—encouraged, even—to suggest topics you’re interested in. I just make no promises to act on them.

Similarly, I hereby renounce my longstanding promise to reply to every email, since I was terrible at keeping it (I think my ‘record’ was an 18-month delay, which, for context, is longer than it took to send a letter around the world in the 1800s). I still read and appreciate every message. If yours went unanswered during the long hiatus, I apologise. Feel free to hassle me again, especially if you had a specific request.

I’m very keen to meet more people, but this time round, the focus is on real-life relationships and community. If you’re in Auckland and want to get a coffee, are looking for a hitting partner (NTRP 3.5 on a good day), or want to learn more about the EA community, please slide into my inbox.

Got a random question? I’ll hang around in the comments for a while and answer in real time, or at the very least, on a timescale shorter than 18 months. Otherwise: first non-meta blog post coming in a week or so.

Not Sure What the Future Holds? Get Your Copy of Optionality Now.