Michael Ashcroft

Thinking Out Loud No. 48 // Friday 10 September 2021 // 5 minute read

Hello everyone!
Getting close to issue 50! Perhaps I'll bake some sort of cake for the occasion.
This week's issue contains:

Making sense of crypto's gravity well

I bought Bitcoin in September 2012. To be precise, I bought 2.8 BTC for a grand total of £20. Today this has a market value of £93,620.80 for a 468,104% return.

Or at least it would if I hadn't lost them.


Back in 2012 when crypto wasn't as user friendly as it is today I sent my bitcoin from the exchange to a software wallet on my laptop. They never showed up. I must have made a mistake.

Before you feel too bad for me, though, even if I hadn't lost them there's no way I would still be holding them today. I would have sold years ago in one of the earlier booms, made some amount of money and felt pleased with myself. At least until I saw the price today.

I say this to make clear that I am not good at crypto. I have only ever lost money on crypto. And I don't plan to talk much about crypto. But there's something interesting happening that I want to explore.

I am now Very Online and, since I quit my job and leaned more into self-employed online business, I've hung out more and more on Twitter. This is almost certainly skewing my perceptions, since that crowd is quite self-selecting, but it seems like so many people are talking about crypto right now. I just joined Nat Eliason's DeFi Orientation course (it's good, but not for crypto beginners) and immediately recognised several different people I knew from different online communities chatting in there.

It's like crypto has created some kind of gravity well that keeps pulling in more and more of the Very Online. What's going on here? I think there are a few factors.

Firstly, there's that self-selection effect I mentioned. The people who hang out a lot in my part of Twitter probably have traits that make crypto interesting to them. They're largely curious people who want to understand the world.

Add to this the fact that many of these people are, increasingly, feral free agents, as @visakanv puts it. They operate and navigate in the world without jobs or strong affiliations, which means their need to understand how things work is important for their survival.

Put another way, if you have a secure job then your ability to make sense of things outside the domain of your job doesn't really affect your security, unless you miss macro trends that cause your job to go away or change dramatically. This is not the case if you're a feral free agent where, in my opinion and limited experience at least, you need to be able to hold a much more flexible and broader perspective to be able to navigate and identify opportunities you could pursue.

Another trait of the free agents is having flexible free time and attention. I have a lot more space in my head now compared to when I worked in consulting or in corporate. I appear to be using that space to look around and go "huh, seems like there's a lot going on over there...", where a convenient "over there" is crypto.

Finally, there's also a tangible sense that some important, world-shaping things are happening in crypto and it's just exciting to be somewhat in or adjacent to that world. I can't code, I only know roughly how a blockchain works and under no circumstances should I be allowed to day trade. And yet I can hang out in these buzzing communities, place some financial bets, play with cool technology that often breaks, and feel like I'm part of something, part of the Great Online Game.

And what is the Great Online Game, you ask? Here's the entrance to that particular rabbit hole, Alice.

Are you already playing the Great Online Game? Do you want to? Let me know, I love finding other players.

Things I have made

No YouTube videos just yet, but I have kept up my writing habit. Here are some new notes I've written this week.

A thing I am making

I am making a new three or four week email-based course called Playful Creativity inspired by an approach I have developed in working with coaching clients.

I've found that a common trap in making things is to try harder to make things, which just gets people stuck. Playful Creativity will help people get out of their own way and allow their natural creativity to emerge easily and playfully.

I plan for this one to be quite affordable, say around $50, because it's the kind of thing I'd like to see scale and allow more people to find joy in their own creativity. I also don't want to be doing launches and things of that nature. Once it's available it'll stay available. although as ever I'll continue to improve and update it and everyone will get lifetime access.

It's fun to play with a second product idea, because I don't want to create a sense of pressure to squeeze money from my Alexander Technique course. I'd much rather pursue a portfolio of small bets approach, as coined by Daniel Vassallo.

Let me know if this sounds interesting!

Things others have made

Speaking of Daniel Vassallo, I recently enjoyed his episode on Paul Millerd's podcast

Daniel walked away from a $500,000 per year salary at Amazon because it wasn't giving him the kind of life he wanted.

"…despite all this, my motivation to go to work each morning was decreasing — almost in an inverse trend to my career and income growth"

Rather than search for motivation by taking another job, he decided to design for the lifestyle he wanted. And now that he has it, his aim is to be able to keep playing the self-employed, self-directed game.

This is my approach as well. I walked away from a c. $100k salary because, to echo Daniel's words, I found my motivation to go to work each morning decreasing. I didn't see that changing unless I made a big change.

It's now been about seven months of self-employment and right now I can't imagine going back. Never say never of course — for the right job, working on the right things, in the right way, in the right place and with the right people — then perhaps.

Time will tell, but for now my plan is to keep playing this game. It's a remarkable amount of fun.


I publish a newsletter called Thinking Out Loud, which chronicles my journey as an online maker of things, but it's also is where I talk about whatever I'm interested in at the time.​ There are almost 1000 of us now, come play!