Unicycle #13 - Reflections, Pirates 🏴‍☠️

As a reminder, I’m Alex Grintsvayg and you’re reading Unicycle. I welcome your feedback - hit Reply or message me anonymously. If someone forwarded you this email, subscribe here to follow along.


Hello dear friends :-)

We’ve been riding the Unicycle together for thirteen whole weeks now 💪. Let’s take stock of where we’re headed and how the journey is going.

First, thank you! I’m so grateful to all of you who read my writing, reply with your thoughts, and text me at 11:55 to make sure I’m not about to blow my deadline (we’ve had some close calls, haven’t we). My goal is to consistently put my ideas into writing and share them. I can do the writing on my own, but I can’t do the sharing without you.

Second, a course correction. Writing these emails has been somewhat stressful. I’d like to go deep on something new every week but I don’t have the time. So while optimizing for writing more, I haven’t been writing better. And when a metric becomes a target, beware Goodhart’s Curse!

To be honest, I did this to myself intentionally. When building a new habit, consistency trumps quality. But now that I know I’m going to stick with weekly writing, it’s time to add the quality back in.

My plan is to focus on one longer essay each month. This will give me time to collect my ideas and get feedback before I publish. I already started the first one (it will be about my approach to solving complex technical problems). It will probably be out in November. To make time for longer writing, the weekly emails will be smaller. I’ll write shorter reactions to things I consume or think about each week. If you see something you want me to flesh out, reply and let me know. I’m always open to feedback.


This week’s email touches on the idea that our lives are shaped by our environment and external incentives. I wrote about this observation in a few previous emails, and I keep coming back to it. Enjoy!

Pirates: Startups of the 1700s

The romantic vision of pirates is that they’re bold and charming swashbucklers, seeking a life of adventure on the high seas. This week I watched a funny and insightful video from CGP Grey that recasts pirates as common people living in an era of few opportunities. They are pushed by economic and social forces to take a big risk, in exchange for a shot at riches and a happy retirement. Less Jack Sparrow, more AirBnB.

In fact, many young companies portray themselves as rebels fighting against an oppressive status quo (we do it all the time at LBRY). Watching the video, I was struck several times by how deep the similarities go.

  • Employees at startups trade safety (stable business model, low legal risk, less effort required) for agency (flat hierarchy, higher personal impact, bigger reward for success).

  • These people are often not well-suited for traditional (Royal Navy / BigCo) jobs. Half the people at LBRY don’t have college degrees (some never finished high school), and we see that as a good thing.

  • The privateering/tech opportunity is present in the market. If your ship/team doesn’t take advantage, someone else will.

  • Clever use of branding can be crucial (more below)

  • Legal uncertainty is a big factor in startup life too. AirBnB famously fought several regulatory battles on their way to dominance, especially in NYC.

I feel obligated to add that startups don’t actually threaten or kill people for not handing over their treasure. If that’s what you’re thinking, try to see piracy in the context of the world as it was 300 years ago. The world was 200 times poorer and 50 times more violent than today. One in nine children died before their first birthday. The War of the Spanish Succession had just ravaged Europe and left tens of thousands of sailors unemployed (and there’s no government safety net). People had completely different attitudes about violence and government (and basically everything) than we do today.

With this frame, watch the video. See if you can spot other parallels.

If you’re curious about how pirates take advantage of branding, here's the companion video about that.

Cheers,
Grin


This newsletter goes out every Friday by 12pm ET. If I’m late, I’ll pay $200 to the first person who emails me about it. Got this after noon? Hit Reply and make me pay! Thanks for keeping me accountable.

Unicycle #12 - Implicit Learning, Explicit Music

As a reminder, I’m Alex Grintsvayg and you’re reading Unicycle. I welcome your feedback - hit Reply or message me anonymously. If someone forwarded you this email, subscribe here to follow along.

Hello dear friends :-)

This Week’s Curious Idea

Implicit knowledge is a fascinating thing. There are things you know, perhaps even know extremely well, that you are incapable of putting in words or teaching to someone else. Many of the things you do everyday are like this: walking, talking (you may think you know the rules of grammar but you don’t), falling asleep. Even something as seemingly simple as swallowing took you months of trial and error to master when you were a baby … or maybe not — some people don’t figure it out on their own and need coaching.

The traditional advice for learning unteachable things is repetition. Keep trying to do the thing until you get it right. That’s what most athletes do (sport skills tend to be implicit). And if they’re really dedicated, they hire coaches. What makes a coach special is they can model in their mind what it’s like to be unskilled.

When my daughter’s hair started to get long enough to braid, I hired a few coaches to help me learn how to do it. That is, I asked the women on my Ultimate team to teach me. They were very enthusiastic and ultimately very unhelpful, because they could not accurately model what it’s like for me as a novice. They focused on superficial details and did not emphasize the basics. Eventually I figured out the tricks (start at the front and aim high) by trial and error and watching Diana do it a bunch.

Next time you’re teaching someone, remember:

In order to tell somebody a thing, you need to know and understand what it’s like to not already know that thing.
~ Neal Stephenson

In Rotation

I’ve been playing three genres a lot lately: chill house, jungle, and full-on psytrance. The former has become my default music while working. DJ Black Coffee fits this genre (I linked him a few weeks ago), as well as songs like this one (the vocals are especially great):

The other two, jungle and psytrance, are were my staple in high school and college but have since fallen into the background. That’s partially because I’ve stopped going to warehouse parties, and partially because my favorite artists switched to other styles or stopped putting out new stuff completely.

So I was very excited to revisit both recently (thanks to the music channel in LBRY slack). The scene has changed, but there’s great new stuff to hear. Here’s a recent jungle track that sounds like it was made in 2000 (that’s a good thing):

And here’s Mandragora, a crazy crazy man making amazing dance music (I like it implicitly 😉). If I ever go to another music festival, I hope he’s there.


Housekeeping

I’m moving the newsletter back to Friday. That works better with my schedule. Sorry, everyone who liked it better mid-week. You’ll get the next Unicycle on Friday, October 23rd.


This newsletter goes out every Wednesday by 12pm ET (but is moving to Friday). If I’m late, I’ll pay $200 to the first person who emails me about it. Got this after noon? Hit Reply and make me pay! Thanks for keeping me accountable.

Unicycle #11 - Goodhart's Curse

As a reminder, I’m Alex Grintsvayg and you’re reading Unicycle. I welcome your feedback - hit Reply or message me anonymously. If someone forwarded you this email, subscribe here to follow along.


Hello dear friends :-)

Last week I took some time off of work and my usual internet regimen to relax, catch up on sleep, spend more time with my kids, and be outside before winter comes.


Goodhart’s Law has been on my mind lately. The short version goes like this: when a measure becomes a target, it stops being a good measure. For example, the level of cholesterol in your blood is one way to measure your health. If your cholesterol is high, your doctor might prescribe you statins to lower it. Now your cholesterol level is no longer a good measure of your health — its a measure of how much medicine you’re taking.

Another way of saying the same thing is that its hard to precisely define a target that matches your true goal. You don’t really care about your cholesterol. You care about a long and pain-free life. We can’t measure that directly so we focus on the things we can measure, forgetting that that’s not really what we’re after.

Sounds obvious when you say it that way. Yet we humans miss this point a lot.

Now that you have a name for this phenomenon, you’ll start seeing it everywhere. I just finished reading Unconditional Parenting. The extremely short summary is that rewarding kids for behavior has a Goodhart problem. If you reward good grades, they’ll optimize for good grades instead of following their interests or challenging themselves.

Same goes for creative work (there’s a huge overlap between parenting advice and management advice, and also sports psychology. that’s a topic for another newsletter). We value risktaking and innovation but we reward safety and incremental progress.

So what are we to do? Is it impossible to optimize for anything we really care about? Sadly, yes. In theory, there’s not perfect solution.

But in practice, you can improve many Goodhart problems by pairing a quantitiatve metric (a precise number) with a qualitative one (a rough assessment). A low grade on an assignment is ok if you tried a new style of writing or explored a challenging topic. Failing to create a sustainable business is a win if you worked hard on something promising and truly new and that didn’t work out.

Ultimate Frisbee does this well. A big part of what’s special about ultimate is Spirit of the Game — the idea that winning must never come at the expense of respecting others, following the rules, or having fun. Spirit rituals are a deep part of the Ultimate culture, so much so that all major events (including national and world championships) track spirit scores for each game and give medals to the most spirited teams.

Mainstream sports optimize for just one thing: winning the game/tournament/season. That leads to unwanted behavior: underhanded tactics, playing to the refs, outright cheating. One could argue that’s all part of the game and you should play to win. I’m sympathetic to that, but it points to a failure of game design. Ultimate shows a better way: you win by scoring the most points AND having the best spirit. Teams are famous for “winning the party” just as much as “winning the tournament”.

What’s a number you care a lot about improving? Do you have a quality metric paried with that number? Take a minute and think about what it might be. It just might help you get closer to the thing you really care about.

Cheers,
Grin


This newsletter goes out every Wednesday by 12pm ET. If I’m late, I’ll pay $200 to the first person who emails me about it. Got this after noon? Hit Reply and make me pay! Thanks for keeping me accountable.

Unicycle #10 - Don't Stay Bored 🥱

As a reminder, I’m Alex Grintsvayg and you’re reading Unicycle. I welcome your feedback - hit Reply or message me anonymously. If someone forwarded you this email, subscribe here to follow along.

Hello dear friends :-)

A short story: You’re watching a movie. The first twenty minutes were kind of cool, but you’re not having fun anymore. None of the characters are interesting, you don’t care about the story, but you keep watching because you know this movie won an Oscar and your friends all rave about it. Still, you’re bored. “Why am I bored?” you ask yourself. “I could be doing something fun. What’s wrong with me?”

There is something wrong, but it’s probably not what you think. And, to give you a quick preview of the rest of this email, the solution is to stop what you’re doing and do something fun instead.

In fact, if you’re bored right now, close this email and go do something else (but first click here to let me know you did). You have my permission. Seriously.

Still with me? Great! So, what is wrong with you? There are two questions here:

  • Why am I bored?

  • Why am I staying bored?

The answer to the first is that there’s a conflict inside you between several thoughts or ideas. The source of the conflict could be conscious or unconscious. Maybe you feel a nameless anxiety that you can’t explain. It’s really caused by a stressful presentation you gave at work and your mind needs quiet to process it, which conflicts with the loud fight scene you’re watching, but you couldn’t tell me that if I asked. Whatever the case, the conflict is preventing you from enjoying the movie.

How do you resolve a conflict that you are not conscious of? You do what’s fun. Philosopher David Deutsch calls this the Fun Criterion. When you’re having fun, you can be sure there’s no subconscious conflict. So if you feel something’s wrong, optimizing for fun will move you in the right direction.

This doesn’t mean you should avoid all effort. “Fun” is not a synonym for “short-sighted pleasure“. Hard things can be fun. Feeling exhausted and freezing cold may not sound fun to you, but it might be extremely fun to a dedicated alpinist about to summit Everest.

Why don’t we do this all the time? Often it’s out of politeness, a social convention that signals belonging. I wrote two weeks ago about the reasons for doing something. Politeness is squarely a tribal thing. You don’t want to leave the movie because that’s not what people like you should do. Maybe you feel you shouldn’t “waste money” since you paid for the ticket. Or your friends would think it’s weird you’re not enjoying yourself like they are.

The good news is that the internet is changing this convention. In the online world of abundance, there’s an infinite amount of really great stuff out there. So our tolerance for boredom is decreasing. Not enjoying a website? Go to another. Bored on Tinder? Swipe left. Even in the physical world, unconferences are promoting the law of 2 feet: if you’re not interested, use your two feet and join another group. You don’t have to finish climbing Everest if you realize you don’t like snow.

Breaking this convention gives you the freedom to try more things without commiting to them. It also increases holds everyone to a higher standard of empathy. I know you don’t have to keep reading what I write, so I think about what you’d actually enjoy. Why read my newsletter, when you could be watching Joe Rogan or browsing Reddit.

Don’t tolerate unintentional boredom. Optimize for fun. It’s ok now :-)


These one-click surveys help me empathize with you. Did this email connect with something in your life experience?

👍 Yes

👎 No


Cheers,
Grin

This newsletter goes out every Wednesday by 12pm ET. If I’m late, I’ll pay $200 to the first person who emails me about it. Got this after noon? Hit Reply and make me pay! Thanks for keeping me accountable.

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