Introduce Randomness

How to evaluate decisions is a good question, NT. As you say, to decide between two things it helps to have a common standard to compare them to. You use time, which is a great system. When I was young, I used an aspirational purchase I liked to make: magic cards. Purchases could be conceptualized in terms of how many packs of magic cards it was equivalent to. That number was always far more visceral for me than an abstract number of dollars, as I think time is for you, and so it made the decision more tangible.

A limitation I’ve found with time is that I find value in doing things myself. I could spend money to have someone paint my house, for example, but I like doing it myself. I learn a new skill and I find more satisfaction in a job well done then just seeing someone else do it for me. That particularly applies when it is something I haven’t done before, or might not feel comfortable doing. For that reason, sometimes I find it useful not to follow my analysis–whether based on time or magic cards–too closely.

Explore vs. Exploit – The Case for Randomness

When I’m faced with a few options, I often do try to find a common baseline to make the comparison. But I also try to introduce some randomness. If it’s something I haven’t done before, maybe I do it even if it seems like the worse option, so I can learn if it’s for me. If doing it will teach me a new skill, that might add a few points too. 

When I get invited to attend an event, for example, I try to err on the side of accepting. They have a cost in time, but there is always a stimulating element of randomness because I’m forced out of my routine and to talk and interact with new people. Sometimes the event is good, sometimes it is bad, but I usually learn something, especially if it isn’t the kind of event I would normally attend. 

Your advice, to include the non-quantifiable, seek asymmetry, and protect your downside, is good. I would add one more: accept randomness. Seek new things. Err on the side of the new, not the old. It’s too easy to stagnate and get stuck in ruts. If you always optimize the same way, you’ll likely always reach the same optimum. If you try something new, you might find you like it even more. I meet too many people who seem to just do what they’ve always done, stuck part way along the path of self-improvement without realizing it. 

We should make mistakes

You finish your post, NT, asking me if I know myself well. I’ve definitely learnt some things about myself, though as I grow and evolve I find I often need to learn those things anew. I do, however, have a far greater stock of mistakes under my belt than I did when I was younger. I’ve learned a lot as a result. So maybe that’s my biggest learning; we should make mistakes. Our growth is the sum of our mistakes.

Mistakes lie at the heart of all of the strategies you mention. We can learn from the mistakes of others, which is particularly important in contexts where making a mistake could have catastrophic consequences; we can learn from experimenting and making mistakes ourselves; and we can learn by reflecting on mistakes we have made in the past and drawing lessons from them. Through it all, we need a growth mindset to realize that those mistakes make us stronger, not weaker, as long as we let them.

For fixed mindsets, as Maria Popova points outs, mistakes are ‘a sentence and a label.’ For growth mindsets, they are ‘motivating, informative input–a wakeup call.’ You can either take a mistake personally or learn from it and do better. 

It has taken me years to realize I don’t enjoy large parties, for example. Now, if I go to a party, I’ll try to stick to conversations in smaller crowds. For the same reason, when I want to connect with others I do so over one-on-one coffees. I am at my best then, and we can take the time to explore ideas and learn from each other more deeply than in a crowd, which I prefer. The only way I learned that, though, was going to parties and realizing they are not for me. In other words, making mistakes. I could have become frustrated at my large-party experience, condemned myself for not finding it easier to connect with people there. Instead, I seek to shape my environment to suit me. 

…as long as we can survive them

Of course, mistakes can have costs. So there is an art to making them in a way that doesn’t sink your ship. If you’re thinking of making a high-risk investment, make it a small percentage of your net worth. Ensure your mistakes don’t cost you or others more than you are willing to pay. As long as a mistake is survivable, you can learn from it and improve, but some things shouldn’t be gambled with. Your health, the happiness of others, your integrity, might all be beyond the pale. But beyond that, take risks! Invest some fraction of your time in moon shots and wild cards, things that likely won’t work but will teach you a lot either way. Try new things even if you expect not to like them. Win or lose, you will learn.

So there’s my takeaway for this week. We should make mistakes! Go forth and take risks. Figure out how to do them in a survivable way. Partway through my thirties, I don’t know if I am wiser, but I am better equipped with mistakes, and that feels like progress. The biggest missed opportunities in my life are those where I could have made more mistakes and learned more, I think.

And then here’s my question for you: do you cultivate moonshots in your life? What bets are you making, and what are you hoping to learn from them, win or lose?