Don't be a donkey
Buridan's donkey—Life as a series of experiments—The teleological fallacy
Buridan's Overthinking Donkey
Have you heard the parable of Buridan’s donkey?
Here’s my version: a thirsty and hungry donkey is halfway between McGillin’s Old Ale House and Mission Taqueria.
The donkey keeps looking left and then right. Unable to decide whether he wants to drink or eat first, he eventually dies of thirst AND starvation.
All he had to do was go to one place first and then the other.
But the donkey was paralyzed, afraid of committing to one option for fear of missing out on the other.
When evaluating career opportunities, I sometimes feel like this donkey. I catch myself agonizing over which new projects to work on, which personal goals to focus on or even whether to transition to a whole new industry altogether. And don’t get me started on crypto!…
I sometimes think, falsely, that the “right” choice will suddenly flash in my frontal cortex one moment, perhaps while I am waiting in line next to the yoghurts in Trader Joe’s. "My life calling is to leverage cloud technologies to help digital healthcare startups scale." As if the choice were so clear and so certain, insulated from the forces of technological disruption, global pandemics and other bang-your-head-on-the-cabinet surprises that can change the game at an instant.
The more I think about it, the more I realize that existential choices such as these don’t have a right answer. Which means if I’m stalling and stalling, waiting for the right answer to appear, I’ll look a lot like Buridan’s hesitant (and unfortunate) donkey.
Meanwhile, the world is steadily advancing… and the one of many opportunities that could have been taken is already gone.
When choosing between attractive opportunities, I think this parable emphasizes that it’s better to make a commitment towards some course of action than to wait for an optimal choice that does not (and cannot) exist.
How can we make this commitment? How can we no longer feel the need to agonize and worry about what the best opportunity really is?
An Experimental Mindset
I believe what gets us there is a mindset that is experimental, that embraces trial and error, that is open-minded and flexible, and that rejects linear I-need-to-have-it-all-planned-out-like-that-guy-on-LinkedIn thinking. You pick something and commit to it for a pre-defined amount of time, and if it doesn’t work, you move on to the next item on the list.
You don't think about what's 10 years down the road because you can't see it yet. COVID taught us that, and we should all give-up on the trying-to-predict-the-future game (economists should too).
I don't think you can sit down underneath a tree and ponder until you figure out what exactly you like best either (sorry Buddha). The process needs to be hands-on, iterative, and empirical—based on the data you gather, not the visions you have while looking down at your feet in the shower.
So what does an experimental mindset look like?
Tim Ferriss has some good advice:
1) Choose an experiment that will still benefit you in some way if it fails
I applied this rule when I chose to start this newsletter, when I was agonizing whether it was “worth it” for me to spend 5-10 hours a week on something artistic when I could be networking, bro. Even if I failed, I knew I’d walk away from the experience with deeper knowledge, stronger writing skills, and some new relationships
Choose to learn a new skill or start a new project with the knowledge that it can still benefit you, even if it doesn't work out.
2) Commit to the experiment for a pre-defined length of time or number of iterations before giving up and moving on. That way, you know when to quit and move on to something else.
This second rule helps you avoid overcommitting to something that is not working. It also helps you make the initial commitment. The new thing you try probably won’t work the first time you do try it. You need to make 4 or 5 podcasts to really tell whether you like it or not (a strategy Tim Ferriss himself employed, when he started his). Besides, the first one is always going to suck anyway.
The first benefit of this experimental strategy is that you limit your losses while still keeping all of the potential gains. If you fail, at least you walk away afterwards with some new asset and perhaps a clearer direction of where to go next.
The second benefit is that, in my eyes, it slowly, over time, opens your mind to see a broader set of opportunities. You can even think of the temporary setbacks or sidetracks as experiments that were chosen for you. What can you learn from it? How can you adapt?
With an open, experimental mindset, it's easier to not put so much pressure on yourself to always be making the right decisions about what to do next, about what you really enjoy, and about what the next best opportunity is. The world changes too much too often to get it all right.
In Antifragile, Nassim Taleb called the teleological fallacy “[t]he illusion that you know exactly where you are going, and that you knew exactly where you were going in the past, and that others have succeeded in the past by knowing where they were going.”
Most of us don’t really know exactly where we’re going. That’s why when we see a lot of interesting opportunities in front of us, we can’t expect to know exactly which one is the best to take.
That’s not an excuse to stall and stall, waiting for the magical right answer.
It’s a reason for a more experimental mindset. It’s a reason for just picking an opportunity and committing to it for a pre-defined period of time.
It’s a reason to not be like Buridan’s donkey.
"Process saves us from the poverty of our intentions."
(1) Antifragile by Nassim Taleb
Check out my newsletter Thoughts from a Bench