Provoking thought

More YOLO

More YOLO
Living the YOLO lifestyle, as visualized by GPT-4o

We had an interesting training on entrepreneurial behaviors at the company this week. We were asked to rank the following behaviors from “Most often” to “Least often” used. We were given them unordered, but this is how I ordered them for myself:

  1. Reflect
  2. Desire to have an impact
  3. Always learning
  4. Endless curiosity
  5. Flexibility
  6. Desire to create
  7. Embrace uncertainty
  8. Believe in oneself
  9. Don’t give up (resilience)
  10. Willingness to take risk

Those that (have come to) know me a little bit, will not be shocked about at least the top of this list.

A productive use of this ranking exercise is to explore the bottom of the list and see if there’s anything we can do there. And dangling at the very bottom (and this was the case for more people) is willingness to take risk.

Risk aversion is an interesting one. It’s one of those things where I can (and will) give you completely rational reasoning why taking risk is a great idea and you should definitely do it more.

But I still don’t do it.

It’s almost like I’m not a rational being.


If you have the same issue, let’s team up and see we can change this.

The challenge: find a way to finally get over ourselves, and take more risk.

You know my go-to solution to solve any problem. You’re looking at it.

The strategy I’m going to employ here is to marry risk aversion with something I do much more naturally: always be learning.


This is where I am, once more, going to switch into motivational speaker mode. To sell this even more: I almost guarantee you that none of this (beside perhaps some obscure book references and hilarious jokes) is going to be new to you.

That said, what I have learned (I’m always learning) is the following: sometimes you need to hear the same thing many times before it actually lands. Sometimes, you need to hear it at just the right time. And sometimes, you need to hear it from the right person. I’m an authority on absolutely everything (you saw where I ranked my self belief), so you should definitely listen to me and do everything I say. My kids do.

In the off chance all those stars align simultaneously, something may finally change. So, let’s give this another shot.

Our kick-off point is our interest in always be learning.

How do we learn?

We can read a book. We can watch a TikTok video. We can take a course. We can read a newsletter from some dude that won’t stop typing. However, I find I learn the most by doing. By putting things into practice, and especially while making mistakes while doing it.

Making mistakes is academically awesome, but personally painful. Yet, when approached correctly, you can extract a lot of learning. What makes things even worse, experience wise, is that the bigger the mistake, the bigger the (potential) learning is.

When I stubbed my toe this morning, it hurt for 20 seconds. I thought: well that was dumb, let’s not do that again. And I bet that for the rest of today I will be extra careful. Perhaps I’ll even put on slippers of some sort (so far I haven’t). There’s few things in my life today that I would attribute to having stubbed my toe (many times) in my life. The amount of learning is low.

Then, there are the more dramatic failures and events. I’ve documented some of these here and there. These are extremely painful to go through as they happen, but are the things that years perhaps even decades later you will still point to as defining moments.

So, it logically follows that the best way to learn as much as possible, as quickly as possible is to constantly do stuff that massively blows up in your face. Fail as much as possible and fail big.

And how do we achieve that? You saw this coming.

By taking more risk.

More YOLO.

As my driving instructor said, as I got super nervous merging onto the high way for the first time: “just close your eyes and hit the accelerator.” He is no longer with us.

Let’s throw in the cliche: “What doesn’t kill you only makes you stronger.”

For legal reasons, I have to emphasize that first part of the sentence.


A whole pentalogy (I had to look that up, it’s the five-part version of a trilogy) made it to The Shelf a few weeks ago. It’s the Incerto series by Nassim Nicholas Taleb. Yes, it’s quite the pretentious title (it’s derived from Latin so that should say enough), but there’s a lot of counter intuitive stuff in there, which is why I love it.

One of the five books part of Incerto is Antifragile. The TL;DR is the following:

Some things benefit from shocks; they thrive and grow when exposed to volatility, randomness, disorder, and stressors and love adventure, risk, and uncertainty.

One example of something acting antifragile in many ways is the human body. When put under significant stress, e.g. when lifting significantly more weight that normal, the body adapts from the experience and starts to build muscle to better prepare next time. Similarly, the way many vaccines work is by making the body a little ill so that it can recover better prepared from when an actual disease infection would happen.

This is a human property, which means we can leverage to make ourselves mentally antifragile as well.

How? By taking (manageable) risk. Letting things blow up (within reasonable margins). Learn from it. Rinse and repeat.

Nothing new under the sun. But worth repeating.

Maybe I’ll listen.