Can you teach someone to be unafraid?

Wil Reynolds
3 min readNov 28, 2022


TLDR: Can you teach someone to be “unafraid” to act when they recognize that the risks are low?

Since I was 14 I always took risks, I calculated the risk and wasn’t afraid of the consequences and I did things that others ask “who told you that it was OK to do that?” To which I respond…what was the worst thing that could happen?

Here are 3 examples of me processing risk and acting w/o seeking permission.

Age 16 — I once tried to help the sneaker company I worked at selling shoes hit a goal. So I hired a friend to stad outside and wave a sign to get people to stop in. Did I ask my boss if that was OK, nope. I just did it. I was pretty sure if I got fired for trying to help him hit his goals, then it wasn’t the right place for me.

Result: We crushed goal, I kept my job.

Age 18 — Freshman year I didn’t have a scholarship. I lived in a dorm with a bunch of other dudes who were on scholarship though. First semester I got a 4.0, I saw kids who partied all first semester get put on academic probation, then they came back in the second semester and kept partying. I got a 3.7. But they had scholarship money and I did not.

So I wrote down their names and went to the financial aid office, and I said here are names of kids I know were on probation and I saw that they kept partying, so I bet a large # of them lost their scholarship $. What happens to the money? Cause ya’ll should have bet on me. No one told me to connect the dots, I just did and figured what was the worst that could happen?

Result: I got a full 4 year ride after my freshman year (paid for both senior years)

Age 22 — I made a list of 6 companies I wanted to work with, put a suit on and started knocking on doors. First company whose door I knocked on, gave me a job in search. The rest is history. But most people have never knocked on a door to try to get a job in their lives, they leave working at companies they really want to work with up to chance. I never understood that.

Result: Altered the trajectory of my life and the lives of countless others.

So recently I was exploring these are all important lessons in my career growth. Heck my life. Why don’t more people “Just f’ing do it” as my buddy Alex Hillman would say.

Alex Hillman w/ JFDI tattoo

So it was in a chat with a co-worker that I asked her…can you teach someone to not overthink things like this and just be unafraid?

Then at a dinner with Alex and Dan, I asked the question…can you teach this, or is is just innate in some of us to not be afraid.

To which Dan Mall said…hold up, let me challenge that…fear is a good thing, it is a good signal to be afraid, to stop and process that fear.

That helped me reframe the question.

Dan went on to say, you can teach people to assess risk. Courage once you’ve processed how “risky” something is, can be taught. Dan then said processing risk is like getting better at meditation, it can be practiced.

So now with that reframe, here’s the question… Can you teach someone to get better at assessing risk, then being unfraid to act when they recognize that the risks are low? Or are certain people just wired naturally / innately to overthink low risks, which can paralyze them from acting. Cause if it is teachable, I would love to learn how to. I see a lot of people in my company and in the world whom I have the highest confidence in, but they don’t always have it in themselves and I’d like to help them break through.



Wil Reynolds

Serial Underdog @seerinteractive doing SEO, Marketing, & Stuff, I am whatever you say I am.