The Road to Mastery Begins With a Step in the Dark

January 13, 2017
dark alleyway

The hardest words to write are always at the beginning. It’s like it brings you back to a place, a primitive place, a place you thought you’ve conquered long ago.

But no.

Every time I’m confronted with a blank page, I’m reminded of how scared I am of the dark.

I don’t know why I’m scared of it and perhaps that’s the scariest thing of all. In the dark, anything could be there.

But you take a step into the darkness, prodded by whatever motivation you managed to grab hold of, and then you take another and another and you find the boogie monster lives solely in your imagination. You might bump into a piece of furniture here and there, but compared to what you had in your head, some bumps are the least of your concern.

The road to mastery is a dark place. This time, the boogie monster isn’t some figment of your imagination. There is no purple monster with the eyes of a fruit-fly, what lies there instead is very real, yet at the same time very make-believe.

“What if I fail?”

“What if I chose the wrong path?”

“What if I’m doing it wrong?”

“What if people laugh at me?”

What if?

And what if you succeed?

What if this is what you’re meant to be doing?

What then?

That’s the thing about the dark, it brings up questions you can’t answer and it scares us to acknowledge that possibility because that would mean we have to come face-to-face with how little control we really have.

The Illusion of Control

Fact is, the matter of both failure and success is a matter of “when” and not “if.” Stumble around in the dark long enough and you’re bound to hit a piece of furniture, trip over something on the floor, or slam into a wall.

In that same vein, stumble around in the dark long enough and you’ll find a door, but because the opportunities for failure are so much greater, it is basic mathematics that we should fail more than we succeed.

At first at least.

Look Dumb to Be Smart

The boogie monster never goes away. No matter what I am doing, whether interviewing for a job or even something I’ve done hundreds of times like writing, the first step is always the hardest one to take. There’s always that possibility of looking dumb, that possibility of slamming face first into a wall.

But many bodybuilders start their journey into weightlifting because they felt inadequate in their bodies. They were too skinny or too fat. So they hit the gym, looking completely out of place.

The best athletes look to square up against the best competition. Dominating lower levels of play does nothing but wax their ego and so they keep their eye out for a challenge. And sometimes they get waxed.

On this road to mastery, there’s going to a lot of looking dumb. I would know, I fail over and over again at my craft.

But with every failure, I gain a piece of the blueprint to success and that’s worth the brief moments of embarrassment.

If you want to be smart, you’ve got to be willing to look dumb.

But how you start? How do you take that first step?

Big Fish Eats Little Fish

People love to spit platitudes such as “the only way to gain courage is to do the thing that scares you,” but they’re empty sentences akin to saying “the best way to get a job is to already have a job” to somebody who is having trouble finding work.

Here’s the thing about courage: it is a calculation of expected value. Risk vs. reward.

Is the risk you’re taking worth the potential reward?

However, when making their calculations, most people make a cognitive error.

Error of Omission

Sometimes the reward isn’t big enough to take upon the risk, sometimes the probability of success is too low to balance out the equation.

But when calculating their analysis, many people commit an error of omission. They see failure as the only risk in the equation when there is another formidable threat in the horizon.


There is comfort in stagnation. It is more comfortable to fail the way you’ve always failed than it is to “die” trying something new and so we give less weight to this state of inaction.

In The Art of Thinking Clearly, Rolf Dobelli describes this phenomenon:

“Such thinking also explains why parents feel it is perfectly acceptable not to vaccinate their children, even though it discernibly reduces the risk of catching the disease…A person who is immune to the disease will never infect others. Objectively, if non-vaccinated children ever contracted one of these sicknesses, we could accuse the parents of actively harming them. But this is exactly the point: Deliberate inaction somehow seems less grave than a comparable action — say, if the parents intentionally infected them.”

But on the road to mastery, stagnation and failure are not comparable actions. Here’s why:


Stagnation breeds self-doubt.

Picture this:

You’re sitting in a meeting.  A topic comes up and everything in your body is telling you ‘say something,” but nonetheless you stay still and say nothing. After you ignore that urge, you lower your head a little bit and you feel a little weaker.

Have it happen enough and eventually, you won’t even get the urge to say something because in your mind, what you have to say isn’t even worth saying.

Every time you fail to do something you think you should do, you lose some respect for yourself and it builds. Self-doubt then becomes a self-fulling prophecy, the doubt you sow internally manifests itself in your work and your lack of achievement.

Embarrassment is brief, but mediocrity. Mediocrity can be forever.

Most people step into the gym because the brief moments of looking out of place is less scary than staying too thin or too overweight.

The best athletes look for the best competition because the brief moments of embarrassment is less scary than possibility of regression.

The road to mastery is a dark place. This time the boogie monster is to your back and the only escape is onto the road to mastery.

And it all begins with a step in the dark.

You Might Also Like


  • Reply Angela January 20, 2017 at 7:21 pm

    A very insightful article. Thank you!

    • Reply January 23, 2017 at 9:04 am

      Thanks for reading Angela!

    Leave a Reply