Riffing on Uncertainty

by Scott - 2 Comments

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Have you ever been scared sh*tless to do something? I bet you that the outcome was uncertain in this situation.

Have you ever done that thing that scared you sh*tless and in one form or another succeeded?

You stood up to the bully on the playground and he backed down.
You got the girl at the bar that everyone was afraid to talk to.
You left the job everyone hated to go build an amazing company.


You conquered fear to achieve success. Fear that was grounded in uncertainty. There is no better feeling.

Uncertainty is a funny beast in my life. I’m addicted to it, yet I simultaneously try to combat it whenever I can.

I love going out in New York. Not because I’m particularly excited about dropping $$ at a bar or restaurant, but because of the prospect of the unknown. I could meet someone awesome. I could see a friend do something I never thought I’d see. I could slap hands with P Diddy. I just don’t know.

It’s the same reason I’ve grown to love entrepreneurship. I could go work at a big, comfortable company with a rigid hierarchy. But knowing what the next 5 years of my life look like doesn’t sound all that exciting to me.

I originally thought the reason I love uncertainty is because I equivocate it to upside. And the perception of upside is the foundation of excitement. It’s the greatest source of energy in my life.

The interesting thing is that I’ve spent a lifetime trying to increase the odds of success in situations where I perceive uncertain outcomes:

  • I went a good school to increase the odds of obtaining the career opportunities I wanted to.
  • I write out the script for a cold call or voicemail I’m going to leave so that I can convey my message exactly how I’d like to.
  • I go to the gym is to increase the odds of being attractive to the opposite sex when I accidentally drop a pass right in front of the group of cute girls on the beach.

*I do/did these things for other reasons too

I’m constantly trying to put myself in pole position when I line up against uncertainty.

It’s an interesting dynamic. Do I love uncertainty because of the potential for upside? Or do I love it because it provides an arena for me to test my mettle in the wild? A way to measure myself.

I think it’s the latter for me. A lifetime polishing your armor is worthless if you never enter a battle…and victories are far sweeter when we perceive the stakes are higher and the challenges more difficult.

I’d probably hate uncertainty if I didn’t perceive it as a force that could be reckoned with.

I hail from a different school. With enough diligence in any scenario, we can master fear and technique to achieve success. Nothing is impossible. When you possess this belief, uncertainty inspires competitive flames. Achieving success in it’s midst becomes a surmountable challenge. This makes it fun.

My best friend who visited last weekend is an officer in the Military. He leads a unit of Army Rangers. He’s spent the last 2 years of his life preparing to lead his men in Afghanistan. During his tenure, the leadership of our government has decided it’s in the country’s best interest to decrease the amount of resources we put into the Afghanistan effort. As a result, there’s a chance that he might never be deployed during his military career.

If he gets deployed, he enters a scenario with the most uncertain outcome(s) and highest stakes. Conversely, if he doesn’t get deployed, the remainder of his military career is pretty low-risk and predictable, discounting an alien apocalypse. He’ll spend the next few years safe on American soil.

Presented with the contrasting scenarios, my friend hungers to be deployed. It’s not that he’s incredibly eager to risk his life or see the awful things war can bring. It’s that he wants to put the sword he’s been sharpening for the past two years to use. He wants to test his skills in the wild to see how he measures up – even in the face of looming uncertainty and a meek potential for upside.

Is there a correlation between love for uncertainty and competitiveness? I don’t think so. I know many people that hate uncertainty who are extremely  competitive lovers of self-improvement. I think that love for uncertainty is correlated with the perception that it’s a state that can be tamed. Uncertainty affords an arena that many avoid, but where some choose to play so that they can measure themselves.

I love thinking about these things because I arrive at a greater understanding of myself. Why do I do think and act the way I do? When we understand this, we’re better able to diagnose and fix the behaviors we want to change. We’re able to get closer to our best selves; an outcome that hopefully yields benefits to the world around us.

“Every day, think as you wake up, today I am fortunate to be alive, I have a precious human life, I am not going to waste it. I am going to use all my energies to develop myself, to expand my heart out to others; to achieve enlightenment for the benefit of all beings. I am going to have kind thoughts towards others, I am not going to get angry or think badly about others. I am going to benefit others as much as I can.”
Dalai Lama XIV

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