How to make life changing decisions in spite of fear
Estimated reading time: 5 minutes
From ‘F**k it, let’s roll the dice’ to a thoughtful approach to decision-making.
Why is it so hard to make decisions, especially ones that can alter the course of our lives? We fixate too much on the decision itself - what should I do - and not enough on finding the right questions to ask ourselves.
At 17 years old, facing a major decision
When I was 17 years old, I grappled with a dilemma that kept me up at night. At the time, I was playing hockey in the QMJHL in Cape-Breton. I was one of the youngest assistant captains of the team - of any team, ever. From the outside looking in, things looked great. From the inside however, things weren’t so great.
I wasn’t getting along with my coach and felt like my hockey career was suffering from it. I had a major decision to make:
a) Stay in Cape-Breton and become the team’s captain the following year. Things would probably work out in the long-term.
b) Ask to get traded to another team and hope that would help me reach my goals of playing in the National Hockey League.
F**k it, let’s roll the dice
At 17 years old, I had no framework to make these kinds of decisions. I tried relying on my dad’s wisdom. Having played in the National Hockey League for 13 years himself, I figured he could make the right decision for me. Or at least point me in the right direction.
To my disappointment, he didn’t guide me in any direction. Instead, he listened and said he’d support me no matter what decision I made. Great parenting, this scenario helped me become the man I am today, but it made my life much harder in the short-term.
I don’t know why, but all I could think of was a scene from the TV show Entourage where Vincent Chase, a movie star, has to make a big decision. Against his agent Ari Gold’s advice, Vince says “F**k it, let’s roll the dice”. Feeling inspired by my favourite TV show, I called my dad one evening and said F**k it, let’s roll the dice! I told my coach I wanted to get traded the next day.
It turns out that relying on your favourite TV show to make decisions isn’t the best idea. It really is a roll of the dice, and you can only hope for the best.
The answer lies in finding the right questions
Throughout the next few year, I started building a decision framework by reading dozens of personal-development books. I realized that my mistake, most of our mistakes, is to focus on the answer when we should focus on the questions. For instance:
Instead of hitting my head against the wall trying to find the answer to ‘should I ask my coach for a trade?’. I should have figured out what questions would help me arrive at the right answer.
I faced another major decision when I turned 21. A decision that would have a profound impact on the rest of my life.
My hockey career wasn’t going as planned, and I had three options:
I could try to grind it out in the American Hockey League and hope to eventually make it to the National Hockey League
I could abandon my dream of being a pro hockey player and focus on my studies instead. I had full scholarship offers from some of the top universities in Canada.
I could abandon my dream and refuse a full scholarship to become an entrepreneur (not my mom’s number one choice!)
This time, I wasn’t going to roll the dice. The first step was to figure out what I truly wanted. Not what society expected of me, or what my parents wanted me to do. What I wanted.
Asking myself ‘what do I want?’ over and over again wasn’t going to provide any clarity. Instead, I thought long and hard about questions that would help me find the answer to ‘what do I want?’.
A few questions that helped me:
In 10 years from now, picture yourself in all three scenarios, how do you feel? What are you doing on a daily basis?
In 10 years from now, which of the three scenarios will you regret the most not having tried?
When I’m on my death bed, which decision would make me the most proud? You can replace the word ‘proud’ with anything. Which would make me the most at peace, the most fulfilled, etc.
What would my best 40-year old self advise me to do? Having gone through the thick and thin of life, what wisdom would he give me? I was adding 20 years in that case. Nowadays I use my best 50-year old self to advise me (I’m 32 as I write this).
If someone has a gun to your head and you have to eliminate one of the three options, which one is it? I use this one a lot in business to ask my colleagues to prioritize: ‘gun to your head, you have to remove one project, which one do you remove?’ The gun to your head is a bit extreme, but it works. Most people, myself included, have a hard time removing options.
These types of questions are immensely more helpful than asking yourself ‘what should I do?’ for days and weeks.
When facing a decision, stop asking ‘what should I do?’ and start asking ‘what are the right questions to help me make the right decisions?’.
A final exemple - should we sign a new office lease?
Earlier this year, I was facing a major decision in business with Ergonofis. Here’s the contexte:
We had outgrown our distribution center and desperately needed more space.
Our leases were coming to an end. We had one lease for our office and one for our distribution center.
We found a great space for our distribution center. It was only 500 meters away from our current office space.
The decision I faced was whether we should:
a) Move the distribution center but keep our office where it is. This was ideal for the office but it separated the team and increased our fixed expenses. It also removed the complexity of moving our offices.
b) Move the office with the distribution center, which had a mezzanine that could be used as an office space. It was a downgrade from our current office space (in terms of design, natural lighting, etc.).
As the CEO, the decision rested on my shoulders. It kept me up at night as I pondered on the decision. I caught myself (again) asking the wrong questions. I kept thinking long and hard about the answer to “should we move our office with our distribution center or keep it where it is?”.
Pondering for hours on that question got me nowhere. The answer became clear as soon as I started asking the right questions:
What’s the impact of each scenario on the team?
How will I feel about signing two separate leases and increasing our fixed expenses if there’s a downturn in a few months?
Who would benefit from keeping our office as is and does it really matter to them?
Equipped with the right questions, I started discussing it internally with our team. I came to the conclusion that we had to move both the office and the distribution center to the same space.
A few months later, I couldn’t be happier with my decision, and it’s all thanks to asking the right questions.
Let’s face it, coming up with the right answer is only step one. What if we’re scared of taking action even though we know what we should be doing? In part 2, I walk you through the exercise I do to face my fears.
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