Play to win, don't play to not lose.
Have you ever asked yourself what the root of your success is? Is it hard work, intelligence, or something else?
Recently, I had a conversation with my friend Dan about this topic. We often assume that success is a combination of hard work and intelligence, but Dan surprised me by saying that he believes the root of his success is his willingness to take risks.
As I reflected on my own experiences, I realized that this has certainly been true for me as well.
Risk taking can mean a lot of different things to different people, but to me, it means playing to win instead of playing to not lose.
When I was a freshman in high school, I found myself in the Eastern Ontario Sectional finals for triple jump where the top 6 make it to Provincials (equivalent to State Finals in the US). For those that aren’t familar, in triple jump is a track and field event where an athlete runs to hop on one foot from a takeoff line, lands on the same foot, leaps forward again onto the other foot, and then long jumps from that foot to land into the sand pit.
At the high school and collegiate levels, there are 3 different takeoff lines to choose from based on how far the athlete can jump. These lines are set 40 ft, 32 ft, and 24 ft from the pit. If you can jump further, you would choose a further starting line from pit.
The score is the distance from the takeoff line you choose to where you land. But if you overstep the line, it’s considered a “fault” and no score is counted. If you take off before the line, your distance is still measured from the line.
Like all the athletes that train, I had a spot on the runway marked for where to start running and the exact count of strides it would take me to reach an optimal speed to take off at the 32 ft line. But whether it was the nerves or the rain that day, I ended up faulting my first two of three jumps.
With one jump left, I consulted my team captain, a senior track star.
“Should I change my starting line to 24 ft? That way if I overstep the 32 ft line again, at least I would have a score and a record of me even competing here. Any score is better than no score”
My captain’s response stays with me to this day.
“If you change your line, you are going to lose up to 8ft off of your score (because I don’t know my stride count for a 24ft line takeoff). You might beat the other girls who are faulting today, but you will not come in top 6. Changing your starting line will not help you win. If you want to advance to Provincials, the only way to do that is with your best.”
I understood immediately. There were only two outcomes - I made Provincials or I didn’t. Faulting or getting a low score would lead to the same outcome. The only way to get to the outcome I want is to do what I knew I needed to do.
Luckily, I didn’t fault my last try and got a score high enough to come 6th - just edging my way into advancing to Provincials.
I think about this experience often and how it applies to the rest of life. In order to achieve the extremely difficult, we often know what we need to do. But we don’t go all out because having a score is better than no score.
A real life example is my journey to Silicon Valley.
I knew I wanted to join an early-stage startup when I graduated in order to get the training I needed to become a tech entrepreneur. I did my research - early stage companies don’t recruit one year out through formal college recruiting pipelines like FAANG, the Big 4 Accounting, investment banking, and consulting firms where most of my friends were heading. Early stage startups hire for what they need immediately - because they don’t know what headcount they might need 1 year from now.
The only way to get a job at an early stage startup was to wait until after graduation to recruit. This was seen as risky to some - to do that I gave up recruiting through my university career center during the school year. I remained not knowing whether I will have a job for months after my friends landed their offers. Even though I felt extremely anxious that I would ultimately fail to break into the tech industry, fall behind my peers in the career rat race, and embarass myself for trying - I knew it was what I needed to do.
If I had recruited and lined up offers to a job that didn’t align with what I really wanted to do, that would be playing to not lose because any job is better than no job and no job would mean losing. I would get a job I didn’t care for, only to be waiting to rack up enough experience in order to take the leap and try to get a job in Silicon Valley 2 years later. If I didn’t play to win now, what made me think I would play to win 2 years from now?
The risk was calculated. I knew that tens of thousands of business graduates from Stanford and Berkeley find jobs in the Bay Area. I may have the disadvantage of a Canadian degree from a lesser-known school, but I decided I was at least above average competent amongst them. If they can do it, why can’t I?
This decision to play to win changed my life and paved my way to becoming an Edtech entrepreneur.
Dan shared similar stories -
Of his friend using financial leverage to bet big on opportunities he was sure about instead of diversifying his portfolio regardless of knowledge and intuition. He got 40x returns.
Of himself not recruiting out of Harvard Business School but instead going to start a startup after putting all his savings into getting the degree. He raised $3M this year developing business planning products and services for brands and D2C merchants.
Of course, there are also many examples of failures. A startup can play to win and lose big.
But the difference between the most successful people I know and the average person is their willingness to play their best card to win big or lose it all time and time again. They get up after every failure and still play to win even if it’s with fear.
Because you can’t win if you’re always playing not to lose.