Three hacks to improve your odds of success

Imagine you’ve set the goal of running a marathon that’s 90 days away. You’ve hired a trainer who says this a less than optimal amount of time, but if you stick religiously to her fitness routine, nutrition plan, and sleep schedule, you’ll be ready come race day. Cheat in any of those three areas, she warns, and you won’t be able to run 26.2 miles on three month’s notice. 

Let’s assume you feel pretty good about your odds of following through in each area. You believe there’s a 70% chance you’ll stick with the fitness routine, a 70% chance you’ll stick with the nutrition plan, and a 70% chance you’ll stick with the sleep schedule. What are your odds of doing all three and showing up ready to run? 

The answer, surprisingly, is only 34.3%. You have three prerequisites to success. Individually, each seems likely to happen. But you need all three to play out as planned. When we multiply your odds of completing each step in the process, the outlook isn’t so rosy. 

This is a relatively simple goal. You only need three things to go right. Now imagine your odds in a more complex and challenging situation—like starting a successful business or winning a coveted promotion. Suddenly, it’s not surprising that nine out of ten businesses supposedly fail or that most people make a tradition out of falling short on their New Year’s resolutions. We aren’t getting unlucky. We’re experiencing the predicted failures associated with big goals and bad odds. But this isn’t a reason to give up. It’s a reason to probability hack. Here are three steps you can take to tilt the odds in your favor. 

1.  Think negative: do everything you can to identify and prevent bad outcomes  

If you flip a coin and call heads, there’s a 50% chance you’ll get the outcome you want and a 50% chance you’ll fail. Our real-life goals are more complex, but the same principle holds. The odds of all possible outcomes add up to 100%. That means, if we can make bad outcomes less likely, we’ll automatically boost our chances of success. 

Many people avoid wondering about things that could go wrong. After all, we’re supposed to think positive, right? Unfortunately, positive thinking won’t prevent bad outcomes, which means it won’t improve our odds. Preparation will. By identifying threats to our success, we can get creative and systematically de-risk our goals. 

When I applied to become the product director of a growing health organization, shortly after graduating college, my odds of success weren’t great. I was competing against a lineup of more experienced candidates. But I didn’t give up or resort to simply manifesting a good outcome. I took intentional steps to make it happen. 

To keep the hiring squad from rejecting me for my youth, I grew a beard to look older. To demonstrate I was up to the task of leading a demanding team, I typed up a spiral-bound plan for improving the department and gave it to everyone I met. To fit in like an existing team member, I read books I knew the team was familiar with, which allowed me to speak their language. The day after an important interview, I woke up to find an email from the CEO. He said I was the most prepared candidate he’d ever seen. Soon after, I was a twenty-one year old department head, on my way to a successful career. 

2.  Multiply your odds with the power of multiple attempts

An 80% chance of failure isn’t necessarily bad. It means for every five attempts, you expect to succeed once. A door-to-door salesman would be absolutely thrilled with that success rate. Knocking on 200 doors per day would lead to 40 sales! For some goals, it isn’t possible or practical to try multiple times. But for goals with a high degree of uncertainty, multiple attempts can actually be the most reliable way to break through. Sometimes you don’t have to beat the odds, you only have to play them. 

Apoorva Mehta estimates that he launched around 20 businesses before founding Instacart, including an ad network for gaming companies and a social media site for lawyers. When COVID hit, his grocery delivery service was in exactly the right place at the right time. Over a span of 10 months, Instacart’s valuation increased by over $9 billion.

Thomas Edison outcompeted his peers and found a practical filament for the incandescent lamp by experimenting with 6,000 different plant materials. Through this inglorious process, he discovered an unlikely winner—carbonized bamboo—and won valuable patents. 

History’s most famous creatives took a similar approach to produce enduring works of art. Mozart composed over 600 pieces of music. Beethoven wrote over 700. Van Gogh painted and sketched so prolifically, he averaged roughly one new work of art every 36 hours for 10 years.

And in the world of product development, Ben & Jerry’s created over 300 discontinued flavors on the road to uncovering classics like Chocolate Chip Cookie Dough and becoming the top-selling ice cream brand in the United States.

Contrary to popular belief, quantity is not the sworn enemy of quality. It’s a clever way to up your odds of producing great work. 

3.  Prioritize low probability steps

Your overall odds of success will never be higher than your most unlikely prerequisite step. For example, imagine you need four department managers’ approval to pursue a time-sensitive idea at work. You think the first three each have a 98% chance of saying yes. The fourth has a 10% chance of saying yes. Again, you need all four to approve. That puts your overall odds at 9.4% — not good. 

One proactive step you can take is first talking to the manager who will probably say no. Why? If he says yes, your odds will skyrocket. If he rejects the idea, you won’t have to waste time talking to the other three managers. This is a clever way to fail fast and focus your energy on projects that are likely to succeed. 

In a production mindset, we prioritize the longest pole in the tent. In a probability mindset, we prioritize the step with the longest odds. Doing so consistently is a reliable way to experience smaller setbacks and get more of what you want in life.  

Every goal that you’re pursuing has two hidden numbers attached to it—a probability of success and a probability of failure. If we can make the first number bigger and the second number smaller, we can rewrite your future. In the context of a single goal, it could change your outcome. Over the course of several goals, it could shift the trajectory of your career. Multiplied across a lifetime of goals, it could redefine your legacy. 

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