
Imagine that you have set a goal to run a marathon within 90 days. You’ve hired a trainer who says this for a less than optimal amount of time, but if you religiously follow your exercise routine, nutrition plan, and sleep schedule, you’ll be ready on race day. If you cheat in any of those three areas, he warns, you won’t be able to run 26 miles on three months’ notice.
Let’s say you feel pretty good about your chances of moving forward in each area. Believe there is a 70% chance of following the exercise routine, a 70% chance of following the nutrition plan, and a 70% chance of following the sleep schedule. What are your chances of doing all three and showing up ready to run?
The answer, surprisingly, is only 34.3%. You have three prerequisites to be successful. Individually, each seems likely to happen. But you need all three to go as planned. When we multiply your chances of completing each step of the process, the picture is not so rosy.
This is a relatively simple goal. You only need three things to do well. Now imagine your odds in a more complex and challenging situation, such as starting a successful business or earning a coveted promotion. Suddenly, it’s no surprise that nine out of ten businesses supposedly fail or that most people make it a tradition not to keep their New Year’s resolutions. We’re not having any luck. We are experiencing the expected failures associated with big goals and bad odds. But this is no reason to give up. It’s a reason to hack probability. Here are three steps you can take to tip the odds in your favor.
1. Think negatively: Do everything you can to identify and prevent bad outcomes.
If you flip a coin and say heads, there is a 50% chance you will get the result you want and a 50% chance you will fail. Our goals in real life are more complex, but the same principle applies. The probabilities of all possible outcomes add up to 100%. That means that if we can make bad outcomes less likely, we will automatically increase our chances of success.
Many people avoid wondering what things could go wrong. After all, we’re supposed to think positively, right? Unfortunately, positive thinking won’t prevent bad outcomes, which means it won’t improve our odds. Preparation will do it. By identifying threats to our success, we can be creative and systematically de-risk our objectives.
When I applied to become a product manager for a growing healthcare organization shortly after graduating from college, my chances of success weren’t great. He was competing against a lineup of more experienced candidates. But I didn’t give up or resort to simply manifesting a good result. I took intentional steps to make this happen.
To prevent the hiring team from rejecting me because of my youth, I grew a beard to look older. To prove that I was up to the task of leading a demanding team, I wrote a spiral plan to improve the department and gave it to everyone I met. To fit in as an existing team member, I read books that I knew the team knew, allowing me to speak their language. The day after an important interview, I woke up to an email from the CEO. He said I was the most prepared candidate he had ever seen. Soon after, I was a twenty-one-year-old department head, on the path to a successful career.
2. Multiply your odds with the power of multiple attempts
An 80% chance of failure is not necessarily bad. It means that for every five attempts, you expect to succeed once. A door-to-door salesperson would be absolutely delighted with that success rate. Knocking on 200 doors a day would generate 40 sales! For some goals, it is neither possible nor practical to try multiple times. But for goals with a high degree of uncertainty, multiple attempts may be the most reliable way to achieve this. Sometimes you don’t need to beat the odds, you just have to play them.
Apoorva Mehta estimates that she launched about 20 businesses before founding Instacart, including an ad network for gaming companies and a social media site for lawyers. When COVID hit, their grocery delivery service was in exactly the right place at the right time. In a span of 10 months, Instacart’s valuation increased by more than $9 billion.
Thomas Edison surpassed his peers and found a practical filament for the incandescent lamp by experimenting with 6,000 different plant materials. Through this embarrassing process, he discovered an unlikely winner: carbonized bamboo, and obtained valuable patents.
History’s most famous creatives took a similar approach to producing lasting works of art. Mozart composed more than 600 pieces of music. Beethoven wrote about 700. Van Gogh painted and drew so prolifically that he averaged approximately one new work of art every 36 hours for 10 years.
And in the world of product development, Ben & Jerry’s created more than 300 discontinued flavors on the way to discovering classics like chocolate chip cookie dough and becoming the best-selling ice cream brand in the United States.
Contrary to popular belief, quantity is not the staunch enemy of quality. It’s a smart way to increase your chances of producing great work.
3. Prioritize low probability steps
Your overall chances of success will never be greater than the most unlikely previous step. For example, imagine you need approval from four department managers to implement an urgent idea at work. You think the top 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 it. That puts your overall odds at 9.4%, which is not good.
A proactive step you can take is to talk to the manager first, who will probably tell you no. Because? 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 smart way to fail quickly and focus your energy on projects that are likely to succeed.
In a production mindset, we prioritize the longest tent pole. In a probabilistic mindset, we prioritize the step with the highest probabilities. Doing it consistently is a reliable way to experience smaller setbacks and get more of what you want in life.
Each goal you pursue has two hidden numbers: a probability of success and a probability of failure. If we can make the first number larger and the second smaller, we can rewrite its future. In the context of a single goal, it could change your outcome. Over the course of several goals, you could change the trajectory of your career. Multiplied over a lifetime of goals, it could redefine your legacy.

