How to win the lottery
or a framework to address luck in outcomes
One of my favorite stories is about a man who really wanted to win the lottery. He prayed very hard hoping that God would help him win. The day of the drawing came and he did not win. Undeterred, he decided to double down. This time he would pray and fast as well. Unfortunately, the same outcome happened. For the next go round, he decided that not only would he pray and fast twice as hard but he would also do good works too. He volunteered to serve orphans, helped old ladies across the street, the whole nine yards. Sadly, when the draw was announced, he was still not a winner. Deeply frustrated, he raised his fists and yelled, “Lord, lord, I have prayed, I have fasted, I have helped the less fortunate. Why didn’t you help me win the lottery?” After a short pause, a deep voice rumbled down from the sky “Son, help me out a little. If you want to win the lottery, at least buy a fricking ticket!”
There are many lotteries in life. The most obvious ones are stuff like the Powerball, Megamillions and other official lotteries. But lotteries are just any game where luck plays a significant factor in deciding who wins or loses. For instance, we all play in the genetic lottery at birth. Some people get genes that predispose them to health and beauty but the less fortunate can find themselves cursed (through no fault of their own) with premature balding, high cholesterol or worse. There’s also the luck of having the right timing to be able to take advantage of your skills. Imagine if Lebron James was born 150 years ago, a couple years before basketball was invented. He’d be insanely talented at a sport that would not yet exist and would likely be a lot less celebrated. This is not really as much a hypothetical as you might imagine. My understanding is that Earl Woods was probably as talented a golfer as his son, Tiger Woods. However, he was born at a time when non-white golfers just did not have the same level of access so he was unable to realize his potential to the same extent.
Other lotteries include selecting a life partner, a career or running a business. Success in those endeavors entail some significant amount of luck. As a society, we tend to want to minimize the effect of luck with sayings like “This is a meritocracy” or “Good things happen to good people” but one of my general beliefs is that better outcomes come from acknowledging reality as it is not as I wish it was. Given this foundational belief, there are a couple axioms that help maximize the likelihood of success when playing these games.
Play lotteries you are more likely to win
If you are offered the choice between a lottery with a one in a million chance of winning or, for the same price, a lottery with a one in a thousand chance of winning, you would be a fool to select the former. This suggests that at the onset of entering a lottery, you should really look for ways to maximize the levers of success that you control. This would seem glaringly obvious but people seem to ignore this one a lot. I want to have a nice, stable domestic life with this person even though we can’t get along for more than five minutes but I’m sure they are “the one” because they are insanely hot or rich or high status or …. (fill in whatever criteria is orthogonal to relationship stability). I want to start a company doing this thing that no one else has succeeded in doing but I won’t do the work ahead of time to figure out why they failed and see if I can avoid those same tar pits that ensnared those that tried before.
Also, some lotteries are rigged. Certain people or people with certain characteristics tend to win. If you want to become a Supreme Court justice in the United States, it helps a lot to attend a law school at an Ivy League university. It used to be that you had to live in NY or LA to be successful in the entertainment business (it may be less so now with social media). Find out if there is some unfair advantage you can obtain (or often, even just table stakes you need) that increases your chance of success and try like hell to secure it. If you can’t position yourself within the favored group,, you should seriously consider if this is a game you want to play or if your time is better spent doing something else..
Play lotteries that announce winners often and quickly
For the same outcome, you should enter lotteries that give you more chances to play. It makes more sense to play a lottery that lets you find out if you win sooner than later. For instance, it can take a long time to figure out if a marriage is going to work out or not. However, you can likely get a sense of how a relationship is going from a few dates and (relatively) quickly weed out people that would definitely not work for you. Therefore, it would make sense to treat dating as an opportunity to show as much of your true self to the other person (rather than trying to project the most attractive version of yourself) so that you both come to a conclusion as quickly as possible whether there is a good long term fit.
In business, you should try to answer the hard questions upfront or as quickly as possible. These tend to be “Does anyone actually want what the business provides? Will they pay enough for it to be sustainable? Can the business find enough customers in a predictable and cost-effective manner?” If the answer to any of these questions is unsatisfactory, you should consider cutting your losses quickly.
Counter-intuitively, the goal should be to find out as quickly as possible if you have won, rather than to actually win. The idea is that the faster you find out that you are barking up the wrong tree, the faster you can change to something else that might work. This approach requires shifting the perspective many of us have with failure. Failure is often seen as objectively bad. People commiserate when a relationship breaks up, businesses go belly up or dreams are unfulfilled. This reinforces that failure is something that should be avoided at all costs and people drag things out for longer than they should. However, it can be useful to think of failure as a tool. It is an indicator that your efforts are best employed in some other manner. No one gets despondent when their GPS recommends a U-Turn. The only problem is if the warning came half-way through the journey or the driver of the vehicle doggedly ignores the directions.
Play lotteries that award prizes you want
This is another blindingly obvious one that gets missed all the time. Lotteries are replete with stories of winners who end up bankrupt, estranged from loved ones or dead. Most people do not really spend the time to think about the full picture of what winning the lottery actually entails and so they sleepwalk into a scenario they do not expect and do not really want to be in.
Earlier on in my career, I took a look at my bosses and realized that I did not want to grow up to be like them. I realized that the things I disliked about their careers were structural to the industry. If I was lucky enough to be successful, I was going to end up in exactly the same position they were in. That’s when I knew I had to get out and find some other industry to work in. Without that introspection, I would have worked really hard, made lots of sacrifices and, if I was lucky, ended up miserable.
I recently listened to a guy write into a podcast advice show wondering where he had gone wrong. He had been immersed in the pick-up artist scene and was now very successful at attracting women. However, all the women he was meeting were (according to him) “shallow gold-diggers” so now he was shocked (shocked!) that his approach of targeting women that would be easily impressed by gaudy shows of wealth and status was attracting women that were easily impressed by gaudy shows of wealth and status. Who knew that could happen!
People make this mistake in less odious ways all the time. You really want freedom and artistic expression but you choose to go to law school because it is safer and more prestigious (or the reverse case where you crave stability and choose to become an artist). You strive for that promotion even though it means working more hours when you really want better work-life balance. Whatever the prize you are going for, make sure it is worth everything that comes with it.
Buy as many tickets as possible
The more times you play, the more chances you get to win. I am often surprised when reading about highly successful people, just how much they did outside of the limelight before becoming publicly acknowledged. Sometimes you catch a glimpse of a movie star in the background of a movie earlier in the career or find out that a famous singer used to do background vocals for someone else. Many famous startup founders had a few unsuccessful companies in their past that no one ever heard of. It makes sense when you think about it. You only need one big success. It doesn’t matter how many dates you went on that went nowhere, how many resumes you sent out or how many ideas that went bust once you are in a good relationship, a great career or have a thriving business.
The insight here is to find ways to give yourself as many chances at bat as possible. Whatever your goal is , you should ask what the first step is and strive to find ways to have that event happen as many times as possible. If it’s a relationship, figure out ways to meet more people in a setting that can lead to a romantic spark. If it’s a career, find more ways to get in front of (or better yet, past) the gatekeepers of your industry. People tend to be more passive than their dreams would require. You should ask yourself what you can do to increase the number of potential chances you have to get what you want. Prioritize the things that can be done quickly and also have a higher chance of success. Then just keep doing that list of things over and over again for as long as possible.
This framework increases whatever odds you have to succeed and you would enjoy your success. It gives you agency over the factors that are within your control and helps you discover where you might have more control than you might otherwise imagine at first glance. Despite all this, nothing guarantees success. You can do everything right and still fail. That is inherent in the design of lotteries. However, the one thing that guarantees failure is if you never, ever even buy a fricking ticket.