Finding Your Personal Lottery 🎟
5 min read

Finding Your Personal Lottery 🎟

Why thinking about the big picture matters.

Earlier this year, I won the lottery. I was making dinner and found myself mentally replaying a conversation with a friend. The Mega Millions prize was approaching $800M and we were discussing what we would do if we won the lottery. After the standard response about buying a yacht, the conversation moved on. But here I was, hours later, still thinking about it. The drawing was at 8:00. I checked the clock:


Just enough time. I grabbed my keys and rushed out the door, leaving my dinner to simmer. A nearby gas station selling tickets had a line spilling out the door, filled with people like myself having the same Sunday night revelation.

I bought my ticket and left the store, humming as I daydreamed about life after the big moment.

For those who know me, this may seem out of character. I consider myself to be a practical guy. My approach to most things in life is generally scientific and I’m not big on gambling. I couldn’t tell you the last time I played a game of slots or blackjack. Why then would I waste money on a lottery ticket, knowing that the odds of winning are infinitesimally small?

I believe that the value of a lottery ticket is not the chance of taking home the prize, but instead the opportunity to imagine your life after winning.

Sure, the chances of winning are small. But playing the game meant that I could allow myself to stretch my thinking by having skin in the game. Until I bought that ticket, it was someone else’s fantasy. By rushing out (and burning my dinner in the process), I did much more than buy a lottery ticket. I bought a dose of perspective.

During the interval between purchase and drawing, anything was possible. My life was like a Schrödinger thought experiment: I was rich and not rich, all at once.

I could seriously ask myself things like:

  • What would I do if money wasn’t a factor?
  • What issues are important to me?
  • Who would I tell first?
  • How do I want to spend my time?
  • What would I name my boat!?

Obviously, I keep a document with all of the answers to these questions. (remember:  practical).

The lottery is a beautiful thing because it gives everyone an equal chance to play. The slogan perfectly encapsulates the feeling I had walking out of the store:

“Hey, you never know.”

The drawing happened, and I didn’t win.

The ticket went in the trash, and I woke up the next morning and got back to work. But something was different. I had an answer to those questions that I asked myself on the way home. My trajectory had been changed, simply by asking myself the question of what if.

We all have dreams that live in the land of what if.

What if I learned a new language. What if I traveled the world. What if I wrote that book. On, and on, and on.

These what ifs are like my lottery scenario, except they are within our control.

Playing the lottery everyday has diminishing returns, and all you’ll likely show for it is an equally diminishing bank account. I’m not recommending this as a good course of action. Instead, I believe that the solution is to find an idea that borders right on the edge of impossible. This is what I think of as my “personal lottery”. It can be a lifestyle, a skill, an accomplishment — anything that brings you closer to the Mega Millions mindset.

As a litmus test, imagine that you had to have a conversation with a complete stranger for 30 minutes. Is there a topic could you talk about and walk away with more energy than when you started? If your personal lottery is in this category, you’re on the right track.

It is often helpful to look for external motivation when deciding on a personal lottery. We idolize people like Elon Musk and Steve Jobs, not only for their vision, but for their ability to show us what is possible. Their missions may not resonate with you, but their success is a benchmark for your own personal lottery.

Paul Graham reminds us that “follow your dreams” is bad advice. Instead, he suggests that people “stay upwind” by looking for promising situations. For your personal lottery, I believe you should take a similar mindset. Don’t choose a big goal just because it sounds impressive. Instead, choose something that brings you energy, and play the game of imagining how it could cascade to become a life-changing event. In your lottery, there is no what if that is off-limits.

Finding your own personal lottery means adjusting your perspective, and thereby your actions. Having a goal in mind isn’t enough. Remember my Mega Millions example: until I went to the store and bought a ticket, it wasn’t real. Similarly, to get the value out of a personal lottery, you need to put skin in the game. Much like a lottery ticket, this should be the minimum investment you can make to convince yourself the outcome is possible. It won’t seem like a wise investment to everyone, but neither does a lottery ticket. Remember, the goal here isn’t to throw money at the problem and hope to strike it rich, it’s to change your outlook.

After you’ve made a minimum investment, tell a friend. Talk about your lottery, and ask them to play the same game. Unlike the Mega Millions, no one needs to split this pot. The act of vocalizing your lottery will make it real, and you’ll have someone who will remind you of your intentions, even when everyday life makes it seem far away.

This concept has given me the freedom to work on things that seem interesting. Following the what if exercise means that I can ask big questions, and keep an open mind for opportunities that fit into my personal lottery. Winning the lottery doesn’t always mean the grand prize — the questions along the way tend to reveal enough to make the exercise worthwhile.

But hey, you never know.

📚 Reading

Astronomers identified a flare coming from the center of the Milky Way. It is generally accepted that our galaxy revolves around a supermassive black hole named Sagittarius A*. The formation conditions of supermassive black holes remain an open area of research, but the result is fascinating: a spherical region of space that creates a force so strong nothing can escape it, not even light. In May, the Keck observatory (located 13,000 feet above sea level at the Maunakea summit in Hawaii) observed an unprecedented event that caused the area around the black hole to flare 75 times brighter than usual. Due to our distance from the center of the Milky Way, we are just now observing this event, even though it happened over 26,000 years ago. Link.

Ebola is now curable. The World Health Organization (WHO) and the National Institutes of Health (NIH) have published extremely promising results from a trial testing an experimental drug to treat patients infected with the Ebola virus. The new treatment is created by extracting antibodies from Ebola survivors and administering it to patients intravenously. Ridgeback Biotherapeutics, a private and majority female owned company based out of Florida, produces the treatment. Link.

A fantastic read from Walter De Brouwer on the collective power of humanity and the increasing pace of innovation. Walter is the CEO of a personalized health company called, and has an optimism that takes over the room. Link.

Cloudflare has filed their S-1. Relatively unknown outside of tech circles, Cloudflare provides important infrastructure for the internet. Cloudfare faced increased scrutiny this month after deplatforming 8chan. Link.

An interesting piece from the New York times on the moderators behind Hacker News. With rising automation and reliance on machine learning within platforms like Facebook and YouTube, it’s refreshing to consider the human aspect of curation. Link.

Stripe has announced a negative emissions commitment and will spend a minimum of $1M per year on purchasing negative CO2 emissions at any price per tCO. It is a good time to be a company developing carbon sequestration technology. Link.

💎 Quote of the Week

“Study hard what interests you the most in the most undisciplined, irreverent and original manner possible.”

Richard Feynman

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