The $10,000,000 Question

Most of the people I know are dissatisfied with their lives. We live in the best age, but all we do is want more. What we crave is more meaning (depth), but what we end up getting is more stuff (breadth).

In short career so far I’ve gone from eating Saltines while living on a leaky, heatless boat in winter to pursuing my dreams on a daily basis. Nothing is easy and straightforward. Some days I’m just as miserable as when I was starting out. Here’s are a few ways I stay aligned and make sure each decision takes me closer to my mountain.

How to find something better than what you’re currently doing

I dropped out of college because it was boring as shit. I wasn’t learning much, and all the wrong stuff. After high school the idea of more school didn’t interest me, but it’s what I was “supposed to” do. Isn’t every middle class kid supposed to go to college? But I knew that dropping out would be enough. I needed a dramatic change–something that would force me to grow. So what did I do? I moved to the Philippines. That seemed pretty dramatic.

It’s scary to make a big change. You never know what’s going to happen and your mind tends to thinks of the worst possible outcomes. For instance I thought I would be sold into white slavery by my Filipino host who I met through a mutual mutual mutual friend. The reality? He’s now one of my best friends, and I was in his sister’s wedding in February. The point is the unknown is terrifying. But moving somewhere isolated let me listen to myself. I was able to find “the thing” that I wanted to do–programming. I didn’t know if it was my life’s work, but hey, it was more interesting than college. I took the plunge and started teaching myself to code.

The $10,000,000 question

My favorite question to ask people is:

“What would you do if got $10,000,000 today?

Most people laugh after I say this so I ask again–if you had $10,000,000, after tax money, what would you do?

I often get the same responses; travel, invest, or both. That’s cool bro, that’s my answer too. What then?

The beauty of this question is you can always drill down. There is a theme to this list as you refine it: buy stuff, donate, give gifts, travel. All that takes about 6 months. So what happens then?

This is where people get stuck. It’s a big scary question that we never address. If I never had to think about money again, what would I do with my time over the next 20, 30, 40, 50 years? Years. That’s a lot of free time for playing video games and travelling. You’re going to want to do something more, but what is it?

Just do f***ing it

Ok, so now you know exactly what you want to do! Just kidding. The goal of this question is to find something that you want to do more than what you’re currently doing. And then do it. It doesn’t have to be your life mission, just something better. People often have very simple, achievable goals and don’t realize it. Spend time with your kids, fishing, or getting involved in your community.

If you’re trading your time for money to have more time to play with your kids, why not just spend more time with your kids? Achieving your goals isn’t that hard when you actually know what you’re working towards. Retirement is the golden period of our lives where we have complete time freedom, but we rarely plan what we’ll do with the time once we have it.

Some of your dreams you can’t do yet. That’s ok too. Once defined, make decisions to get you closer. If you want to spend 6 months volunteering in Bali, start with 3 weeks off and try Bali out. Or somewhere closer. All this “some day” shit is just that–shit. If you know what you want, go get it. If money’s the blocker don’t spend on things you don’t need! I guarantee you if you’re motivated enough you can save money by eating Ramen noodles and PB&J for a month. No, not ideal or fun, but we’re talking your life goals here. It’s worth the sacrifice.

Measure each decision against where you want to be. Seeing how your actions bring forward or push back your goals can be a powerful motivator. Don’t focus on perfection; focus on progress.

If you’re looking for some Monday inspiration, watch Shia LaBeouf scream a lot. Just do it inspiration.

How to refine your passion

You change, your goals change. As you progress you may find that your goals are less inspiring. Or you need to level up your goals as you level up. Improve your goals as you grow. I wanted to be a programmer and now building products and ideas is more interesting than coding. I still have lots of fun building MVPs but wouldn’t be happy only writing code for the rest of my life.

A good way to envision your goal is as a distant mountain. As you get walk towards it, you might notice it’s more to the left or right. As long as you make decisions that get you closer to the mountain you’re doing well. Just don’t go further away from it.

I picked this concept up in a commencement speech by the amazing writer Neil Gaiman (). Continue to refine your goals, actions, and commitment and every step you take will get you closer to your mountain.

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