How I Make Extremely Scary Decisions

It Started With a Motto

For a long time I’ve tried to live the motto: Memento Mori.

It’s like the grim cousin of Carpe Diem.

And the older brother that went to college and has his life together of #YOLO.

Memento Mori means to remember that one day, you too, shall die.

We’re given one lightning fast chance at life and then it’s over. (I know this is starting as a bit of a downer, but it improves as you read, I promise).

It drives what I do in my family, my faith, and my business.

It’s with that mindset that I’ve made massive changes and taken radical action in my life. More so in the last year than at any other time previously.

Because of this motto, I have:

• Made a personal brand for myself from the start, having no fear of putting myself out there
• Then started my own jiu jitsu company.
• Raised almost $3,000 to send jiu jitsu gis across the word
• Raised over $2,000 for a cancer charity
• Started a podcast that’s been downloaded over 111,000 times
• Coached other entrepreneurs, especially dads, on starting and growing their online business

Taking action on all of that involves getting over a LOT of fear.

And the reason for that is a secret that I recently heard echo’ed by Jeff Bezos, the founder of Amazon:

I went to my boss and said to him, “You know, I’m going to go do this crazy thing and I’m going to start this company selling books online.” This was something that I had already been talking to him about in a sort of more general context, but then he said, “Let’s go on a walk.” And, we went on a two hour walk in Central Park in New York City and the conclusion of that was this. He said, “You know, this actually sounds like a really good idea to me, but it sounds like it would be a better idea for somebody who didn’t already have a good job.” He convinced me to think about it for 48 hours before making a final decision.

So, I went away and was trying to find the right framework in which to make that kind of big decision. I had already talked to my wife about this, and she was very supportive and said, “Look, you know you can count me in 100 percent, whatever you want to do.” It’s true she had married this fairly stable guy in a stable career path, and now he wanted to go do this crazy thing, but she was 100 percent supportive. So, it really was a decision that I had to make for myself, and the framework I found which made the decision incredibly easy was what I called — which only a nerd would call — a “regret minimization framework.”

So, I wanted to project myself forward to age 80 and say, “Okay, now I’m looking back on my life. I want to have minimized the number of regrets I have.” I knew that when I was 80 I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the Internet that I thought was going to be a really big deal. I knew that if I failed I wouldn’t regret that, but I knew the one thing I might regret is not ever having tried. I knew that that would haunt me every day, and so, when I thought about it that way it was an incredibly easy decision. And, I think that’s very good. If you can project yourself out to age 80 and sort of think, “What will I think at that time?” it gets you away from some of the daily pieces of confusion. You know, I left this Wall Street firm in the middle of the year. When you do that, you walk away from your annual bonus. That’s the kind of thing that in the short-term can confuse you, but if you think about the long-term then you can really make good life decisions that you won’t regret later.

I have a wife just as awesome as Jeff.

She’s with me 100%.

She’s equal parts co-founder and Ride-or-Die.

She has that loyalty you just can’t buy.

But that also means her loyalty deserves respect, even reverence. You don’t abuse loyalty like that just because you can.

And it’s also true that, like Jeff, my wife married a really stable guy in a stable career path.

Teacher>Assistant Principal>Principal>Retired. That was my jam.

But then it wasn’t.

And if you’re like me, you can’t un-learn your entrepreneurial DNA.

So we set out on this new path based on what I *wasn’t* going to regret when I was 80.

So every time a big pivot or opportunity comes my way, I think about this framework.  And sometimes it sucks and I lose a lot of money. And other times it pays off.

A Framework For Making Extremely Scary Decisions

When you think of a framework, you typically think of grids and boxes and matrices and all of that jazz.

But not with this. It’s a simple yes, or no.

And that’s because failing is really hard.

But, in the long run, not trying is far, FAR worse.

There’s a very good chance that you, reading this right now, are thinking about making a major pivot in your family, business, and life.

So just answer the simple question:

When I’m 80, will I regret having never tried this?

I’d love to hear your thoughts in the comments below.