The psychological benefits of taking risk

When I was in the sixth grade, my English teacher asked the class to consider if we would rather be moths or cockroaches. The distinction, as he explained it, was this:

Moths live quick but thrilling lives. They flutter around with wild abandon living almost their entire lives in a state of excitement but ultimately meet their destiny in a blaze of glory, flying just a bit too close to the flame.

Cockroaches, on the other hand, live long but monotonous lives. They trade glory for longevity, traveling in darkness and avoiding danger at all costs.

I always thought that I'd rather be a moth. If you're going to live, you might as well really live, right?

Like many young men, that philosophy led me to take more than my fair share of risks with my body (barreling down icy ski slopes), my health (enjoying maybe a few too many adult beverages), and even with my career (quitting a high-paying job and moving cities without a safety net).

But as I’ve gotten older—especially in my 30's and into my 40's—I’ve certainly become more careful—with my body (exercise, diet), my finances (investing long-term), and my relationships (learning to bite my lip more every year).

An objective look at my behavior would likely show that I am more risk-averse at 42 than I was at 22. (Some might say more boring, but let's stick with risk-averse).

Much of this is a natural progression. In our teens and twenties, we test our boundaries. We try to figure out who we are. We aim high, and as a result, tend to hit both higher highs and lower lows in every part of our lives.

But by the time we hit middle age, things stabilize. We find partners and settle into long-term relationships. We better understand our talents and weaknesses professionally. And we (hopefully) get a handle on our finances.

If we're lucky, we get families, and houses, and investment accounts.

And who could complain about any of that?

But of course, the irony in acquiring all of these things is that we now have something to lose. And the natural reaction to having more to lose is to risk less.

So we become more conservative.

We stay in that 'safe' job longer than we should. We balk at trying that new hobby or sport. We're less open to meeting new friends.

We're comfortable. Maybe too comfortable. Starting-to-look-like-a-cockroach comfortable.

And then comes the blowback. We get bored or depressed or disillusioned. We think "Is this it?"

And we’re faced with the sudden reality that it’s not the mountain top that makes us happy or that keeps us motivated. It’s the climb.

Put another way, we are wired to always be reaching for what's next.

Those things are more obvious in our 20's and 30’s: financial success, a loving mate and family, a stable/lucrative career.

But by the time we hit our 40’s? Or 50’s? Or 60’s? Not as obvious.

And we risk falling into the trap of complacency. Of thinking “Yes, I guess this is it.

And it is at exactly this moment when our ambition dies. When we stop trying to get better.

But guess what—it doesn’t need to be this way.

We can, and in fact, need to, keep reaching. In our careers. In our finances. In our health. In our relationships.

Enter Moonshots.

A moonshot is a particularly ambitious initiative that has a high chance of failing, but if successful, would have material, positive consequences.

The futurist Peter Diamandis compiled a list of humanity’s top-50 moonshots over the last 20 years, which includes things like:

  • Putting all the world’s information at our fingertips (Google)

  • Mass production of electric vehicles (Tesla)

  • Sequencing the human genome

All feats that seemed impossible just a decade or two ago, but which have now been accomplished.

So what do Google and Tesla’s achievements have to do with you and your motivation to get out of bed in the morning?

A lot, actually.

Believing that things can get better, and actually taking steps toward such goals, can have incredibly positive impacts on our psyche.

It’s the reason why people book their next vacation as soon as they get back from the last one. Because we all want and need something to look forward to.

And that’s what moonshots provide us with—not just in technology, but in all areas of our lives. Lofty targets give us a reason to hope.

So how can we implement moonshots in our own lives?

By thinking big. I’ve already told you that for me, 2021 is about 10x growth vs. 10% growth. And we can only achieve that type of dramatic change by smashing through mental roadblocks that have held us back for too long.

How about some examples? Here are just a few from my own experience—both past and present to give you a sense of what I’m talking about:


  • Quitting my job — I quit my job in 2012 and moved to Charlotte, a city where I knew no one. I was told I was making the biggest career mistake of my life. Walking away from a high-paying job that I could have stayed comfortably at for decades. It sure was scary, but I wanted more. I wanted another challenge professionally. I wanted a better climate and a better place to raise my kids. So I shot my shot. So far, it’s worked out.

  • Writing a book — I had serious imposter syndrome when I sat down to write my first book, CFA Confidential. Who was I to write a book? I was in sales before that! I had no writing credentials. And just to make it particularly egregious, I then had the gumption to FedEx copies of the manuscript to the world’s top-20 investors. A serious moonshot. I never heard back from 19 of them. But one of them responded. Charles Brandes. He’s a billionaire and one of the richest living Americans. He loved the book and his quote now graces its cover. Seven years later, the book still sells. Who gave me permission to do this? No one. I shot my shot.

  • Starting a podcast — I started a podcast for my company in 2018. I had zero experience on a microphone and not one person told me it was a good idea to do. We’ve now recorded 50 episodes and have over 5000 subscribers. What gave me the right? Nothing. It was a shot.

  • Crazy streaks — I had a goal of working out every day for a year. That’s crazy. I ended up going 483 days and wrote about it here. I also had a goal of not drinking for a year. That happened, too. Who was I to do these things? No one. I just did them. I took a shot. Don’t worry though… they certainly haven’t all ended well. Case in point: My year without dessert. It ended after a month. Damn you, sugar. Too strong to resist.


  • Growing an audience — So now I’m taking a moonshot on growing an audience. Did you know I have a goal of having 5000 Twitter followers and 1000 newsletter subscribers by the end of this year? Probably not, because this is the first time I’m telling anyone. And guess what? I’m not even close! Today, I have 639 Twitter followers and 245 newsletter subscribers. A long way to go, but just a couple of weeks ago, those numbers were 535 and 153, respectively; they’ve grown quite a bit recently, thanks in part to this tweet. Will I achieve this goal? Probably not. But I’m going to try. It’s a moonshot and it’s written on a whiteboard right in front of me, so it’s kind of hard to ignore.

The thing I love about moonshots is that they give me a chance. It may be a tiny chance but it’s a chance. I’m in the game.

Pick your cliche:

  • You can’t win if you don’t play.

  • You miss 100% of the shots you don’t take.

The point is the same. I can go to bed every night knowing that I have placed a bet that has a chance of going amazingly right, and which could be life-changing for the better. That is a major psychological boost compared to having a “this is as good as it gets” attitude.

Ultimately, risks are worth taking. And big, ambitious, unlikely goals make life more fun to live.

Let me remind you as I’ve done before that we only get one spin around this planet.

Let me also remind you that people who are no smarter, no more talented, and no more motivated than you or me are setting goals today—probably at this very moment—that are way, way more ambitious than anything I’ve even discussed here.

So let me ask you: What moonshot are you taking? And if you’re not? Exactly why not?

Thanks as always for reading. I’ll be back in your inbox next Thursday morning.

Have a great week.



Photo credit: Sanni Sahil

Extra credit

If you’re wondering why I want to grow an audience, it’s because I believe we’re entering a new type of economy that will be driven more by individual contributions to the world and less by corporations. Think: the ‘gig economy’ on steroids. In fact, I think right now there is an almost unbelievable opportunity to create and sell things online. People are minting fortunes daily on platforms like Twitter, Youtube, Gumroad, Teachable, TikTok and others… not just by entertaining, but by teaching. Having an established audience helps you get your message out there when you’ve got something to say (or even sell). I’ll write more on this soon but if you have ANY type of skill that you can teach to someone else, you are a candidate to do this. Why not shoot your shot?

THE LOST SECTION!!! - I killed the below section of the article because I thought it would be too distracting—but speculative investing can also be considered taking a moonshot. Just do so at your own risk!

  • Buying Bitcoin — I’ve been buying Bitcoin since 2017. Here’s my thesis: It’s entirely possible that a new asset class is being created before our eyes and that this so-called “digital gold” will become a common allocation for almost every investor on the planet. If that happens, there are massive amounts of money that will flow into Bitcoin over time, and the law of supply and demand means that that should inevitably push the price higher—maybe materially so. Today, the price of Bitcoin is roughly $36,000. Some ‘experts’ think it should be worth $400,000. Others say $3,000. Guess who’s right? I have no idea. No one does. There is a very real chance that Bitcoin goes to zero. Why? Who knows—there could be a problem with it that we can’t see today or another technology could take hold instead. So, I’ve invested some money that “I can afford to lose” (meaning it won’t materially impact my life if it does go to zero) but it’s also meaningful enough that if Bitcoin does end up being a homerun, it could materially impact my life for the better. In essence, I’ve decided (with this very small and very speculative part of my portfolio) that I’m holding it either until it goes to zero OR it pays off my mortgage—whichever comes first. In other words, it’s a moonshot. And there’s a positive psychological benefit to knowing that I own a small piece of something that could be transformational. If you want to get smarter on Bitcoin, here’s a good intro podcast with Naval Ravikant on Tim Ferriss. And if you want to learn more about the crypto ecosystem (aka picks and shovels) which I’m increasingly thinking is the way to actually invest in this trend, here’s a great recent podcast with Chris Dixon from the VC firm A16z. By the way, please don’t take this as any type of encouragement to invest your own money in Bitcoin. If you want to know what I think about taking financial risks, especially with money you can’t afford to lose, please read this. Invest at your own risk. Thanks again for reading!

    Subscribe now