How to Take Smart Risks Without Being Reckless

Wake-Up Call #24

This hat, worthy risk, or straight-up reckless?!?!

When I was 16, we had this game we used to play.

Roof riding. A few of us had licenses already and we were all, frankly, morons. 

We’d take the cars, one, a 1960s VW bus, the other, a 1970s Plymouth Duster, out to the end of Sands Point late at night. I grew up in Port Washington, the Long Island peninsula that the Great Gatsby’s East Egg was based on. Sands Point, was the bougie, quieter tip. Windy, wavy, bumpy roads, lined with massive, old Maple trees.

After midnight, you’d barely see other cars.

We’d stop in the middle of the road. One of us would climb up, spread-eagle, face-down on the roof of the WV bus, fingers clutching the rain gutters. The other would lie face-up on the hood of the Duster, arms overhead gripping the windshield edge. Hanging onto, well, everything you could, which amounted to very little.

The game: for the driver to hit the gas, swerve, avoid trees (not always successful), stop short, do donuts, all in the name of trying to knock the idiot on the roof or hood off.

Sixteen year-old stupidity masquerading as fun.

We knew it was risky, especially the VW, nothing to really hold onto, and a reputation for tipping if you took a turn to hard and fast. But, we were high-school-boy invincible. The fact that one of the drivers had already totaled two junkers before graduating high-school, without a single hospital visit, made us feel like fortune was on our side. Or, at least, his.

Hindsight. We’re lucky to be alive. It was straight up reckless. Insane.

Fast forward. Middle-age. I’m talking to a leading adolescent psychiatrist and researcher. He describes the state of the adolescent brain as “all gas, no break.”

Science tells us that part of the brain that controls impulse, literally, doesn’t fully form until the age of 25, which is now considered the end of adolescence. Until then, there’s a physiological basis for recklessness. That’s not a license to be a dope, or forgiveness for repercussions, but it’s a partial explanation rooted in something beyond judgment.

But, what about as we get older?

How do we do the dance of identifying, then taking risks that expand, maybe even define, our lives, while not being utterly reckless?

Or, on the other extreme, how do we avoid becoming so fear-driven and cloistered that we stop taking any meaningful risk and, as a consequence, stop living, and growing, and glowing?

Risk isn’t a bad thing, just by its nature.

It’s actually the gateway to a lot of what makes life good. It signals that something’s on the line. That you don’t know how it’s going to end. That, in some way, it matters to you. Risk is an essential element of growth, and possibility.

If there’s zero exposure, the thing you’re considering is either so sure, or devoid of stakes that, even if it works out, won’t matter to you. Nothing is on the line. Which is safe, but also profoundly stifling. It stops us from doing things that open the door to growth, connection, and expression. It keeps you writing a life-story inside a cage draped in a blanket of smallness.

Nearly everything good in life comes on the other side of our willingness to step into the unknown, when the stakes are real.

But, then there’s that recklessness thing.

At a certain point, risk tips into indefensibility.

Our task is try, best as we can, to suss out what is worthy risk versus straight-up reckless. 

How? 

Many times, if we get quiet for even a minute, look at the obvious facts, and check in with our intuition, we’ll just know.

Roof riding? No analysis needed. Just stupidity.

Then there are those other times, grayer lines, it’s not so easy.

In those cases, think about three things:

• Stakes - what is the value of the thing being risked? How are you measuring that value? Meaning, money, status, connection, impact, time, stories, etc? Can you quantify it?

• Probability - What is the likelihood of success and/or failure? And, if there’s no easy way to determine this, are you okay with that?

• Recoverability - Is there a realistic path to recovery and/or redemption upon failure? What does it look like? And, even if a path is available, what is the added cost?

The scenarios are endless:

Joining a startup team or raising money to launch your own venture to build a product or platform that’d change millions of people’s lives? 

Snowboarding in trees on a deep powder day? Or, in the back-country? With avalanche training? Without? Riding the park and learning to jump? 

Working in a job where you’d learn a ton, but potentially be assigned to projects or accounts you could care less about?

Introducing yourself to someone you think you’d love to start a relationship with?

Taking a gap year or sabbatical to work more on you than work?

Writing a book, before building a platform to help it find an audience?

Everything worth doing involves risk.

Trick is to step into risk that holds the potential for growth, without crossing the line into recklessness where the stakes, probability, and recoverability no longer justify the means or the end.

So, what’s your take?

How do you do the dance between worthy risk and outright recklessness?

What’s your take? Intuition? Data? Spreadsheets? Just say yes?

With a whole lotta love & gratitude,

Jonathan

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Wake-Up Call #24 | Where’s your Risk/Recklessness Setpoint?

I’ve increasingly found that many of us have a certain risk tolerance setpoint. Especially as the stakes get high. I’ve also noticed this can be change across different domains. You might be very comfortable risking vulnerability in the domain of relationships, but not at work. Or, risking time on learning, but not on love.

Think about your Risk Setpoint. When the stakes are high (however you define that), are you cautious/risk averse, somewhere in the middle, risk-seeking, reckless even?

Where does your natural inclination lie? And how do you feel about this?

Is it limiting or exposing you in any way that bothers you?

How might you tap the three metrics—stakes, probability, recoverability—to reimagine how you step into the unknown in a scenario you’re exploring right now?

Noodle on it, move with it, write about it. And, if you’re inclined, share in the comments.