If you had life over again: what would you do differently? Part 2—More Risk

A bunch of 95ers were asked this question and what they said is intriguing and instructive. Answer #2 was: they wish they’d taken more risks. Here are my thoughts on their answer.

This is a tricky one. More risk means more chance to fail. More failure means…well, what does that mean? Is failure all bad? Might it sometimes make you a better more resilient person?

That’s just one way the ‘risk’ answer is is a tricky one.

Risk and the desire for risk is highly personal. Some of us are just wired for more of it.

There is a guy, Alex Honnold, who, a couple years ago, climbed the face of El Capitan without a rope. Did you hear that? –No rope! No rope to catch him if he fell two thousand feet. With nothing but his two feet and two hands he climbed one of the highest cliffs of granite in the world. Now that, my dear brother, is taking risk.

Here’s what Alex says about it: “I talk about risk versus consequence. I don’t think I’m taking a risk because I’m not going to fall. But there is an extremely high consequence if I make a mistake.”

What? I’m sorry, that makes no sense to me. Even when he explained that comment on a podcast, I shook my head, confused. This is a guy who takes on enormous risk with almost no fear...like none. They even documented it in an F-MRI machine.

That, my friends, is a wired thing.

I knew someone else years ago who was extremely risk averse—I would say at the other end of the spectrum. She didn’t trust banks with her money or companies with her credit card. She didn’t invest her money in anything. She was insured way beyond her net worth. And she took every health caution known to man. She was wired for caution and safety and control.

Now, ask Alex Honnold to live her kind of life and I think he’d probably ask you to shoot him.

Ask her to even stand at the foot of El Cap and look up—much less climb it without a rope—well, you may as well take her out as well.

Taking risk is highly personal.

Risk, itself, is neutral—neither good nor bad. It can be good and stretch you and cause you to grow and enrich your life. But it can also do the opposite.

So, how do we learn from those 95ers who wish they’d taken more?

Maybe the solution is to take smart risk. Maybe the key to that is knowing yourself. Actually—that is the key. Knowing yourself is one of the most important things in life—and risk-taking. Knowing your weaknesses, your tendencies, your blind spots, your loves, your nature, your inclinations, your appetites, your aspirations, and your risk tolerance.

There it is: your risk tolerance. What is enough to excite you? What is so much that it keeps you up at night? You know…tolerance.

I’m in the financial field and this is one of the biggest concepts of all: know your client’s risk tolerance. But most people don’t know how tolerant they are until they are asked to answer questions like these.

1.      You are on a TV game show and can choose one of the following. Which would you take? $1,000, or a 50% chance at $5K, or a 25% chance at $10K, or a 5% chance at $100K?

2.      You just finished saving for a once-in-a-lifetime vacation and you lose your job, what would you do? Cancel? Go modest? Go as scheduled? Extend and go first-class?

Once you know your tolerance, then you can make a smart move.

My eldest son, Jess, recently took a big risk and I think he did it smartly.

Jess, now thirty-eight, taught middle school for ten years and loved it. He was well-loved and many students claimed he was their favorite teacher ever. Because Jess had struggled as a student, he was able to relate to and reach those who also struggled.

But he wanted more in his career…more income and more stimulation. So he took the risk of leaving the solid salary, good benefits, and future pension of a teacher, and opted for a career in real estate with all its ups and downs.

This was a huge decision for him and his family and he talked about it for years with his wife and me and others. He prayed to God a thousand times for wisdom and strength. He journaled about it extensively. He listened to hundreds of podcasts of those who had done something similar. He desperately wanted to take the risk but he wanted to do it smartly. In a nutshell he came to know himself and what he, personally, needed and wanted.

Now he’s delighted that he took the leap. It has been extremely stressful but also enlivening and harrowing and thrilling and stretching. In the past year he has grown in ways he could have never imagined. He is using his talents. He is learning new things. Now, a year later, he can’t even imagine not having made this move.

He found the sweet spot of risk, if you will, the Goldilocks zone: ”Not too hot, not too cold, but just right.”

And maybe that’s the key for all of us.

Know thyself.

Know thy risk tolerance.

Put thyself out there.

And don’t be one of those 95ers who regrets what you didn’t attempt.