Worth The Risk?

If we measure risk with regret, how does your life stack up?

“Non, Je Ne Regrette Rien” -Edith Piaf

“No regrets/No Tears Goodbye” - Tom Rush

“You know, if I had a chance to do it all over again/ I wouldn’t change sh*t” -Eminem

In my wellness newsletter I share articles I find useful for optimizing wellbeing. Last week, I offered a short read on “Risk and Regret”. The gist is that risk can be measured in regret: “We spend so much time quantifying risk when the answer is just figuring out what you will and won’t regret” (Housel). 

How risky are you? 

What regrets do you live with, if any?

Drawing back from those very big questions, let’s start here: what is your attitude on risk-taking? What emotions fire when you think of being risky?
(Do you picture Tom Cruise singing Bob Seger? I just aged you. Ha!)

Risky is often associated with immaturity, while risk carries many “grownup” connotations. “I am taking a risk” hits different than “I am a risky person.” 

Risk is a financial investment. Changing jobs. Risk is a noun, an idea. Perhaps that makes it feel controlled. 

Risky feels like impulsivity and recklessness. Behaviors that elicit raised eyebrows. Risky is meeting a stranger who slid into your DMs. Free Climbing. Risky is an adjective, a descriptor. Perhaps that makes it a bit more wild? 

The deeper we entrench ourselves in routines, the more uncomfortable risk becomes. It’s normal, but is it a good thing? In many ways, the arc of adulthood is about seeking stability and creating roots. Are the roots you’ve planted a strong base for a good life? Or are they snaring you and preventing growth?

Both, most likely. 

The question isn’t whether or not you should become riskier. No one’s asking you to scuba with sharks. 

The question is, are you avoiding risk and playing it safe in ways that will lead to regret? Maybe you want to scuba with sharks.

It’s fair to say I’ve become a risky person. I’d like to think I balance that with wisdom to avoid foolishness. My first taste of risk came after 7th grade. Before that, I was a pretty timid kid. But that summer, my dad and I had a ton of adventures. We hiked, we bungee jumped, we raced go-karts–all things I’d never wanted to do before. Each adventure got my adrenaline pumping and butterflies beating hard in my chest. 

And I freaking loved it. 

It helped me see that I could be daring. I could push through fear to experience something wholly new. Something that I’d have wished I said yes to if that fear had held me back. 

I did get hurt. I fell off a log and narrowly missed breaking a rib on the hike. But even that was a good lesson. I learned that pain and danger can be part of the experience. Pain didn’t prove my fear correct. It taught me that risk can come with a price, and that’s okay, too. The reward in that case was an awesome experience and an appreciation of proper hiking shoes. 

Those lessons stayed with me and became part of my core belief as I grew up. That summer of adventure gave me the confidence to keep growing and go out on my own. To leave home and move to NYC. To become a Spartan racer. To say yes to the madness that 2020 brought.

And certainly to flip the table on my life after years of careful construction. 

I like to say I don’t believe in regrets. Obviously, I don’t question the existence of the concept. Rather, I don’t like to live with regret. There are many things I wish I had done differently. Most have to do with wishing I’d acted with more kindness and gentleness, either to others or to myself. But I don’t regret even my most painful memories because they brought me here. Every risk, every leap into the wild unknown, made me more of who I am today. More of this quirky, passionate, inspired human being who I’ve become. And, yes, I can acknowledge moments where I was too hard in my approach. But I had to be that way to learn how to become soft again in just the right way. 

One morning on my soul journey in Scotland, I was on the brink of what I knew would be a life-changing moment. As I waited for it to begin, I sat and journaled. And what I said was, 

I don’t know what all today holds. But this is what I want, and I’m not worried about the pitfalls.

If I fall, at least I jumped. 

I fell. Hard. In so many ways. But every moment of pain had its complementary moment of triumph and pleasure. I risked a lot to find myself. I paid a high price. And I have no regrets. 

One could argue that’s an easy thing to say when you’re through it all and living a beautiful life. And indeed it is. But here’s the thing, and I want to make this very clear:

I never had any regrets. Not even when I was sorrier than I ever imagined I could be. Not even when I was more broken than I ever knew I could be. I had made my choices. I had leapt. I knew the risk and accepted it all. I knew that it would change me, and I was ready for the change. I needed to go through the fire, and I knew (thought) I deserved the hurt. 

So maybe I am risky. Maybe diving with sharks is a crazy dream. Maybe I shouldn’t talk to strangers. I’m definitely not free climbing, so at least that’s something, right? 

Or maybe I’m comfortable with risk. Maybe I know some things will scare the hell out of me, and that’s why they’re worth doing. I got into (indoor) rock climbing because a friend said, “How do you feel about heights?”

Me: “They scare me, so I try to face the fear when I can.”

Him: “Cool. We’ll go climb.”

And, I love climbing. I love living. I love leaping into the wild unknown when my intuition says it’s the right thing to do. But I also am confident to say no thanks when it doesn’t feel like a risk I want to take. 

It’s knowing the difference, I suppose, that makes me wisely risky.

What do you think? 

Are you risky?

Do you live with regret?