Biggest Lesson I've Learned In 2024

Our desire for certainty steals a whole lot of time from our lives.

Days. Weeks. Even years.

When I think about the hours I’ve spent torturing myself over different decisions, that were not life or death, it blows my mind. And frustrates me. The time I spent determining which way to go could’ve been better spent starting, figuring out how to get over the wall when it appeared, and having the strength (and courage) to figure out how to fix it when I become stuck.  

Not to mention all the hours of complete misery we put ourselves through over something that “might” not go our way or the anticipation of the worst possible outcome (which rarely happens). And of course, there’s that lifelong and timeless foe we all struggle with: worrying over something we have absolutely zero control over. 

Like I said…Days. Weeks. Even years.

But where I’ve encountered this the most over the past few years is questioning the certainty of success. Putting myself through mental angst over things to creatively pursue, based on whether or not it will all work out in the end. Trying to look into a crystal ball deep down I know doesn’t exist.

From the time we are children, our parents make decision after decision to try and guarantee our success the best way they can. I do it for my own child now. It’s a natural parental process we follow to do our best at setting up our children for the best possible future in adulthood. Nothing wrong with that. 

But my larger concern is whether or not we lose our ability to take worthwhile chances. To go for things, boldly, without guarantees, and under the uncomfortable cloud of knowing this might not work out…but that it’s still worth pursuing because it makes us better, and stronger, and builds us in ways we can’t fully understand or recreate in any other way. 

Life feels like it’s never been more uncertain. But whether or not this is true – does it have anything to do with how we should view success, ambition, and the pursuit of worthwhile goals?

When we think about putting time and effort into anything in life, we have this ingrained tendency to go down the list and make sure that we aren’t “wasting our time” or putting effort into something that won’t pan out.

This is exactly where our decision-making skills stall out and find themselves lost in a sea of uncertainty, drowning in all the possible scenarios that will prevent us from achieving whatever we’ve set sail to achieve.

A successful businessman in my hometown told me something in my mid-30s that I’ve never forgotten: 

“Everybody will tell you all the ways a deal can’t get done. You just have to figure out the one way it can get done.”

I think that’s true about success in general. If we set goals based on certainty or favorable odds or most likely scenarios…are we setting goals or self-imposed boundaries?

Because despite what we tell ourselves about any success story in the world we admire, there was no guarantee — no perfect playbook, no script. 

Instead, it was determination. Confidence in thy self. Willingness to get dirt thrown on their face. And, no doubt a little ‘positively naive’ as I call it. 

When you study the stories of your heroes you’ll discover that they weren’t nearly as “qualified” for the success as you might imagine. You’ll learn their story wasn’t inevitable as it reads in the biography or memoir. The beginning chapters are almost as boring and uninspiring as our own often feels.

Certainty is nowhere to be found.

Somewhere in our lives, we started chasing certainty — guaranteed success. Sometimes out of entitlement, or personal or family security, but often out of personal peace of mind, so we don’t have to deal with an ounce of rejection or failure. At the core, we simply fail to stretch ourselves beyond what we believe we’re capable of today.

And the merits and concerns on this are understandable. Life is hard enough. Who needs failure, rejection, and just-not-being-good-enough to add on top of all that life throws our way?

I get it. By 18, I was in complete survival mode already. So the thought of pursuing something hard or taking chances or stretching myself beyond what I could imagine or having the courage to chase something without guarantees was absurd. I was just trying to make it to the next day or week.

But as I look back on every great thing in my life, it was filled with uncertainty. Will she say yes? Will they give me a chance? Do I really have what it takes to complete this? Will this idea ever work? Will they ever call me back or take my call? Can I get this done? Will this finally be the time it works? 

One uncertainty after another. Just as any success, in any field, has ever faced. Not knowing, what we know now. From hall-fame athletes and dynasty sports teams to your favorite writers to the billionaires you see on tv to the local entrepreneur you admire. Success was never guaranteed, it was earned while dealing with uncertainty.  

Hacking the algorithm to go viral or finding that guaranteed foolproof path to success doesn’t actually exist. You may never find the perfect path to success. You might never find the finish line on that big project or ever turn a profit in that dream business or become a bestseller or land that dream job. 

But you are sure to guarantee your results if you don’t get started. If you delay for too long. If you fail to get off the sidelines and into the arena where it’s there, and only there, you truly begin your apprenticeship of success. If you aren’t willing to test your meddle, see if you can stretch, and be willing to take a few shots to the face.

We need to be asking questions like, Where can I get better? Where can I push myself to put more effort in? Why can’t I be good enough over time? How can I use this to make me better? Even if I fail, is this the path that makes me better? 

We need to get started, without the guarantees. Despite the doubts. With a willingness to face the wind at our face, not just when we feel it at our backs. And with strength of mind and fortitude, we will work through the hard and uncertain times with the courage that the tasks require.

That’s the only way.