How to make the most of any opportunity

When I come across any “life’s biggest regrets” articles, memoirs, or reflections, what I find across them all is that people’s biggest regrets revolve around missing out on opportunities to do things in life. An NPR article put the concept of regret very succinctly when quoting author Daniel Pink after he spent years researching human regret: that it is “an emotion distinct from sadness or disappointment because of the agency involved in it.”

Pink found that “regrets of inaction outnumber regrets of action 2:1.” Meaning that we tend to, by a wide margin, regret opportunities we didn’t try to take, over ones we did but were wrong about.

If we look at other resources, like Forbes’ The 25 Biggest Regrets In Life…, which chronicles a long list of common regrets, we can see all of these as opportunities not taken. For example, the regret of “Working so much at the expense of family and friendships” may be seen as missing the opportunity to spend time with loved ones. The regret of “Not applying for that dream job I always wanted” is a potential opportunity wasted.

The list of lists goes to practically infinity. To hammer home the impact, a Google search of “End of life regrets” yields 64.8 million results.

At the end of it all, I realize this is something so many people struggle with. It’s also something people frequently come to me for advice about. Despite becoming a bobsledder, starting a non-profit, pushing bureaucratic limits in complex organizations, and running a marathon, I’ve still turned away more opportunities than I’ve gone after. And I’ve turned away ones I should have taken, taken on ones I should have declined, and succeeded where I didn’t think I could. How do I think about it?

Well, I might not always get it right. But here’s my approach…

Five steps (or considerations) to make the most of any opportunity.

1. Recognition: Of the opportunity in front of you. And that the opportunity is for you.

Any opportunity starts with choosing to see it.

I’ve learned that highly driven people see many things as opportunities. Is it challenging? Is it opportunistic? Is it frustrating? Was it a failure? Great. It’s an opportunity to grow and get better.

When stuff comes our way, even things that look like problems, we get to be the one who can choose to see the opportunity in it. That’s on us. The more we look at life that way, the more opportunities we’ll have. Simple as that.

But once we’ve recognized something as an opportunity we should ask: Is this an opportunity for me or is this for someone else?

That’s important math to run. If it’s for you it means it’s something you can lean into, find passion in, or see an eventual outcome you want - it’s an opportunity that you can see yourself staying up late to work on and that gets you up in the morning, whether you enjoy that or not. You will do it because you see a path to success that you can impact.

If it’s not going to do the above for you, it still might be a great opportunity… for someone else! Pass it on and in the future, great opportunities will be passed back to you.

2. Start with a growth mindset.

When there is some kind of opportunity in front of us (including one that presents itself in the form of a challenge) that we’ve decided is for us, we need to start with a growth mindset: believing in our ability to grow and get better at whatever it is we’re facing.

It can be easy to look at a thing and see all the ways it can go wrong. (And sure, as we progress in taking on the opportunity we will look for roadblocks and figure out how to get through them.) But first, we need to generate some momentum and motivation. And that starts by choosing to see the potential within the situation in front of us.

I like to do this by asking questions like:

How can I make this work?

How might I be able to learn and get better from this?

How can I turn this situation into an opportunity for something positive and worthwhile?

For more on what a growth mindset is, how it works, and how to cultivate it - this Psychology Today piece is good.

3. Learn everything you can.

My background in sport has taught me the value of being prepared. You can’t go blindly into something and expect to succeed.

I’ve taken this approach into pretty much every area of my life.

As soon as I started to develop Classroom Champions, I went down a massive rabbit hole of learning. I learned everything I could about leadership, education, social-emotional learning, school systems, the psychology of adaption of tools, and more.

As soon as the possibility of running the NYC Marathon came up, I started learning everything I could about long distance running. As part of that effort, I sought out experts and engaged a coach.

Whatever the opportunity is, you’ve got all kinds of resources at your disposal. These days, the bigger challenge is probably making sure you get the right information. Think critically and seek out trusted sources to make sure what you’re learning is credible and reliable. If it goes against your intuition, question it without dismissing it. Seek more information but be careful not to only look for data that tells the story you want. Challenge yourself here.

The more you learn, the less likely you are to cheat yourself. You’ll know the facts. When I learned about long distance running, it became very clear to me that I can't cheat the miles. Among other things, I can't teach my body to burn fat over glycogen without training. I can't shortcut that; there isn't a supplement that I can take. There isn't a there isn't a mindset that I can get myself into. There isn't a meditation I can do. There isn't a weight that I can lift. The only thing that I can do is get out on the road and teach my body to metabolize energy in the way that it needs to happen on race day.

And I won’t lie - that realization had a bit of a “DAMN, this is going to suck” element to it. And once I recognized that, I leaned in and it’s now what it is. This past weekend’s 20 mile (33km) run was simply what I needed to do. I decided it didn’t suck and thus I looked at it positively.

This is why learning is so valuable; it prevents us from missing an opportunity (or screwing up our chances of success) due to ignorance.

From there, you can turn what you learn into a plan.

4. Reduce Variables and Create Redundancies

When you’re building a plan, don’t build it on the assumption that everything will go right.

Build it on the assumption that things will go wrong. Because they will.

A strong plan takes into consideration what could go wrong. From there, you can try to reduce the variables (the things that could screw up your plan). And you can build in resilience so any variables will be less likely to destroy your efforts.

I’m a fan of the KISS method: Keep It Simple, Stupid. The more complex and convoluted your plan, the more chances there are that something will go wrong.

But even if your plan is relatively simple, you still want to make sure your preparation is robust enough to handle any curveballs that could show up.

During the start/push of the second of four heats at the 2010 Winter Olympic Games in Vancouver, running downhill on ice at full speed, as I loaded into the sled and reached across to allow myself to get in, my left hand glanced off of Justin Olsen's butt on the load into the sled — something I’d never done before — and my hand at first missed the wall of the sled, which is a necessary element of getting in.

In other words: I almost fell face first into the sled in front of a global audience in the biggest moment of my life. The result of which, without question, would have been ending our chances at any Olympic medal.

Fortunately, we had built our plan to reduce variables and create redundancies, which meant that if just one thing went wrong, we would give ourselves the best chance to be okay. It would take more than just one thing going wrong to undo us. I had taught myself to get into the sled in an imperfect situation; we had taught ourselves how to go forward and withstand a little bit of error.

So, rather than falling flat on my face, here’s what happened instead. Since part of standard our load into the sled was me putting my helmet into Justin’s back to brace the energy created upon entry, we had created both a more efficient way to get in and a redundancy if something went wrong. Because of my mistake, Justin felt more pressure on his back from my helmet than normal, but he was braced and ready for it. I was able to use his back to brace my weight, lift my hand and reposition it, and then get in without any more than a 2-3% loss in execution.

When we got to the bottom, Curt could tell the timing was off by a mere tenth of a second or so and asked what happened… to which I replied, “I’ll tell you later.” Knowing it could have been catastrophic, the debrief was better suited to the Olympic Village than standing on the finish dock with cameras rolling and microphones everywhere.

Images left to right: First image: The left circle shows Olsen’s proper hand position, while the third athlete (me) has a circle around an improperly placed hand; Second image: My helmet circled, pushing hard into Olsen’s back; Third image: My hand properly placed a split-second later.

To watch that moment, this YouTube link will get you right there.

One more word about variables: so often, WE are the ones who are most likely to mess up the opportunity in front of us, not some external factor.

So, as you look for potential roadblocks and plan around them, consider this: How are you most likely to get in your own way?

If you aren’t sure, talk to your friends — the ones who will be really honest with you. Ask them to call you on your shit or point out your blindspots. Be brutally honest with yourself so you can prevent yourself from being your own biggest obstacle.

5. Just start. And commit to it.

At a certain point, you just have to get out there and get started.

Overcome the limbic friction, the fear, whatever it is that is standing in your way.

Put it in your head that this opportunity won’t be around forever - they never are - and give yourself the motivation to get started with what might feel like an imperfect plan. (Also remember there are no perfect plans, so…)

Eventually, if you don’t do something about it, either the opportunity will be taken by someone else, or the peak moment of the opportunity for you and others will be gone.

And, if you’re going to make the most of any opportunity, you have to start.

Once you’ve gotten started, commit to it. And by that I mean be willing to put yourself in a place where it will hurt if you fail. Be willing to make it important enough for yourself that if it fails, it's gonna hurt.

Oftentimes, when considering an opportunity, we look for ways to avoid being all-in, at least emotionally. We trick ourselves into thinking it’s not that important, that it doesn't mean that much to us. But really, we’re just preventing ourselves from committing.

If you fail, or things don’t go the way you want them to go, it’s going to hurt. But if you don’t commit, if you tell yourself it doesn’t matter, how much less will it actually hurt? Maybe 10% less, at best. (If you recall, this was the reasoning for choosing to believe the Buffalo Bills would win the Super Bowl last year. And I can tell you, I have no regrets about that!)

So as you move towards this new opportunity, give yourself permission to commit to it.

The bad news is that you might fail, and it might hurt. But the good news is that I’ve learned over the years, from my own life and from just about every successful person I’ve ever met, that a low point in life is almost always the impetus for something great.

In the long-term, failure is only true failure if it a) kills you, or b) you don’t learn from it. Short of those two outcomes, it’s not failing.

So go ahead. Start the thing. Commit to it. If you succeed, great. If it doesn’t work and you’re still alive, you get to control whether it was a failure or not.

- Steve