Crossing Over: Methods For Climbing Mastery Curves

John Otterbein
9 min readApr 30, 2019

Basketball was never my strong suit growing up.

I remember playing when I was around ten years old in a recreational league. I dreaded handling the ball and continuously felt out of touch with the flow of the game. I used to hide behind other players, so our point guard, Richie, couldn’t beam a pass at me. Quite the competitive spirit, I know. It was clear from an early age that my basketball career would be shortlived.

My parents, unsure of how to drain me of my extra energy, so I wasn’t ravaging around the house like a Tasmanian tornado, decided to throw me in a pool and enroll me on a local swim team. It worked like a charm. I finally chilled out. Swimming was my go-to sport through college, but I stopped immediately after graduating. As most retired swimmers know all too well, it’s astonishingly miserable to jump back into a cold, foreboding pool after grinding out laps for countless years. I needed a new form of exercise.

So, after getting back into watching basketball with friends in my mid-twenties, I revisited the sport with a renewed sense of interest and devotion. Instead of shying away from how terrible I was, I dove into the deep end of the court. I started to enjoy the process of methodically progressing into a legitimate player. The more I played, the more the beauty of basketball slowly began to dawn on me — the rhythm, movements, coordination, repetition, endurance, and, most importantly, the sound of the net swishing behind a perfect shot. I was hooked.

But improvement didn’t happen overnight.

It took years for me to notice even a fraction of a difference in my skillsets. My ball-handling skills were non-existent, my shot was painfully inconsistent, and the only thing I had going for me was my defensive tenacity (which is what players with no offense typically hang their hat on).

I was awkward and clumsy on the court, to the point where I felt out of place. I couldn’t help but flashback to those painful memories of basketball in my youth, but my newfound obsession never wavered. I hung tight and continued to show up to the courts every single day.

I became obsessive about this one workout, consisting of five to six sets of twenty made-shots (makes). Each group of twenty makes were comprised of different ranges, a varied selection of moves, and fluctuated in their intensity (some involved explosive movements while others focused solely on shot repetition). The workout lasts as long as it takes to complete each subsequent set.

Small, incremental improvements became intoxicating. They kept calling me back time and time again. The comfort I felt on a basketball court now compared to a few years ago was astounding to me, mainly because I genuinely didn’t feel like I had what it took improve at something that had once been so foreign and intimidating.

The basketball court started to feel like a second home.

The result nearly two years after first adopting this routine has been pleasantly surprising and reconfigured my relationship to earned achievement and competence — which brings me to why I’m writing this:

My long-term obsession with basketball has become my model for approaching progression of any kind. More and more, I find myself overlaying my basketball mindsets and methods (which I’ll outline throughout the rest of this article) on top of other areas in my life where I could use some help systematizing my improvement.

After pondering and parsing the core tenets that have led to my marked improvement, I’m going to unpack them and show how they apply to other areas of life.

Repeatable, Simple Actions

This first tenet may not come as a surprise, but let me tell you, it’s one of those timeless pieces of wisdom that can’t be repeated enough (get it?). Let me unpack this phrase a little bit more. Repeatable, simple actions are the smallest and most simple actions (derived from the skill you’re trying to improve at) that you can revisit with the least amount of resistance. If the skill you’re trying to acquire is complex and multi-faceted, take the time to locate the minute actions (look closely; they can be microscopic) that form the foundation of that skill.

In the case of basketball, it’s most complicated form would probably be a player with an excessive amount of fluidity, precision, and refined decision-making against other high-level players. That’s the destination on the horizon. That’s the dangling carrot. But that’s also quite the gap to bridge because it’s difficult to say how one goes from having virtually no skills to being the most lethal threat on the court. So, that’s where I started my quest and began to look at all of the different, smaller skills I’d need to hone in on to improve.

Once I started chipping away at these fundamental building blocks over and over again (lay-up lines, shooting in rhythm, dribble drilling, left-hand development, crossovers, etc.), they all started to improve simultaneously gradually. No matter how many times I bricked a shot or lost control of my handle, I simply retrieved the ball and started again. And again. And again. The improvement began to become more and more noticeable, which fed back into sharpening all of these different skills.

But here’s my favorite discovery about pursuing the track of repeatable, simple actions:

An improvisational and creative potential eventually emerges from sequencing simple skills acquired from diligent repetition. Because once you master enough repeatable, simple actions, you start to combine these simple elements into more complex and unpredictable patterns, and you do so with more style and swagger.

Think of a chess player building out their arsenal of opening moves, mid-game scenarios, and end-game techniques. This armory must be patiently built-up over endless games and hours of practice, but new combinations and insights will begin to emerge once the moves become second-nature.

Applying this tenet to other domains, if you want to learn how to code an application, the first action you might take is familiarizing yourself with Html functions until you’ve memorized them. If you want to write a short story, start by repeatedly showing up to compose a short paragraph, sentence, or just following one word with another. The entry barriers for these small actions are much lower than the notion of immediately ascending to the highest forms of the skill, i.e., coding a best-selling application or making it onto the New York Times Bestseller’s List.

Find the smallest action and repeat it to climb up onto the higher shelves of skill development. The key is to dig until you reach the bedrock of repeatable, simple actions and follow them until new levels of combinatorial creativity follow.

Now you may be asking, “when will I find time to locate these repeatable, simple actions so I can start to fire away at them?”

Which brings us to the next tenet:

The Inescapable Trade for Time

Chew on this for a minute:

There comes a time in life when time will start to make choices for you unless, of course, you beat it to the punch. As you grow older, doors will begin to close despite your futile attempts to hold them open. The word child is practically synonymous with the word potential. But that incredibly malleable time in life doesn’t last forever. Time will slowly but surely shrink your windows of opportunity, gradually turn you into stone, solidify characteristics about you that can no longer be left open to the winds of change.

And that’s not meant to sound hopeless or defeatist; it’s meant to be an air horn in your ear. You should befriend the time you’re given at this very moment because that’s all the time you’ll ever have.

Suppose you don’t willingly trade your time for repeatable, simple actions that push you up mastery curves (which will ultimately enrich your life with a purpose by way of proficiency). In that case, time will advance without you in mind. Sure, it can be challenging to trade time for skill willingly, but isn’t it just as challenging to live a life without the incomparable joy of being good, even masterful, at something? Don’t be on the wrong end of the deal when dealing with the inescapable trade for time.

An exciting side of this idea is how it changes as you pursue repeatable simple actions. As you chip away at your skill’s foundational bedrock, you start to enter a mutually beneficial relationship with time in contrast to your previously dysfunctional one. Instead of fleeing from time’s inexorable advance, you willingly enter into its steady current with a goal to swim towards. And now I’ve unintentionally arrived at a metaphorical crossroads between finding your flow state as you agree to trade your time for repeatable, simple actions, and let me tell you, it feels great to come around full-circle.

Let’s keep going.

Failure Should Drive You Forward

Just because you’re trading your time for repeatable, simple actions and slowly climbing up the mastery curve of your choosing doesn’t mean you’re not going to trip over failure — quite the contrary. Failure is going to be your close companion the whole way up the mountain. When I say failure here, I’m not necessarily talking about an epic fail or a massive setback. When I say failure, I’m referring to the tiny missteps and mistakes along the way that help to sharpen your skills — like all of the shots I inevitably miss as I’m trying to improve.

Even now, after years of not leaving the courts until hitting 100 makes, there are still days when I miss 5–6–7 shots in a row. Does it boil my blood and make me want to high-tail it home? You bet. But I stay, recenter my focus, and keep grinding until the ball goes through that net one-hundred times — no questions asked.

Because at its core, failure is the impetus that continues to drive you forward in your pursuit of mastery.

If I knew for a fact that I’d never miss another shot, then why would I even bother going to the courts? It’s like using cheat-codes in a video game — sure, it’s fun for a few minutes, but the game will start to feel empty and pointless because progress wasn’t earned.

There’s always room to improve, and that’s what keeps us coming back for more. Sure, my shot is way more accurate than it used to be, but I’m still missing shots all of the time. Take Kobe Bryant as an example — you’d consider him to be a masterful player, right? He took over 26,000 field goal attempts throughout his illustrious career and made just south of 12,000 (a respectable 44% from the field). He missed more than twice the number of shots he made, yet he’s considered one of the most dominant players in the sport’s history.

Even the most supremely skillful people are failing all of the time. Nobody has summited a mastery curve; even if you have to peer straight up and hold a flat hand to your brow to block out the sun as you try to find them up in the clouds, they’re surely still climbing.

Hopes and Systems

“You don’t rise to the level of your hopes, you fall to the level of your systems.” — James Clear (Atomic Habits)

This quote beautifully sums up the point I’m trying to make — hope may help you choose a direction, but it’s not going to foster marked improvement. Hope is fickle, temporary, and transient. Hope will vanish at the smallest signs of hardship. You can’t build mastery on top of the quicksands of hope. You’ll need something sturdier and substantive. That’s where systems come into play.

What good will hope do for my game? Other than deluding me into thinking I’m better than I am, hope is almost good for nothing. Hope should be feeding your systems, not your ego. And when I say “system” in this context, I’m talking about a routine that’s firmly baked into the casserole of your day. My system is the 100 makes routine that I never diverge from. It’s always the same. I don’t have to think, plan, or strategize on how to get better anymore because now all I have to do is show up and run through the system over and over again. The results take care of themselves.

In the greater context of climbing the innumerable mastery curves available to us, I strongly encourage you to build your very own systems for methodical improvement by:

  1. Finding the repeatable, simple actions that you can pour your time and effort into;
  2. Willingly accept that time will make choices for you if you don’t beat it to the punch (so choose something now);
  3. And befriend failure as the impetus that will continue to sharpen your skills and drive you up mastery curves.

Now get out there and start climbing up some curves!

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