How to Time Your Leaps and Set Yourself Apart

Using the Sigmoid Curve to reinvent yourself, take risks, and accelerate growth

In January 1961, a nineteen-year-old, unassuming kid from Minnesota hitched a ride and headed eastbound for New York to pursue a career in music. He wanted to get closer to the heart of the folk music in Greenwich Village and see if he could cross paths with his idol, Woody Guthrie. Over the next three years, he would release four critically acclaimed albums and become widely regarded as “the voice of a generation.”

The world would soon know that kid as Bob Dylan. And it was precisely that moment in time — after four successful albums — when he decided to completely change his sound from his acoustic roots and “go electric.” As he defied expectations, he threw the folk community into a fit of rage.

The obvious thing would have been to stick with what was working and fallen in line with his audience’s expectations. But validation was never Dylan’s primary motivation. He cared more about his own growth as an artist, seeking meaning over influence at each step of his career. As a result, he achieved exactly that — lifelong influence.

Dylan resonates with people because his songwriting tracks his own development as a human being. Each album reflects who he was — his observations, experiences, and imagination — and who he refused to be at each point in time. Dylan’s life is a master class in embracing the impermanence of identity and authenticity.

In the almost six-decades since, he’s altered his voice and bridged different genres. Beginning in folk, moving towards rock, and experimenting with country and Christian albums along the way. His entire career demonstrates a remarkable ability to shift strategies and reinvent himself.

But Dylan is not alone in this. Most top performers are obsessively focused on reinventing themselves and changing strategies as they near the top. It’s what gives them their edge and helps them lock into a “learn + grow” pattern while circumventing the decline.

Houston Rockets guard James Harden works tirelessly during the NBA off-season to experiment with new shots and develop new moves. But it’s not like his existing repertoire stopped working during the previous season. This is just how he challenges himself to stay engaged and push the limitations of his own game. Harden never confines himself exclusively to the things that have worked in the past. He’s always looking ahead, focused on accelerating his own growth.

As a result, Harden is able to suspend his opponents in a cloud of confusion — they never know what to expect and rarely have time to adapt. Harden’s ability to reinvent himself creates a walking nightmare for other teams on the court. The best they can often hope for is that he’s having an off night.

The same mentality applies to Tiger Woods changing his golf swing at the top of his game. And it’s the reason companies like Apple, Amazon, and Google have been able to sustain success over decades.

This is not to say that you’ll never miss. Bob Dylan’s released albums and experimented with sounds he would likely laugh at today. James Harden’s had his share of flops that didn’t quite work out. And Apple’s launched failed products — some you’ve heard of and others that have died before ever making it to market.

But it’s much easier to recover if you’re out there taking risks, looking forward, and committed to a growth mindset.

The Sigmoid Curve

Growth comes from allowing yourself, your strategy, and your sense of authenticity to evolve. At a certain point in time, the strategy that worked for you up until now will falter. That’s part of life.

One way to adapt is to think of personal growth as a sigmoid curve — an S-shaped curve that follows learning, growth, and decline. The goal is to maintain an upward trajectory. This means hijacking the curve and your experiences, as best you’re able to, when you reach the peak of a growth curve.

Sigmoid Curve Personal Growth

In the early days, growth is nonlinear. Outcomes rarely match input. Think about starting a new job — for the first six months you’re just trying to keep your head above the water. Eventually, things start to come together and you reach an accelerated period of growth where you begin to realize some of the rewards and outcomes you set out for.

But you likely won’t get through life on a single strategy without it growing stale or ineffective. 

Remember, life is motion. You will evolve. Obstacles will evolve. Context will evolve. That’s why it’s important to shift strategies when you’re at the top of your game. Otherwise, you often end up giving back the gains you’ve made.

If you want to keep moving forward and reinvent yourself, you have to outwit the inevitability of the sigmoid curve. As James Kerr suggests in his book, Legacy, “The key, of course, is when we’re on top of our game, to change our game; to exit relationships, recruit new talent, alter tactics, reassess strategy.”

Bob Dylan, James Harden, and every top performer who has sustained success over the course of decades demonstrate a fundamental understanding of this principle. They seldom give back the gains they’ve made. Instead, they build upon them. They remain insatiable in their desire to learn and grow. Even when it comes at the expense of personal comfort and opens them up to outside criticism.

Close to six decades later we can step back and admire someone like Bob Dylan’s trajectory — how he pushed himself to grow, defy expectations, and channel that into his art. Time makes this seem inevitable, as if all he had to do was fall in line with destiny. But that fails to take into account the years of criticism, outrage, and uncertainty he faced.

Staring Down the Criticism

The real challenge is that when you reinvent yourself and shift strategies, you’re sure to be criticized. People hate change. And people are convinced they know what’s best for you. Pair these and you’re guaranteed to face a barrage of commentary from those without skin in the game. Critics will be quick to point out that you should have stuck with what was working instead of taking what appears to be a step back into a learning phase.

Dylan was shredded by the folk community when he went electric. Harden gets ridiculed by the press every time he goes a few games and struggles against his own limits with a new shot.

Reinventing yourself is not for the faint of heart. But it’s a risk that pales in comparison to remaining still and failing to evolve.

If you listen to outside advice and never switch things up, you all but guarantee a life void of meaning and a spiral towards irrelevance. By clinging to the same strategy, tactics, or identity for too long, you fall out of harmony with the motion that defines life.

And this is how you wake up to John Daly, Sugar Ray or Blockbuster staring back at you in the mirror. The same people who told you to stay the same have abandoned you because you’ve abandoned yourself.

Timing Your Leaps

Above all else, you have to allow yourself and your own sense of authenticity to evolve. That’s the only path towards peak performance, and it demands occasional discomfort.

To outwit the sigmoid curve, you have to make a series of carefully timed leaps. The trick is knowing when to make those leaps.

Sigmoid Curve Leaps

When you feel like you’re nearing the top of your growth curve, that’s when it’s time to start thinking about what you can switch up. This might mean testing a new strategy or taking on more responsibility. Or it might mean pursuing a new career path or an outside learning opportunity. Or perhaps it’s just switching to a new team to preserve your sense of engagement and continue challenging yourself.

A shift in strategy doesn’t always need to be drastic. But it does need to be deliberate.

Otherwise, things become too easy and too familiar within the confines of your comfort zone. And when you become trapped in a decline, it’s all too easy to cling to an expired identity and give away the progress you’ve made.

Much of life is knowing when to shift strategies — when to call it quits, when to stick it out, when to evolve your approach. If you can perfect this, you can bypass the decline phase altogether, and jump from one “learn + grow” period to the next. And this is what sets apart the top performers in every discipline.

It’s difficult to realize when you’re nearing the end of a growth phase. It requires first developing a deep sense of self-awareness and prioritizing room for reflection. This should be paired with experience — both personal and vicarious.

The usual signs are when you start to notice a decline in personal engagement and the meaning you find in the work. This signals that it’s time for a new approach.

Remember, you’re a human being. Emotion is an inherent part of your decisions. The best you can do is pause and create space for reflection. The more dispassionate you are in coming to a decision, the more you should trust it.

For example, when you’re pissed off at a manager, that’s not the time to make abrupt decisions. Create space. Allow yourself to be upset for a few hours. After a week, when you’re less entrenched in that moment, you can see things for what they are and make a more rational decision.

When I feel a calm sense of it is what it is, I’m not upset, but I accept it’s time for a change that’s when I know it’s time to switch things up and test a new strategy. When I’m in an emotional state — especially when I’m upset and playing through imaginary conversations in my head — that’s when I know I need to pause before making a decision on a potential leap.

Allow Yourself to Evolve

It’s easy to get locked into a rigid thought process with a single strategy if you stick to the map without ever looking up. But when you stop reaching for absolutes, you’re able to embrace the motion inherent to life. Everything is fluid.

The best thing you can hope to do is remain in harmony with your own sense of authenticity and the motion that defines life. By embracing this, you’re able to better challenge yourself, embrace a growth mindset, and create meaning.

If you want to create your best work and make a meaningful difference in the world, you’re going to have to grow to get there. This comes from timing your leaps and finding the courage to reinvent yourself — especially when it feels uncomfortable, counterintuitive, and the world least expects it.

Bob Dylan’s determination to evolve as an artist and his refusal to accept what people expected of him helped him grow into one of the greatest songwriters of our era.

James Harden’s ability to reinvent himself every NBA off-season is what allowed him to go from the sixth man behind Kevin Durant and Russell Westbrook is his early days with the Oklahoma City Thunder to an MVP and the cornerstone of a franchise.

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In visualizing the sigmoid curve, you’re trying to jump at the precipice of growth and catch hold of another learning curve one layer above — just as Dylan and Harden demonstrated. This is how you lock yourself into a “learn + grow” mindset.

Strategies are tools that you can use to take thoughtful action and connect your guiding principles with your day-to-day. Put them to use for you. Blend them. Change them. And always be willing to shift directions when something’s become stale or no longer works for you.

Above all else, allow yourself to evolve. Growth is born from a willingness to leap before you feel ready.