The Vehicle vs. The Destination: Why Crazy Career Changes Aren’t as Crazy as We Think

Being Weird Isn’t a Weakness.


I love finding unusual paths towards success. 

I love seeing freaks win by letting their freak flag fly.

I love learning about people who have stumbled, who have failed, and who almost quit on life. My work is about people who’ve tried everything and the kitchen sink before arriving on the path for them…

This piece is about this false contradiction that exists between certainty and success. As a society, we seem to believe that not having a singular focus from the time you graduate high school is somehow a weakness. 

We seem to believe that the “best” way to live is to leave high school knowing exactly what you want to do with the rest of your life, and then committing to that for decades.

It’s true that many of our most celebrated humans followed a straight-and-narrow path. 

Beyoncé was winning singing and dancing competitions from the moment she could enter one. Rory McIlroy was chipping golf balls on national TV as a 4-year-old. So while this typical path may indeed be the story of many rockstars and celebrities, has it ever resonated with you? Have you ever felt that, because you weren’t chipping golf balls on national TV as a 4-year-old, you missed the boat? Maybe you’re 20. Maybe you’re 30, 40, 50, or even recently retired. Do you ever feel that there’s no hope for you to achieve *your* dreams or goals? That you somehow made a wrong turn in your life that you can’t come back from?

I’ve felt that. Especially because I’m blessed to know so many highly successful people in this world. Some of them were child prodigies that never had money worries a single day in their life. But many more of us—an order of magnitude, certainly—are struggling. 

We struggle with our work, we struggle to find our place in an over-crowded universe, and we struggle with the fact that we may not be as special as we once thought we were.

Well I’m here to explain a concept to you that our society doesn’t seem to broadly recognize yet:

Ross’s “String Theory” for Careers

How is it that someone can be a musician, a writer, a businessperson, an accountant, a tennis player, an eco-warrior, a mom, and more? 

Crazier still: How can someone change their career so dramatically throughout the course of their life? Is this just weakness? Is this just making constant mistakes?

If you watched someone go from professional tennis player to accountant, would you say they’re insane?

How can someone only care about being a DJ one day, then only seem to care about saving the planet the next? Is this person fundamentally broken?

Well gather ye round, because I know how…

Have you ever seen a video of artificial intelligence learning how to “walk”?

You can find other examples all over the internet. How does machine learning solve the problem of walking, you might ask? Well, you *don’t* teach a robot how to move. Instead, you put the necessary motors and joints in place for movement into the object, then you simply give it a destination, say, the other corner of a room. Through trial and error alone, machine learning figures out what motors it has, how it can move those motors, and what actions bring it closer to that target and what actions don’t. 

This is exactly how humans learn to crawl and walk. We arrive in the world kicking randomly as we discover what our body is, how it can move, and what its limitations are.

Given enough time, our machine-learning-driven object will eventually “walk” to its destination. And the wild thing is, there are infinite *ways* that this object can reach its destination. Some of these ways might look a lot like animals we know, others might look truly alien or even downright hilarious. But the robot gets there. Only through repeated action does the robot learn what it’s actually capable of. It maps out its own body and capability through experimentation, continuing sequences of actions that cause forward progress and abandoning actions that don’t. Do this long enough, and the object will reach its goal. It may not be pretty, but it will get there.

I think we’re the same, more than we give ourselves credit for.

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Step One: Find Your True Objective

The problem is we don’t realize what our true objective is.

If I say: what’s the common thread that links being a musician, being a writer, building a company, being a marketer, or being a scientist? Things that seemingly have NO relation to each other whatsoever in our modern career framework? 

This is the key. We need to find what connects seemingly disparate ideas.

We’re all humans. Often there IS a connection in our own lives, whether we realize it or not.

If the true connection is: “I want to make a difference and I want to connect with people.” Then it’s easy to see how all of the above professions can be a subset of that larger goal. But we forget our larger goal sometimes.

There can be no doubt that musicians can make a difference and connect people. Scientists can, too. A company is a way to make a difference in the world, and it’s also a way to connect new cohorts. 

So, like the robot in our machine learning example, our job is first to find our own objective in life. Our big objective. 

In my case my objective is: “To connect with people and to make people realize that we are all fundamentally one and we are all in this together. We must work together to achieve common goals, and the lines that divide us are arbitrary and meaningless.” 

I’ve tried many things to reach this objective. I’ve loved dance music because it has no words. No language. Music without words can be a truly globally unifying force, because it’s understood in every culture in exactly the same way. This brings us all together. But it’s just one tool to achieve my larger objective.

Good writing can do the same and so can many other pursuits.

So as humans, first we set our bigger objective for our life, not knowing how we will achieve it. Then, we must be open to the possibility that, like our robot example, there are literally infinite ways we can achieve our goal. 

Step Two: Experiment Like Hell

As we move through life, we try things out and we learn more about ourselves in the process. We discover our own capabilities and limitations through action. We discover that we can’t dunk, so maybe basketball isn’t our vehicle. We discover that we don’t have Mozart’s ear, so maybe music isn’t our vehicle. We discover that we’ve never had writer’s block a day in our lives, so maybe writing is our tool. Maybe speaking is our vehicle. Maybe comedy is our vehicle.

We learn through elimination what we’re capable of and how we can best achieve our over-arching goal within the context of our unique set of circumstances. This might mean that we have to let go of some of the vehicles we particularly enjoy, instead settling on vehicles that are better suited to our abilities and talents. 

But lo and behold, now we have a mental framework that tells us how an individual can be and try several things without it being a weakness. It’s merely evolution doing its thing.

Now flash back to our robot trying to walk. What if the robot never tried to move? Clearly it would just sit there. It would never achieve its goal. It’s only through continuous imperfect action that this object can eventually learn what works. We’re the same. Only through continuous action and activity can we discover what it is that will get us to our goal. And for some of us, this can take decades. For some of us, the first thing we try will give us forward progress. But this is just as much random chance as a group of people being asked to pick the door that has a prize behind it out of 100 doors. We can only assume the other 99 doors have tigers behind them, cuz why not? 

If you put 1,000 people through this gauntlet, a percentage of people will pick the right door the first time. But 99% of people wouldn’t. In such a context, would we celebrate the people who happened to guess the right door the first time? Of course not. We’d congratulate them, sure, but we wouldn’t celebrate them.

Such forces of luck and chance are ever-present in our lives. A tiny fraction of humans will pick the right profession the very first time, and they will make forward progress immediately. Many more of us won’t. So while we place undue attention on those who picked the right door from childhood, we need to understand that we’re all evolving and that we’re all just trying to find the path that works for us.

That’s why I’ve interviewed so many people who made drastic and profound shifts in their career. It might seem random for someone to go from corporate manager to professional bodybuilder, but are you now able to create a mental model of how this seemingly random change of heart can make perfect sense?

So it’s time for all of us to separate our vehicle from our destination. It’s time for all of us to understand that experimentation is the key for us to find the unique path that’s best suited to who WE are. 

Step Three: Go Easy on Yourself

And it’s ok if we don’t get it right the first time. It’s ok to try and fail and to try something totally new. 

The key is just to reframe how we see the problem.

Ask yourself “What is my destination?” and “Am I using the right vehicle to reach it?”

That’s a start.

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