Finding A Goal That Is Right For You

Answering The Question
Image by Peggy und Marco Lachmann-Anke

I have done incredible things, but I have never achieved any­thing great on my own. Every record I’ve set, every stroke I’ve taken, and every mile I’ve hiked is made possible by my teams. Every member of the team may not have been with me at the finish line, but they were the ones who ultimately made it pos­sible for me to be able to cross it at all.

Every team I build is meant to do something impossible. Doing the impossible in this case means accomplishing a goal that subverts the expectations of rational people.

Your impossible could be hitting a massive sales quota, starting an innovative new company, or just making sure the people you’ve hired get to keep their jobs for another quarter. The impossible is all around us, but so is adventure, and adven­ture can beat the impossible if you do things in the right order. The very first step is answering the question why? Not for your team, not for your boss, but for yourself.


Why should you give all your time and effort to this par­ticular goal? If you don’t know why you’re doing something, if you don’t have a crystal-clear image of the success you’re chas­ing and the reason you’re chasing it, then you will never lead a high-performance team. You might be able to scrape together a few solid returns out of a burned-out group of overstressed individuals, but it won’t last.

If I didn’t have a strong why for my team and from my team, we would not have won our world record. We would not have made it across the ocean. We probably would have never even tried.

If all this sounds emotional, that’s because it is. Leadership is way more right-brained than people give it credit for. Building strategy is important. Setting timelines is important. Project management is important. But if you don’t own the emotions of your team, then you don’t really have a team at all.

The First Step In Finding "Why"

The only way to reliably build teams that succeed is to find your why and instill it into the hearts and minds of the people you’re supposed to be leading. Believe it or not, the first step in finding that why may in fact be quitting.

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Quitting is not a failure. Most people have heard that “it’s not how many times you get hit that matters; it’s how many times you get back up,” and that’s what they believe.

This saying is inspirational as hell if you’re in a Rocky movie. But in real life, it’s wildly off base. I’m not here to teach you how to be good at getting up. I’m here to teach you how to learn the right lessons from your time on the ground so that when you do get back up, you cannot be knocked down again. And neither can the members of your team.

When we were rowing in the ocean, whenever one of us took a dip in the water we were tied with a rope in case the currents changed suddenly. The last thing you want is to be untethered in the middle of endless water watching hopelessly as your boat disappears over the horizon.

However, we also always kept a knife on the deck as well. This knife was meant to cut the rope in the event an unex­pected wave shifted it into a position where it was actually injuring one of our teammates. In life, your why is just like that rope.

Not All Goals Are Cre­ated Equal

Some people are too afraid to bring out their knife. They cling so tightly to an opportunity that they don’t realize it’s actually strangling them to death. They prefer that choking consistency to the terrifying possibility of being set adrift in an ocean of raw possibility.

Direction is good. Goals are good. But not all goals are cre­ated equal, and you need to test and be intentional with your goals to make sure they reflect the unique abilities, emotions, and goals of you and the team you are leading. Then you need to lead the team to the success you promised. In this book you will learn a process in which both of those things can be accomplished.

It starts with finding your why, which may mean calling it quits on a goal that is wrong for your team. But how do you know when the time is right? How do you know if an oppor­tunity is keeping you tethered securely or choking the life out of you?

Leadership Lesson: Understand Suffering and Sacrifice

Quitting is nothing more than weighing two variables and finding that one of them has stopped being worth it. These two variables are something that every human deals with on a daily basis: suffering and sacrifice.

Humans have a knack for understanding the amount of suf­fering and sacrifice that they must endure to reach their goals. The trick is that you need to start doing this consciously and channeling what you find into a decision that leads to a why, which leads to a team, which leads to an impossible victory.

As an example, let’s look at two different corporate histories.

Airbnb is a company that enables people to open their homes to paying guests. That’s a wild idea even today, when as of this writing the company is currently poised for a mas­sive initial public offering (IPO). But it was absolute insanity back in 2008 when its founders, Brian Chesky and Joe Gebbia, started trying to raise millions for a company most people were sure would be used exclusively by serial killers.

The duo persevered, however, and held on to their idea. The hook, they believed, was the ease and intimacy of people sharing their homes with other people, giving guests the ex­perience of really living in the city they’re visiting. That idea was too powerful to give up, and today the insane company is projected to receive a post-IPO valuation of $190 billion.

That’s one path. But let’s consider another.

Very few people have heard of Game Neverending, an inno­vative little internet-only video game from a company called Ludicorp. The creators of Game Neverending dreamed of creat­ing a fully immersive digital world, complete with fluid social interactions and a real, dynamic economy. The game had trou­ble getting funding—and players—and soon Ludicorp was on the verge of collapse.

In the final days of the game’s life, one enterprising pro­grammer launched some simple photo-sharing functionality into Game Neverending’s social system. Photo sharing quickly became the number one activity among the game’s band of diehard players. This put Stewart Butterfield, Ludicorp’s co­founder and chief executive, in a tough position.

Butterfield could ignore the success of photo-sharing and leverage the company’s remaining funds into a last-ditch effort to make the game a success—a direction that was championed by most of his employees. Or he could abandon his dream of running a gaming company and start building a photo app.

The decision was difficult, but eventually Butterfield de­cided to scrap the game and launch a photo company instead. He gave his new start-up an era-appropriate, vowel-discarding name: Flickr.

Flickr became, in a pre-Facebook world, the number one photo-sharing website on earth and was eventually acquired by Yahoo! in 2005 for an estimated $22 to $25 million.

As humans we have an innate desire for comparison. Are Chesky and Gebbia geniuses for holding on to their idea and building a multibillion-dollar company? Was Butterfield a master strategist for pivoting to photos and earning himself a respectable fortune of his own? The answer to both is the same: not really.

These men aren’t special or unique. For every one of them there are thousands more who refused to pivot, or did pivot and ended up with nothing. The lesson here is not that they were successful. It’s that they became successful by finding and respecting their own thresholds for suffering and sacrifice.

Every human has an undefined threshold for both suffering and sacrifice that they are unwilling to go past. We don’t talk about it. We can’t measure it on any objective standard. But it’s there, and it’s there for everyone.

A Noble Quitter: Quitting Is Not Failure

A noble quitter is someone who understands where that line is and learns to respect it. Quitting has gotten a bad name from people who are unaware or unwilling to define that threshold and therefore decide to stop before they ever hit it. There is no honor or reason in that sort of quitting.

My adventures have taught me that while we all do have a threshold for suffering and sacrifice, it is usually much higher than we think. A person who would be capable of leading a high-performance team takes the time to learn exactly where their line is. Because once you know it, you can tiptoe right up to the edge and actually go further than all the other people who flamed out a mile back because they couldn’t imagine they could make it that far.

The Path To Doing Difficult Things

The path to doing difficult things is not mindless enthusi­asm. It is to learn about yourself. Learning about yourself is the only way to block out negativity, endure past adversity, and meet the goal you’ve set. It means testing yourself. It means earning your own self-confidence and paying through hardship. Then you will have the right to say to your team, “This is what we have to do.”

Quitting is not failure. Quitting is realizing that this one goal isn’t right for you and your team. Failure, real failure, is never finding a goal that is right for you.

My path to success started the day I quit on something I’d wanted my entire life. That was the first step in a journey that would lead me to discover the process of finding my best goals, forging strong whys, building exceptional teams, and leading them to impossible successes.

©2019 by Jason Caldwell. All Rights Reserved.
Excerpted with permission from Navigating the Impossible.
Publisher: Berrett-Koehler Publishers.

Article Source

Navigating the Impossible: Build Extraordinary Teams and Shatter Expectations
by Jason Caldwell

Navigating the Impossible: Build Extraordinary Teams and Shatter Expectations by Jason CaldwellWorld-record endurance athlete and professional leadership coach Jason Caldwell draws on his amazing experiences to show how anyone can build and lead teams that accomplish incredible things. This book is a distillation of Jason's worldwide speaking programs delivered to packed crowds at Fortune 500 companies and universities worldwide. It is the answer to a question he is constantly asked: How were you and your teams able to accomplish such seemingly impossible goals? And it's also a guidebook that can teach anyone how to do the same. (Also available as a Kindle edition and as an Audio CD.)

click to order on amazon


Another Book by this Author: WHAT IF

About the Author

Jason CaldwellJason Caldwell is the founder of Latitude 35, a leadership training firm that operates around the world. He is also an adventure racer who currently holds over a dozen world records across five continents. He has worked with companies such as Nike,, and Santander Bank and has offered programs at institutions of higher education including Columbia Business School, the Wharton School, and the Haas School of Business at the University of California, Berkeley.

Podcast/Interview with Jason Caldwell: Building & Leading an Extraordinary Team


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