Becoming Someone Who Can Survive Their Dreams

What I wish I knew about ambition and failure

We are the music makers,

And we are the dreamers of dreams…

Yet we are the movers and shakers

Of the world for ever, it seems.

Arthur O’Shaughnessy

“The credit belongs to the man who is actually in the arena…who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.

Teddy Roosevelt

January 26, 2016 was a gut punch. At 9:18 that morning, I/we told the world we were closing the business we started 4 years ago. 9:18 that morning was when I had to tell about a thousand people that I was a failure. And it sucked.

Maybe you’ve lost the state championship game in front of a sellout crowd, this was my first bout with a big, public failure.

I have thought about that day almost every day since. And a decade later, I’ve only started to think I understand.

So to start 2026 off, I want to share what I’ve learned – what I wish I knew beforehand and what I think you should know now.

This is not some feel good b.s. about how failure really is a blessing in disguise. There’s no toxic positivity here.

Instead, I want to write honestly about ambition, about attempting to do big things, and what we all should know about reaching for greatness. I want to unpack what I’ve learned, what I wish I knew, that it might spare you some heartache along the way.

You need to understand why you want to achieve something

You need to understand that I really needed to be successful.

It’s not that I wanted the money, I needed the love.

Up to that point, I had seen that a decent dose of smarts + a high capacity for hard work opened the doors to almost everything that I wanted in life. I could see my own potential…

But riding alongside academic achievement was a strong sense of loneliness, of feeling different. How would I fill this sense of loneliness? I had a work ethic, a creative mind, and a dog with a bone level of determination/obstinance/refusal to take no for an answer.

So entrepreneurship felt like the best choice.

The gamble I made was simple - I would create something. That act of creation would allow me to be seen and valued in the way I felt I was lacking. At least that’s what I’ve been able to unpack with my therapist.

These were my motivations for reaching for greatness. You have yours. It’s just really important that you know what they actually are.

I didn’t understand any of this at the time. Instead, I was running towards something with a whole lot of my psyche riding on an outcome.

“Anything in life worth doing is worth overdoing. Moderation is for cowards”

- Shane Patton

Ambition is powered far too often by a selfish motivation, a need to do a specific thing in order to think/feel/be a certain way. The late pastor Tim Keller referred to this as “the work beneath the work.”

In Ancient Rome, ambition was the literal ‘going around’ required to attain political office. Even to this day, the word’s meaning includes this desire for “rank, fame, or power.” Ambition so often requires others to fall, so that we can rise.

Why do you want to achieve?

To attain power over others? To receive status in someway? How about to achieve something that will outlive you and attain some sort of immortality.

Whatever your reasons - they won’t work.

We know that because it never does. How many quotes from how many successful people do we have to read? Here are 3 of countless others.

“Why do I have three Super Bowl rings and still think there’s something greater out there for me?” - Tom Brady

“I think everybody should get rich and famous and do everything they ever dreamed of so they can see that it’s not the answer.” ― Jim Carrey

“the life of money-making is one undertaken under compulsion, and wealth is evidently not the good we are seeking; for it is merely useful and for the sake of something else.’ - Aristotle

Even consider something as fickle as fame. As Scott Galloway noted in his recent book Notes on Being a Man, people may know your name, but they don’t know the real you. You may desire fame so you aren’t forgotten. But the crowd moves on quickly and moreover, the you they know is 2-dimensional, not the you that desperately wants to not be forgotten.

These common motivations for achievement are about delivering psychological or spiritual rewards. Why should we think that the answer to those sorts of problems would be found outside of the psychological or spiritual realms?

We quickly fall for the head fake – something that looks like it may give us what we were looking for. But is using the wrong tool to solve the problem.

There is both an honorable and dishonorable type ambition. Sure ambition can be about proving oneself.

But the other form is an ambition that is an aspiration, the seeking of a goal. There is an implied lightness to this. Certainly there is work and a strong pursuit, but it is not competitive with others.

We shouldn’t avoid ambition then at all costs. Instead, we should get the inputs, our reasons for it right. It is good to have big dreams, to want to do big things. These dreams are what propel the world forward.

But we should focus first on becoming the people that can survive our dreams - whether they come true or not.

Outcomes won’t be determined by ability

“There is no man living who isn’t capable of doing more than he thinks he can do.” - Henry Ford

Whether doors open or close for you will have little to do with your ability, in an absolute sense. Most things do not require you to be the best in the world. Better than most yes, but not Michael Phelps.

I believe and have been convinced from my own experiments that it is possible to move into the top 10% of nearly any domain based on effort and practice alone.

Now, of course, there are a select few domains in life that require 1% talent - professional sports comes to mind. But if you are 99.9% of people, that’s not going to be your path. For most, the top 10% of your field will be enough to provide you with the opportunities that you desire.

At the same time, you simply do not know what you are capable of.

It is widely known that Steve Jobs was a jerk to work for. Beyond demanding, at times cruel, and yet, those who worked for him exhibited tremendous loyalty. Most jerks have massive turnover, not mass accolades.

What made Jobs different?

His ability to get people to do things beyond what they believed they are capable of.

Far too often, our internal beliefs of our own capability are massively limited.

We do not see the possibility, nor believe we are capable of what is required. We see/hear an analogous message out of the US Special Forces, who repeatedly emphasize that when you think you have hit your limit physically, you are really nowhere near it.

Bottom line - ability won’t be what limits the outcomes of life, which is good because we do not really know what we are truly capable of.

Learning to be patient and impatient

“Why does he write like he’s running out of time?”

Hamilton, Lin Manuel Miranda

Ambition is a function of both motivation and intensity. If we want to get somewhere, we generally want to get there as quickly as possible. Or as Elon Musk’s stated, “Stop being patient and start asking yourself, how do I accomplish my 10-year plan in 6 months?”

Urgency can be an asset and a liability. It is a powerful fuel that can burn brightly to push achievement. And in fact, many things can move a lot more quickly than we realize. Urgency can also lead to impatience and the risk of making choices too soon.

Knowing when to quit and when to persist is one of life’s true mysteries. The risk is we choose to stop doing something right before the breakthrough of success.

Time is a great paradox. It is both quite short and limited, but also long. We perpetually feel rushed and short on time. But across the entirety of a lifetime of 80+ years, it is undeniably long.

Consider a story that Jensen Huang (founder of Nvidia) shared.

When his kids were still at home, they spent a summer in Japan. While visiting a famous temple, Huang came across a gardener who was using bamboo tweezer to tend to the moss of the garden.

“I walked up to him and I said, ‘What are you doing?’” said Huang. “He said, ‘I’m picking dead moss. I’m taking care of my garden.’ And I said, ‘But your garden is so big.’ And he responded, ‘I have cared for my garden for 25 years. I have plenty of time.’

The gardener knew something important - the push of urgency is often based in a scarcity mentality.

We have to do these things at these speeds b/c we do not have time to delay. If we do not get to our desired destination now, we may never get there at all.

And yet, some things will take far longer than we imagined. And still others, will never come to pass.

Hence the paradox of time.

Life is long [hopefully] and we have plenty of time. And yet, much can be accomplished quickly if we will push. We should be both patient and impatient

What then is the path of wisdom?

Taking one step forward each day.

My executive coach pushes me to each day write down the 2 (maybe 3 things) I want to accomplish. While not seemingly large in number, the daily push forward repeated with great frequency makes for a tremendous amount of progress.

They say part of Elon Musk’s managerial genius is that each week he picks the most glaring problem in his businesses and he spends the week trying to solve that. If each week you are solving the biggest issue (and you have a great team to keep everything else in motion), you cannot help by to see a tremendous amount of progress.

Steve Martin once told an interviewer about learning to play the banjo, “if I stay with it, then one day I will have been playing for forty years, and anyone who sticks with something for forty years will be pretty good at it.” That interview happened in 2007, and in 2012, Martin and the Steep Canyon Rangers, were nominated for a Grammy for Best Bluegrass Album. Martin started playing banjo at the age of 17, the Grammy came at the age of 67 - a full 50 years later.

The destination is uncertain and progress will be slow

16 years ago, I began an annual process each December of setting goals for the year ahead. I built a list of goals across 10 categories. Now years later, I’ve been able to accomplish 90%+ of those goals.

We know from the success literature that goal setting is motivating and clarifying. People who set goals are in fact more likely to achieve them.

And yet, many longer-term dreams and ideas simply are too far out of reach to set a goal to attain them.

Professors Kenneth Stanley and Joel Lehman in their intriguing Why Greatness Cannot be Planned highlight that goal setting as a process works best for incremental improvements. In these situations, there is a clear relationship between current state and the desired future state. A goal provides a clear and understandable bridge between the present and the future.

The problem Stanley and Lehman call out is that the “the challenge of ambitious problems is that their solutions are more than one stepping stone away.” Sometimes, we have dreams of doing things that have never been done before. When that is the case, it is not always clear what the next logical step is.

Consider the invention of the vacuum tube. Vacuum tubes became integral to the design of the earliest computers such as ENIAC in 1946. But the vacuum tube itself was invented in 1904. It was not obvious in 1904 that this technology was going to assist in the development of computing.

So let’s call this the first problem of goal setting - we may not know where we want to go and if we do, we may have no idea how to get there. In fact, getting there may not even be possible.

The second problem of goal setting is the problem of developmental plateaus.

We all know of the concept of a learning curve - the idea that something is hard to learn at the beginning. Once you master some basic skills, you begin to be able to enjoy the activity. So while, it may take you a day or two to learn to snow ski - you are a long way from being Mikaela Shiffrin.

But let’s say you wanted to ski at her level. If you wanted to progress to that level of expertise, your progress will not be linear. You cannot chart out when you will reach that milestone on a table or calendar.

Instead, with any complex skill, we learn new skills and then may see a long period of time before we are actually able to advance to the next level. I shot golf rounds in the 80s for decades before I was able to card my first round in the high 70s.

These plateaus make goal setting a challenge. We do not know when we may run into a plateau that slows our progress. While we are on the plateau, we may worry that we have hit the limits of our ability and that our goal may ultimately be unachievable.

Plateaus can persist for a long time. Some times, it is our skills that must change for us to move to the next level. Sometimes, it is ourselves who must change to be ready for the next level. Who knows how long it can take to become the type of person who is ready for the next level.

Goals then are a two-sided sword. On the one hand, goal setting is really important. If you aren’t doing it regularly, you are missing out on achieving what all you are capable of.

At the same time, the big goals - the dreams you may have of changing the world, making a new invention, reaching new heights of art - these goals don’t have a linear path from today to achieving them.

Stanley and Lehman offer that the right response to his reality is that our focus should be on learning. If we are pursuing creativity and learning, and persist in doing so, we create the conditions for serendipity. And serendipity is what opens the path to the big goals, or reveals entirely new dreams we never would have come up with.

One of my favorite movies is Jiro Dreams of Sushi. This documentary is a beautiful and inspiring profile of a master sushi chef in Tokyo. There is a scene in the film that discusses how the chef, Jiro Ono, is the only one allowed to purchase a particular type of rice from his rice vendor. Ono spent an untold amount of time mastering what is required to optimize the cooking of this particular type of rice. Anyone else cooking with the same rice would be unable to have as good a final product.

I have to imagine that along the way, Ono had no idea what he was after. He just kept iterating and trying new ways to further improve and refine the production of the rice.

There is such an inspiring degree of persistence in the face of the mundane in this example. And yet, also tremendous creativity to keep developing new and better ways to improve the rice. As the documentary portrays, this level of rigor was incorporated across the entirety of the sushi making process.

Along the way, he no doubt discovered new things about making sushi, so much so that he is regarded as a master chef.

But at the outset, he focused on learning in the minutia. Then he just kept learning.

Conclusion

"The master of the art of living makes little distinction between his work and his play, his labor and his leisure, his mind and his body, his education and his recreation, his love and his religion. He simply pursues his vision of excellence in whatever he does, leaving others to decide whether he is working or playing. To him, he is always doing both."

Lao-Tzu

There is a quirky little book written called Finite and Infinite Games written by a professor named James Carse. The core idea of the book is that in life there are some games we play where the whole point is the chance to win. Sports easily comes to mind. But, there are a lot of games in life where the whole point is the chance to keep playing the game. These are what Carse calls Infinite Games. Simon Sinek popularized this idea in his own book called The Infinite Game.

Most of life is not a finite game. We may play sports while we are growing up or even into adulthood. Or you may have an intense game of Settlers of Catan over the holidays with your family. These sorts of games with clear rules and clear winners/losers are welcome amusements and diversions from our everyday life.

Everyday life for nearly all is more likely to be an Infinite Game.

No one thinks of winning the game of golf. In the same way, there is no finish line in a career. There is a choice to begin doing something and keep doing it, and then maybe stop. Classic infinite games.

And so, we must be cautious when we bring a desire for a certain outcome to an infinite game. Outcomes based thinking can be toxic and set you up for heartache and disappointment.

And at the same time, we should not let the lack of a specific outcome spurn us from valiant effort. The over and under-achiever commit the same fundamental error.

We should attempt great feats, make notable quests, dream big dreams because we can. There is nobility in the attempt. The pursuit itself reveals something of who we are, but more over molds us into who we might be.

Those who don’t even try are less than they might be as people. Their lives will be less full as a result. Moreover, as those who share bonds of common humanity, we all will be worse off by their lack of ambition.

There is a hotel where I stay regularly for business travel, nothing fancy, a generic Marriott property. But the star of the hotel is the man who runs the breakfast buffet.

We all know a hotel breakfast can be hit or miss. But this gentleman opens his doors promptly each morning at 6. The buffet is spotless. He has great music playing in the kitchen. And he greets guests as they comes in. The hotel is fine, but watching him work is one of my favorite parts of the trip.

Its so easy to imagine the opposite. This is not a high prestige job, and I’m sure it’s not the most high paying. But here is a guy who is doing great things in common places.

Ambition must be powered by the right motivation, for it to be durable and sustainable over time. This gives us the mental framework then to both be urgent in working towards change, but patient to know that some things take an inordinately long time. As we go, we focus on learning, on creativity, attuned to the fact that sometimes where we think we are heading is not where we end up. And in fact, that destination may be even better than what we were capable of dreaming when we set out along the way.