Can We Stop The Whole “Go Big or Go Home” Stuff When It Comes To Following Our Dreams?

When Hernán Cortés landed in Mexico in 1519, he burned his military’s fleet of ships, removing any thought of retreat or return to Spain. His military would have to conquer the land or die tryin’. (Cortés was Spain’s equivalent of 50 Cent.)

Against incredible odds, Cortés’ military caused the fall of the Aztec empire and brought large parts of Mexico under the rule of Spain. If anyone embodied the “Who cares if we’re ready! Let’s do this!” mentality, it was Cortés.

Cortés’ story is often used in business writing targeted at would-be entrepreneurs and lifestyle designers. This imagery resonates with a lot of people. We like the concept of single-minded passion. And burning ships make for good desktop backgrounds.

But it’s important to remember that normal people don’t burn their ships. Crazy people do. Just because this strategy worked (once!) doesn’t mean that you and I should adopt it as our de facto approach to life.

But that’s exactly what many twentysomethings have done. When it comes to our dreams and passions, we’re boat-burners. We go big or go home. We burn the boats or go back to Spain. We sprint after our dreams or sit in misery. It’s now or never.

There is no middle ground.

Granted, there is a time and place to go all-in. But twentysomethings like to do it for no good reason.

For the millennial, passion requires recklessness. And I believe it is this reckless, boat-burning ideology that holds many twentysomethings from actually pursuing their passions.

Which is why I’m here to advocate for the middle ground. You don’t have to go big. You don’t have to go hard. You don’t have to wake up at 4 am. You don’t have to move to a beach in Mexico.

You can go medium.

“Get busy living or get busy dying.”
 — Andy, Shawshank Redemption

Let Curiosity Drive You

The conventional “Follow Your Dream!” mantra conjures up the image of a recent college graduate striking out on her own. Of becoming her own boss. Of assuming the title of “expert.” Of doing it her own way.

But what if following your dream requires the opposite mentality?

In his book Mastery, Robert Greene talks about the need for a “self-directed apprenticeship” on one’s course to finding an ideal vocation. This apprenticeship is a developmental period of 5–10 years that (generally) follows formal education. The purpose is not money, title, or fame, but rather the transformation of one’s mind.

This type of apprenticeship can often be confused with traditional internships or soul-sucking “pay your dues” scenarios. But actually, the most beneficial apprenticeships are those that give the learner freedom to shape her education. The self-directed apprentice does not need to be motivated by money or title. Her motivation is primarily a thirst for more knowledge.

The self-directed apprentice is driven by an immense curiosity (not a rigid framework for learning) that fuels the task of internalizing a large body of knowledge.

It is this thirst for knowledge that transforms a dreamer into a master. It is this submission to a process that creates the most creative minds in history. The apprentice finds her individuality not by going solo, but by subjecting herself to the criticism and instruction of others.

But the process is slow. And who is willing to admit that they are not disciplined or skilled enough to be their own boss? Who is patient enough to submit to long a process of self-directed learning before they strike out on their own?

My caution to you boat-burning and dream-chasing twentysomethings is to find your apprenticeship before you chase your dream. This is a practical way to “go medium” without going big or going home.

Do you need to find some personal sensei for this? Probably not right now, but eventually. Mentors are valuable. And since everyone wants to be their own boss these days, mentors are pretty easy to find.

But even more important than a mentor is having the attitude of an apprentice. Apprentices are driven by curiosity and discipline, not graduate school tuition. They don’t wait for mentors; they hunt them down. They have enough respect for their dream that they assume the role of “learner” rather than “expert.” They follow their dream as an apprentice long before they strike out on their own.

To “follow your dream” in the traditional sense would mean to declare yourself an expert as soon as possible and go it alone. Instead, “go medium” and become an apprentice. Learn as much as possible under the best people. Learn 10x more than your colleagues. Read more books. Ask more questions. Let your curiosity be the engine driving your dream, not the unrealistic demands of a “now or never!” timeframe.

“In this new age, those who follow a rigid, singular path in their youth often find themselves in a career dead end in their forties, or overwhelmed with boredom. The wide ranging apprenticeship of your twenties will yield the opposite — expanding possibilities as you get older.”
 — Robert Greene, Mastery

Follow The Dreamers, Not Your Dream

For some unfortunate reason, “follow your dreams!” has become a widely-accepted piece of advice for unhappy people with terrible day jobs. It’s so culturally-ingrained that I find it hard not to say, myself. If feels helpful. It feels empowering. And it’s way easier than, “How are you qualified to do that?” or “Your dream sucks.”

And since no one is going to tell us that our dreams suck, how are we supposed to know if we should follow our dreams, let them go, or save them for later?

The most common question we ask ourselves is, “Do I know how much work that will take?”

But that’s a dumb question. Everyone knows the answer: a lot. More work than I am currently capable and for longer than I expect.

A better question is: “How will I connect with the people that can make my dream a reality?”

Most dream-following is about finding the person(s) with the other half of our dream. If I want to be a musician, I will be successful when I find people who dream of listening to the kind of music I write. If I want to be a businessperson, I will be successful when I find enough people who dream of of owning the product I create.

But finding those people is tricky, even after 10 years of self-directed apprenticeship.

So how does one get to know these dream-fulfillers?

Don’t follow your dream. Be the other half of someone else’s dream. Rather than chase a dream and hope someone is willing to make it a reality, chase the dreamers and make their dreams a reality.

The purpose of this isn’t to suppress your passion. You’re not putting your dream on the back-burner. You’re just being creative about how you express it.

When you get in the business of other people’s dreams, you’ll find that it takes a little bit more creativity to make things happen. Your skills won’t be quite as intuitive. You’ll need to broaden your horizons. You’ll need to do projects out of your comfort zone. But that’s the thing about following a dream: if you’re on the right path, going out of your comfort zone should be exciting.

More importantly, a focus on fulfilling the dreams of others will cultivate relationships that will move your dream closer to reality. Sometimes, the best way to follow your dream is to follow someone else’s. (At least for now.)

“No individual has sufficient experience, education, native ability, and knowledge to ensure the accumulation of a great fortune, without the cooperation of other people.”
 — Napoleon Hill, Think And Grow Rich


Following a dream comes with an unrealistic pressure to make everything perfect. And when everything needs to be perfect, mistakes are not an option. And if you’re not willing to make any mistakes, it is quite difficult to learn from them.

It’s kind of like a game of poker. In poker, a player goes “all-in” with one of two attitudes: confidence or fear. A player can be bluffing and still have confidence that he will win; his move is calculated, not reactionary. Otherwise, a player moves “all-in” because he is low on chips and feels like he needs to make up for lost time; his actions are motivated by need, not thoughtfulness; he feels like he is running out of time, so his actions are reckless.

At some point in your life, you’ll have to pull the trigger and go all-in on your dream. You’ll need to burn your boats one day. But if you’re making that decision because you feel like you’ve wasted too much time already — and not because you’re ready — then you will be motivated by fear. You will be afraid of mistakes, rather than seeing them as a learning opportunity.

Risk is an important component of success in any venture. Like poker, life is made up of big and small risks. The more small risks you take, the more prepared you will be to take larger risks. The confidence you learn from small risks will be the same confidence you have when you take big risks. And hopefully — if you take enough small risks — you’ll never need to resort to taking big risks just to survive.

So when it comes to “following your dream,” save the drastic measures for later. You probably don’t need to drop hundreds of dollars on specialized equipment (yet). You probably shouldn’t quit your day job (yet). You probably shouldn’t move (yet).

Instead, take small risks. Learn from small mistakes. Take risks on a scaled-down version of your dream. Take risks on something that isn’t your dream. You should be excited about the biggest risks in your life, not terrified. If following your dream conjures up more fear than excitement, maybe it can wait. Work your way up the risk ladder so that your big, “all-in” risks are made from a place of confidence, not fear and necessity.

“If you only take small risks, you are only entitled to a small life.”
 — Robin Sharma

In Closing

I don’t know what your dream is, but I bet that it is awesome. But just because it is awesome doesn’t mean that the best course of action is to pursue it with reckless fervor. “Following your dreams” — in the conventional sense — means to take incredibly drastic and selfish action. That will get you nowhere in life.

Instead, reconsider your all-or-nothing approach to following your dream and remember these principles:

– Following your dream should not be about recognition, but an internal transformation.
– Following your dream should benefit others, not just yourself.

– Following your dream requires small risks before big risks.
– You can (and should) “go medium.”
“The practical dreamers have always been, and always will be the pattern-makers of civilization.”
 — Napoleon Hill

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