Oscar winners, SoundCloud rappers and college drop-out start-up millionaires would have you believe that with enough drive and persistence we can all pursue our wildest dreams and reach the top of society as long as we don’t give up.
While some of us will, most of us won’t. Here’s why:
Consider the failures first
It is true that the ones who take risks are often the ones who succeed. They’re also the ones who fail horribly.
When a person takes a risk and succeeds they learn a dangerous lesson: that risk always pays off. We believe that if we do something and succeed that we must have succeeded because of our action, instead of because of dumb luck.
You wouldn’t take the financial advise of a lottery winner who says the way to get rich is to buy lottery tickets. Taking the advice of Will Smith on how to become a successful actor is equally stupid.
The wisdom of successful people is not useful without taking into account the people who did exactly the same thing as them and failed.
For every rich rapper there’s 500 fast food cashiers with a horrendous unfinished mixtape perpetually in the works. For every start up millionaire there are a hundred IT support technicians making glacial progress on an app they say will change the world all while living in their mother’s basement.
Just because it’s your dream doesn’t mean you’re good at it
Believing in yourself is important; knowing yourself is more important.
Loving something and having skill are distinct and unrelated traits. All the desire in the world won’t make you talented. Know your weaknesses.
Loving music doesn’t mean you can sing. Enjoying basketball won’t make you taller or increase your lung capacity.
Just because you’re good doesn’t mean anyone will pay you
Even if you love something and you’re good at it, that does not mean there’s a job in it. If no one will pay you to do it, it’s a hobby not a job.
You like to dance and you’re good at it, but you live in a rural town with no demand for dancers. You move to a better city, but the competition is so high that you’re now in the middle of the pack.
There are millions of people with the same passion as you and we hope there are enough spots to fit us all. Here’s the problem: that’s mathematically impossible. Only ten percent of us can be in the top ten percent of any given field.
Don’t put all your emotional eggs in one basket
“Shoot for the moon. Even if you miss you’ll land among the stars.”
It’s a beautiful sentiment. However, when you make your goal the moon, missing and floating aimlessly among the stars can feel like a hopeless defeat.
Following your dream will blow up in your face if you rest all of your capacity for happiness in the ability to fulfill that one dream.
If you get in your head that you want to be the best boxer in the world and that anything less is a failure you have now created a world view such that there is a more than 99 percent chance that you will be unhappy with your life. Burdening yourself with delusionally high expectations is an unnecessarily difficult approach to life.
This all sounds very dire and cynical, but here’s what you should do instead:
Be Okay with Being Okay
Following your dreams means finding happiness even if you don’t achieve them. This is an essential part of a healthy and passionate life.
You want to be a stand up comic? Well, there are a lot of rungs on that ladder. You may not necessarily be a Louis CK or a Kevin Hart, but you might get the chance to make your entire livelihood on comedy. Making 40,000 dollars a year touring, doing college gigs, and writing on shows is better than working the traditional 9 to 5 for a lot people. So what if you never achieve world fame? You’re doing what you enjoy and surviving doing it.
Going after a dream and getting mediocre results is not the end of the world. It’s okay to try and never make it.To have tried is better than to have never attempted. Not reaching your wild pipe dream at 35 is not the end of the world.
A real nightmare is going to bed every night in a big memory foam bed in a comfortable house with a nice wife that you never really liked that much. When you’re taking the train every day to a job you hate to support the two kids you weren’t ready to have, you’ll spend your days fantasizing about a road not travelled.
Don’t spend your life wondering and living in regret, but don’t bet everything on success either. Be okay with the possibility of failure and learn to redefine what success can look like.
Diversify your Dream Portfolio
There are many ways to get trapped in an unhappy life, but luckily there are just as many ways to find happiness.
You can learn to be passionate about many things. The skills and traits of one passion may translate perfectly to another: the socializing, creativity, and showmanship you admire about being a singer you may also find in pursuing teaching or political lobbying. And you’ll actually get paid to do it.
Don’t make your job your identity
When we’re asked as children what we want to be when we grow up what is actually being asked is, “What do you want to do to make money when you grow up?”
In adulthood, the question “So, what do you do?” is followed by the implicit words “to make money”.
We are taught that our main source of income is what we are (“I’m a doctor, a lawyer, a stripper, a teacher, a waiter”) and that we don’t have the right to claim other identities (“I’m a philosopher, a youtuber, a rock climber, a sculptor”) if they don’t bring us money.
The root of this is a flawed work life culture. Your work should be enjoyable and happy, but it does not need to be the main focus of your life.
Get a humanities degree in something “impractical” because it’s what you want to learn and talk about even if it’s not what will make you income. Fill your life with the things you enjoy doing and the people you like being around. Income is secondary to this.
Just because you work in a trade doesn’t mean you’re only a tradesman. Being a writer with a masters in Medieval Anglo-Saxon Art Theory who happens to make all her money as an electrician is a perfectly valid life set up.
Think of yourself as a business
When thinking about how to make money think about what makes money. Look at what the economy in front of you is actually demanding, or look for an economy that is demanding what you want to supply.
If you can follow your passion and figure out how to make money doing it, then fucking do it. If your dream is to be a miner in a mining town and you’re good at mining, then you’re in luck, but if your passion is less obvious you may have to get creative or adjust your expectations.
If someone told you twenty years ago that you could make a living playing video games 30 hours a week it wouldn’t have been believable, but there’s a thriving scene of competitive players and Twitch streamers doing exactly that. This is an economic reality and therefore a viable dream.
Enjoy the journey
Do you actually enjoy the day to day of your passion or do you just like the idea of succeeding in it?
If you’re only in it for the endgame, you shouldn’t be in it.
If you enjoy how you spend your days, that’s about as happy as a person can ever hope to be. Happiness lies not in where you land, but in the flight itself. ⠂


