A framework for chasing dreams

Here is a dartboard.

In your hand is a dart. Where are you going to try and throw it?

You could aim for the bullseye, a tidy 50 points.

Better yet, you could aim for triple twenty, 60 points.

Regardless of where you aim, you are probably going to miss. Unless of course, Michael Van Gerwen is one of the few hundred people who read my writing.

If you are at the pub, with friends, beer in one hand, dart in the other, chances are your fate is sealed. Despite your complete lack of skills, you are going big.

It’s bullseye time.

The shakespearean tragedy that follows, was inevitable, the publican knew what was going to happen before the sisal fibers last brushed against your fingertips.

The dart ricochets off the pub wall, clangs loudly against the floor and everyone is now looking at you.

Well that was shit.

But I have an important question, how and where would you throw the dart if your life depended on it?

If everything rested on where you set your sights, where would you aim?

Well in this theory I have made up, everything does rest on it. By the end of the article I hope to convince you that your life and career are essentially throwing a dart on a board.

And the sad reality is that most people miss because they are not aiming in the right place.

Let’s imagine the dart is us. The bullseye is our dream, it can be a job, vocation or achievement. There are many patterns to our dreams: the professional athlete, the novelist, the actor, the musician, the painter, the President… Some dreams may even be more operationalised than that: to play in the NBA, to win the Pulitzer prize, or an Oscar.

But this isn’t a normal dartboard. The bullseye’s size is inversely proportional to the size of the dream. You want to be president, the bullseye is the size of the pupil of a bird. You want to be a bus driver, the bullseye is almost the size of the board.

Probability is the key determinant of the size of the bullseye. Here are some probabilities for some common dreams.

0.3% — Chances of making it in the NBA

0.0002% — Chances of becoming famous actor

0.00006% — Chances of starting a $1 billion company

These odds are fairly horrific. But every year, millions of young people aim big, and change the course of their lives in the pursuit of greatness. For some, this might mean enrolling in three years of acting school or waiting tables to pay for the recording studio.

But it’s important to note, that some people are exceedingly good at throwing darts. They are the top 0.0001% of talent. For the dreams, where skill is the major deteriming sucess factor, like sport, then it might actually not be that risky for you if you are the best. The problem is most dreams don’t just hinge on skill. They hinge largely on luck, regardless of talent. Acting. Writing. Painting.

And the irrefutable, undeniable, mathematical reality is that almost every single one of these young people will fail.

And that’s completely okay, if they can find happiness in failure.

But what breaks my heart is when the pursuit of a dream leads to an unhappy life. I have seen it many times before, we all have.

It is the high school sports coach who hates kids but wanted to be a professional athlete.

It is the unfulfilled copywriter for BHP who wanted to be a poet.

It is the tired minimum wage worker, who wanted to be an actor.

Usually, the story unfolds like this, a young adult aims for the bullseye. Then after a decade of trying, and making limited progress, they miss. They might take another shot, and miss again.

Then in their thirties they have children, and their life changes. Dreams become selfish in a world where a helpless being depends on you for survival. Then, almost always the dream is relegated to the background as financial security becomes the all consuming focus for the young family.

And this is where the trouble arises.

No one wants to admit it, but pursuing the dream had a cost. A decade of chasing a skillset that might have no real commercial benefit. You can play basketball really well? Nice, meet Excel.

You are back to square one.

All your peers who gave up on their dreams a long time ago and pursued stable jobs now have stable finances.

You are not selfish, you need to support your family so you take any job you can find. Anything that is even remotely adjacent to your motley skillset accumulated in the pursuit of greatness.

You accept compromise, after all this time. And you hate it. And it doesn’t pay well. And now you’re bitter.

I think this story illuminates three harsh truths about the dreams we have for our lives:

1. Most dreams are just lottery tickets
2. Most people stop playing this dream lottery when they have kids
3. The pursuit of dream lottery can cost a decade of the most productive years of our lives

Now I am not the grinch of dreams. I have them too, probably too many on the list. And as we know from conditional probability, if you have more than one wild dream, your chances are fucked.

So why am I trying to ruin the dreams of all young people aspiring to do great things?

I am not. I simply want to encourage a new way of thinking about dreams and life careers that will save people a lot of sadness. I call it the Dartboard Approach to life.

If dreams are the bullseye, then the rest of the board is the sample space of the likely life options from pursuing that goal, weighted to its relative probability.

For example, if the bullseye is to become a famous Hollywood actor, the next ring might be being a Broadway actor. Then the next one down could be being a voice actor. Then an actor in a local theatre company, then an acting teacher at a reputable university, then an acting teacher at your local high school, and finally waiting tables. This is an example of the sample space of life careers that exist by aiming in this direction.

So waiting tables would be the wedge on the board valued at one point, it is our hypothetical worst outcome for aiming for your dream. In the middle, let’s say at 10 points is being an acting teacher at a local high school.

Now before you pick holes in this thought exercise, why is this useful?

It tells you where you should aim, you are throwing this dart as if your life depended on it, remember?

It allows us to think probabilistically about our future. While it sounds boring, this could save your life.

If we see where we are likely to end up if we fall short of our dream career, we can think about whether we would actually be happy. Even better, we could aim for the bullseye for the first few throws, and then we could take another shot at a safer option that we would also like.

For example, if you go to acting school in pursuit of acting in movies, you may also love teaching and be completely okay with a salary of $60k teaching students in a local high school. In this sense, there are some places we can land on the board where we mostly can’t lose.

In this case, you should follow your dreams.

Maybe waiting tables for 12 hours a day, looking after your child for 4, and then going to auditions every other second makes you feel content. If you are one of these rare souls, then pursue your dreams doggedly.

You can’t lose.

But if you are very honest with yourself, and you know deep down that the other career paths on the board would not make you happy:

Then you probably shouldn’t follow your dreams, pick a different board.

Pick a board, with an aspiration where everything related to that pursuit would make you happy. Where even the failures are successes.

All dreams are not created equal. Pick a board that is more contingent upon skill and has less random variability. Many dreams have gatekeepers that have arbitrary selection criteria. Casting agents, writing agents and art curators. For some aspirations, you are the master of your own fate based off how good you are. No one is going to deny Michael Jordan from being in the NBA, because sports leagues are some of the best meritocracies we have in the world. This is a blessing. It means if we are not delusional, accept genuine, candid feedback, and give 100%, we can seriously improve our odds of making it or knowing when the dream is impossible.

When I was young I had two dreams. To start a company and to write fiction full time. I plan on doing both. But the first game of darts I intend to play properly is running my own business.

Because I love it. I love the ugly parts of business, making models, thinking about branding, talking to customers. It’s weird, but it’s just something I intrinsically enjoy.

And if the bullseye of starting a billion dollar company has a 0.00006% chance, almost every other tile on that board is something I still enjoy doing. Being a product manager, being in tech sales, and being in marketing for a tech company.

Hell I even loved being a VC, arguably the ultimate soft landing for failed entrepreneurs ;)

I can’t lose by throwing this dart.

Being a failed writer, I would not be happy.

Because I looked deeply at the sample space of likely lives this would lead to, and after deep self reflection, awareness of my own flaws, I know it wasn’t for me.

So to all future dreamers or even those who are unsure about what to do with their life, make your own dart board of possibilities.

Choose carefully where to aim.

The bullseye probably won’t happen but will you still be happy if you miss?

If you won’t be, find a different board to play.

One where you can not lose.