What if you knew you would fail?

👋 Hey friends,

"What would you do if you knew you could not fail?"

This is one of those motivational mantras designed to help us push past our fear of failure. If success was guaranteed, we'd have the courage to pursue our wildest dreams: start that company, write that book, or publish that YouTube video.

We'd approach our work with a sense of ease and creativity rather than the crushing weight of perfectionism. We wouldn't burn ourselves out chasing some elusive finish line, convinced that we're never working hard enough. We'd actually enjoy the process instead of treating it like a test we might fail. Our self-worth wouldn't rise and fall with every small victory or setback.

It sounds idyllic – because it's a complete fantasy.

What are the odds?

In my day job, I'm a growth engineer. I spend my time testing ideas and running experiments to figure out how to increase customer acquisition, activation, and monetization.

My role is essentially to de-risk ideas and deliver often uncomfortable truths about their odds of success or failure.

So, here's my professional assessment about the likelihood of being successful in nearly anything: it's abysmal.

Only 10% of businesses started this year will be around in 7 years. 3% of books sell more than 1,000 copies. 1.5% of all active YouTube channels have more than 50,000 subscribers.

Take almost anything meaningfully ambitious you want to accomplish in life, and the numbers will humble you quickly.

No matter how hard you work, how naturally gifted you are, how convicted or desperate you are to succeed – the reality is that it would take an enormous amount of random, uncontrollable luck to achieve traditional markers of "success".

The odds are not in your favor.

I know this feels discouraging. But once we accept this reality, we can ask ourselves a much more revealing question.

What would you do if you knew you would fail?

If you knew with absolute certainty that your venture would fail, your book would go unread, your work would remain largely invisible—what would you do?

Would you give up? Just not try at all? Well, then good! Life is short. Save your time. Do something else. Release your ambition. Go spend more time with people you love.

Feel at peace knowing you made a pragmatic decision that saved you years of pain and disappointment.

There is another option, though. We can accept the inevitability of failure...and try anyway. Not because we're delusional about the odds, but because we can't help ourselves.

It's like deciding to hike a mountain knowing that the summit is blocked, inaccessible, and permanently shrouded by clouds. Reaching the top and seeing the view isn't the motivator. We climb because something inside of us just needs to feel in motion.

The pursuit is no longer of success, but of curiosity, learning, discovery, and adventure. And here's what I've noticed: embracing the certainty of failure looks a lot like embracing the certainty of success.

If you knew you were going to fail anyway, you'd stop taking every setback so personally. You wouldn't be so hard on yourself when things didn't go according to plan. You'd find genuine joy in the daily work because the pressure to "make it" would evaporate. You'd be kinder to yourself and others because you'd understand that we're all just figuring it out as we go.

You'd feel free to experiment without the paralyzing fear of wasting time or making the wrong choice. You'd work on your own terms instead of constantly looking over your shoulder at what everyone else is doing. And you'd stop being swayed by the endless parade of people claiming they have the secret formula for success, because you'd know that failure is the only guaranteed outcome.

A lot of people try to motivate themselves by declaring, "Failure is not an option". But I've started to embrace the truth that...

Failure is the only option

We can't choose to be successful. That takes luck. But we can choose to fail. We can choose to take a shot, have a go, make mistakes and learn.

One of the quotes I have hanging in my office is:

"Experience is what you get when you didn't get what you wanted"- Randy Pausch

But I'm starting to realize how freeing, inspiring, and cathartic it is to have experience be what you wanted.

And interestingly, for the part of us that still, deep down, wants to achieve, experience increases our odds of success.

Second-time founders are 5% more likely to succeed than first-time founders. An author's second book is 7% more likely to sell more than 1,000 copies. YouTube channels that actively publish for more than 3 years are more likely to reach that 50K subscriber milestone.

Although it's small and although it's still completely out of our control, our odds of success increase the more we fail.

So, rather than trying to be inspired by the delusion that we'll succeed, we should embrace that the only thing that is certain is failure.

And if we truly accept that fate and are willing to pursue something anyway, that in itself is a kind of success. Because it means we've found something we simply enjoy doing.

And, in this life, that's special.

Until next time,
Drew

This essay is dedicated to my grandfather, Harry Lister.