The Philosophy of Hacking

“The impediment to action advances action. What stands in the way becomes the way.” ~Marcus Aurelius

It’s 3:00am. You’re slouched in your chair, tormented by the glare of your laptop screen, as it reminds you, beckons you – even taunts you – to finish what you started. But you’ve hit the wall, so to speak, and you’ve tried every way around, through or under it… and it won’t budge. Not even the dangerous amount of rapidly-chugged energy drinks coursing through your veins can keep you on task. You start to nod off, you check out; “Just a quick nap,” you think to yourself as you fade away.

Fast forward a few hours.

The judges have announced their verdict – and the winner is you! After pinching yourself to make sure you’re actually awake, you look upon the crowd… beaming, triumphant. You high-five your teammates. A few hours ago, it all seemed hopeless. How foolish that seems now! And yet, there was a path between then and now, a path you could follow because you, like most hackers, are a natural philosopher.

Whether you realize it or not, you follow the Philosophy of Hacking. Rooted in Stoicism, this philosophy implores us to have the right outlook, take the right action, and have the will to power on, even as the obstacles keep coming… until we ultimately triumph and succeed. This post will give you a taste of this powerful way of living – I hope it inspires you to go deeper, and let it guide your life.


Stoicism (1)

“A Stoic is someone who transforms fear into prudence, pain into transformation, mistakes into initiation, and desire into undertaking.” ~Nassim Nicholas Taleb

Stoicism, the Philosophy of Hacking, originated in Ancient Greece. The Stoics – which included philosophers Seneca and Epictetus, as well as Roman Emperor Marcus Aurelius, amongst their ranks – advocated a way of life ruled by logic and correct action, free from impulsiveness, reactiveness, and destructive emotions.

Sound familiar? It should. Mr. Spock, and in fact, the entire Vulcan race, is modeled after the Stoics: logical and rational… yet calm, profound, and even spiritual. Calculated, analytical, and reserved, he provides a perfect contrast to Captain Kirk’s brash impulsiveness. Yet Kirk also represents certain Stoic virtues – namely, his willingness to take action and sheer force of will – that also manifest in today’s hacker culture.

This dynamic between Kirk and Spock perfectly illustrates Stoicism. You can even describe a Stoic as someone who “Thinks like Spock, Acts like Kirk.”



“Mind like a mirror.” ~Zen Proverb

What makes something good or bad? (Google it… it’s ok, I’ll wait).

The answer? We do. Or rather, our perception does. People, places, things, events… they just are. They’re neither good, nor bad – and in fact, “good” and “bad” are entirely artificial constructs.

This is a huge collective hurdle. We perceive setbacks as “bad,” and this prevents us from objectively evaluating and solving problematic situations. When you hit that wall at 3:00am at a hackathon – do you freak out about how screwed you are, or do you see your situation for what it is? Neither good, nor bad – just another task to be solved.

Everything is negotiable, and everything’s solvable, as long as we see clearly enough to find the solution, often hiding right under our noses.

Hackers know this. Design thinking, which is very influential in the tech community, emphasizes exactly this. Objectively, and without prejudice, evaluating the situation – or “problem” – in order to find the right solution. So, if there’s a rock in the way… do you go around it, or move it aside? If you’ve hit a wall at 3am, do you debug, reiterate, or pivot completely?

You may not have a map, but a cultivated, clear perception will serve as your compass. With the right thinking, you already know where to go…



“Just Do It.” ~Nike Slogan

…So now you have to go there. Having the right perception is just the first step (which will still put you ahead of most people alive). Once your thinking’s in order, it’s time to act on it.

It sounds simple enough, but most of us struggle with this. We come up with a million excuses to not take action, and most of them are a variation of “I’m scared to fail.” Deconstruct any excuse you’ve ever made to not do something – “I don’t have time, I don’t have money, I don’t know how” – and it all comes down to choosing complacency and safety over the possibility of experiencing the sting and humiliation of failure.

But hackers, to their advantage, seem utterly immune from this fear. In fact, they live in a culture that encourages – even celebrates – failure! Michael Jordan once said that “before you can taste success, you have to taste failure.” Thomas Edison, after finally finding the right filament for a little invention he called the “lightbulb,” described his previous failures as such: “I have not failed. I’ve just found 10,000 ways that won’t work.”

Removed from this fear of failure, hackers are not afraid to take a leap of faith, to take their chances, to risk everything. From Steve Jobs to Mark Zuckerberg, Silicon Valley is filled with people who put themselves out into the world – in direct defiance of legions of haters, common wisdom, and seemingly the universe itself – and profoundly changed the world around us.

How many of us have similarly big ideas, but just never get around to acting on them?



“Never give up, for that is just the place and time that the tide will turn.” ~Harriet Beecher Stowe

Now, this may seem contradictory, but it’s an important part of the Philosophy of Hacking: sometimes, you can’t change the world.


I know, shocking. Or rather, it’s more correct to say you can’t force a change in the world. But you can be steadfast in your will, and keep hammering away, until the world is ready to be changed.

Allow me to illustrate…

In 1983, Steve Jobs expressed how he wanted to “put an incredibly great computer in a book that you can carry around with you and learn how to use in 20 minutes.” Furthermore, this device would carry “a radio link in it so you don’t have to hook up to anything, and you’re in communication with all of these larger databases and other computers.” Sound familiar?

Moving on… In 1993, Apple released the MessagePad, an early tablet running on a platform called Newton. Though technologically advanced (for its time), the MessagePad was panned and ultimately bombed. Since then, others had tried – and similarly failed – to launch tablet computers.

Until 2010, when Apple introduced the iPad.

Steve Jobs knew since 1983, nearly 20 years before he announced the iPad, what he wanted to introduce to the world. It took decades of iteration, failure, swimming against the current – but eventually, finally, the world gave way and rewarded his sheer persistence.

That is what the Stoics refer to as will. A seemingly contradictory trait, it involves having both the perseverance to keep doing the right action, even when the whole world seems against you… and at the same time, having the courage and humility to recognize your own limitations, when to take a step back, when to let things be.

After all, Apple didn’t immediately follow the Newton up with the iPad – it waited, patiently, until the market was ready, and until it had perfected the concept. Then it leapt.



“That which does not kill me, makes me stronger.” ~Friedrich Nietzsche

It’s important to realize that the challenges never stop. Just like Apple didn’t stop after the first-generation iPad, you too will have to solve endless obstacles and fight countless battles in your lifetime.

It never stops. With each solution, comes new problems. With each goal, new challenges. With each answer, new questions. So you’ve won the hackathon… now, you’ve got a team to wrangle for 12 weeks as you go through the HACKcelerator program, and after that, a room full of investors to wow at Global Demo Day. And even if you succeed there, you’ve got to figure out how to keep your ever-increasing customers, investors and employees happy as you get closer and closer to an IPO.

But don’t despair, for even though you can’t stop the waves, you can learn to surf. As the ocean of life continues to toss ever-bigger waves at you, Stoicism is the surfboard on which you’ll ride them to ever-bigger victories. You might even learn to enjoy the ride!

Both the hacker and the Stoic embrace the neverending obstacles, and indeed thrive in them, for they know they’re priceless vehicles for growth and realization that will always provide insight and strength – if only one looks within them.



“It is the power of the mind to be unconquerable.” ~Seneca

Going back to the hackathon – what happened between 3:00am and the judging? Since you follow the Philosophy of Hacking, you let go, took a step back, and copped a quick nap. Then, with a clear mind, you saw the way forward – a new way that you hadn’t seen before.

Recognizing this, you tapped into your iron will, and decided to give it your all. Taking the right action, you rallied your teammates together and got in the zone. You were on fire, and you couldn’t wait to pitch to the judges. They were impressed by your enthusiasm, and with the calm and collected confidence with which you answered their questions.

Like LeBron James sinking an impossible three-pointer right as the buzzer sounds, you clinched it. You won it all, thanks to the seamless marriage of perception, action and will that allowed you to turn a blockage into a breakthrough, a problem into a solution, an obstacle into a way.

Everything’s solvable. Everything’s instructive. Everything’s valuable. This is the Philosophy of Hacking, and it’s why hacker culture has affected so much change on the world. The rest of us would do well to live by it.


Special thanks to Ryan Holiday for introducing me to this life-changing philosophy through his excellent primer, “The Obstacle is the Way.” Read it in full if you want to master the Philosophy of Hacking.