The Freedom of Failure

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Freedom of failure — how hard we are on ourselves, all the time

When was the last time you sat back, smiled softly at yourself with the thought — “well done, I’m so happy I did that”?

If you can remember doing this, or even a version of this in the recent past, then kudos to you. For the rest of us — the ones living a daily grey, grim PTM with ourselves — this one is for you.

We have seen big business heads claim this as a superpower — the freedom of failure. And every time they do, it feels like something super luxurious, expensive, almost impossible to get for ourselves. Perhaps because we have only ever seen the high and mighty talk about it. It feels like a members-only club, and nobody slid an invitation under your door.

But let’s go back further. Growing up, did you have the freedom of failure?

When you did not say the times-tables like a song, you were made to memorize them — repeatedly, endlessly — until you got them right or the person administering the task (the admin) gave up on you. I use the word admin deliberately, because that is exactly how it felt. A task to be completed, not a moment to be enriched. When you were stuck, did anyone come up with a different way to help you remember? Did they try memory techniques, make connections, explain the concept differently? Mostly the answer is going to be no. Did anyone ever say — “It’s okay if you don’t know this, you’ll have calculators and computers for the rest of your life anyway”? Almost certainly not.

Times tables is just one of many things children are told they must know. Being good at a sport, riding a bike, dancing, singing — the list is long and the grace period is short. The deeper question is — are we doing anything different with our own children? Or have we simply become the admins in their lives now?

What we absorb subconsciously as children is what we practice as adults. If we were taught that failure is just another attempt — which means you get another chance at trying again, perhaps with a different method — then that creates a safe space. A space where you are unafraid to try once more, where you stay open to tools and aides, where you naturally start becoming solution-oriented. So many of us have sat across interviewers who asked us to “think outside the box” — but if as children we were kept firmly inside the box, and reprimanded every time we dared to step out of it, how do we suddenly find that out-of-box thinking on demand? Are we magical pills we don’t know about? Do we quietly slip into Hogwarts and brew something with Professor Snape?

Back to our very Muggle world, then.

Another space where this phrase gets used often is startups. Reality TV has given all of us a peek into that ecosystem — and we have seen some founders who carry the freedom of failure lightly, while others are at a very real do-or-die edge. Neither is wrong. Every founder knows from day zero what they signed up for. Failure is the fifty percent possibility they all live with. What they hold in their hands instead is the opportunity to pivot — which comes at a cost, but it comes. What I admire most about founders is their resilience, their never-say-never attitude, their hunger to keep learning. Whether or not they have the luxury of failing freely, they carry the lessons forward. And that never goes to waste.

Then there is Tina.

Tina was a homemaker who had chosen that path after quitting two jobs — once to accommodate a marriage, once because of a relocation. Her years went into raising children, running a home, holding everything together quietly. All through this time she was also earning as a freelance artist, which meant no fixed salary, no security, and an unpredictable stream of customers. Every time she hit a low, she had to start from zero — rebuilding, re-proving herself, beginning again. Years later, her spouse asked her what her contribution to the family was and what she intended to bring to the table going forward. That question stopped her cold.

While she technically enjoyed the freedom to fail — the breadwinning pressure had rested on her spouse, after all — nobody had ever asked her whether she liked it. Nobody knew what she went through each time she failed or had to start again. Nobody asked. Nobody stayed around long enough to find out.

As that question about contribution kept circling in her head, she found herself quietly jealous of her spouse’s stability — the regular salary, the increments, the sense of structure. She had given up those opportunities twice. She would not be compensated for either. When well-meaning friends told her to look on the bright side and appreciate that she had the freedom to fail, their words landed like a slur, not a comfort.

Tina is not a victim — she would be the first to say that. She has owned every decision she ever made, including the breaks from formal employment. But the freedom of failure that others so cheerfully assigned to her was not something she chose consciously. It was something that had happened to her. And only she knew that this freedom — the one others envied her for — quietly broke something in her each time a failure came.

She now craves stability. Her search is on.

So freedom of failure is not always a rosy bouquet. Sometimes it is a difficult corner you find yourself painted into, through circumstances and choices that no longer feel entirely your own.

Another space where the freedom of failure quietly lives — mostly unacknowledged — is in relationships. Especially the long ones. Marriages, friendships, partnerships. We enter them with the best of intentions, and sometimes we get it right, sometimes we don’t. A misread situation, a wrong word at the wrong time, a decision taken without fully thinking it through. And what do we do with that? We carry it. For years sometimes. The guilt, the “I should have known better”, the mental replay of how things could have gone differently. Nobody hands you a handbook at the altar or when you shake hands on a new friendship saying — here, you are allowed to get this wrong sometimes. So we hold ourselves to an invisible, impossible standard — of always saying the right thing, always being the bigger person, always getting it right.

What if instead, we treated a relationship rupture the way a good therapist would — as information? As a moment that is telling you something about yourself, about the other person, about what needs to shift? That single reframe can take enormous weight off and replace it with curiosity. And curiosity is always a better starting point than guilt.

Then there is the career pivot. The person who spent twelve years in banking and one fine day decided they wanted to design furniture. The engineer who took a sabbatical to write a novel. Society does not go easy on these people. The raised eyebrows, the quiet judgment from family, the “but what about your career graph?” The person themselves is usually their own harshest critic — what if I fail, what if I wasted all those years, what will people say? The pivot itself is rarely the hard part. The permission to pivot — the permission to say, that chapter served its purpose and I am now turning the page — that is the hard part. And yet, every single person who has come out the other side of a brave career change will tell you the same thing: the worst that happened was not nearly as bad as the fear made it out to be.

So what does all of this tell us?

Failure — whether it shows up in a classroom, in a marriage, in a balance sheet, in a career, or in the quiet corner of a freelance studio — is not the opposite of success. It is part of the same journey. It is a pause, not a full stop. A comma in the middle of a sentence that is still being written.

We don’t need a TED talk or a prime time startup pitch to claim this freedom for ourselves. We need something far simpler and far harder — the willingness to be a little gentler with ourselves. To say: I tried. It did not work out the way I hoped. Let me sit with that for a moment, and then figure out what comes next.

The always-successful ones — the ones the world looks at and says “they have never failed” — perhaps they are the ones who need this permission the most. Because the pressure of an unbroken record is its own kind of prison. And no one should live in a prison of their own making.

So the next time you stumble — and you will, because we all do — try not to call it a disaster. Call it data. Call it a detour. Call it the universe nudging you, gently, toward a slightly different path.

And then, without too much drama, keep walking.