What Failure Is Trying to Tell Us

One of my favourite shows growing up was Gilmore Girls. My school friends and I would rush home after school to watch each episode and then discuss it endlessly. And, of course, we were all madly in love with Jess #TypicalTeenageGirls.

What is funny is that, all these years later, my friends and I still occasionally talk about Rory, the show’s protagonist. I am fascinated by how realistically she was written, particularly as she grew older. Rory was intelligent, ambitious and hardworking, but she was also someone whose sense of herself had been shaped by being told, repeatedly, that she was exceptional.

You do not need to have watched Gilmore Girls to understand this essay. But when I started thinking about the difference between struggling and failing, I kept returning to Rory’s story.

There is a particular story we like to tell about hard work: “if you want something badly enough, remain disciplined and refuse to give up, eventually things will work out”.

It is appealing partly because it gives us a sense of control. Effort becomes a kind of contract with the future: if I keep doing my part, life will eventually do its part too. Except, of course, life has never agreed to this arrangement.

People can spend years chasing a goal, enduring rejection and making sacrifices because they assume difficulty is simply part of the journey. Perhaps success is taking longer than expected. Perhaps the breakthrough is just around the corner.

Sometimes they are right. Sometimes they are not struggling towards something at all. Sometimes they are failing at it.

We often treat those two experiences as interchangeable. We describe a difficult period as failure, while a failing strategy becomes something we simply need to struggle through. But I do not think they are the same.

Struggle tells us that something is difficult. Failure tells us that something, at least in its current form, has not worked. Both contain useful information. But they may be asking us to do very different things. And Rory Gilmore’s story makes that difference unusually visible.

Winning

For much of Gilmore Girls, Rory is doing what Rory has always done. Winning.

She becomes valedictorian at Chilton, a prestigious private school. She is accepted into Harvard, Princeton and Yale. Teachers praise her. Her grandparents believe she is extraordinary. An entire town seems invested in the idea that Rory Gilmore is going somewhere important. Even my friends and I were invested in her trajectory. I genuinely studied harder at school because of Rory.

And even when life becomes difficult, things have a habit of working out for her. When Rory first arrives at Chilton, she is academically overwhelmed. She falls behind, doubts herself and has to work extremely hard simply to catch up. But look at how that chapter ends. She graduates as valedictorian and finds herself choosing between some of the best universities in the world.

I related to that part of her story. When I moved from Vienna to London, I had to adapt to an entirely different education system. Until then, all of my schooling had been in German in Austria, so there was a lot to catch up on, alongside the inevitable self-doubt. I remember thinking about Rory while completing my A-levels.

That is what makes her Chilton years so important here. The struggle becomes part of the success story. Difficulty does not challenge Rory’s belief in who she is. In the end, it reinforces it: she struggled, worked harder and succeeded. Rory knew how to struggle. What she had very little experience doing was failing.

Failure is Information

Failure and struggle can look similar from the outside, but psychologically they can teach us very different lessons. Struggle followed by success reinforces the story we already believe about ourselves:

“This was difficult, but I was capable.” “I worked hard, and eventually I succeeded.” “I was right to believe this path belonged to me.”

Failure can ask a more uncomfortable question: “What if it doesn’t?”

For people who have experienced failure repeatedly, that question may arrive quite early. You work incredibly hard and still do not get the grade. You apply and somebody else gets the opportunity. A relationship ends. A career does not unfold as imagined. A door stays closed no matter how many times you knock.

It can be devastating. Sometimes it is also unfair.

But people who have had the opportunity to properly fail and then continue building often learn something useful: effort is not a guarantee. The world does not owe us a particular outcome simply because we worked hard for it. That sounds pessimistic until you realise how liberating it can be. Once effort and outcome are separated, failure no longer has to mean something has gone terribly wrong. Something simply did not work. Then the question becomes: why?

Was the strategy wrong? Do I lack a skill? Do I need more experience? Am I in the wrong environment? Or am I trying to succeed at something that no longer fits me?

Sometimes failure is telling us to keep going. Sometimes it is telling us to change how we are going. And sometimes it is telling us to stop. The difficult part is knowing which.

When Failure Becomes Identity

Rory seemed to have much more difficulty making that separation. For her, failure became something more personal. It was not simply, I failed at this. It was, maybe I am not who I thought I was.

Nowhere is that more obvious than during her internship with Mitchum Huntzberger. Rory had wanted to become a journalist for most of her life. By Yale, journalism was no longer simply something she was interested in. It had become part of the future she expected for herself.

So when she landed an internship with Mitchum, one of the most powerful figures in the newspaper industry, it felt like an important step towards that future. Rory did what Rory always did. She showed up. She worked hard. She tried to do everything properly.

And then Mitchum gave her his verdict: “You don’t got it.” It was brutal. But it was also one man’s opinion. He may have been right. He may have been wrong. Perhaps Rory lacked initiative and could have developed it. Perhaps she needed more experience or a different newsroom. Perhaps reporting was not ultimately where her strengths lay.

There were several possible interpretations. Rory seemed to hear only one: “You are not good enough to be the person you thought you were.” And that is a very different kind of failure.

Because when an outcome becomes fused with identity, curiosity becomes much harder. Instead of asking, “What can I learn from this?”, we start asking, “What does this say about me?”

This is where external validation becomes complicated. Rory had spent most of her life surrounded by people who believed she was extraordinary. Harvard, Princeton and Yale reinforced the same story. Validation can encourage us, motivate us and make us work harder. But it becomes dangerous when we use other people’s belief in us as evidence for who we are. There is a subtle difference between knowing you are capable and knowing that other people think you are capable.

I think part of the reason I find Rory so interesting is that my experience has often been the opposite. I never really had the luxury of consistent external validation. If anything, I became accustomed quite young to being underestimated. People would form an impression of me and then revise it once they knew me better or saw what I was capable of.

That was not because I was deliberately hiding anything. I have simply encountered enough conscious and unconscious bias over the years to recognise the pattern. It was frustrating. But it also meant I could not rely heavily on other people to tell me what I was capable of. So I started collecting my own evidence.

Not to prove anybody wrong. That distinction matters to me. I have never wanted my life to become a reaction to someone else’s expectations.The evidence was for myself.

I would do something I had doubted I could do and remember it. I would struggle through something difficult and remember that too. Eventually those experiences accumulated into something more durable than praise. Self-belief. And, over time, confidence.

Perhaps that is one of the quieter ways confidence is built. Not by repeatedly telling yourself that you are exceptional, but by gathering enough evidence that you can trust yourself when somebody else does not immediately see what you see.

Rory, by contrast, had spent much of her life receiving that evidence from other people. And if other people have the power to convince you that you are exceptional, they also have the power to convince you that you are not. That is why Mitchum’s criticism lands as something much larger than one bad review. He is challenging an identity that had been reflected back to Rory for most of her life. And she did not yet seem to have enough distance between the two.

When There Is No Plan B

There is another moment in Gilmore Girls that becomes more interesting in hindsight. Jess asks Rory what she would do if journalism did not work out. It is a perfectly reasonable question. Rory does not seem to think so. The possibility genuinely unsettles her, almost as though she had never seriously considered that the future she imagined might not happen. And perhaps she had not.

Journalism was not simply one career Rory wanted to try. It had become part of the story she had been telling about her life for years. Which is why Mitchum’s criticism threatens more than a career. If journalism does not work out, then what? Who is Rory without that future? This is where I think optionality matters.

I have written before about the value of creating options in life. Not because we should remain permanently uncommitted, but because a life built around a single possible outcome can become surprisingly fragile. Optionality gives us somewhere psychologically to go when reality changes. It allows us to say: I wanted this. I worked for this. It did not happen. What else might still be possible? That is different from giving up. Sometimes changing direction is simply a response to new information. Rory seemed to have very little room for that kind of thinking.

After Mitchum tells her she does not have what it takes, she drops out of Yale. On the surface, she is walking away from university. But I think she is also avoiding another test. Trying again would mean risking another answer. Another editor might agree with Mitchum. Another attempt might produce the same result. And sometimes not trying feels safer than collecting more evidence.

One rejection can be dismissed. A second becomes harder to explain. A third may force us to reconsider the story altogether. So avoidance can become a strange form of self-protection: “if I stop trying, I never have to find out whether the thing I fear is true.” But you also lose the opportunity to discover that it might not be.

This does not mean abandoning something the moment it becomes difficult. Struggle often requires persistence. The challenge is recognising when persistence is still serving the goal and when it has become a way of avoiding what the evidence is telling us.

Optionality does not mean caring less about what we want. It means allowing for the possibility that one path may fail without treating that failure as the end of possibility itself. Perhaps the more resilient position is to leave enough room in our identity for more than one version of who we might become. To be committed without becoming trapped. Because sometimes the path fails. That does not necessarily mean we have.

What Paris Knew

Paris Geller, Rory’s classmate and friend, gives us a useful contrast. Like Rory, she is highly intelligent, ambitious and intensely hardworking. But Paris has much more experience with disappointment. Harvard rejects her, despite the fact that she had imagined attending for years. Things do not always go according to plan for Paris. And she does not exactly respond to failure gracefully.

She melts down. She catastrophises. She gets angry. But what she rarely does is stop. Failure can embarrass her. It can devastate her. It does not usually convince her that she no longer belongs in the race. If anything, uncertainty makes Paris create more options. By graduation, she is applying to both law school and medical school. If one path closes, others are waiting.

There is something almost excessive about it, but underneath that excess is resilience. Harvard can reject Paris without Paris concluding that she is not intelligent. She can fail at something without immediately needing to become someone else. And this is where the difference between Rory and Paris becomes most interesting.

It was not intelligence or ambition. They were both brilliant and worked extraordinarily hard. The difference was where they located their sense of certainty. Rory had spent much of her life having her identity reflected back to her by other people. Paris had spent much of hers pushing forward whether other people approved of her or not.

That does not mean Paris was immune to validation. She wanted recognition, status and success as much as anyone. But Paris had also accumulated a great deal of evidence about herself. She had strong academic credentials, leadership experience, an extraordinary breadth of knowledge and a long history of working intensely towards what she wanted.

She had also failed before. That part matters. Paris knew that disappointment could be humiliating and painful without being definitive. She had already gathered evidence that she could lose something important, recover, and continue building. So when somebody rejected her, their judgment entered an existing body of evidence.

It did not automatically replace it. Harvard could decide that Paris was not right for Harvard. That did not erase everything Paris already knew about herself. Perhaps that is what self-belief actually looks like. Not believing that you will always succeed. Not assuming every rejection is somebody else’s mistake. But having enough evidence of your own that somebody else’s judgment becomes one piece of information rather than the entire case.

Evidence, however, has to work both ways. We cannot collect only the evidence that tells us to persist while dismissing everything that suggests we may need to change direction. At some point, repeated failure may itself become useful evidence.

And that brings us back to the tension at the centre of this essay: knowing when the evidence is telling us to keep struggling, and when it is telling us that something is no longer merely difficult. It is not working.

Self-belief should give us the confidence to continue when continuation makes sense. It should also give us enough security to change course when it does not.

Reading the Evidence

Perhaps this is where the distinction between struggling and failing becomes most useful. Neither tells us automatically what to do next. Struggle does not always mean keep going. Failure does not always mean stop. The harder task is interpretation.

We often look for certainty where there is none. We want a clear sign that persistence will eventually pay off, or equally, that it is time to walk away. Life rarely offers information that neatly.

One rejection may mean very little. Several may still mean very little in a highly competitive process. Repeated failure in exactly the same way, however, may be telling us something different.

Perhaps the strategy needs to change. Perhaps we need more experience. Perhaps the environment is wrong. Perhaps our strengths lie somewhere adjacent to what we originally imagined. Or perhaps this particular path is simply not working.

The difficulty is that we are rarely neutral interpreters of our own evidence.

When we desperately want something, we can turn every setback into proof that we simply need to work harder. When we are frightened of failing, we can turn one setback into proof that we were never capable in the first place. Both distort the information. One makes us persist long after persistence has stopped being useful. The other makes us retreat before we have learned very much at all. Underneath both reactions, I think, is identity.

The more tightly we attach ourselves to an outcome, the harder it becomes to assess that outcome honestly. If becoming a journalist is not simply something I want to do, but evidence that I am intelligent, ambitious and going somewhere with my life, then changing direction becomes psychologically expensive. I am no longer changing careers. I am changing the story I tell about who I am.

And we do this outside work too. A relationship, marriage, friendship, creative ambition or imagined future can quietly become evidence that we are lovable, talented, making the right choices, progressing as we should. Then letting go feels like admitting all of those things were untrue.

But one thing failing does not invalidate is everything that came before it. A marriage can end without having been meaningless. A career can change without the years spent building it becoming wasted. An ambition can turn out not to suit us without proving that we were foolish to pursue it.

Telling people simply to “embrace failure” does not seem particularly useful. Failure is not inherently wise. It does not arrive carrying a lesson neatly labelled for us. We have to make sense of it:

We have to distinguish between a difficult chapter and a failing strategy. Between one person’s opinion and a meaningful pattern. Between discomfort that comes from growth and discomfort that comes from repeatedly forcing something that no longer fits. There will not always be a clean answer.

Perhaps that is part of becoming more comfortable with failure too: not knowing immediately what it means. Allowing ourselves enough distance to ask better questions before turning the experience into either a tragedy or a motivational story.

Rory’s problem was never that she struggled. She was very good at struggling. And it was not simply that she failed. Everybody does. What made failure so destabilising was that she had so little distance between what happened to her and what she believed it said about her.

Maybe that is the distinction I keep returning to. Failure should be allowed to change our plans. It should be allowed to challenge our assumptions. Sometimes it should even change our minds about ourselves. But it should not be granted the authority to define us entirely.

The challenge, then, is not simply learning how to fail. It is learning how to read failure.

Perhaps maturity is not becoming less afraid of failure. Perhaps it is becoming better at understanding what failure is trying to tell us.

“You may encounter many defeats, but you must not be defeated”

- Maya Angelou