Failure – A millennial's musings

The pain of dreaming big

Every commencement speech tells you to dream big. I want to clarify that dreaming big specifically relates to who you become – not what you have. Fantasising about Ferraris doesn’t count. In this model, they are a possible side effect of delivering something valuable to the world.

Dreaming big comes naturally to those who are ambitious, but some people don’t. Why don’t they? Freud is my friend here. Not dreaming big is less painful than dreaming big. Big accomplishments come with increased responsibility, hassle and resentful friends. Nobody likes those things. I think every human being can relate to this. At the same time, convincing yourself that something that is out of reach isn’t worth it has a name. In Ancient Rome, they called it sour grapes. Literally, the expression comes from this: you cannot reach the grapes, so you convince yourself that they are sour – so you don’t have to keep reaching. It’s a form of nihilism: “it’s not worth it anyway.” Personally, I never suffered from this. Grapes are yummy. However, I have another issue.

Dreaming big focuses on the future. It stretches you. It sets a vision on what should be in your head. However, when you snap out of the big dream – it really hurts. Looking at reality will inevitably cause you to question what is responsible for the discrepancy. This may be another reason that stops people from dreaming big. Furthermore, even if you have the audacity to dream big, feeling bad about yourself in this manner hampers your chances of achieving your dream.

Happiness is most certainly a function of expectations, not reality. In fact, to make it nice and mechanical, let’s (over)simplify: Happiness = reality – expectations.

It is easy to be happy if you have no sense of entitlement. This is a nice way of saying it. It is stoicism in a sentence. Let’s try this: it is easy to be happy if you have low expectations. Hmmm. This calls into question the idea of dreaming big. It seems that reality hurts more when you have big dreams as happiness becomes a negative “number”. While there is technically a difference between a dream and an expectation, but I think for anyone who really believes in their dreams, it is kind of the same thing.

The only solution I can think of is patience. Patience means that you don’t expect is all and expect it now. I recall dreaming of being a doctor. I knew no bigger dream at the time. It didn’t hurt so much when I was 17 and on track – though the dream was still only a dream. It becomes more complex when you are an adult. When you see others who achieve humongous things at an exceptionally young age, when you start comparing yourself to others – your patience seems to die a sudden death. For me, thinking about Mark Zuckerberg or the chap who came up with Snapchat makes me feel like I am already late to the party.

Another bit of common wisdom comes to mind – don’t not compare yourself to others. Is it good advice? Comparing yourself to others is part of understanding reality. I believe that self-awareness and awareness of reality are paramount – hence my interest in mindfulness. So comparing yourself to others it’s at least in part useful. However, it has to be balanced with feeling good about yourself – I don’t think anyone ever achieved anything through hating themselves. In fact, comparing yourself to others could even be pleasant – look at you doing better than some of your classmates. Twisted, but true. Apparently, that’s the same mechanism behind people watching the Kardashians being ridiculous. I don’t know. I’ve never gone there. Looking up to a role model – our fundamental way of learning – is a form of comparing yourself to others, only here you strongly believe that one day you can become a version of this person.

I think it is good advice in the sense that in the long run, you’re only ever fighting against your former self. If you are trending upwards, it doesn’t really matter where you rank in the short term.

Lastly, it is important to get good at dealing with failure. It is my rule that if something hurts too much – a rejection, a failure, whatever – I am taking it personally. The only way to approach this is like a game. A sort of hobby. The moment you begin to take it personally, you lost. There is a temptation, especially among overachievers, to bet their self-esteem on achievements. Bad idea. Just like in negotiating – you should never put yourself in a situation where you can’t walk away from a deal. The way to do that when it comes to expectations is to remember that you are distinct from your mission – no matter how much you love it.

After all, dreaming big is about who you become. Winning is a long game, so big dreams, patience and a good understanding of reality will be required.

Should we avoid losing?

Freud is famous for all kinds of weird reasons. I believe it is more of a reflection on society than it is on Freud. He got some stuff right and some stuff wrong. One of the things that he managed to articulate incredibly well is this simple concept: we are driven by wanting pleasure and avoiding pain. In this simple equation, avoiding pain is much more important. In other words, we will forego pleasure in order to avoid pain. I remember learning that lesson when I was 7: I am sure I’ve done a lot to learn it through my own mistakes, but what got really etched into my brain was my cat’s behaviour. My lovely cat, she was probably about 5 months old then, got on top of the kitchen counter while no one was looking. I may have been an accomplice in her trespassing. She speedily made her way to the divine smelling milk that was getting heated up on the hob. As she put her pus into the pan, she must have burnt herself off the edge of the pot. She jumped right down with a loud meow. She didn’t get seriously hurt. What fascinated me though is that she never went near the hob again. Ever. Even if I put her regular cat food bowl on the switched off cold hob. She would just proudly sit there and wait for me to put it back where it belongs. My cat made a decision – and it was final. Avoiding pain is key.

If you come to associate something with pain, you will probably fear it to some extent. So the question is: should you be afraid of losing and associate it with pain? On the one hand, it means that you will avoid losing. Is that the bottom line though? Winning isn’t the same as never losing.

I don’t know whether losing in some shape or form is part of the obstacle course. Maybe you can just get through a life of poetry in motion without ever losing. I don’t think I can think of any examples of it though. It is important to remember that the people we think of when we think of success generally have some control of what is put out in the world about them. So we are looking at a highlight reel. However, considering some really famous actors, politicians and business people – it is easy to think of things that were outright flops. Cringy films, awkward public statements, bad investments, a personal life that could be on Jeremy Kyle – it all seems part of everyone’s journey.

As somebody who has a clear sense of agency and whatever control that humans can have over their own lives, I envisage life as a series of option trees. Every time there is a fork in the road – that’s when life is shaped. Moments of choice are what shapes that part of our lives that we can control. However, I have been making the assumption that if I make the right choices, I will never experience losing. Hence, losing equals bad choice – my bad choice. I am starting to question that assumption.

It is important to take a step back and consider what we call losing. What do we call failure? Is failing simply falling short of our expectations? In that case, for anybody who likes philosophy and mindfulness, it is immediately obvious that losing happens in our heads – not in real life. Expectations are great, but a dose of humility can be a real treat when we get so carried away so as to believe that we are owed our preferences at all times.

Not to sugar coat it – because it is true – but losses now can mean large gains later. While that’s a metaphor for our experience, it is quite literally a description of an investment: debit now for credit later. To continue with the investment analogy what really matters is how you compound it. Does a loss mean new learning and information that adds to your overall game or does it mean debilitating poison that stops you from carrying on? It is clear that the latter option is better. So maybe being afraid of losing in and of itself is damaging. I don’t know for certain that losing is unavoidable. A consultant psychiatrist I used to work with and revere used to use this metaphor: if you want to box, prepare to get punched.

It’s not easy though, to find a balance. If you focus too much on being OK with losing, you will get too comfortable with low standards. This seems to logically make sense. There’s an interesting analogy I would like to draw. I have discussed the Stoic attitude to death in this article. Essentially, not fearing death is one of the most liberating things that a person can do. This goes against all logic: surely, if you stop fearing death you are more likely to die? Yes and no. It seems that literal life-or-death situations are thankfully exceedingly rare for most people. Unless you actively seek out dangerous situations, you are unlikely to die prematurely because you adopt this belief. However, you are more likely to take small risks – as now, they are framed in this bigger perspective and seem not that huge at all. So could it be that by de-vilifying failure, it is possible to make better decisions rather than worse ones?

If you focus too much on always winning, losing becomes too scary to deal with. I don’t think it is better to assume that losing is inevitable than to assume it is possible to avoid it. Assuming anything is always risky business though necessary to simplify things. Sometimes we will lose because the timing isn’t right, sometimes it will be completely beyond our control – but we have to keep our eyes on that part of it that is within our control. I think the key is to not think of losing as detracting from your final wins – that are surely ahead of us. Winning is a long game and losing is just a lesson that refines our approach and let’s us know how to do better next time. Failure is a form of constructive criticism or a reflection of conditions beyond our control. Should we be afraid of failure? All in all, I think it is too high a price to pay as it constricts our ability to get to the big wins. Should we avoid losing? I don’t even know if that’s completely necessary. It’s not the actual end result. If you make a P&L statement analogy, high costs don’t mean no profit.

In medical ethics, they often talk about an act of commission and acts of omission. In other words, to act and to not act are equally consequential. In the medical context it is something like this: you cannot euthanise a person by actively injecting potassium chloride in their veins, but you can allow someone to die by choosing to not instigate active treatment (in most parts of the world). In our culture, we have come to see failure as a negative consequence of an act of commission. Doing something outside of what is prescribed is an act of commission, meaning it takes more deliberation and implies more responsibility. It is much more likely to cause strong emotions if it doesn’t go right than ending up with the same result from doing nothing. So what about acts of omission? The definition of failure has to allow for acts of omission. I think failing to invest in something worthwhile or to tell someone you love them is as bad as investing with poor returns or being rejected. However, if we only concentrate on avoiding losing, we are bound to miss out.

Moving from Freud to Frankl, it’s important to consider the meaning of failure. I think the visceral fear of failure comes from the meaning people have been conditioned to attach to failure: you are failing because you aren’t good enough. I mean you may as well take a gun and shoot your sense of self. What is enough? Enough is completely in our heads. Maybe you are failing because you aren’t that good yet. It’s describing the same facts, but the way it makes you feel is completely different. A much better question to ask would be: how can I use this? Looking at failure from more than one angle instead of fixating on a bunch of assumptions is going to help. If you can make use of it, then there’s nothing to be afraid of.

Our brains are somehow wired to move towards the thing we think about the most. Those who survive car accidents tell how they could only think about the thing that they crashed into – rather than thinking of the gap that they may have been able to drive through safely. Budgeting for the downside is good, but once a decision is made, it has to be a fleeting thought at the back of your mind. You can’t focus on avoiding failure and expect success. Even in those forms of financial investments where avoiding losses is the foundation of all success, the game is to put yourself in situations where losses are least likely – rather than trying to predict them, e.g. in trading. In venture capital, it’s the opposite – you only need one smashing success. While we can’t be completely unaware of our surroundings, the focus has to simply be on winning.

I think it is time to start letting go of the fear of losing because that way we’re risking missing out on something really great. Losing requires humility to accept our own mistakes non-judgementally and use them. Only this way, we have a chance of winning in the long term.

Mindfulness and fear of failure

What is dealing with losing like for people? I am not talking about dealing with rejection. When other people are involved – that’s different. Losing, failure. This kind of thing.

I think the practice of mindfulness has taught me something really valuable on this front: we shouldn’t be quick to judge. In reality, calling something a success or a failure is quite closed-minded. It was easy back in school and college: if you get an A you’ve won, anything else – you’ve lost. If you score a goal, you’ve won – and so on. It’s not that clear cut in academics and sport in the medium term, and it certainly isn’t clear cut in life – because its a long game. I won’t really know what was a success and what was a failure until I am on my deathbed.

Looking back, things that seemed like overwhelming successes in the past lead me down pathways I soon abandoned. Being the best at something, winning competitions – the conventional definition of success – often leads to a tree of really tough choices and pressure of other people’s expectations. Success brings it’s own set of challenges, hence it is difficult to sustain it.

On the other hand, what seemed like giving into my weaknesses turned out to be huge wins. Giving up on relationships – huge relationships that really mattered in my life – at the time it seemed like shameful quitting, like a black mark that I could never wash away – yet I am liberated by my choices everyday. Getting invested into other relationships without knowing where it is going, uncovering my vulnerabilities – that felt like it could only end it tears, but in reality it turned out to be the biggest gift. Career pivots felt like controlled failure. Nasty people judge you, and nice people pity you. Of course, knowing what you want makes it all irrelevant, but nobody likes to feel that lonely.

The other things that matters when thinking about fear of failure is what do we actually fear? Who is the toughest judge? The career pivots were experiences in my life when other people felt I was failing whereas I knew I wasn’t. That taught me something: I fear not trying more than I fear letting irrelevant people down. I think a lot of people worry about letting people they care about down: their family and significant others. We make this erroneous assumption that we can make other people happy without doing what’s right for ourselves in the long run.

Martyrdom is a hiding place. Hiding from judgement; hiding from the accountability that going after our dreams brings. It’s a way to blame others for not doing what’s really hard. The most ironic thing is that it will probably come as no surprise to the people we are trying to please that we’re not happy, but they will never even suspect the weight and severity that we assigned to their opinion. There’s nothing malicious in this. In fact, the harm is done by ourselves: assuming that the people who are meant to care about us simply won’t understand. There’s a way to present our troubles in a way that is open and vulnerable rather than an acid test. Chances are that the people who care will come around to see our reasons.

Mindfulness is the best way to uncover our assumptions, that’s why I love it so much. No amount of reading or soul-searching will help to understand what’s going on inside unless we practice. Reflection to mindfulness is like stretching is to exercise. They go incredibly well together, but let’s not skimp on our practice either.