The other day somebody asked me: What would you do differently if you could start again? I had to stop for a moment because it’s a simple ask but it requires a well-thought-out answer.
You can read the question from several angles but it boils down to: what do you regret?
I’m not so smug as to tell you that I’ve lived a life with no false starts, naive decisions and bad choices. I’m actually going to tell you that the very reason I’m so happy about where I’m at is because I have done things worth regretting.
In our own way, we’re all trying to find a way to deal with the possibility of living a life we regret. On the one hand, we have people who think that means regretting things we did. On the other, we have folks who think it means regretting that which we did not do.
The first group often seem to be living as if there are no consequences to their actions. These people might say it’s pointless to worry about regretting something because who knows if you’ll ever be around long enough to regret it anyway.
The latter group is living as if every risk should be limited as far as possible. These people might argue that this is the only way to live sensibly, any other approach lacks foresight and responsibility.
Depending on your character and experiences, you might lie anywhere on the spectrum between these two poles. But if you were ever to seek out advice about minimising the number of regrets you have in your life, it doesn’t take long to find reams of it on the internet. There are whole lists of things young people should avoid doing so they won’t be plagued with regrets further down the road. These lists get repetitive quickly. Work harder, look after your body, be more adventurous, don’t take people for granted, spend less time watching TV or on social media. Of course, I broadly agree with all of these points – but only because I’ve been there.
I’ve made plenty of mistakes. Mistakes are worth making. But they aren’t worth repeating. We make mistakes because we’re wrong, stupid, ill-informed or any other number of unfortunate adjectives. We avoid repeating them because we develop some degree of wisdom.
In order to understand why we end up with regrets and how we can minimise them, we first need to understand the difference between stupidity, wisdom and how they are inseparably linked.
What is stupidity?
You can make a mistake and not be stupid. You can choose the incorrect answer and not be stupid. You can totally miss the mark and I still won’t peg you as stupid.
That’s because stupidity isn’t about being wrong or messing up. These things can be passed off as just inexperience or being misinformed about a situation. No, stupidity is something much more personal and deep-seated than short-term failure.
In my eyes, stupidity is a combination of a lack of self-reflection and the habit of continuing to make the same decision regardless of your knowledge. There’s the famous adage from Einstein, that insanity is doing the same thing over and over again while expecting different results. Well, stupidity is simply doing the same things over and over again knowing that they’ll produce the same results. There is a subtle difference.
The insane, we might suggest, don’t have enough perspective to see the loop they are caught in. That’s unfortunate but it’s explainable. The stupid have a modicum of self-awareness and can see that they are repeating their errors. But this knowledge doesn’t cause them to course correct. They continue anyway.
A few weeks back I wrote about how mistakes are just opportunities for learning that have been inaccurately categorised. Making a mistake and not realising it’s an opportunity to learn is forgivable and something you can work on changing. But the truly stupid person is well aware of what’s happened. They see the lesson in front of them and they choose to ignore it. This is an important distinction.
We can make many mistakes and not be considered stupid. But when we throw ourselves into the same old problems with the same useless solutions, that’s when we start moving toward stupidity.
What is wisdom?
At a first glance, it would appear that wisdom is the polar opposite of stupidity. When we make a mistake we learn from it so that, moving forward, we are able to operate on this new found insight. We have advice about what to do in a given situation and we live by it. This is why wisdom appears to become more abundant with age. The older we get the more experiences we’ve had, the more mistakes we will have made and the more our advice about life is able to accumulate.
We can illustrate this point by imagining two elderly citizens. One is a perennially disappointed and bitter grandfather who will always tell you about the ills of this world. Not many people enjoy talking to him for too long, it gets depressing rather quickly. The other is a wise old woman who doesn’t feel the need to accost people with her disappointments but instead shows the path worth walking through her conduct. Despite not speaking over others, she tends to hold people captive in conversation and is visited often by people of all ages.
The bitter grandfather only has perspective on his side – he’s been around long enough to resent the way the world has changed and imagine how it could have been better. But that’s just memory. He’s not adding anything to the situation aside from negativity.
The quiet elderly woman is what we might refer to as wisdom. She has seen and heard enough to simply be the way she knows she should be. Her mistakes or disappointments have not become something she lectures others on. Instead, to paraphrase Gandhi, she has become the change that she wished to see.
Sam Harris describes wisdom as little more than the ability to follow your own advice. This is how our elderly woman lives. This is why she’s wise. While this definition is a good start, it also reveals to us an interesting question: how do you arrive at having good advice in the first place?
We can find good advice everywhere. My girlfriend is forever telling me that if I want to lose weight then eating lots of Ben & Jerry’s ice cream is a bad idea. But when that tub is in front of you, well, let’s just say that conceptual knowledge is not always easy to recall.
If your sweet tooth is anything like mine, then obtaining the wisdom to eat less Ben & Jerry’s in any one sitting is only arrived at by being naive enough to overdo it once or twice.
The impossibility of pure wisdom
We often frame opposites as having a hard divide. Wisdom is wisdom and poor actions are poor actions. One you arrive at through age and experience and the other by being young and naive. But these two attributes are not mutually exclusive. In fact, they are dependant on one another.
We have two definitions now. One for stupidity and one for wisdom. What this has shown us is that regrets are not a product of a life lacking wisdom, but rather, one lived in stupidity. But the most interesting insight comes when you take this a step further and realise the fact that wisdom never arises without a little stupidity.
While a life of wisdom is something we should aspire to, we don’t get there by being flawless. The flowers of wisdom require some dirt upon which to grow. Generally, that means a degree of pain or discomfort in our lives through which we can nourish our own insights.
But this wisdom doesn’t just appear by virtue of having made mistakes. We need to exercise some self-reflection and honesty. When we truly absorb something and learn from it, we are strong, better and wiser.
When this happens regret becomes an impossibility. If we are wiser and stronger as a result, then to not have experienced such a thing would, by definition, leave us worse off.
That means you need to eat that tub of Ben & Jerry’s at least once to understand why it’s a bad idea. You need to binge on Netflix and put off chasing your passion before you know why that truly sucks. But more importantly, you need to be honest with yourself about it afterwards. So you shouldn’t regret the tub of Ben & Jerry’s. But you reflect on it.
Regrets arise when we are able to gain some perspective on a situation but fail to fully form that perspective into something useful and insightful. It’s a lack of deep reflection. If you’re truly reflective then you don’t make the same mistakes over and over again. You look back, understand that the course of action you took was not ideal and then you recalibrate for the next time. That’s what life is about. Not sitting around listing the things we’d never do again given a second chance.
Every mistake is who you are
The question still remains: what would I change about my past? Would I go back and avoid stealing that ice lolly? Would I not get in that fight? Or maybe I wouldn’t lie about where I’d been to my girlfriend?
Well, actually I wouldn’t. It’s important that I did those things. I don’t want to do them again and I wouldn’t recommend them to anyone. But those poor choices are mine and they’ve taught me about what it means to be a better person.
The world is full of these kinds of situations. Black and white questions that are harmless enough but which conceal a deeper question about our lives and how we live them. Perfection is only achieved by embracing the whole mess of life for what it is. Not by picking and choosing the parts that suit you best.
You are the sum of all the things you’ve ever said and done, all the experiences you’ve had, every action you’ve ever taken. Any positive skills and wisdom that you’ve gained are intimately wrapped up in all the other missteps and half-starts you’ve had.
You’re human which means you’ll screw up every now and then. Hopefully, you’ll learn when it happens. But don’t worry about messing up in the meantime. If you need to worry, then worry about not screwing up enough. Worry about not learning from the things that go badly.
So drop the regrets. Stop making lists of them. Stop regretting and start reflecting. Because anything worth regretting is probably worth learning from. Choose the one that makes you a better person moving forward.