The Ultimate Mistake

Is life one big continuous mistake or is it just a long series of separate mistakes?

If mistakes aren’t the whole shebang, they definitely constitute a major chunk of it. At least that’s been my experience. I’ve also noticed a slightly unsettling feeling that as I get older I’m actually making more mistakes than I used to. What am I to make of that?

Consciousness, Living Meaningfully and Machiavellian Mistakes

I could be mistaking an increase in my awareness of the my mistakes for an increase in the frequency of my mistakes. Maybe I’ve just become conscious of a larger percentage of my mistakes while the actual number in any given period hasn’t really changed all that much. This scenario would seem to be good. Knowing I made a mistake is the first step towards not repeating it.

Or I might be mistaking an increase in the significance of my mistakes for an increase in the frequency of my mistakes. Maybe it just feels like I’m making more mistakes because my mistakes are becoming more important to me. If I had finished reading Thinking Fast And Slow I bet I could have found some solid evidence to back this idea up. Unfortunately I loaned the book to an ex-girlfriend before I finished it.* Instead try this thought experiment out:

Imagine you are on your deathbed many years in the future reflecting on the course of your life. How would you feel about how you lived if the mistakes you made during your life had become less and less meaningful to you as you grew older? How would you feel if the mistakes you made had become increasingly more meaningful to you as you grew older?

I don’t particularly like the idea that my biggest mistakes are still ahead of me, that doesn’t sound super fun. Less fun however, would be looking forward to a life that doesn’t mean as much as it used to. How could a meaningful life not include also include meaning-full mistakes? They appear to be a required part of living a worthwhile life.

The third possibility is that I am indeed making more mistakes than ever before. If so it’s useful for me to determine what kind of mistakes they are. Niccolo Machiavelli had considered this:

“All courses of action are risky, so prudence is not in avoiding danger (it’s impossible), but calculating risk and acting decisively. Make mistakes of ambition and not mistakes of sloth. Develop the strength to do bold things, not the strength to suffer.”

If I find them to be mistakes of sloth, I’ve increased my awareness around these mistakes and have taken the first step in not repeating them. If I find my mistakes to be ones of ambition it’s a sign I’m boldly moving towards the things that are important to me.

Regardless of the reason, the feeling that I’m making more mistakes appears to be a good sign. Becoming more aware of my mistakes, making more significant mistakes or actually making more mistakes all mark the path towards a better way of living. The more signposts the better, right? The real mistake would be to ignore all those useful signposts.

Major Mistakes

Over and over again really successful people have made the following two observations about mistakes:

1) Mistakes will continue to happen. Forever. Forever? Forever ever.**

“Do not fear mistakes. You will know failure. Continue to reach out.”
― Benjamin Franklin

“Have no fear of perfection – you’ll never reach it.” 
― Salvador Dalí

Mistakes have never stopped happening yet. In all likelihood they probably won’t stop happening anytime soon.

2) Recognizing mistakes is how we learn.

“Failure is simply the opportunity to begin again, this time more intelligently.”
— Henry Ford

“I have not failed 700 times. I’ve succeeded in proving 700 ways how not to build a lightbulb.”
— Thomas Edison

Negative feedback gives us clues to how the world works and allows us to improve on past efforts in a significant, non-random way. Making mistakes is critical for the baby learning to walk and the scientist studying the universe.

It’s not impossible to learn without negative feedback but it’s a hell of a lot harder. Imagine a game of Battleship where the rules had been modified slightly so that Player A is permitted to record both her “hits”and her “misses” as normal but Player B can only record his “hits” but not his “misses”. Who would you put your money on?

If mistakes can help us learn to live a better life and they are also inevitable then how could I possibly blow it? There appears to be two ways:

Major Mistake #1: I die.

I can’t learn from a mistake if I die from it. Others might, but I won’t. This is an extremely small percentage of the possible mistakes I can make. It’s possible but in most situations I’m pretty aware when I run the risk of making a mistake that could kill me and will do everything I can to prevent making this type of mistake.

Major Mistake #2: I avoid or ignore the signposts. 

Based on what I now know about mistakes that don’t run the chance of killing me why would I ever choose to avoid or ignore them?<

Avoiding Shitty Feelings

Mistakes sound great until they become my mistakes. Standing face to face with one of a big, ugly mistake of mine doesn’t feel so hot. Similar to a Donald Trump rally, my mistakes often trigger a complex and confused chain of emotional reactions that have the unfortunate result of leading me to believe the exact opposite about my mistake. This mistake shouldn’t have happened and it’s proof I’m not making progress. A deeply ingrained notion that dates back no doubt to years of gold stars, red ink and SAT scores. This feels shitty.

But underneath that there’s a much more deeply ingrained fear. It’s the fear I’m making major mistake #1: I might die from this. Thousands of years ago making a critical mistake had a much more likely result of dying as a result. Being exiled from your clan or misidentifying a sabertooth tiger had a good chance of getting you killed. Luckily for most of us today, that is not our reality. For most of us, the risk of dying from our day to day mistakes is extremely small to non-existent. That being the case, it’s much more likely that this fear is just another shitty feeling.

If I’ve sighted a mistake it has already breached the outer walls of my defense, which usually include a formidable combination of excessive planning, procrastinating and worrying.


When these all have failed I reach into my trusty quiver of ways to not feel like shit. Ignore this, minimize this and distract me from this are all reliable strategies at this point. For more formidable adversaries I may need to resort to heavy artillery and unleash blame something or someone else and (for especially dire situations) run away.

All these strategies are aimed at either preventing the mistake or avoiding the experience of my mistake and all the not-so-great feelings that come with it. This is major mistake #2.

For one this approach is insane. Mistakes are inevitable. I’ll be building walls and firing off volleys for the rest of my life. What’s worse though is that each shot fired shoots down a chance for me to grow as a person.


Cultivating a better attitude towards my mistakes is uncomfortable and hard. It requires laying down the weapons and embracing the not-so-great feelings that my newfound friends will inevitably drag along with them.

Not easy to do, but it probably won’t kill me either.



*Probably one of my mistakes.

**Forever ever?

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Hello. I’m Alasdair.

Hello. I’m Alasdair.

I believe that being aware of who I am and mindful of who I am becoming is the best investment I can make in my life —and that when we focus our efforts within, the rewards naturally flow outward to those we love and through the communities we belong to.