February 22, 2023
min read

Why Certainty Will Destroy You

Montaigne was a man of uncertainty. Throughout The Essays, are ramblings on complex topics such as fear or moderation, life or death. He’d develop exhaustive arguments. He’d seem to be heading towards a conclusion… only to completely undermine himself by appending it with “… I think”.

That’s exactly why he was, and still is, so relatable. His uncertainty in his arguments, no matter how well thought out, was what made centuries of readers seem themselves in his writing.

Montaigne spent his life thinking, looping back on his own arguments, drawing inspiration from the world and coming so close to reaching a definitive conclusion only to be plagued by uncertainty.

I don’t know about you, but that’s exactly how my brain works. I’ll think about all the possible outcomes and make a pro-con table only to end it all with “… I think?”

Uncertainty has always made me uncomfortable. I thought as long as I planned enough or got enough information, I’d be able to make the right decision. I’m guessing you’ve felt the same.

Unfortunately, the world doesn’t work that way and no amount of planning or information will ever bring us complete certainty.

We spend way too much time planning out our lives that we forget there’s an infinite number of things that could happen that would flush our perfectly crafted plans down the toilet. The world is changing, fast.

There’s a chance you’ll get fired tomorrow. There’s an even higher chance your job could get automated in a couple years, no matter what your job is. There’s a chance you’ll get dumped. But there’s also a chance you’ll be offered your dream job or you’ll meet the love of your life. All those things will radically change any plans you’ve made, no matter how great they are.

But there’s also one other thing that could happen that could destroy our plans… and it’s even more unpredictable than any of those above.

We could change our minds.

It’s easy for us to believe that who we are now is who we’ll always be. We subconsciously expect that things we like now, whether it’s people, food, or a specific lifestyle, will be what we like forever. We can’t see ourselves changing.

It makes sense if we’re learning and growing every day… this is the most enlightened and knowledgeable we’ve ever been and it’s hard to see what comes next. But everything we know and think now could, and is probably, completely wrong. We only need to look back on our embarrassing selves from 5 years ago to confirm that point (I just looked back through my Facebook pictures… so. much. cringing.)

The point is, a million things in this world, including ourselves, could break down the most well-crafted plans.

What’s the point of productivity and goal setting strategies if they’re all ruined by the slightest unpredictability? Does that mean we just throw our cards in the air and see where they land? I thought so.

Then I listened to the Tim Ferriss podcast with Derek Sivers. (Yes, I refer to this a lot because it is literally a pot of gold. Seriously, go listen to it now.)

He put into words something I’ve always believed:

“The best plan is the one that lets you change your plans.”

Derek Sivers

It all comes down to one word:


This video with Gary Vaynerchuck sums it up: Let Go Of The Things You Can’t Control and Move The F*** On.

Montaigne, Sivers, and Vaynerchuck all have one thing in common. They show an awareness, and even an embrace, of their uncertainty. It’s their certainty of their uncertainty that gives them the strength and confidence to move forward. It causes them to always keep their mind and options open.

Doubt is an uncomfortable condition, but certainty is a ridiculous one.



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