The Regret Society

And my secret theory as to why people love Casey Neistat

My working thesis is actually more about human nature, we’ll get to Casey.

It’s also about our interactions with the things we own. I’m not really sure where I’m going with all this; roll with me.

I don’t think people hate change. I think people hate regret.

Because change is inevitable and endless. It’s guaranteed. And most of us are pretty okay with that fact. Sometimes, change is super beneficial and we’re glad that it happened / we did it / the change was made.

Except, every change opens up the potential to wish it were back the old way.

The regret of making a change is worse than the regret of not making one.

And so, naturally, we’re inclined by the path of least resistance to make fewer changes, to live in a world that is somehow both optimized and static.

This, of course, is impossible.

(also, just to clarify, that bolded part isn’t objectively true — it’s how we see it)


The nature of permanence is also a factor here.

Regret is only weighty if the change is permanent (or, at the very least, the amount of consequence for changing back is unacceptable). Regret is the function of being locked in to a decision. Committing to the choice.

We hate that.

This loops around to psychology like FOMO and analysis paralysis, but in essence we generally try to keep our options as open as possible in order to always have the choice of jumping from one path to the other in the event that we’ve chosen the ‘wrong’ path, or one we don’t like anymore.

And why not? Choice is the right of freedom, and that’s downright American!

The side consequence is that in an effort to never commit to something and block off the other choices, we tend not to choose anything at all and then the regret of never doing anything is just as bad (worse?) as the regret of choosing the wrong / sub-optimal one (assuming there is a ‘right’ one).

So often the answer is simply to pick the best and execute. Then, stop worrying about it since you can’t change the past now. Read the stoics again if you want more thoughts / a guide on that.


What I really wanted to talk about is a seemingly rare ability to make permanent-esque changes to objects. Both as a designer of these goods and an observer of friends, here’s a fascinating thing:

  1. People will always be in shock and horror when you drill into something, paint something or otherwise modify it beyond stock.
  2. People love that you’re able to do that, because they themselves aren’t.

When I say aren’t able, I don’t just mean that they aren’t designers and don’t know how to drill things (though, this might be true) but that something deep down in our psychology screams to not do those things in case we accidentally and irreversibly damage them.

This is the Casey Neistat appeal, because it’s a cornerstone of his life and how he works. His cameras, his drones, his skateboards, his house and workshop and glasses: the first thing he does to them is something generally permanent.

And, even though he’s not an industrial designer, I have great respect for this attitude: if he finds something wrong, he’ll problem solve a way to fix it and then just go and do it. Others, perhaps, would go to an Amazon comments section and whine about something they themselves could fix.

There’s a few other bits to live in there: we all love a man of action. We love people who do instead of talk. We love people who show us how to do it too, even if we’ll never face that problem ourselves.

We love people who are seemingly regretless, the people who are infinitely cool are the people who are comfortable with doing and being anything. It’s not that they’re masters of making the right choices, it’s that they’re masters of being okay with the choices made and they places they find themselves in.

And we love people who have the gumption to change and shift the entire world around them if they aren’t.

Casey, then, is a master of his domain.

There’s something kingly about that, right? Powerful. We like that too.


So why don’t we all just do that? Be masters of our surroundings, physically shift things to work with us via grinders and sledgehammers and blunt but effective methods? Why aren’t we cool people too.

Much like most human-ness, fear.

Also like much of human-ness, the fear of something bad happening is often worse than the actual bad thing itself.

The fear of having regrets is often (always?) worse than actual regret.

(this one is bold because I genuinely believe this)


It’s really easy to implement this attitude too: start small.

I’m famous for painting stuff. Usually black, sometimes not.

This is my daily driver. My old camera was blacked out too: prevents those bright white CANON reflections from messing up your pictures when shooting out of glass windows. Regrettably, I do need to know what size the lens diameter is for filters — that stupid white text mocks me.

These are my GoPro batteries. Candy red and yellow, because that’s just the colours that were laying around.

These are my winter wheels, and that’s the third colour they’ve been sprayed.

People ask where I got tiffany blue Plastidip (the removable colour favourite in the car community) and I smile: it’s actual spray paint. Way cheaper and comes in hundreds of colours. Lots of compliments on these so far.

Just, you know, commit. Do what you like with the things you own.

I put hooks in my walls at my last place to hang a hammock in my bedroom — it was great for years to sit in the sun and read; rock gently in the summer breeze with the window open.

Ended up costing a few hundred bucks out of my rent deposit. Worth it.

Painted a wall without asking, actually, and the landlord didn’t even notice, so ¯\_(ツ)_/¯ I guess. Any fear about doing it before was misplaced entirely.

The fact is, these examples are pretty minor in the grand scheme of things. In a decade from now I probably won’t even own any of them. The odds of me being on my deathbed at 80 and thinking “I shouldn’t have sprayed those wheels blue when I was young” is basically nil.

So all in all, like any decision making, it comes back to consequences: do you accept the end results of the things you choose? Often there really isn’t much consequence at all for making changes to things you own and want to improve. It’s not about what you can and can’t do as rules, it’s about what you do and don’t want as consequences, and then accepting the result either way.

Because acceptance is the antidote to regret.