We live at a time where you gotta break the rules

The old career rulebook has been dying for years and playing by those rules is likely to lead you to a dead end.

It was 1am last night and i was chatting with this 17-year old kid via Substack messages.

No it wasn’t dirty or anything like that. Get your head out of the gutter… hahaha

Rather he was a creator who was interested in promoting my side biz, Reviv. Which is a health brand/tool that uses biomechanics related to teeth to solve all kinds of health issues.

Anyway he apparently has been pushing out content in an adjacent space for awhile and I was impressed with the way he thought. Despite the fact that he was still in high school.

All I knew was that he lived in London and was very savvy on who the major creators were in this space and what they were doing.

I had no idea if he got good grades, nor did I care.

I had no idea if he even planned on going to college.

And he’s actually very similar to another guy that i’ve been cooperating with for the same thing for a few weeks.

A couple of decades back I would have never even considered working with teenagers like this. I would have looked for people that have a strong educational pedigree and experience.

But the game has completely changed. And today i’m gonna explain what i mean.

Playing by the rules is getting shittier and shittier

I've come to realize that breaking the rules is actually a good thing nowadays. And I say this as someone who spent most of my early life following them religiously.

Times have changed. When I was growing up, following the system worked pretty well. Get good grades, go to a good college, land a good corporate job - boom, you were set.

But that shit doesn't work anymore. The game has completely changed, and yet many young people haven't figured that out yet.

They’re still trying to get the perfect grades, so that they can get into the big name college. And hopefully that will help them land a good job.

But those ‘good jobs’ are a lot fewer and more far between these days.

More importantly, they’ll lay you off at the drop of a dime. And so I wouldn’t be surprised if the tenure of new grads into such jobs is less than a year on average.

The percentage of people that will have truly fulfilling careers working for others in this coming generation will be <5% in my opinion.

And the rest of the 95% will either be pushed out or even if they stay in… they’ll probably end up in jobs they don’t like.

I was a person that rarely broke the rules growing up

I was the ultimate rule follower. Got straight A's in school.

Teachers loved me - I was that annoying kid who was often the teacher's pet.

Graduated near the top of my high school class and was voted ‘smartest in my class’ of ~270 or so. It was a public high school in New York where being smart was very not cool.

And so being voted ‘smartest’ was the equivalent of being voted as the biggest dork in the class. So rather then feel proud it was more something that i got made fun of for.

But I went on doing everything right. Went to an ivy league college. Got a good strategy consulting gig out of college. And I thought i was on my way.

I played the career game by the textbook and ended up not liking it

I read all those management books. You know the ones - "How to be a Great Leader," "7 Habits of Highly Effective People," all that shit.

I did everything they said. Built relationships. Played politics. Climbed the corporate ladder.

Most of my 20's and 30's were spent working for the machine. Making other people rich while following their rules.

Also working for a lot of people that would have made horrible entrepreneurs. Rather they were good at this game in which the corporate got bigger and they took home more salary and bonuses.

But when I looked at them and the folks above them… i never wanted to be them.

It seemed like a waste of a life. You do all that and retire one day and then probably think to yourself…

What was it all for? I mean that is how i spent my precious time on this earth.

Do those corporates give a damn about me now that i’m retired?

Answer… no. They absolutely don’t give a fuck about you. You mean jack shit to them.

The main thing you have to show for the most valuable years of your life is some money in the bank and perhaps some friendships and memories.

That’s not gonna be me.

Now I break lots of rules and love it

These days? I love breaking rules.

I do a fractional role leading tech in a startup because I still love being involved in tech.

I take care of a couple of clients of Taskbeasts where most of the work is executed by vetted freelancers and i just oversee the process to make sure it runs smooth.

I run my D2C brand, Reviv, which leverages my learnings from the past decade about dental biomechanics and their impact on health. A topic I am very passionate about.

We help people get results that traditional medicine says are impossible. We break the medical establishment's rules (legally, of course) and get people healthier.

I don't work normal hours. I don't do recurring meetings. I manage a bunch of people directly through Clickup and love to say stuff like… “We have no culture. I am not going to try to get to know any of you.”

And you know what? I love it. I'm happier and more fulfilled than I ever was following the rules.

The old way seems revolting to me now

Contrast this with the frustration i often felt with in the corporate world.

Where you’re continually optimizing for how some other person or group of people deem your 'performance’.

And often this person is just a person that was created by the ‘system’.

Meanwhile you’re focused on things that optimize shareholder value. With the hope that you’ll be rewarded if that happens.

Screw all that… I’m going to do things that optimize for things that I truly care deeply about. Rather then some faceless shareholder.

And if someone makes a bit more money than me because they played the old game well…. I couldn’t give a shit.

I’d much rather enjoy each day i work… knowing that i’m playing my game by my rules.

I think our kids are served best if they color outside the lines

AI is going to wipe out a lot of those "safe" jobs that everyone's parents want them to get. Being a good rule-follower isn't going to save you when ChatGPT can do your job better than you.

And from what I’ve heard… AI already operates at the level of a person that has about an IQ of 150.

So trying to continue to be smarter or more educated than AI is a very unwise bet in my view.

You need to be interesting. Different. Someone who thinks outside the box and isn't afraid to try new things.

That is how you’re gonna stay ahead of AI and continue to create value in this new world. At least in my view based on the things i’m seeing now.

Going to a good school doesn't guarantee anything anymore. That's why I don't push my kid on grades. I push him to think differently, to question things, to find his own path.

The 3 key principles of this new mindset

First, don't follow the herd. When everyone's zigging, that's probably a good time to zag.

Second, don't expect the system to lead you to the right place. The system was built for a world that doesn't exist anymore.

Third, you create value by doing things that others aren't doing. And you’re often going to fail if you try to play the same game as many others… because there is just too much competition in today’s global world.

Closing thoughts

The world rewards rule breakers now more than ever. Look at Elon Musk - he breaks pretty much every management rule in the book, and he's the richest person in the world.

The old playbook is dead. The people who will thrive in the next decade are the ones who can write their own rules.

So my advice? Start breaking some rules. Not the legal ones - I'm not trying to get you arrested. But break the "rules" about how you're supposed to work, how you're supposed to manage, how you're supposed to succeed.

Because the people still following those rules? They're going to wake up one day and realize the game changed while they were busy playing by the old rules.

Don't be one of them.