The Definition of Insanity

Fighting the cycle of career frustration.

Jack Raines
November 16, 2021

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Practice Makes Perfect

In August 2019, I was watching film from football practice with my coach, Jeremy Hawkins. As a defensive end, it was my job to blow past the offensive lineman across from me and sack the quarterback. How do you get past an offensive lineman? Don’t let him get his hands on you. If I let my opponent get a good grip on my pads, I was toast.

Hawk queued up eight plays. They were all the same: the ball snapped, I hit my opponent in the chest (instead of staying outside the frame of his body), and I got blocked. Eight plays. Eight losses.

“Ever heard the definition of insanity?” he asked me.

“No sir.”

“The definition of insanity is doing the same thing over and over again, and expecting different results,” Hawk told me. “You went down the middle of this guy eight times, and you caught eight losses. You want different results? Switch up your play.”

We spent the next hour reviewing some different pass rush moves. The next morning, I switched up my actions and sure enough, the results changed. I stayed outside, knocked his hands down, and won my reps.

Insanity cured.

In football, insanity is easy to identify. I got my ass kicked eight times because I did the same wrong thing eight times. I changed that thing, and I no longer got my ass kicked.

Insanity in your professional life is not so obvious.

Corporate Insanity

I previously wrote about Indefinite Optimism, a phrase coined by Peter Thiel. Basically, we (99% of young-ish workers) have heard the same message for years. “Go to school, get a degree in _______, then get a job with a good company. Keep building your resume to climb the corporate ladder. You’ll be set.” so we follow those steps, and assume the future will take care of itself.

There are three problems with this message:

  1. We never learned why this was the right path
  2. Every step is merely preparation for the next
  3. We never considered what being set actually means

So you’re 22-23 years old, you have followed that path perfectly, and you get that job. But you don’t feel “set”. You feel underwhelmed.

This is it?” you ask yourself. “This is the next forty years? Should I try something different? No, I just need to keep going. It’ll be worth it once I get that promotion and pay raise.”

You shake off the thoughts and decide that you just need to get to the next level. This was your first job, after all. So you work even harder at the unsatisfying thing, because that’s all you know. You get promoted. Make more money. But nothing changes. You’re still in the same spot. Just with a promotion and more money.

Sound familiar? You’re not alone. I’ve talked to dozens of 20-somethings about this very phenomenon, and it seems like everyone has gone through this.

You might make more money or have a more prestigious position, but you won’t suddenly wake up one day fulfilled. You’ll likely grow bitter you ask yourself, “What am I doing wrong?”

Here’s an inconvenient truth: Seeking fulfillment by doubling down on the thing that isn’t fulfilling is never going to work. What was the definition of insanity? Doing the same thing over and over again, expecting different results. 

The problem is, we spent our formative years learning that this is the path to success. So when it doesn't feel like “success”, we think that we just haven’t arrived yet. So we attack it with stronger resolve. The idea of making a bold change enters our mind, but it sounds too risky. We don’t dare deviate from the path.

“Maybe I’ll take that chance some day, but I need to get further in my career first.” 

Work hard, move up, more prestige, more money.

But if more prestige and money didn’t alleviate the problem last time, do you really think it will help this time?

The cycle repeats itself.

The law of inertia states that objects in motion tend to stay in motion. The law of career inertia states that it becomes exponentially difficult to make a career change the longer you stay on the same track.

There is an opportunity cost associated with staying on the same path. While you’re doubling down on stuff that you don’t like, you are sacrificing opportunities to attempt anything new that you might like. And the longer you focus on the stuff that you don’t like, the less time you have to experiment with these different areas.

I do personally believe there’s a little more to life than clocking in and out for 40 years til we can retire. The struggle is figure out that “more to life” part.

Breaking the Cycle

We spend 22 years learning a recipe to success, only to see that reality rarely matches our expectations. We may briefly flirt with the “What if I try something different?” thought, but then it’s gone. So we get back to work.


This cycle never breaks itself. You can either learn that from observing other people’s career regrets, or you can experience it yourself.

If you want to exit this cycle, you have to break the inertia yourself.

Unlike the path to conventional success, there is no road map here. No one, myself included, can give you a tried & true formula for finding career satisfaction. But I can tell you how to look for it.

Take action. Experiment. Iterate.

This isn’t one of those exercises where you can think your way to a solution. You have to get in the trenches and try stuff out. It could be small things like requesting different projects at work. Or maybe you start freelancing online. Or a thousand other things.

A lot of these things won’t work. But one day, something clicks. You finally have a minor breakthrough. You get paid to do something on your own. You applied for that long shot job and landed an interview. You enjoy your role with a new team.

Lean into that and keep going. Build on it. Here is what your flowchart looks like now:

Now you’ve gone from new things that you might like to new things that you do like. Keep building on that.

I do want to point out that career frustration doesn’t mean you should just quit your job on a whim with no plan. In a world where plenty of jobs are still remote, you have time to explore these other interests while you work your day job. Keep doing both until you can afford to make the switch full time.

Did I quit my job? Yeah. But I also had other online gigs lined up, a solid chunk of money saved, and grad school coming up in a year. What I’m doing now is the result of months of meticulous planning and doing.

What’s the Alternative?

Taking that leap of faith and trying something new is risky and scary. But what’s the alternative? Not taking that risk and getting stuck in the cycle of career apathy? No thank you.

It’s a difficult question that most people don’t want to confront: What do I do with my life? But it’s a question that needs to be asked, because life isn’t going to change itself. If you aren’t happy with what you’re doing, it’s on you to take steps to remedy the situation.

Mark Twain once said, “Twenty years from now you will be more disappointed by the things you didn't do than by the ones you did do.” I would go do more things.

That’s all for today, let’s have a great Tuesday 🤝


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