The hidden risks of linear career paths (and why you should start a business instead).
4 min read

The hidden risks of linear career paths (and why you should start a business instead).

As early as kindergarten, we start asking kids what they want to be when they grow up. The answers start off innocently enough - “an astronaut! A firefighter!”

By the teenage years, the answers might be more practical - “doctor, lawyer…”

An enlightened few will say - “engineer, marketer, designer.”

John Lennon was once asked what he wanted to be when he grew up.


True. But rather trite.

Jobs are generally good. They provide money, which usually makes you happier. If you’re looking for the lowest volatility and best expected value out of a career, the answer is simple - get a good job.

The two most common career paths I see are

  1. chasing money with a high paying job to buy more things (status)
  2. chasing freedom with a high savings rate and lower-cost lifestyle

Both those options have their own set of risks.

Get a high paying job

Landing a high-paying job leads to the highest expected salary, but high-paying jobs can lead to unexpected downsides.

Careers known for high pay tend to lead to the trappings of wealth - bigger house, expensive cars, private schools, status-chasing social groups, and country club memberships.

Those things can be nice, but working for the purpose of getting those things is a road to hell. Especially for the current generation of wage-earners.

I don’t know anyone rich under the age of 40 whose primary goal was to buy "the dream house." All my rich friends started companies, with no goal in mind but to build something valuable.

The last generation of wealth could pull off the wages --> wealth formula. The doctors, lawyers, dealmakers, and bankers. The country club members. The hammered by 4pm drive your golf cart back to your villa crew.

Nothing against them, but they aren’t generally people I enjoy spending time with.

Many tech employees aren't that much better off here - it's really hard to walk away from a $350k salary at Netflix, private schools, and a $2m mortgage.

The unforeseen risks of chasing money through a high-paying job are always feeling a step behind, constant stress, and the risk of becoming a bit of a jerk.

Save a lot of money

The other path to wealth is the “wealthy barber” approach - have a good job, live within your means, have a high savings rate, and invest in index funds.

Many of these people are more satisfied than clout-chasing, high-flying, corporate burnouts. At least it’s a path that gives you a feeling of control.

Often these folks have rich lives outside of work - sports, hobbies, and interests. I tend to like them better than the country club generation.

Meaning is found in the freedom provided by living below your means, which is certainly better than finding meaning in living above your means.

The highest risks of this path are complacency, boredom, and a similar obsession with money (but in the opposite way of the high earners).

Strangely, these two paths don't often intersect. Most high-paying job people tend to live slightly above their means. Whether it's nature or nurture, I'm not sure.

Both options lack something most humans are searching for.

Optimizing for expected value is too simple of an equation when it comes to careers. Careers are a multi-variate equation.

You'll spend more than 1/3 of your life working, and money is just one variable.

Careers can provide a lot more than just money.

Purpose. Agency. Ownership. Flexibility. Freedom. Fun.

Unless you’re a pro athlete, there’s a limit to the amount of purpose your hobbies provide. I don’t yet have kids, so maybe offspring solve the underlying ennui of working a job you know just doesn’t matter. But I’ve spoken to many people who still feel that - even with kids.

The third option is the most overlooked when it comes to solving that multi-variate career equation. Entrepreneurship.

Start a business

No matter what business, building something from nothing injects purpose straight into your veins.

You’re the direct line of delivering value to customers. You’re providing jobs for people that allow them to live and thrive. You’re creating something. You’re more than a cog in the machine. You're in control.

But for some reason, we discourage starting businesses.

Parents don’t want their kids to be entrepreneurs. They’re scared they’ll end up destitute. Jobs worked for our parents - they worked at the same company for 40 years, bought a house that went up 2000% in value, and we all lived a decent life.

Education is the next enemy of entrepreneurship - a conveyor belt designed to push you towards gainful employment. High school is measured by how many kids go to college. College is measured by how many graduates get jobs. The incentives are aligned to create millions of debt-burdened 22 year olds with shitty career prospects.

The education system is designed by rule followers, and entrepreneurs don’t follow rules. Unfortunately for education, that lack of rule-following is the only that’s ever created lasting value in the last 1000 years of society.

It seems we should be encouraging it more.

In terms of expected value, the risk may be a little higher. But the rewards are so much richer. It also might be the only good alternative left for young people.

The world looks more daunting for anyone under the age of 30 than it has in a while. Houses are expensive, debt is high, and most jobs suck. Boomers got the best economic ride in history, and it won't be repeated.

Oh well.

Fortunately, it’s the best time in history to start a business.

Demand is though the roof. Technology is better than ever. Billions of people are potential customers. Startup costs round to zero.

Starting a business gives you control of the input variables. It lets you control your time, your pricing, and your output. It lets you choose how much you want to work. It gives you the chance to get rich.

Consider the non-linear path.

If you plot out your career trajectory for the next 10 years, and you don’t like how it looks - change it. A linear path will create linear results.

The winding path of entrepreneurship might seem a little crazy looking forward, but will make sense over long enough time frame. You just need to zoom out.

The zig and zags will create huge leaps, and you'll end up somewhere you never imagined. That somewhere will be better than if you followed the boring path.  

Sometimes the best decision is simply the most interesting. The weirdest.  The scariest. The volatility of a non-linear path is high, but the risks are overstated.

The biggest risk is looking back on your life and realizing that you never gave it a shot.

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