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The Danger of a Traditional Career Is You Can Go from One Safety Net to the next (Out of Habit)

by | Feb 6, 2023 | Startups

Many careers die due to a lack of risk.

The owners of those careers don’t know life took a big dump on them and they won’t find out until it’s too late — or never.

Risk is a concept we’re programmed to avoid. We think we’re taking enough risk but most of us aren’t. So our careers stagnate and our lives feel like they’re missing something.

Yet we can’t put our finger on it.

Let me explain what you may not know about risks, so you can reach the next level of whatever career or life games you want to play.

Treating career risk like it’s an index fund

Finance writer Jack Raines points out that too many people never commit to a career path. They keep their options open.

It seems smart to do this. You’re diversifying yourself the way buying stocks inside an index fund allows you to invest and not think about markets.

Will Manidis describes it best:

The most disturbing trend is the amount of people treating life like an index fund.

He argues the days of taking big career risks are gone. He says it’s easier to never make a decision than it is to commit. He says it’s popular to never choose one path and go all in.

And even if you’re bold enough to start a business the temptation to hire people to run it for you is huge.

That way if the business blows up you can go “wasn’t me, it was those dumb adult babies running my company, bro.”

This type of career is built on anti-risk.

I hate the index fund life. I’ve also told people for years that index funds are not what they’re made out to be. Yes, you can invest money into a safe bucket of 500+ companies and make a mediocre return after inflation and taxes for the rest of your life.

But what if you invested that money in self-learning, traveled the world, or used it to start a business? They all carry risk but they can produce 10x the returns a stock market index fund ever could.

Risk is good for you. Risk is where living begins.

Most people are living life trying not to lose. That’s why they never win. Take risks — Dakota Robertson

From one safety-next to the next (by accident)

Jack Raines also quotes Harvard Professor Mihir A. Desai.

Mihir says a career with no risk causes you to become a habitual acquirer of safety nets. This thought slapped me in the back of the head.

I built a career on safety nets. I never wanted to have a gap in salary. I chose big companies to work for because startups had the risk of failing.

The lie we’re told is climbing the corporate ladder is smart. As you go higher up you are taking on more risk. Leading people is hard, dontcha know.

But the ladder is made up of back-to-back safety nets. The risk you take with higher up positions is small. Even if you do get fired (like I did) from a managerial position, recruiters will be all over you like a pig in sh*t.

As soon as a recruiter sees the logo, they smell blood in the streets and a juicy commission about to be devoured.

You can get fired plenty of times on your pursuit to climb the corporate ladder and always land another job (eventually). The world isn’t short of email jobs — where you show up for Zoom calls all day, every day.

The standard corporate job carries the illusion of risk. Really it’s a crack addiction to safety nets in disguise.

“If you’re always avoiding risk, you risk missing out on life”

(Steven Barlett)

I felt like I missed out on life.

In 2011, I walked away from a successful business I loved. I hid away in a bank job from 2011 to 2021 out of fear. I had a decent online income but refused to take the plunge and quit corporate life.

Finally I had the guts to do it. I agonized over it for months. Without a doubt it’s the best decision I’ve ever made.

But if I had leaned into career risk more, I could have quit sooner and got access to what I have now. The thought that trapped me is “what will I tell recruiters and hiring managers if it fails?”

This thought was stupid. My job involved me dealing with stacks of recruiters. I saw plenty of examples where mass failures actually impressed them — they made a candidate stand out.

Yet I lied to myself and still thought failure was risky.

Avoiding danger is no safer in the long run than outright exposure. Life is either a daring adventure, or nothing — Helen Keller

We’re deathly afraid of randomness

A career without risk lacks randomness.

This seems smart because then you know all the risks and can’t get smacked in the face by an angry Mike Tyson type. But a life without randomness is the ultimate hidden nightmare.

When everything is predictable it’s hard to have the energy to wake up and win the day. You become stagnate and stuck in the dangerous status quo.

You actually start to fear change which leads to greater stagnation.

Randomness has some risk but it’s also what makes a career great. I started working in a bank call center and then accidentally got a cool job helping tech companies come to Australia.

It’s the sort of job any young graduate would dream of, and I was grossly underqualified and didn’t even have a finance degree. The only reason I got the job is I embraced randomness.

I did stupid things I was told not to do.

  • I helped departments that weren’t my own.
  • I rang executives by getting their number from the company directory without booking meetings with their personal assistants.

In a way, I felt like I had nothing to lose. I was recovering from mental illness and couldn’t eat at a client function without throwing up. Everything that could go wrong already was going wrong.

I wanted randomness to take care of my decisions because I sure as hell wasn’t fit to. After a while I learned that randomness is what helped me deal with all these issues.

And randomness brought me to a farmer who wanted a wife and gave me the best job of my life.


There are only two options…

The Danger of a Traditional Career Is You Can Go from One Safety Net to the next (Out of Habit)

Image credit: Janis Ozolins via this tweet (follow him)


The career path of no risk is the riskiest

Right now we are seeing the career effects of a lack of risk.

Smart, sophisticated people working for brand-name companies are getting laid off as if they’re a piece of dirt that needs to be swept out into the gutter and then pissed on.

They can get another job. Yes. But because it’s been a long time since they’ve taken a risk some of them are defeated.

  • Their ego is destroyed.
  • Their self-worth is nuked.

They’re trying to transition from comfort to the discomfort of the real world. I speak to people in this situation every day.

Many of them can’t do it. A lack of risk becomes habitual. Breaking the habit is like giving up drinking after being an alcoholic for 30 years.

This is the danger of risk aversion. Risk-taking is a muscle memory. Don’t use the muscle, and it vanishes out of sight.

Famous motivational speaker Jim Rohn says it’s all risky. From birth you’re born into a risky world where death by an out of control yellow school bus can happen at any time.

He says if you think taking risks is risky, wait until you get the bill for not taking any. That’s what the recent layoffs are showing.

Final Thought

Life is so damn risky you die at the end. So if the answer is death no matter what, what the hell are you waiting for? Take a career risk or risk doing the same boring sh*t for the rest of your life.

Without taking risks all you’re left with are painful regrets.

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