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If You Don’t Take a Risk in Your Career, You’ll Be Doing the Same Boring Job for the Rest of Your Life

by | Apr 4, 2022 | Success

So many people have careers they hate.

They’re afraid to admit it and pretend everything is okay. Yet deep down they know they’re living below their potential, and drastically below their ambition. It pains me to see. So much life … wasted.

Risks create your career path

No risk, no dream career.

That’s the harsh truth. Last year I took the biggest risk of my career. I quit my safe job that took ten years to get, during the middle of a pandemic.

People thought I was freaking nuts.

They didn’t understand one thing. In 2015 I had a near-miss with cancer. It turned my life upside down. I went from dreaming about my future career over decades, to living my career one day at a time.

Something hit me: If I don’t take a risk and bet on myself, I’m going to regret this decision for the rest of my life.

So I quit. No stable income. No million-dollar daddy to support me if I failed. No secret trust fund to lift me up by my bootstraps if I failed.

All I had was my savings and what I’d learned about writing.

It still may not work out. But at least I tried.

Playing it safe gets you nowhere

As for weighing the risks/rewards, I’ve long been puzzled by how life is the only movie in which no character makes it out alive, yet most of the actors insist on playing it safe — Genius Turner

Most people that play it safe in their career don’t even realize what they’re doing. A buddy of mine is 63. He’s due to retire in two years.

He hates his job with a passion.

“Why don’t you quit?” I said softly over coffee.

“I’m close to the end now, may as well finish in a job I know back the front.”

It made no sense.

You’ve got two years of your career left. You have enough money to retire already. You’ll never work another career ever again before you die. Why the freaking hell would you stand still?

If anything, if it were me, this is where I’d go wild and take all sorts of whacky jobs. I don’t get how death doesn’t motivate people in their careers.

It’s weird.

They know they’re on the path to the cemetery, yet somehow, magically, the reality of “every day we’re slowly dying” hasn’t hit their brain.

Where does a safe career get you anyway?

You say yes. You don’t speak out of turn. You don’t do job interviews because you might get rejected, or maybe an existing colleague finds out and tells your boss. You never miss a deadline. You work more and more long hours to keep up with the workload?

For what? Nothing.

A safe career got me nowhere. All I did was build up a stockpile of regrets and sit on them every day over lunch while feeling lost.

Only when I started taking risks did crazy opportunities I could never have dreamt of start to appear.

Like the time I wrote about losing my job and feeling like a failure. That post gained me more career supporters than meeting my KPIs or being on time to warm my office seat ever did.

The biggest career risk is not taking a risk.

Most jobs lead nowhere

Took me a long time to realize this. If you hit the cruise control button and stay at a safe speed in your career, the path will lead nowhere.

Think about it.

Is your boss motivated to give you a promotion? Nope. They’re too busy and aren’t even thinking about your career.

Will your employer give you career opportunities? Nope. They’re too busy trying to meet revenue targets.

Will an opportunity come out of nowhere from LinkedIn and slap you in your gorgeous face? Nope. (Well, unless you write on there daily — most don’t.)

So if no one is coming to save your career then what do you think is going to happen? Do you think experience matters? Do you think your current or future employer will fall to the ground in excitement because of the number of years you’ve worked in the same job? No way.

Most jobs require one year of learning. This learning turns into experience that’s repeated every year until an employee interrupts the pattern and realizes this nightmare.

You know it’s true. Most jobs aren’t hard to learn — or even master.

So, what’s going to make your career lead somewhere then?


You’re the one that has to take your career by the curly ones and make it happen. That involves risks.

A salary is the real risk

A salary is meant to be a guaranteed amount of money you can bank on.

I’ll tell you something wild. When you get a loan to buy a house or car, or rent a home, you do an application form.

On it, you list down your income so the reviewer can see you can afford what you’re signing up for. Affordability is based on your salary continuing.

Yet, a salary can be cut off in a heartbeat. A salary is a guarantee of nothing. It’s no more stable than freelancing or contracting. In the old days when my grandpa still worked, you could bank on a salary.

Now the safety blanket of a salary is no more.

Companies are moving to more flexible models of employment. They prefer an on-demand workforce as opposed to a giant fixed cost that has a range of skills they don’t always need.

Guess what else is crazy?

That safe salary is melted away by inflation (currently 8.2% in the USA) each year. All of this happens in a world where 99% of investments can’t even earn you more than 8.2% in returns!

So, your safe salary is melting away like an ice cube left out in the hot sun, while you continue to work harder busting your nut each year, thinking you’re getting wealthier by playing it safe, when you’re actually heading towards an eventual financial crisis.

But inflation will slow down, they say. LOL. You think businesses will lower their prices again or gas will go back to the cost it was three years ago?

Not gonna happen.

The real risk most people miss

A recession tsunami comes out of nowhere.

When it does, your employer panics and fires your boney ass. Look at March 2020. Look at the 2008 Financial Crisis. This is when the wake-up call makes those safe employees go deaf from alarm bells.

Businesses prioritize profit over humans — that’s the meaning of capitalism. Your safe career means nothing to them.

Smart risks you can take (NOW) to upgrade your career

Let’s finish with a big bang. Here are risks you can take.


This is the polite way of telling an employer you want to try out different jobs without raising any alarm bells.

Secondments lead to new jobs in the same company. Use the code word.

Proactive job interviews

“Always be interviewing” is my motto.

Job interviews teach you so much. You get good at selling yourself. You get great at high-pressure situations. And the job you don’t get forms relationships with hiring managers and recruiters of jobs you’ll eventually get.

Talk to people from competitors

I love making friends with my competitors. Because they will one day want to hire me if they like my work. Few understand this.

Pretend to be ruthlessly at war with your competitors in front of your boss. But after hours, get to know them.

Trade industry (not company) secrets to help build the relationship. Then when you’ve had enough of your boring job, call them and say “Hey, are there any jobs going over there?”

Remember: Competitors are future employers. They can be better employers, too, when a sudden wrong turn happens at the management level of your current job (aka a series of dumb decisions).

Write on LinkedIn

LinkedIn is an opportunity magnet.

Share what you know on there and your InMails (direct messages) will light up brighter than a Christmas tree.

Write short text posts. Daily is best.

A side hustle

Don’t get upset by this buzzword. It’s just an after hours project you work on that can one day make money online.

Think of it as an insurance policy against bad employers.

It’s your backup plan in case a new job doesn’t break your boredom cycle the way you hoped. Or it can create passive income that buys financial assets that sets you free from ever working a job again.

Closing Thought

Life is meant to be lived.

Doing the same job for far too long is the definition of insanity. You’ll become lifeless and lack any emotion if you do.

It’s time to come alive again by taking smart, calculated risks with huge payoffs that will obliterate career boredom. This is the way.

Are You Operating With Maximum Energy?

For those who are tired of dragging through the day, who want to get back the fire they once had, who are ready to reclaim your natural energy… this is your book.

Unleash the fire within