Don’t Let Your Eulogy Say You Played It Safe

By Gerald Walsh ©

A friend of mine, Peter, who I hadn’t seen in a while, approached me at an event recently. I put out my right hand to shake hands with him but as I did, he awkwardly extended his left hand instead. I hadn’t noticed that his right arm was in a sling, held tight to his body.

When I asked him what happened, he said he had been playing on his son’s electric hoverboard and, well, you know the rest of the story. Let’s just say it didn’t go well for Peter.

My initial thought was: Why are you, Peter, at your age, playing around on your son’s hoverboard? I thought you were smarter than that?

He must have seen the puzzled look on my face because before I could say anything, he said: I would never want them to say in my eulogy that I didn’t try anything new.

Peter’s comment got me thinking about careers and specifically why so many people take the safe route and do not pursue career paths that will make them happy.

Inevitably, they end up having regrets at the conclusion of their careers.

What holds most people back is fear

And, in fact, many of you will lead what I call a “fear based career.” Meaning that most of your career choices will be governed by an underlying fear that prevents you from doing what you really want to do.

I know several people who have been held back by fear.

There’s Lisa, a CPA now in her late 30s, who deep down believes she is not worthy of success. Growing up in a rural community in a family that had  money and substance abuse challenges, Lisa knew that if she didn’t leave she would end up working in meaningless jobs.

But to this day, she still believes that passing her CPA exam was a “fluke.” That the marker made a mistake. That she didn’t deserve to pass.

This feeling of not being worthy of success has caused Lisa to bypass jobs she is clearly qualified for – believing the company would never hire her anyway. She is reluctant to ask for raises for fear of being turned down. She’s even reluctant to ask her boss for performance feedback as she’s afraid of what she might hear.

There’s Jim, a marine biologist, who has a fear of being judged especially in job interviews. Everybody feels some anxiety in an interview but Jim’s fear goes far beyond the normal levels of anxiety most people feel.

Even though he is always well-prepared, his mind is so focused on all the bad things that could happen that he comes across as stiff and unnatural. Jim leaves a bad impression and is not getting job offers.

There’s Cory, who could not come to terms with being fired from his $200,000 job when his company downsized. Cory’s entire identity and status was so wrapped up in his previous job that he refused to apply for jobs that paid less than his former job. Not surprisingly, Cory never found a comparable job and over two years burned through his savings. He ended up broke and living in his parents’ basement at age 50.

There’s Jamie, a human resources director, who feels like an imposter in leadership team meetings and sometimes wonders why she is even there. She has even turned down a promotion to VP of human resources because she didn’t feel she was “quite ready yet.”

Here’s the question I’d ask you to think about:

Are you going to play it safe through life and allow your fears to hold you back from reaching your career potential?

As you consider your answer, remember two things.

First, how you define ‘career potential’ is totally up to you.

You might define it as making a lot of money. You might define it as working for a not-for-profit. You might define it as working in a regular 9-5 job where you leave your worries at the office and spend evenings and weekends with your family.

One definition is not better than the other. You own the definition – not your parents, teachers, or peers.

Second, the average life expectancy in Canada is 82 years. You don't want to be that person who looks back at their life and has regrets. By the time you’re 82, it’s likely too late to start that company, write that book, go for that great job, or try your child’s electric hoverboard.

Remember, there’s a great temptation to place it safe through life. But in the end you will regret the risks you never took.


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Gerald Walsh is an executive recruiter, career coach, public speaker and author. He is the author of “PINNACLE: How to Land the Right Job and Find Fulfillment in Your Career.You can follow Gerry on Twitter @@Gerald_Walsh