How to Avoid Common Career Regrets and Mistakes

green ways

“Regrets, I’ve had a few. But then again, too few to mention.”

By Priti Dadlani

We’re lucky if that refrain from Frank Sinatra’s signature hit song holds true as we review our careers.

Research suggests we feel the most regret about missed opportunities. In other words, we regret the things we didn’t do rather than the ones we did do. The split is about 75/25.

That’s certainly true in my case.

Near the beginning of my journalism career I had a “now-or-never moment,” a chance to work at the Sun Herald newspaper in Biloxi, Mississippi.

At the time, I was a rookie reporter with a couple of years’ experience working at The Record newspaper in Kitchener, Ont., the town where I grew up and where my family lived. I had been named Novice Reporter of the Year by the Ontario Newspaper Association.

The Sun Herald offered me a reporting job covering municipal politics. The hiring process happened over a series of phone calls with senior editors at the paper.

The beat sounded exciting. Biloxi’s economy relied heavily on gambling revenue from casinos and part of the job would be to try to uncover and write about corruption.

Acting against my career instinct, I turned down the job. But I often wonder how my career, and indeed my life, would have played out if I had gone to Biloxi.

Tech entrepreneur Daniel Gulati writes about the Top 5 Career Regrets in the hope “that by exposing what others are most disappointed about in their professional lives, we’re maximizing our chances of minimizing regret in our own.”

Gulati came up his list by informally polling a diverse group of 30 professionals between the ages of 28 and 58:

  1. I wish I hadn’t taken the job for the money. This was by far the biggest regret. Research has shown that happiness caps at a salary of $75,000 and no matter how much more than that you make, you don’t report being any happier.
  2. I wish I had quit earlier.
  3. I wish I had the confidence to start my own business.
  4. I wish I had used my time at school more productively.
  5. I wish I had acted on my career hunches.

Number Five relates to my regret about not going to Biloxi. Gulati describes it “as the importance of identifying these sometimes unpredictable but potentially rewarding moments of change, and jumping on these opportunities to non-linearly advance your professional life.”

Career regrets can make you vulnerable to “should have thinking,” says Priscilla Claman, in her article Coping With Regrets.

She outlines a process for replacing the “should haves” with “what ifs,”and reframing the regret into something positive.

The process involves naming the regret; brainstorming with trusted friends and colleagues about how to think differently about it; compiling a list of “what if” scenarios that relate to the regret; and then acting on one or several of the scenarios.

Closely related to the topic of career regrets is that of career mistakes.

Eric Barker writes about the 5 Most Common Career Mistakes on his blog, Barking Up the Wrong Tree:

  1. Doing inadequate research about whether the field or job you want to work in will be a good fit for you.
  2. Being swayed excessively by money and ignoring less tangible measures, like fulfillment, respect, and good co-workers.
  3. Escaping “from” a job rather than moving “to” one.
  4. Overestimating yourself and thinking that your current company is the problem and not accepting that you may be part of the problem.
  5. Thinking short-term and hopping from job to job instead of being smart enough to stick with a good thing.

On the subject of regrets, British Poet Laureate Ted Hughes sums it up best: “The only thing people regret is that they didn’t live boldly enough, that they didn’t invest enough heart, didn’t love enough. Nothing else really counts at all.”

His quote appears at the end of an infographic created by Happify on How to Live Without Regrets. I love infographics because they beautifully illustrate a lot of complex material in a simple way.

What career mistake have you made? Would you do if you could magically rewind your career?


2 thoughts on “How to Avoid Common Career Regrets and Mistakes

  1. The only career regret I have is not setting up shop in Silicon Valley sooner but better late than never. Totally agree with being bold and much better to have taken a chance than never ventured out.

    • Yes, taking risks is part of business and indeed life. As Anais Nin said, “One’s life grows in proportion to one’s courage.” Thanks for reading!
      Priti D.

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