Motivation

How to Know When to Retire or Change Careers

Tom Brady. Cher. Tina Turner. What do they have in common? Besides being at the top of their respective game at one time or another, all three second-guessed their initial decision to retire. They returned for one more season and a few additional farewell tours.

You might not knock on your former company’s doors months after blowing out the candles on your well wishes in retirement cake. However, in this day and age, it is likely that you might find yourself not content to totally hang up your work hat.

Here’s how to know when it might be time to retire from career No. 1, what to know about making your next move and how to take care of your mental health during the transition.

How to know when to retire or make a change

International Coaching Federation certified Professional Coach Jen Carman noted that changing careers has become increasingly more common in the last few years. “Employees are reevaluating their priorities—both personally and professionally,” she says.

According to Second Wind Movement, several signs to know that it might be time to retire can include being emotionally burnt out, a decline in health, no longer identifying with your work and being financially prepared to leave the workforce. 

“If your current career no longer aligns with your goals, don’t be afraid to consider a change,” Carman says.

Ten years ago, business development consultant John Bassett was ready to make that change—or so he thought. After managing a successful loyalty program at 3M Company, he retired to volunteer, travel and “relax.”

“I joined SCORE (Service Corps of Retired Executives) and gave counsel to start-up companies for a few months,” Bassett says. “I played more golf, but I had difficulty as my ‘work identity’ was a stronger factor in my happiness than I realized.”

What move should you make?

If, like Bassett, you realize your work identity strongly factors into your happiness, you’ll face a decision of what to do next. So how do you determine the path ahead?

“Working with a certified career coach can be a great way to further determine your priorities, gain clarity and set goals,” Carman says. 

Carman also recommends taking a class to test the waters or learn more about a new subject matter. “It can be a great way to gauge your true interest level,” she says. “Likewise, if there is a certification that will make you more marketable, invest in yourself. It will pay dividends.” 

Lastly, Carman says, never underestimate the power of your network. “Sometimes all it takes is one conversation to get that ‘in’ you might be looking for!”

That’s exactly what happened with Bassett’s Plan B. When he announced he was leaving 3M, his customer PSS asked him to serve on their advisory board.

“I accepted as it would provide some business inclusion, with three meetings a year,” he says.

At one meeting in Texas, Bassett witnessed a new safety product PSS invented. He knew he could assist PSS in launching it, which would dovetail nicely with his newly realized desire to increase his work contribution. He called the company’s president and explained his plan to expand his work impact.

“I drew up a job description and compensation plan, and he hired me to work with the management team,” Bassett says. 

His work schedule now varies based on projects, meetings he attends or leads and ad hoc coaching requests. “When I travel for business, I work full time,” Bassett says. “When I’m at home, it’s usually around 15-25 hours per week.”

Take care of you

Transitions bring about uncertainty. This could wreak havoc on your mental health, thereby disrupting the momentum and productivity in your career search or second career. Carman recommends listening to your mind and body to stay on track.

“Figure out what works and makes YOU feel your best,” she says. “It’s different for everyone.” Carman personally prioritizes getting enough sleep and moving her body as much as possible.

“I also connect with family and friends, and make sure I have enough ‘me’ time to properly recharge,” she says.

And if you find yourself particularly stressed, reach out to a family member, friend or medical professional. “Most importantly, don’t suffer in silence,” Carman says. “We are all human and it’s okay to ask for help.” 

Knowing when to retire or make a change is worth it… and it all comes down to relationships 

Bassett feels like he is now living his dream in this phase of his work life. It was made possible, he says, through positive relationships. “Every opportunity I’ve had from day one came as a result of a relationship I developed.”

He also believes that all the jobs he held throughout his career influenced and prepared him for his current role. “Some of those key elements included keeping myself open for change, considering the team, not just myself, and treating people as you’d like to be treated. Don’t burn any bridges!” he says.

Photo by Prostock-studio/Shutterstock


Jill McDonnell is a Chicago-based content writer and communications professional. She has a bachelor’s degree in magazine journalism from the University of Missouri-Columbia and a master’s degree in public relations and advertising from DePaul University. She is currently at work on a psychological thriller novel.


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