Fresh start after 50: How to land a job later in life

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I’ve received questions from readers in the post-50-year-old age group. One had lost a relatively senior position and was having a tough time finding a comparable job; the other wanted to transition to a different profession than the one he had been in for more than two decades.

Both were feeling stuck and discouraged and wondered if they would have to accept that they were past the point of being able to find the kind of positions they’re seeking.

Unfortunately, career experts admit, there isn’t a way to sugarcoat the challenge of finding a new job once you’ve celebrated the Big 5-0.

“Being 50-plus can be an added complexity in a job market that typically favors younger, and less expensive, employees,” said Lisa Schmidt, a certified career coach and founder of Worksphere Consulting.

That is especially true for those looking for senior-level positions during the current pandemic, according to Susan Peppercorn, executive career consultant at Boston-based talent consulting firm ClearRock Inc.

“It’s difficult for someone in their 50s at a senior level to find a comparable position under the best of circumstances. Current economic conditions due to the COVID-19 pandemic have increased that level of challenge exponentially,” she said.

That doesn’t mean these “older” job seekers should just throw in the towel. Here, career experts offer tips on how to best prepare for the job search.

Assess your financial resources

“Many people do not have the financial resources to wait to find the perfect role. In those cases, you may want to consider a job that will help you pay your bills while you look for something that aligns with your talents,” Peppercorn said. “If you are in a financial situation where you must bring in income immediately, then an immediate flow of money is a top priority and so is a job.”

Research prospects in your industry of choice

You might have to reconsider your goals or expect a longer wait if you’re looking for work in what Schmidt calls “a highly disrupted or shrinking field such as publishing, or oil and gas.”

Could be an opportunity in disguise?

“Is there something you have long wanted to do professionally that this break in employment can be used for?” Schmidt asks. “For instance, have you wanted to train for an entirely different career but lacked the time to do so? Or would you consider taking on a role as an instructor in your field of expertise if you always wanted to teach?”

Have two resumes

This is a good idea for someone who needs to find work quickly, according to Debra Boggs, co-founder of D&S Professional Coaching. One version should be for higher-level management roles, the other is scaled back to appeal to a wider market of mid-level positions. “This way, a candidate isn’t applying for mid-level roles with a resume that makes them appear over-qualified, but they still have the higher-level version on hand,” Boggs said.

Consider contract work

It can be an excellent alternative to waiting for the ideal role to arrive. “Contract employment allows you to test out an employer environment without a long-term commitment while building your capabilities,” Peppercorn said.

Social media profiles should portray you at your best

They always should, of course. But in the current climate, LinkedIn has become more important than ever. “With COVID-19, networking has shifted to LinkedIn,” said Damian Birkel, founder and executive director of Professionals In Transition. “Make sure your LinkedIn profile is complete, easy to read, search engine optimized and full of quantifiable measurable benefits.”

Your profile should “make clear what problems you are uniquely positioned to solve” as well as “the impact you have had as a leader, as opposed to the activities you did in your previous positions,” Schmidt echoes. “If you have a profession that can be leveraged into different industries, get really clear on your transferable skills, knowledge and talents. Know what you are good at and get good at describing it. Consider a personal website and business card as promotional material ... for you!

Birkel also suggests leveraging LinkedIn in other ways.

“Participate in discussion groups. If you can afford it, move into the paid level of LinkedIn,” he suggests. “It gives you access to hundreds of excellent courses. That alone is worth the money each month to pay. In addition, you will be able to contact anyone you desire.”

Evaluate opportunities for growth

“Compensation and title are not the only measures of career trajectory,” Peppercorn points out. “Will this new opportunity teach you something new that can be transferable in the future? Today’s ever-changing business climate appreciates someone who has a variety of experience and has taken risks.”

Making sure potential employers know about all that experience and risk-taking is what likely will land that desired job.

“I think it’s less about the path you choose or have to choose,” said Peppercorn. “It’s more about how you tell your story.”

Kathleen Furore is a Chicago-based writer and editor who has covered personal finance and other business-related topics for a variety of trade and consumer publications. You can email her your career questions at

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