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Jan. 22, 2021, 2:10 p.m. EST

Retired too soon? How to re-enter the job market without skipping a beat

It’s not easy to re-emerge as a hotshot job candidate

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By Morey Stettner


Getty Images/iStockphoto

You retire awash with relief. You’re thrilled to kiss your working life goodbye.

A few months pass, maybe a year. And your relief has turned to regret.

You’re bored and restless. You yearn to return to the workforce. But you can’t reclaim your old job—perhaps it no longer exists, it’s filled or you burned bridges on the way out—so you wonder how and where you can restart your career.

Let’s say you’re recharged and ready to embark on a new professional adventure without a desperate need for money. You can be choosy.

Read: I have a seven-figure nest egg. Am I saving too much for retirement?

Still, it’s not easy to re-emerge as a hotshot job candidate that employers snap up. So what should you do?

“Think about your passions,” said Christine DiGangi, senior editorial director at the Balance, a New York City-based personal finance platform. “Think about what you always wanted to do but never had a chance to do.”

Ask yourself three questions:

1. Do I want to work full-time, part-time or as an independent contractor?

2. Do I prefer self-employment or working for an employer?

3. What core skills or knowledge have I accumulated in my old job(s)—and how might that carry over into another line of work?

Flexibility helps. If you’re intent on working full time, don’t lock yourself into a box. Consider part-time openings, consulting or freelancing.

“There are fewer full-time positions,” DiGangi said. “What’s booming is gig work” such as tutoring, data entry and driving for hire.

Read: Older Americans are sinking into debt. How to reverse the trend

Many parents with children at home during the pandemic have cut their hours as freelancers, creating opportunities for seniors who want to fill the gap. From offering music lessons to serving as nannies to preparing meals for harried families, retirees may opt to return to work on a per-project basis and test the waters.

As you identify the key skills or knowledge you’ve gained over your career, scan the employment horizon for ways to transfer your strengths to another type of job. If you spent 30 years as an insurance claim adjuster, for instance, your expert negotiation skills might help you succeed as a real-estate agent or arbitrator in dispute resolution.

When interviewing with hiring managers, play down your status as regretful retiree who’s eager to get back in the game. Instead, emphasize how your experience and qualifications fill the bill.

“Don’t market yourself as a retiree,” said Catherine Collinson, president and chief executive of Transamerica Institute in Los Angeles. “Frame it differently,” perhaps by explaining the one-year gap on your resume as a chance to recharge your batteries or lay low during the pandemic.

Unsure what kind of work might appeal to you? Expand your network and strike up conversations.

“Use social media tools to see what’s out there and what has changed,” said Maria Heidkamp, director of program development at the Heldrich Center for Workforce Development at Rutgers University. “If you’re interested in a certain industry, follow people posting articles [in that field] and comment on them. Join industry groups and meetups.”

List some of the top influencers in your area of interest and contact them. Research their background in search of commonalities (did you graduate from the same school?). Search online to see if they’ve been quoted in the media, written white papers or developed a slide deck for an industry presentation.

Rather than ask for a job or informational interview, reach out to them to talk shop. Praise their work. Ask intelligent follow-up questions about what they posted. Explain that you’d like to learn more about their business and ask them to recommend resources.

“It’s not surprising to want to reengage on the work front after you retire,” Heidkamp said. “But it gets harder to find a full-time job with benefits,” so you have to get creative to build relationships with a range of potential allies.

Morey Stettner is a personal-finance columnist for MarketWatch. He is the author of "The New Manager’s Handbook."

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