Snagging Your Dream Job After 50

Editor’s note: This article is part of The Great Unretirement, a Next Avenue initiative made possible by the Richard M. Schulze Family Foundation and EIX, the Entrepreneur Innovation Exchange.

For whatever reason, some people fail to follow their passions early in life and find themselves in a career that may pay well but isn't intellectually or personally stimulating.

Some find that passion later on.

Whether they write the Great American Novel, take up a career in the arts, open a restaurant, found a winery or become a therapist, many people pursue major career transitions after turning 50.

Kristine Cherek is one example. She spent much of her working life in male-dominated fields — first as a corporate attorney at an international law firm, then as a senior executive of a real estate company and later as a law school professor. Over time, Cherek says she grew increasingly frustrated.

Finally, she left her traditional career to write a book, "Tread Loudly: Call Out the Bullsh*t and Fight for Equality in the Workplace." The book fuels her work helping other women achieve their career potential and teaching executives and emerging business leaders on workplace culture. She speaks at universities, professional groups and companies ranging from early-stage startups to corporations listed on the New York Stock Exchange.

Others have taken similar journeys.

At age 50, Barbara Palmer was laid off from her job and, while she felt it might have been "easier to play it safe and find another executive role," she added that she "felt emboldened by having older children, more self-awareness, and trust in myself that I could be successful at something less traditional or expected." Palmer says that she had changed jobs earlier in her career — both by choice and through layoffs —so she was less anxious about this departure. She also had a strong support network.

"All of this allowed me the confidence to pursue a less traditional path, one that may have felt riskier earlier when I had small children and less experience," she says. Palmer added that she also was confident that if things didn't work out, she could always go back to the tried and true.

But things did work out for her. Today, through her company Broad Perspective Consulting, Palmer coaches professionals on their next careers.

Jan Cullinane was a science teacher early career; she loved the work, she says, but grew tired of changing jobs every few years as she followed her husband, a CPA, to new cities when he took on new clients. "I reached the point where I wanted to be in control of my own time and my own schedule, and was ready to forge a new path," she says.

Today Cullinane is the author of retirement books that offer "holistic" advice beyond financial considerations for a boomer audience. Her first book was published in 2004, with others following in 2007, 2012 and 2022. She also serves as a "Healthy Living" columnist for Ideal Living and gives talks on retirement, drawing on her experience as a teacher.

Even while in college in her 20s, Virginia Stockwell says she recognized that she didn't have the same passion for a chiropractic career as other students. But she persevered, graduating with a Doctor of Chiropractic degree "and a mountain of debt," she says.

For the next five years she worked in the field but finally decided she couldn't "keep living a life that didn't feel authentic." So she took a corporate job. But that didn't prove to be the right fit either.

It would take her a few more tries — running a medical transcription business and working as a realtor — before the financial crisis of the early 2000s led her to launch a personal chef business. While Stockwell was successful in each endeavor, she says it wasn't until she was in her 50s that she finally found a career that "feels like the right fit."

Today, Stockwell is a business coach who helps other coaches and consultants turn their expertise and life experiences into online courses and memberships. It's a role, she says, that "brings together all the lessons I've learned from my many pivots into work that feels fulfilling and aligned with who I am now."

It's not at all uncommon for people, even those with decades of experience in a single career, to long for something more.

According to a ResumeBuilder.com survey of people aged 62 to 85, 12% of retirees say they are likely to start working again (25% already did so). While the top reasons for returning to work are inflation and the high cost of living, many older returning workers also point to a desire to continue contributing and an interest in pursuing passions missing from prior jobs.

TopResume career expert Amanda Augustine says there's really nothing unusual about craving something new after a long career. "As life changes, it's only natural that your career aspirations might evolve too," she says.

If that has happened to you, there are a number of positive and proactive steps you can take to position yourself for the job of your dreams — even if your background and experience is in an entirely different field.

Palmer uses a scorecard exercise to help people evaluate what's most important to them in pursuing a new career pathway. This involves:

• Listing all of the things you would like to consider. It helps to gather everything in one place. Are you looking for remote work? On-site? Do you want to lead others? Are you interested in working in a specific location? A certain industry? A particular culture? "The list is unique and personal to you," Palmer says. "Some of the elements may not matter for now but may come into consideration down the road so list them and we can deprioritize them at this time."

• Prioritizing. What are your "must haves," "nice to haves" or "does not concern me at this time" elements?

• Using the scorecard. Score every opportunity you're considering based on your list. In addition, Palmer suggests, you can also use your list of attributes to ask the right questions during interviews.

• Continuing to refine. The scorecard should be a living document, Palmer notes. "Today, you may value compensation and growth opportunities, but in a few years, you may want to understand policies around caregiving, flexible work schedules or bereavement. All elements stay on the list, but their value or priority may change over time."

Shifting from one profession to another may seem impossible, but it does not have to be. It's not only paid experiences that matter, says Augustine, who points out that volunteer work, freelance projects or even relevant hobbies are all fair game for demonstrating your interests and aptitudes. In addition, she says, "Many of your current skills — like communication, problem-solving and leadership — are valuable in other industries."

It's important, though, Augustine says, to "speak the language of our new industry." Be sure to reframe your experience using industry-specific terms. "Research trends, attend events and conduct informational interviews to learn the language, then update your resume with relevant keywords," she advises.

Preparation and education are critical, says Cullinane, who learned how to prepare a proposal for her first book by reading "The Complete Idiot's Guide to Getting Published" by Sheree Bykofsky. "This has been my second career for more than 20 years, and I'm still loving it," she says.

This time of year is ideal for considering a career shift, says Renee Barber, Global Director for TYR Talent Solutions. "If you're planning a career change in 2025," she advises, "now is the time to research industries, identify needed skills and position yourself for success. Change isn't easy, but the rewards can be transformative."

Stockwell agrees. "If there's one thing I've learned, it's that finding your dream career doesn't have a deadline," she says. "By your 50s, you have the clarity and confidence to finally build something meaningful and authentic."

Lin Grensing-Pophal 

Lin Grensing-Pophal is a freelance business writer with a background in HR/employee relations and marketing/digital marketing. She is accredited through SHRM, the Society of Human Resource Management, as a Senior Professional in Human Resources and Senior Certified Professional. She also is a member of the American Society of Journalists and Authors and the Association of Ghostwriters.  Read More