S3-EP4: Kerry Hannon on Pajama Jobs, the New Age of Remote Work, and Why Older Workers May Benefit

Oct 23, 2020


Debbie Weil speaks with career and retirement expert Kerry Hannon on how COVID has changed the way we work, why WFH (working from home) is here to stay, and why older workers may benefit.



Today, Debbie talks to Kerry Hannon, author of the new and well-timed Great Pajama Jobs: Your Complete Guide to Working from Home. Kerry is the author of 14 books and an expert on career transitions, entrepreneurship, personal finance, and retirement. She writes regularly for The New York Times, MediaWatch, Forbes and other media outlets, including NextAvenue.org.

BTW, her dog, Zena (pictured on the cover of her new book), is “PERFECT,” she tells Debbie. The dog barking in the background belongs to her neighbor.

Kerry answers the question: will we ever return to the office or is remote working here to stay? Debbie wishes WFH (working from home) had been an accepted phenomenon decades ago when she had small children.

Kerry shares some key skills that can make working from home more effective (good communication, discipline, technical literacy) as well as tips for older and more experienced workers, including the semi-retired. She makes the point that work is not just about the money.

They also talk about ageism, still a pervasive issue in the workplace, and how remote work might alleviate it by focusing attention on performance and productivity.

Finally, they talk about one of Kerry’s favorite topics: cultivating resilience by learning new skills. Expand your brain, she says. Adopt a beginner’s mind, stay open, and take risks. Consider living and working in a foreign country that is welcoming to location-independent workers.

Perhaps not compatible with our pandemic world right now, but travel and living somewhere else are often part of a gap year dream.


Mentioned in this episode or useful:

A few job boards recommended by Kerry:

Places Kerry recommends to work remotely (once the pandemic is over):


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Thanks to our media partners

Encore.org, our newest media partner, is an ideas and innovation hub tapping the talent of those 50+ as a force for good. Founder and CEO Marc Freedman is an award-winning social entrepreneur and author, most recently, of How to Live Forever: The Enduring Power of Connecting the Generations. Looking for a great gap-year transition program? Check out Encore Fellowships, which match skilled, seasoned professionals with social-sector organizations in high-impact, paid assignments.


Modern Elder Academy is a program dedicated to navigating mid-life transitions. MEA, based in Baja California, Mexico, provides the place and the tools to start reframing your lifetime of experience. Grow whole, not old. Founder Chip Conley is a New York Times bestselling author, award-winning hospitality entrepreneur and a rock star of the mid-life transition movement. His newest book is Wisdom @ Work: the Making of a Modern Elder.


Next For Me is an important new resource for the 50+ crowd focused on rewriting life. Taking a gap year or timeout may be the best way to figure out "what's next" when you're in this stage of life. Founder Jeff Tidwell explains, Next For Me "connects and inspires our generation to evolve our post-50 lives through new work, a new purpose, or a new social contribution."