Retirement. You could wing it. Why not design it?

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The Very Early Registration discount (45%) ends on June 21st. Learn more here.

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In our last conversation, Dan Pontefract gave us a demographic wake-up call. The future of work is aging, and longer lives will require new thinking about careers, retirement, and contribution.

Today, Scott Siff brings that to the practical level: how do we create better pathways for people who want to keep contributing, but not necessarily in the same way? And what are employers missing when they overlook experienced talent?

His story begins with his father’s frustrating search for a new job in his 70s, and builds into a larger conversation about age bias, unretirement, labor shortages, and the need to redesign work for longer lives.

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Bio

Scott Siff is the founder and CEO of Pivoters, a job-matching platform focused on helping people 55+ connect with employers seeking experienced talent. His story begins with his father’s frustrating search for a new job in his 70s, and builds into a larger conversation about age bias, unretirement, labor shortages, and the need to redesign work for longer lives.

Siff is also a founder and Managing Partner at Quadrant Strategies, a Washington, D.C.-based strategy research and communications firm. His background includes advising senior leaders, Fortune 50 companies, and high-profile political figures on public affairs, brand, reputation, crisis, competitive positioning, and strategic communications.

Earlier in his career, Siff served as CEO of BAV Consulting, Vice Chair of the global research firm PSB, and worked at the U.S. Department of Justice as a prosecutor and later as counsel in the Environment Division. He earned a B.A. from Harvard University, Phi Beta Kappa, and a J.D. from Harvard Law School, where he was an editor of the Harvard Law Review.

Scott Siff joins us from Washington, DC.

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For More on Scott Siff

Pivoters

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Other Retirement Podcast Conversations You May Like

The Portfolio Life – Christina Wallace

The Unretirement Life – Richard Eisenberg

Working Identity – Herminia Ibarra

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Best Books on Retirement

Our reccomendations and summaries are here

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Mentioned in This Episode

The Future of Work is Grey – Dan Pontefract

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About The Retirement Wisdom Podcast

There are many podcasts on retirement, often hosted by financial advisors with their own financial motives, that cover the money side of the street. This podcast is different. You’ll get smarter about the investment decisions you’ll make about the most important asset you’ll have in retirement: your time.

I help people who are retiring, but aren’t quite done yet, discover what’s next and build their custom version of their next life. A meaningful retirement doesn’t just happen by accident.Schedule a call today to discuss how the Designing Your Life process created by Bill Burnett & Dave Evans can help you make your life in retirement a great one — on your own terms.

About Your Podcast Host

Joe Casey is an executive coach who helps people design their next life after their primary career and create their version of The Multipurpose Retirement.™ He created his own next chapter after a 26-year career at Merrill Lynch, where he was Senior Vice President and Head of HR for Global Markets & Investment Banking.Joe has earned Master’s degrees from the University of Southern California in Gerontology (at age 60), the University of Pennsylvania, and Middlesex University (UK), a BA in Psychology from the University of Massachusetts at Amherst, and his coaching certification from Columbia University.In addition to his work with clients, Joe hosts The Retirement Wisdom Podcast, ranked in the top 1% globally in popularity by Listen Notes, with over 2 million downloads. Business Insider recognized Joe as one of 23 innovative coaches who are making a difference. He’s the author of Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy.

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Wise Quotes

On Rethinking Work“At 55, you may well have 30 years of work life left, but you probably have 25 really good years, which is the same length of career as from the ages 25 to 50.”On What Employers Are Missing “There’s a pool of 40 million unused workers ready to go, better workers, and they’re sitting there on the sidelines, begging to get in the game.”On Reframing Aging

“A 65-year-old today is like a 45-year-old 20 years ago. And I’m not saying that theoretically, that’s what the science is finding.”

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