The Retirement Wisdom Podcast

What If You Pivot Instead of Retiring? – Scott Siff

June 18, 2026·29 min
Episode Description from the Publisher

Retirement. You could wing it. Why not design it? Our next group proram starts in September and is limited to 10 people. The Very Early Registration discount (45%) ends on June 21st. Learn more here. _______________________ 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. __________________________ 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. _______________________ For More on Scott Siff  Pivoters _______________________ Other Retirement Podcast Conversations You May Like The Portfolio Life – Christina Wallace The Unretirement Life – Richard Eisenberg Working Identity – Herminia Ibarra _________________________ Best Books on Retirement Our reccomendations and summaries are here _________________________ Mentioned in This Episode The Future of Work is Grey &#8211; Dan Pontefract _________________________ 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 &#38; Dave Evans can help you make your life in retirement a great one — on your own terms. About Your Podcast Host <article class="post-705844 podc

Podzilla Summary coming soon

Sign up to get notified when the full AI-powered summary is ready.

Get Free Summaries →

Free forever for up to 3 podcasts. No credit card required.

Listen to This Episode

Get summaries like this every morning.

Free AI-powered recaps of The Retirement Wisdom Podcast and your other favorite podcasts, delivered to your inbox.

Get Free Summaries →

Free forever for up to 3 podcasts. No credit card required.