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The Retirement Wisdom PodcastTransition Coaching for Career and Retirement Author: Retirement Wisdom
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Design a Phased Retirement – Anna Rappaport
Episode 387
Monday, 19 January, 2026
Last call… Design Your New Life in Retirement New Groups start on Thursday 1/22 & Friday 1/23. Join us…and design your next chapter. Learn more and sign up here _________________________ Bio For decades, Anna Rappaport has studied how people actually transition out of full-time work—not in theory, but in real life. And what she’s learned may challenge how you’re thinking about retirement. Anna Rappaport hasn’t just studied retirement—she’s been living a phased retirement for three decades and is still going strong at 85. As a former Society of Actuaries President and one of the profession’s most published and respected retirement experts, she has insights you’ll want to hear. So, today, we’re focusing on phased retirement, but not as an HR policy. We’re talking about it as a life strategy—one that blends purpose, flexibility, and relationships. Anna introduces a powerful framework she calls the Life Portfolio—Health, People, Pursuits, and Places—and explains why money alone is never enough for a fulfilling next chapter. If you’re wondering Who will I be when I retire?, this conversation is for you. Anna Rappaport joins us from Chicago. ________________________ Bio Anna Rappaport is the founder and president of Anna Rappaport Consulting. Anna is an actuary, consultant, author, and speaker, and is a nationally and internationally recognized expert on the impact of change on retirement systems and workforce issues. She is a phased retiree and is passionate about women’s retirement security. Anna is a past-President of the Society of Actuaries and chairs its Committee on Post-Retirement Needs and Risks and its Aging and Retirement Research Initiative Steering Committee. Anna spent 28 years with Mercer as an employee benefit consultant, before she founded her own firm, Anna Rappaport Consulting, after leaving Mercer. _________________________ For More on Anna Rappaport LinkedIn A Conversation With Anna Rappaport & Steve Siegel: Solo-Agers Disconnect Thinking About the Future of Retirement _________________________ Podcast Conversations You May Like Retiring: Creating a Life That Works for You – Teresa Amabile The Portfolio Life – Christina Wallace Is Your Company Ready for the Aging Workforce? – Paul Rupert _________________________ 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. About Retirement Wisdom 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 1.6 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. __________________________ Wise Quotes On The Portfolio You’re Ignoring “The Life Portfolio assumes that the individual has enough money. So this is on top of money—it’s not instead of money. That’s really important. The four quadrants are: Health, Pursuits, People, and Places. If you’re not in good health, nothing else matters. But pursuits—the things that give you a sense of purpose in your life—that’s critically important. And here’s the key: you need a portfolio of them, not just one or two. Because you can always lose one or two. If your pursuit is playing tennis, you might not be able to play tennis anymore. If it’s work, it might disappear. So people should try to do a few things, see what they like, zero in on it, but not be limited to one thing.” On The Reboot, Rewire, Retire Concept “Rather than saying ‘Okay, I’m done with work, I’m going to play golf all the time,’ Reboot is thinking about this life portfolio. What can I do that brings value to my life? We went around the table asking what people were most concerned about regarding retirement. The biggest issue wasn’t money, wasn’t health, wasn’t caregiving—it was ‘who am I going to be when I’m not who I was anymore?’ That was a real wake-up. Rewire is getting ready—building new skills, keeping up your contacts, maintaining your skills. Those are critical things.” On Preparing for Phased Retirement “The preparation you should do is not when you’re ready for phased retirement—it should be way before that. Think about career planning where you’re always focusing on how you’re creating value. You need to have ways of creating value. If you have a good relationship with your employer, you can work something out. I was probably the most published and well-known retirement person in my firm at Mercer. You need credibility. Learn to use their words, not ours—if I’m talking actuarialese to my client, they’re like ‘what?’ But if I’ve translated that to their language, it’s a lot better.” On Identifying Where You Add Value “I think the big benefit for employees is that they have much more satisfying lives. There are also a lot of people who they get near what like the traditional retirement ages and they want to spend more time with their grandchildren. They want to take more vacations. They want to pursue a hobby, but they don’t just want to say, my work life is over. And it gives them a variety of options. So I think there’s a lot of benefit. It’s really a way of this gradually changing pursuits. And it may involve money and it might not involve making more money. But it does involve value. Now there can be, and we had a Society of Actuaries essay on employees and both, we’ve discussed the value a number of times. We’ve also discussed the routes to phased retirement because it’s not an easy deal that just automatically happens. Not usually. For employers, it’s a different thing. Depending on the kind of employer and the kind of job that people have, it lets them keep value that people have contributed. And what I want to say is that if we look at employees, and of course it varies by type of employment, there’s firm-specific human capital and there’s general human capital. And for example, if you were a currency trader, you could probably move into one job to another in two minutes. But Joe, you were a human resource director, and you had years and years of history, a lot of firm-specific human capital. What we have not done a good job of, and this is a speech I’ve been making for 25 years, probably maybe 30, is identifying what are the things that you contribute, that you really contribute value. It might be that 10% or 20% of your job, you’re doing something where you’re contributing a lot of value. And what I think is really important is for the employee to figure out how they can contribute a lot of value and the employer to figure out, and for them to reach a meeting of the minds.”
