Advice to Pre-Retirement Self: Be Less Sure

What’s next?

Don’t drift. Design.

Our next small group coaching program starts in April.

Learn more here.

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Who are you when you’re no longer your title? For many high-performing professionals, that question can feel destabilizing — even frightening.

Michael Kay is a CFP, a financial life planner, the author of the new book How To Craft Your Chapter X: A Guide For High-Performing Men to Discover Meaning (and Joy) In Retirement. He’s been through it himself—the excitement of the new chapter, and then, six months in, the wall he didn’t see coming.

Today he shares what he’s learned about reopening the aperture, grieving what you’ve left behind, and finding out who you were before you were your job. This is a conversation every high-achieving man—and the people who love them—needs to hear.

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Bio

Michael F. Kay is a coach, teacher, author and retired CFP(R). Through his books, workshops, speeches, and the Chapter X community, he’s helped thousands of women, men, and families master their financial lives—and navigate the transition from full-time work to what comes next.

He’s written three books: How to Craft Your Chapter X, The Feel Rich Project, and The Business of Life. His insights have been featured in The New York Times, The Wall Street Journal, Fox Business, Forbes, and Psychology Today. Today, he publishes weekly essays for the Chapter X newsletter, hosts the Chapter X podcast, and shares his thoughts on LinkedIn. He is the former president of Financial Life Focus, a fee-only multi-advisor financial life planning firm.

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For More on Michael Kay

How To Craft Your Chapter X: A Guide For High-Performing Men to Discover Meaning (and Joy) In Retirement

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Podcast Conversations You May Like

The Inspired Retirement – Nathalie Martin

How to Prepare Mentally for Life After Work – Joseph Maugeri

Art Cure: The Science of How the Arts Save Lives – Daisy Fancourt

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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.

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.

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Wise Quotes

On Saying No in Retirement

“If it’s not joyful, I’m not going to do it.”

On Perspective

“As we get older and we start focusing towards career, that aperture narrows. And so when we get ready to step into this next chapter, whether it’s our choice or not, we are at our narrowest. So we need to, mindfully and intentionally—I think that’s the right word—look to reopen that aperture.”

On Returning to Music – For Fun

“I got the trumpet out and had it cleaned, and I found a teacher, and I started playing again, and I put up on my music stand, ‘fun’—the word fun—to remind me. Because if you miss a note, I was like, ‘You suck.’ All these things that come back. And so I had to keep reminding myself: this is for fun. I am never going to be a touring professional musician. I’m never going to play with Blood, Sweat and Tears or Chicago. This is for fun. And it just takes the discipline to keep reminding yourself—have joy in the music, have joy in the doing. The joy is in the journey, not in the destination. Because the destination is the journey.”