The Boomer Woman’s Podcast, episode 224
Helping the Men We Love Find Purpose Beyond Work with Michael Kay
Retirement isn’t just a financial decision. It’s an identity shift.
While women often spend years thinking about what comes next, many men reach the end of a career only to discover they don’t know who they are without the job that has defined them for decades.
In this thoughtful conversation, retirement coach Michael Kay explains why leaving work can be unexpectedly difficult for men, why so many struggle to talk about it, and how women can create safe conversations without trying to solve the problem for them.
We explore:
- why identity can become wrapped up in a career
- why “retiring to something” matters more than retiring from work
- how couples can prepare together for life after full-time employment
- the importance of individual dreams alongside shared goals
- why golf isn’t a retirement plan
- creating meaningful friendships beyond the workplace
- how unexpected job loss changes the conversation
- why curiosity is one of the best retirement skills we can develop
Whether you’re approaching retirement yourself, already there, or watching someone you love struggle with the transition, this conversation offers thoughtful ideas for creating a richer next chapter.
Listen below.
Agnes - in conversation with Michael Kay
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About the guest: Michael Kay
I started working (legally) at age 13 when I could apply for working papers. By the time I graduated from college, I’d cleaned garages, picked weeds, worked for a butcher, baked bagels, hauled musical equipment, took care of pets, children and plants, played in rock bands, worked in a glass warehouse, installed sun control film, construction, bookkeeping, parked cars, worked in a bookstore, grocery store, college admissions office and served as a Resident Assistant in the dorm. I’ve probably left out a few odd jobs here and there.
I graduated college with a degree in accounting and hit the workforce during a time when no one was hiring. Luckily, I was hired by a mid-sized CPA firm and embarked on a ten-year journey that led me through luck, fate, or magic to financial services. I found out quickly that I sucked at selling things and, applying my CPA training, created (ultimately) a fee-only Registered Investment Advisory firm where I didn’t have trade advice for the purchase of a product. On the way, I discovered financial life planning, which changed my life, business, and relationship with clients and then the magic took over.
By the time I turned over the reins to my partner, I had built a firm of professionals who cared deeply for their clients. It was very satisfying. During my career, I wrote two books on Financial Life planning (one for professionals and one for consumers), countless articles for business publications, spoke all over the country to professional and consumers audiences and even spoke to the largest financial planning conference in India.
I created Chapter X, a community for men transitioning to life after their careers. I became a Certified Life Coach to help others identify their values and move towards them. Life is messy and sometimes having someone to provide support and some very pointed questions helps.
After a 50-year hiatus, I’ve returned to my first passion, music and am having a blast. I’ve also turned my attention from writing non-fiction to fiction and having fun creating characters and stories to entertain others. I volunteer helping some elderly folks who have trouble figuring out their bills, mail, etc., and hopefully serve as a good companion. I am physically active between weight training and yoga.
My college sweetheart, Wendy, and I have been married since 1977 and we are blessed with two wonderful children and three delicious granddaughters. Oh yeah, I can’t forget our Biewer terrier Phoebe…she rocks!
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