The Boomer Woman’s Podcast, episode 224

Michael Kay

Understanding Men's Post-Career Transitions with Michael Kay

Michael Kay talks to mid-age men about the transition from work to whatever’s next.  He approached me asking if he could share how we mid-age women could support the men in our lives, how to have those non-threatening conversations.  His request was like having the tables turned when I hadn’t thought about their turnability.

Michael explains:

  • Why post-career is so difficult for men
  • Who has the most difficulty with transitions? (Great insights and he is candid, even as he is also a man.)
  • How so many facets of post 9-5 life aren’t considered, aren’t discussed well before the big day comes. (Just like we women don’t think about, don’t always know what we aren’t considering)
  • The conversations we mid-age women might have with the men in our lives when they’re considering the next chapter… and when they won’t. 

We both try to be honest about gender differences while maintaining respect for the opposite gender.  Except I do slip a few comments in…

Listen below.


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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!

Michael’s podcast:  Chapter X with Michael Kay
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