Episode summary
Ep 485: Exercises to Help Clients Better Navigate the Transition to Retirement After Having Done ...
Financial Advisor Success (Kitces)
· · 1 hr 30 min · Hosts: Michael Kitces, Adam Van Deusen · Guests: Michael Kay
Summary
Michael Kay argues that retirement is not just a financial transition but a psychological one, and that many high-performing professionals underestimate how much identity is tied to work. He says he entered retirement with plans, hobbies, and even new credentials, yet still fell into a period of depression because he had not truly grieved the end of the firm and the role he had built over decades. The deeper issue, in his telling, was not missing the work itself but losing a core part of self that had been reinforced since childhood.
He recommends that advisors help clients create space for reflection instead of rushing straight from employment into the next chapter. That means asking values-based questions, exploring what gives meaning, imagining contingencies if golf, travel, or other plans fall away, and discussing social support as workplace relationships disappear. Kay says the transition often exposes old habits around hustle, obligation, and difficulty saying no.
His broader point is that retirement can become more satisfying when clients accept that joy, flexibility, and purpose may look different than they did during their careers. In his own retirement, that has meant music, writing, coaching, community, family time, and a firmer boundary around what is worth doing.
Key takeaways
- Michael Kay says retirement can trigger grief because many professionals have built identity around work for decades.
- Kay argues advisors should ask clients what they value, not just what hobbies they plan to do.
- He says retirees need backup plans if health or other limits interrupt their first-choice activities.
- Kay emphasizes that social structure matters, especially for men, because workplace connections often disappear after retirement.
- His own retirement improved when he learned to say no to activities that were not joyful.
Notable quotes
“I had never grieved the loss of the thing I had created”
“Until you sit in the crucible of change and feel the heat of becoming something else or someone else”
“If it's not joyful, I'm not doing it. Hard stop”
How the episode opens
Welcome to the Financial Advisor Success Podcast, where you go behind the scenes with financial planner, speaker, and consultant Michael Kitces to hear stories of how leading financial advisors navigated the inevitable challenges that arise on the path to success, and get insight from leading industry consultants about how to break through to the next level in your advisory business. And now, here's your host, Michael Kitces. Welcome everyone.
Welcome to the 485th episode of the Financial Advisor Success Podcast. My guest on today's podcast is Michael K. Michael is a retired financial advisor and a current life coach and author who helps high-performing individuals successfully make the transition to retirement.
What's unique about Michael though is how he has developed questions and exercises that financial advisors can use to help clients and themselves make the transition to retirement. In this episode, we talk in-depth about how while Michael identified plenty of activities that would fill his time in retirement, he found he didn't give himself enough time to process the transition from leading a financial firm to taking on other pursuits. How Michael considers the retirement transition to be a grieving process requiring thoughtful consideration given that many successful professionals have a multi-decade relationship with their job, which can become part of their identity.
And how Michael found that acknowledging that his previous professional success was enough helped him gain the closure to move on to the next phase of his life. We also talk about how Michael finds that advisors can support clients by having them think through how they will fill up their entire weeks in retirement going beyond just a few hobbies, and along with contingency plans if health or other issues prevent them from pursuing their initial plans. How Michael suggests that clients think back to their first day at work to remember what that major transition felt like, including the nerves they might have had at the time.
From the episode’s captions: roughly the first two minutes, lightly cleaned. Keep watching on YouTube →
Topics
- retirement transition psychology
- client exercises
- retirement planning beyond income
- social structure changes
- purpose in retirement
Watch the episode
Summary, takeaways and quote selection by Octagon. Quotes are short excerpts; the full conversation is in the episode.
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Financial Advisor Success (Kitces), this episode and its artwork belong to Michael Kitces. Octagon is not affiliated with the show; this page is an independent summary.
