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Exercises to Help Clients Better Navigate the Transition to Retirement After Having Done It Yourself

Nerd's Eye View

Apr. 14, 2026
Podcast

My guest on today's podcast is Michael Kay. Michael is a retired financial advisor and a current life coach and author who helps high-performing individuals successfully 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), 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), and why Michael finds it important for those nearing retirement to consider how their social structures will change along with the transition (as they will no longer have the experience of seeing coworkers on a day-to-day basis).

And be certain to listen to the end, where Michael shares how the ability to say "no" more often than he did during his working years has led to greater satisfaction in retirement, how Michael’s work building and participating in an online community has brought him meaning during his retirement journey, and how Michael has found success in retirement in part by recognizing that his new avocations are still making a difference in the world (even if it’s a different type of impact than he had during his working years).

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