Confessions of a Retired Advisor  

One year after selling his practice, he reveals the biggest challenges and lessons learned.  

By Michael Kay
Michael Kay
Michael Kay

It’s been a little over a year since I sold my firm to my partner and stepped away from 99% or maybe 99.9% of my involvement. It’s been a year of exploration, some missteps, some interesting learning and finding comfort in my discomfort.

There have been lessons, small and large.

For example, instead of receiving a biweekly paycheck, I had to rearrange cash flow and pay estimated taxes. I also basically put my financial life on autopay and autopilot to minimize time and effort. For some, this financial rearrangement triggers feelings of insecurity and instability. But the fact is, managing your money after the paychecks stop should not be a time-absorbing quagmire of uncertainty. As a professional, I was undaunted; but it still meant a shift in operations was necessary.

A new framework

The bigger challenge was creating the framework of a routine that was flexible yet had some structure. There were times when I felt low and like I was stuck in the mud. The shift from absolute engagement of career, where I pretty much knew what work needed to be accomplished, to a free-form open day to be filled with satisfying activities was challenging. After all, a life time focused on accomplishment doesn’t disappear overnight.

“There were times when I felt low and like I was stuck in the mud. The shift from absolute engagement of career, where I pretty much knew what work needed to be accomplished, to a free-form open day to be filled with satisfying activities was challenging.”

I made the decision that my “job” was to focus on not judging myself for days where I “meandered” and couldn’t tally anything in the win column. I really needed to be equally okay with days where I was really engaged along with days where not much happened.

As I encourage those in the Chapter X community to find things that have meaning to them, I needed to listen to my own good advice. What do I love doing? I found the answer in my distant past: my formative years where music was the centerpiece of my life. After 50 years of keeping my trumpet locked in its case, I decided to start again. I needed to line up a bunch of things, like finding where to have my old horn cleaned and oiled, a teacher and a different mindset.

No joy? No thanks

My teen years were immersed in music which included a teacher who broke me to tears weekly and an unremitting self-loathing of not being “good enough” even though I was, objectively, a pretty good player. In my late 60s, carrying around unremitting self-loathing is hardly productive; it’s a formula for misery. While I loved performing and even the hours of individual and group practice, my drive as a teen to be “the best” took a great deal of joy out of it.

In this stage of life, my mantra is to find joy in the activities I pursue and to slow down from the breakneck pace of life “before.” I made the very conscious decision to pull back from things that were not interesting, meaningful and joyful.

For example, I started playing with a local jazz ensemble which has been mega-fun and the other members of the group are enjoyable and fun to be around. Then I started to play with a local community band, which I found to be laborious and not particularly welcoming.  After two rehearsals, I stepped away, unwilling to devote hours of practice that were not fun, enjoyable or meaningful to me. Hard stop!

Staying strong and involved

I try and maintain a rigorous schedule of physical training and other self-care modalities targeted to staying healthy. I admit that sometimes it feels pretty self-indulgent, but that’s part of realigning thoughts and actions. After a lifetime of “squeezing in” a workout or the occasional massage, I am committed to doing what is necessary and important to stay healthy, mobile, flexible and strong.

Additional Reading: Life After Career: What Successful Men Need to Know 

The biggest hole, as it were, is in social involvement with others. As a committed introvert, getting out there is a challenge, but getting involved in two musical groups has been a bit of a lubricant for meeting new people. I need to do better in reaching out to others and continue to build and strengthen relationships. The challenge exists in battle between my ears.

Okay, this is the part where I attempt to offer some advice.

1. Take stock

Unless you’ve already gone through the process of transitioning from work life to your Chapter X, I suggest you start with taking stock. How are you feeling about leaving your career in the rearview mirror? Are you excited, joyful and revved up, or are you worried, nervous, anxious or less than enthused? If it’s more the latter, consider what or who you need to work with to help you parse out all the pieces. After all, life in Chapter X is a blank canvas of time to be invested in activities that bring satisfaction. If you’re stuck, find a life coach who can help lead you through an inquiry process meant to develop a path.

2. Check your financial, physical and emotional health

Devote yourself to making sure these areas are properly covered. If you have the “I don’t ask for directions” mindset, perhaps it’s less than useful right now. You want to think less about independence and more about interdependence. Who do you need/want to help you on your journey?

3. Listen to your inner voice

If you’re hearing a lot of “shoulds,” it’s probably time for you reconsider how helpful, meaningful and true those feelings are. “Shoulds” grow from the soil of guilt or shame and, trust me, it’s infertile ground. Replace each “should” with “I want” or “I care about …” Finding what you really care about and what lights you up is a journey of varying lengths and complexity, depending on the person — and it’s different for everyone.

4. Rediscover curiosity and the joy of new learning

 This one’s a big one, because whatever direction you take that is not your prior work, you begin as a novice.

Going back to my reclaiming of music, I never learned music theory. After all, I played a brass instrument and I played the notes on the page. In my new adventure, I am starting to learn theory, which is necessary if you’re going to learn how to improvise. I have to admit, it’s daunting and requires a lot of memorization. But my goal is to be able to play joyfully and learn the language of jazz and how musicians communicate through their improvisational skills.

My mindset needed to change and while I feel the tug of dread at my lack of knowledge and ability, I am embracing the challenge and remembering to smile after each attempt, even if it sucked.

5. Being a novice can be fun

Going from mastery to novice is a hurdle that stops some people dead in their tracks.  After all, you’ve spent decades growing and honing your skills to gain mastery. Now those skills or achievements are of lesser importance; instead, look for the magic in learning something new and failing miserably. I guarantee, it isn’t the first time in your life and you’ve survived thus far.

6. Be real

Developing self-awareness of your own flaws, foibles and faults is important so that you can focus on being at peace with who you are, what you value and what’s real for you. If you’ve spent your life being powerful and in charge, rest assured it’s fleeting and in this stage of life, it’s just not so important.

Aging is not for the faint of heart; it’s a seismic shift in every way. But let’s not waste the time granted us by wallowing in self-pity, self-loathing or fear. Living life to its fullest (however you define ‘fullest’) is the order of the day. You can go home again, even if it’s a different home.

Michael Kay, author of “The Business of Life” and “The Feel Rich Project” joined the financial services industry in 1985, after nearly 10 years as a CPA. He founded Financial Life Focus LLC in Livingston, N.J., in 2001 and recently transferred ownership to his partner. Michael has been married to his college sweetheart for 44 years. His Chapter X project is available at along with his podcasts (Apple, Spotify or wherever you listen). Reach him at, on Twitter (@michaelfkay) and on LinkedIn.


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