April 24, 2026
When I finally made the decision to retire from my career, I set about preparing for the experience. My goal was to create a successful second stage, to not waste the wonderful opportunity to in effect start a life all over again. Free at last from my responsibilities, what could I fashion?
I had spent 45 years working on Wall Street. For the first 20 years, a client-facing financial advisor at Morgan Stanley and its predecessor firms. And then for the final 25, senior partner in a portfolio management group there, managing billions of dollars for clients across the country and around the world. I had a wonderful career, loved my team, my firm, our clients and advisor-partners. Can’t emphasize enough how a career-glow enhances your frame of mind when you leave.
But the first 20 years were up close and personal. Over the years, I watched and assisted dozens/hundreds? of individuals, mostly corporate or professional, make the transition to retirement. My role was of course as their financial advisor, figuring out the money, but as you probably know, one inevitably becomes quite close and your role includes advising on a wide range of issues. And it seemed I was asked a lot.
In addition, I’ve spent most of my life in what I’d call a club-centric life. I moved around and, in the process, was a member of eight country clubs of which I lived in four. So even though I worked full time, my life was surrounded by those who had already taken the journey, clubs of course being chock full of the retired.
So, as I embarked on the journey to learn more about retirement, this time for myself, I had what I thought was a strong base of knowledge to at least get me started…life had given me opinions.
I found many things you would expect and were predictable. Stay active and all of that. But you know, the more I read and watched and listened and learned, the more I came to believe that a good portion of the advice given to people, while invariably well-meaning, was either misleading, or flat out wrong, or didn’t address some things I thought would be important.
In a way, I could say that everything you’ve come to believe about retirement is wrong but that would be a stretch. But I can say that a lot of what you are told or have come to believe is wrong.
Retirement is one of those subjects where everyone is an expert until they actually get there. And then they learn on the job. We spend decades picturing what it’ll look like, absorbing conventional wisdom from financial magazines, brothers-in-law, and that one coworker who retired at 58 and won’t be quiet about it. Then we arrive, look around, and realize half of what we were told was nonsense.
Let’s knock down a few of the big ones.
“You’ll need 80% of your pre-retirement income.”
Maybe. Maybe not. This is the financial planning industry’s favorite number, and like most favorite numbers, it’s a rough average dressed up as a rule. Some people need 60%. Some people need 110% because they finally have time to travel, golf, eat out, and discover their spouse has expensive hobbies they were too busy to notice. The honest answer is that you need whatever you need, and that number is personal. The 80% rule exists mostly because it makes for a clean slide in a seminar.
“You’ll be in a lower tax bracket.” This one gets a lot of people. Sure, your earned income drops. But between Social Security, RMDs from your IRA, pension payments, and whatever dividends and capital gains you’re throwing off, plenty of retirees find themselves in the same bracket they were in during their working years. I know I am. Sometimes higher, once one spouse passes and the survivor is filing single.
“I’ll just keep working if I have to.”
About half of retirees leave the workforce earlier than planned…health issues, layoffs, having to care for an aging parent or spouse. You don’t always get to choose your exit date. Working until 70 sounds great when you’re 55 and healthy. It sounds different when you’re 68 and your back has a different opinion. I retired at 75 and don’t feel I waited too long.
“I’ll be bored.”
This one is the flip side of the same coin. People who spent 40 years grinding away assume they’ll be restless. Most aren’t. They’re tired. They sleep in, read, putter, see grandkids, and genuinely enjoy not having a calendar full of meetings about meetings. Boredom tends to hit people who have no hobbies or interests outside work, which is a clue to start cultivating some before you hang it up. But then, they begin to find their way and sleeping in is replaced by getting up early…tee time at 9 or bridge game at 9 or breakfast with friends or charitable…
“Medicare covers everything.”
No. Medicare covers a lot of things, covers other things partially, and covers some things not at all. Long-term care? Basically nothing. Dental, vision, hearing? Minimal. Most retirees end up with supplemental insurance and still write plenty of checks. You will probably make a Medicare supplement, purchased from an insurance company, your first retirement purchase.
Retirement isn’t a finish line. It’s just a different chapter with its own rules, and the people who do it well are the ones who figured that out early. People ask me when I retired. I tell them I haven’t yet. Which is the truth!
I will tell you the single best thing you can do for yourself, your spouse and your family (who will have to put up with you and take care of you eventually), is to know yourself as well as you possibly can. And have a realistic view of what can today be the endless years unfolding after you leave your primary career.
I know if you love a sport, for example, and look forward to long days of playing, stretching out, you have a lot of company. But just remember that your body will rebel at some point, whether through arthritis, a bad back, a shoulder tear or any of a hundred geriatric failures that have to be addressed. So, just know that if you build any sport as central to retirement, you’re going to have to redo that at some point. Fill the inevitable gap that will open up.
So, do not, do not, do not, neglect the mental and social aspects of life. Eventually, it is my expectation that I won’t be able to do much more than watch a movie, go out to dinner, read a book. I’m not going hiking at Yellowstone, jump out of airplanes, run 10K’s. Thus, as your physical world inevitably narrows, make sure your mental world can pick up the slack. And, get to the physical stuff first while you can (one reason I’m so adamant that people need to travel NOW and not postpone).
We’ll do more on this subject in future pieces. Everyone has an interest in this, whether in the immediate future, or well down the road.
Thoughts, questions, or reflections? I’d love to hear them. You can reach me anytime at anthony@workingprofit.com
