That 80s TV show, Who’s the Boss was must-see-TV every Tuesday night in my house.  We laughed watching Angela and Tony, her “housekeeper” spar about who was the boss and who was the housekeeper.  Who actually wore the pants?  Well, here’s what I just realized is the scariest thing about retirement:  Unlike the moving tapestry in that TV show…now YOU ARE THE BOSS…

From birth until now…you always had a boss.  First, all kids are supposed to at least pay a modicum of attention to what our parents said. (Admittedly, once you are a parent, it often doesn’t seem that way….)   From toddler-hood to college or grad school, our teachers joined the rule setting team. Once you joined the working world, you traded teachers for real bosses and we all spend our entire working life morphing into a new person every x years as bosses changed.  Sometimes we were better employees than others and sometimes we had better bosses than others.  But the power all along the route did not lie with most of us.



So many people I’ve talked with were happy in their careers until external forces toppled them.  I know that many of them would be extremely jealous of Pat, who sits in a position where—at the moment—there don’t appear to be storm clouds brewing and she continues to be as engaged and successful as ever in the job she has done for many years.

At an age when many of her peers are considering retirement, Pat remains one of the leading investment professionals in her area of expertise….in fact, she’s a household name in the field.  She’s been involved in the markets since her niche was in its infancy and after her decades-long career, she’s still going strong.  She manages a 10-person investment team, responsible for managing somewhere near $10 BN.  You’d think that it would be time to give up those days that begin before dawn and end way after dark. But…you’d be wrong.  She is as motivated and involved as ever—with the passion and skill that have propelled her throughout her respected career.

This isn’t to say that she hasn’t thought about packing it in.  Being the ever-thoughtful person that she is, she’s gone through all the pros and cons.  Her conclusion– there’s almost nothing on the retirement side of the scale.  With that mind set, she knows that she is incredibly lucky to be in a position where the external threats to her career seem almost non-existent.

It was interesting to talk through her thought process on this decision, because her thinking echoes that of many people who don’t want to retire—even though they’re in that retirement age zone.  A key force keeping her away from the door marked “retirement” is the terrifying question “What’s next?” she admits.  “Who am I if lose my power base?  How do I define myself without my career?  If I walk out, I’ll have nothing to trade.”  Going down that road, she fears a future where she would walk into a room and have little to contribute or talk about…versus now, when everyone wants to know what she’s thinking.  Adding to all of that is the fact that she continues to be incredibly good at what she does, really enjoys it and continues to be stimulated by and respect the team that she’s hired.   Again, what’s not to like?



Let’s start with the premise that there’s no shame in being a “normal person.”  Right?  If that’s true, then the corollary is that a normal person doing normal person things should be behaving normally and accepting the new normality.  Right?  Well…in my case NOT RIGHT.

So, let’s start out by listing just a few of the normal person things I did during my first week of retirement: 

  • Got up at every day at 7 am
  • Went to the Gym at 7:30
  • Had post workout latte and egg white sandwich on Tuesday at Starbucks at 8:45.   I mean I just HAD to do that because guess who was scheduled to come the first day of retirement???  My cleaning person who comes once a week. The chances of her coming on Day 1 ain’t that high—well 1 in five, but let’s not be so literal.    And I’m not sure that I could have faced being home during cleaning for the first time in how many years.  (Well that motivation isn’t normal, let’s be honest….but the action of going to Starbucks IS normal behavior)
  • Walked uptown when all the worker bees were walking downtown
  • Enjoyed a Ladies who lunch lunch….and the ladies didn’t come to Rock Center to meet me.   I went uptown to meet them.
  • Got my hair cut at 2 PM
  • Didn’t put on makeup every day
  • Did NOT wear a dress or skirt…not even once!!
  • Talked to my kids during the day, without saying:  “Gotta go”
  • Noticed the paucity of emails.  (I mean, just now the only people who have emailed in the last half hour are Huffington Post and Amazon. So, there is no need to check email slavishly, which is just shocking and demands a discussion

Yup….Let’s digress for a minute to talk about EMAIL.  One thing I prided myself on while working was responsiveness.   If a client or prospect or whoever got in touch with me, I was ON IT.  I was the poster child for being on top of things; Score an A for me!! To earn that A, I NEEDED to be checking my EMAIL all the time, because it MATTERED.  Well, you know what…Now it doesn’t MATTER at all.  And there’s not so many emails anyway.  And this is a major major change.  I mean…almost as big as realizing that my office email doesn’t exist for ME.  Just part of life, but the difference in behavior and focus is just staggering.



Andrew found a very lucrative and part-time “turnaround” career after he retired from his corporate division President job at age 55—at what was the height of his career.  This definitively was NOT his chosen time to leave the corporate world.  In a horrific scenario, he had to leave when he was told he suffered from a fatal disease with a year to live.  (Spoiler alert—Since I am writing this story 20 years later, you now know that this was a shocking misdiagnosis.  He is alive and well and smiling at me!!!).   Anyway, back then….by the time it was determined that this was a malpractice-worthy medical mistake…he’d left his job, couldn’t get it back because they’d offered the plum position to someone else and the only jobs at the company weren’t nearly as desirable.  Clearly, the amazing news was that he was going to live a long and productive life—the difficult task was finding a new productive life.  

Become a consultant again was his first stab at getting back in the game after a 9-month hiatus.  After all, he thought, he’d been a consultant in the radio industry before…but, “the phone never rang”, he said wistfully.  Instead, he shifted gears and started calling brokers in the industry to help him identify radio stations in need of a turnaround.  The first station he uncovered needed a General Manager, so Andrew stepped in with the goal of turning around rock- bottom ratings and an almost unheard of loss around in order to sell the station.   With a one-year contract, he moved to New England, while his wife stayed working in New York—and for that year, a commuter marriage ensued.

While the story of how he did manage to achieve those goals and bring the station up to a #6 market rating is somewhat beyond the scope of this blog, it’s such a great story that I just can’t keep it to myself.  So…here’s a quick synopsis.   Is there anyone who doesn’t know about Don Imus…and his “choice words and commentary” about anyone and anything?    Well…as Andrew was taking over the station, Imus was looking to expand his reach beyond New York City, so Andrew convinced him to use his station as that stepping stone.  Just after the deal was struck, Imus had surgery, so the station could play only outdated reruns…not the deal Andrew had signed on for.  Smart businessman that he is, Andrew refused to pay Imus until he went live.  When Imus did go on air, he BLASTED Andrew by name for delaying the payment.  If you know Imus, you wouldn’t be surprised at the insulting, demeaning and histrionic vitriol that came out of his mouth.   While Andrew was hurt, distraught and clearly emotionally bruised, the ratings did start to climb!  And after a year, with those incredibly improved ratings, management sold the station and almost everyone walked away happy.   Andrew’s ego and self image still smarted, … until…he heard Imus unleash a similar attack  (albeit for a different reason) against the next station manager he worked with!  When Andrew finally confronted Imus after the whole affair, Imus gave him a brotherly pat on the back, grinned without a hint of contrition or apology and explained: ”You know— it’s all only an act…don’t you???”



When you graduated from high school?  College? The day before you had kids? 

The point is that these are all huge transitions: endings and then beginnings.  In the world of Hakuna Matata, that’s the circle of life.  Getting back to my narrative….Today was MY LAST DAY OF WORK.  It is actually RETIREMENT DAY.  That is rather significant, don’t you think?  So, I look back to other transitions and how I felt then….and NOW.

Speaking generically and I imagine for everyone (since we’ve all gone through at least one of the above), there’s always a sadness at an ending, just because it is an ending.  And endings mean that whatever it is you were doing the day before is now history and you’re not quite sure what you’ll be doing the next day.  If we are all brutally honest, we also say…hmmmm….I wish I had done this or that better or differently.  Like, I should have gone to one less party and studied a little more.  Or, I should have gone to one more party and studied a little less. You get my drift.  The idealized vision of what we thought would happen isn’t always the reality of the actual experience, right?

So here’s the thing.  Looking through the rear view mirror, I really don’t have any regrets about my career, honestly.  I say this without bragging and with 20-20 backwards vision.  Things have just always worked out for me in my career and without my having necessarily had any plan of action or strategy.  It just happened and it always seemed to work out just right. 

I mean how many people have had this experience:  You’re working for a firm that blows apart and you’re on the wrong side of the split and so you lose your job.  But then you find a job instantly and start your great new job on the EXACT day your SIX MONTH severance starts!  (I admit it…that was me.)  And not only that, the old job ended after I’d been there 5 years and 3 days, when the first pension vesting date was 5 years.  Things like that just happened to me.  Whether it was financial services or my real first love–City government during the Lindsay years in New York City when public service was where all the smart people went–I have had amazing jobs, worked with exceptional people and moved ahead albeit with normal bumps in the road that pop up in everyone’s career.  

So, I really don’t look back and say that I wish I had done this or that differently.  I achieved what I wanted to achieve AND was able to spend time with my wonderful family along the way and met a whole lot of great people in the process. AWESOME and continually struck by lucky lightning bolts.  Maybe that’s why this transition is actually a bit easier for me now than it was getting out of high school or college…because I did have regrets back then.  But not now!



If you heard a business person use these words, what would you think?    “Passion about what I do, setting and achieving goals, seeking new challenges, mentoring and coaching, creating new structures, putting pressure on myself to achieve more.”  Right, you’d think that’s just how people with careers they love talk about their work.  Well in Grace’s case, these are the words she uses to describe her RETIREMENT CAREER!

By way of career background, she never set out to be a banker, but fell into it and then thrived.  She moved up the ladder of a local bank and survived a number of mergers until one last acquisition by a foreign bank.  Not uncharacteristically, they assigned coveted jobs to their own staff, while quashing the jobs of highly paid career employees in the acquired company.  Undaunted by she leveraged her non-profit banking experience and contacts to take on a senior development job at the State Community Foundation.   Several years into this, she spent an agonizing 6 months analyzing whether to retire.  Bottom line, there were parts of the job that just weren’t satisfying and she decided to move on to Retirement.

One of the very early…and still lingering biggest difficulties Grace faced as she moved out of the working world was accepting the word “retirement”.  In her world view, THAT word applied to someone else—not her!  When your identity has been tied up in your career, who are you when the words “here’s what I do” no longer define you?  Definitely, she was not about to lose her identity to the lack of a title or job description.  



If you happen to be in the underground Rockefeller Center walkways any weekday between 12 and 2, you’ll see a long line of people snaking down the corridor waiting patiently to snag their healthy, fresh and tasty lunch from JUST SALAD.  Furthermore, you’ll see about half the people with their pre-purchased bright orange, green or white heavy plastic bowls which both help the environment (because you don’t use a new one every time) and make your salad tastier and bigger (because you get not one, but TWO free ingredients in your salad.)

While working, I go to JUST SALAD about three times a week and truly look forward to my “Thai Chicken Crunch with no wontons  and apples instead of wontons, please and chop it into the orange bowl.”  As I am writing this, I know that JUST SALAD withdrawal symptoms are going to set in EIGHT DAYS FROM NOW when I join the ranks of the not-working class and can’t walk downstairs to get my delectable lunch.  

And that thought lead me to think about all the other similarly “not-life-altering-things” that will change on Retirement Day—


  •  I will never again answer the phone saying “Susan Leader” in that monotone professional voice.  I get to say..Hello..or Hi fill-in-the-blank

  •  I won’t have business cards to introduce myself and make people remember me.  Thank heavens we now have smart phones to exchange contact information without that piece of paper.

  •  Those key cards that get me into the building?  GONE.  If I come to visit friends, I’ll have to get registered with security and then suffer the indignity of waiting in that endless line downstairs in the building I once called home.

  • I won’t have to wear all those business suits any more…and guess what’s even better–someone else who needs them is more than welcome to them.   Hello Dress for Success–a truck load of 20 years of suits and blazers is coming your way!!  I wish the new recipient as much success in them as I had.

  • Anyone who emails me at my prior business address will assume that I have disappeared off the face of the earth…along with that email address which will cease to exist.

  • To add insult to injury, my W-2 information will be lost to me forever.  It stays here, while I go elsewhere.

  • My iphone will be considerably easier to operate when I get rid of that Compliance-mandated MobileIron security app with the 6 digit password and other complications.

  • If I haven’t collected all my flex spend dollars, they too will go up in smoke.  (Stop writing and submit those forms NOW)

  • I’ll have to give up my beloved Outlook and use not-so-user friendly GMAIL instead.   Seriously, Google, can’t you figure out how to create archives????

  • I WILL have time to clean out my closets and drawers…which frankly look like they haven’t been cleaned in five years.  (Oh wait… it’s actually more like 7 years)  Who had the time or inclination to do that?

  • I WILL save so much money in airplane and train tickets because I’ll be able to plan personal travel at the “cheap times”.  And then of course, I will eat up those savings in scheduling more flights and trains..so it will be a wash.

  • I WILL and have planned a lot of trips.  Admittedly, paying for them is another matter, but I will deal with that question later

  • Etc…etc…Etc….


The very very excellent news for me, personally, is that I am TOTALLY and FULLY OK with all of this.  You remember the denial period that I talked about, which was followed by the acceptance mode.  (With apologies to Elisabeth Kübler-Ross because this is clearly not death-like).  But her stages of grief do provide a good construct.  Anyway, with those 8 days to go, I am so ready to go over to the Dark side.  It’s sort of like the days before your first child goes away to college—by the time the day comes, you’ve been so busy obsessing about it that you’re just ready to give up the obsession and the fact of your child leaving home is sort of secondary.  



If Column A was to continue your stressful, travel-filled, more-than-full-time job and Column B was a 2-3 day a week law practice at a firm where your name was still on the door and you could earn enough money to pay both your AMEX bill and for some expensive hobbies…I’ll bet many of you would pick Column B.

And that’s exactly what Andrew did. He had built a very successful practice specializing in insurance law. Starting with nothing but his law degree, he put up his shingle before he was 30 and 25 years later, the business had mushroomed. He had brought in two partners, 30 lawyers and the firm was a magnet for insurance-related business, both domestically and in London. And it was Andrew who had made that happen. Fortunately for him, he was building this business before this business niche became incredibly competitive, with fee cutting and fee-auditing processes the name of the game—a whole new profit-squeeze environment.

And then at age 58, he had health issues. After open heart surgery, Andrew said he didn’t have the desire, drive or energy to continue that singular devotion to growing the business any more. Facing his own mortality, he didn’t want to kill himself working—“It was great while I was healthy…but not when you have to face the fact that your days might be limited.” At the same time, he admitted, the business itself had changed dramatically and the profitability of all firms had suffered. “In a sense,” he admits, “if I was going to get sick, my illness happened at the right time.” What that meant, he continued was that “it was anything but a pleasant time for the industry, my firm…and for me.”


And Dr. Freud asks:  How does it feel? The six months before I retired……

Retirement Whatever That Is, Susan Leader, One Baby Boomer’s Guide to Retirement

Honestly, I’ve been acting really strangely over the past six months, I say to the bearded Doctor in the chair. “Tell me about your symptoms,” he asks with a kindly smile…And here’s what I would have answered…if I had been on that couch talking to him.

First of all, I’m usually an amazing sleeper. In fact, that’s probably my greatest skill set. And yet, I now wake up at 3 in the morning, stare at the ceiling for a while pondering everything and nothing…and then maybe go back to sleep, or maybe not. That’s just not me and even I know that it has to do with this looming TRANSITION. I mean…next to having your first child, which changes your life forever, this has to be one of life’s most jolting moments. Accept that, my dear, says the Good Doctor, and maybe you’ll go back to your old sleeping habits.

But if you add to that the extra glass of wine that I drink every day….even when dining alone…..is that a problem, I ask? And then I say…well maybe this is all due to Trump-alaise (short for Trump malaise). I mean…I’m in good company with this sleeping/drinking disorder, right? And then I realize that I had this before November 8th…so this is one thing I can’t blame on our new President. And the Doctor assures me that this too will pass…to which I respond, it had better!



There we sit, John and I, at the Regency Bar and Grill, bastion of the power lunch in NYC, looking like any other deal makers.  Except that we’re not.  We’re probably the only retired people in the room.  I suppose the other diners would have known that if they’d stayed long enough to see that we were the last to leave while they went back to their deal-making offices.  

The shattering irony of our discussion which focused on the “loss of power and identity and connections in retirement” in a room filled with networking business executives is pretty striking.  Seriously, can you imagine the head turning from those power brokers if they’d heard John say this:  The crux of retirement for me is “the loss of the sense of self which is only magnified by the fact that you’re not at the center of the action anymore—No one needs to stay in touch with me now.”  He goes on to talk about the “ego satisfaction of the job and the fact that “so many high powered guys have a sense of bravado” which needs to be fed.  “Everything I did was attached to my business success…everything my parents taught me.”  And when that ego satisfaction is gone, it’s a hard fall.  All of a sudden he admits “you realize that it wasn’t YOU that people sought after— it was your position.  When you’re in the JOB, you’re the person people seek out. But your Power stemmed from the business you worked for…and without that business, you’re just a regular guy, whose calls are maybe returned several days later…or never.  He jokes that when he was the CEO, he could call anyone…and “I never got put on hold, and now… I’m always put on hold!”  Now, there’s a proof statement if I ever heard one!!!