How many people can say that they started a new late-life career at age 63—not many.  And yet, that’s Rachel’s story.  “Not only that,” she admits with a smile: “these years have been the most satisfying of my professional life”.  At a time when most people are playing bridge, golf and going to lectures, she is productive, making a difference in people’s lives and is incredibly fulfilled—with control over her time as well.  It’s just a very compelling story, I think.

Rachel has a broad based background in education and social work.  At the same time, she wasn’t afraid to try new things, broadening out to educational policy research and college admissions.  She was very happy in all those endeavors and would have continued…and then her husband decided that they were moving out of state.  Not only did she have to pack boxes…she had to pack up her career and start again at age 60!  Having spent a year in her new home in Florida doing nothing productive and feeling “totally out of it with no purpose”, she knew that action was required!



I just love this quote from Harry:  “People who are happy don’t look backwards.  If you walk backwards, you’ll trip.”  That’s how he concluded our conversation about his career and quasi-retirement.  He’s lived this mantra and honestly, if more people followed this, maybe they’d be as content and comfortable in his skin as he is!

For his whole life, Harry has looked forward, seized opportunities, made the best out of them and has never bemoaned the wiggles and waggles along the way.  By his own admission, he’s really never found the need to strategize and plan and rather just moved forward.  Raised into a “classic blue collar family”, the only lawyer he ever knew was Perry Mason.  (sorry to you non-Baby Boomers who don’t know who that is.  Hint:  He was on TV.)  Any way, he ended up in Law School where he did well, went to work for the firm where he had a summer job and stayed there for his whole law-firm career.

In one of those all-too-familiar stories, this mid-sized firm, where he’d worked up to managing partner, started to pull apart at the seams by the last 90s.  No one’s fault…It was just the competitive environment which squeezed out the not-so-big firms.  After that, he took a General Counsel position at a mid-sized retailing company and then became “of counsel” at a law firm started by some of his ex-colleagues.  He was brought in “as the grey haired one”—an advisor with some clients who ask for his assistance.  But importantly, for him, he’s out of the legal rat race chasing hours.



When you listen to Robert talk about his career, you hear a whole lot of stories—as he moved successfully from one endeavor to another when he “got bored” or something different came along that interested him. Diversity, change and a commitment to community service are the hallmarks of his career. So, it was no surprise to me when he talked about his seemingly seamless shift from his working career to his “retirement career”. He just figured out something else he wanted to do and never looked back. And to that I’d say…there’s a whole lot of people who would just love to have that skill.

I suppose that at the bottom of his wanderlust was the fact that he was a trained lawyer…but didn’t particularly find the practice of law…well…for him…that stimulating. After several years working in his father’s law firm, he got restless and took up a friend’s offer to set up motorcycle dealerships across the country–which is about as far from the law as you can get, I’d say. And then after returning to the law again when he’d sold enough dealerships, he hitched his star to an insurance business. And that expanded to his own firm which provided all manner of financial services—pension management, insurance writing, actuarial services and estate planning. You’d think that responsibility, in addition to numerous civic and board obligations, would keep him in one place. And you’d be wrong.



I had lunch with one of the most successful women I know. In male-dominated financial circles, she is truly a household name and she’s earned every one of those achievements through hard work and talent. Adjectives people would use to describe her—brilliant, no nonsense, not afraid to take on challenges, incredibly thoughtful and understandably self confident. She retired a couple of years ago and her comments on the challenges she faces are definitely worth sharing.

From my perspective, Laura is one of those people who I might have expected to work long into her 70s. And I do believe that she could have stayed in the business as long as she wanted…but chose not to. And in this context, she concluded that one of the reasons she’s happy that she retired is that “the older I get, the more I realize that there are no guarantees. Frankly, the idea of putting off and putting off and putting off things you want to do just gets scarier and scarier. You just have to do things when YOU CAN! ” Like many of us…of a certain age…she’s watched too many people see their life plans derailed by illness.

From there to the challenges: First… and this is often the elephant in the room: Retirement Marriage. Married for 47 years, Laura cites the proverbial motto: “You’re married for better or for worse…but NOT for lunch.” The issue, she explains, is that in retirement your lives must re-synch in a way that works for both people. And if you have different retirement life patterns, that’s a real challenge. Laura is ultra-Type A and her husband is the opposite. When they were working, this difference didn’t necessarily cause either one much stress. But now, as she says: “He can be downstairs in front of the TV and on the internet, reading for 7 hours without a peep. Meanwhile, I am pacing like a caged animal!!! If I don’t get into the City for meetings, or lunch, or have some prep to do for a Board meeting, I would go out of my mind.”

Another difference that’s difficult to bridge is retirement attitudes. Laura’s mantra is that “I want to contribute, while I still have my marbles, my skills and my expertise. My view is that in retirement, you need to use your skill set to make a difference in someone else’s life. I can use my financial expertise and contacts. Teachers can teach and coaches can still coach.” Others are more self contained, like her husband, who clearly enjoys the intellectual pursuits of retirement. That difference can be frustrating.

Clearly, they both have identified their differences and are working through them. On the really positive side of that equation, is their shared love of travel, gourmet food, cooking and some very favorite and shared pastimes. And they do indeed travel together, and love it. In fact, as we spoke, she had just come back from 2 weeks in Hawaii!!

Laura and I are business friends and that actually is another challenge she faces. Having spent 200% percent of her working life WORKING, she didn’t have time to develop what we all call “girl friends.” If you had watched her rise in a very male-dominated world and seen the commitment it took to get there, you’d certainly understand this. With time on her hands now, she muses that she just doesn’t have that support network of friends to fall back on and she’s loathe to impose on other people’s time. One of the prices of that huge work success is the lack of a cushion afterwards. And then again, we agreed to go to the ballet together…and I feel that we’ll be doing more of that!

I’d say that a challenge that she doesn’t face is lack of things to do or a lack of some structure in her life. She is a sought-after professional in her industry and fortunately for her, she’s someone who has a tremendous amount to contribute. No grass is growing under her feet, that’s for sure! At the same time, she knows she’s entering a new chapter and that’s still a work in progress.


During our lunch, the three businesswomen of “retirement age” talked honestly and openly about a range of topics that we’re thinking about.  You know how those conversations just morph from one subject to another.  Here’s a sampling of our thoughts and conclusions:

Our Goal for Retirement:  We’re all pretty Type A people, so of course, we need to have goals…whether it’s in our jobs or retirement.  Helen synthesized our thinking in such a beautiful way:  “You spend 2/3 of your life working and you know all the components of that and what made it fulfilling.  And now you’ve got this whole white space ahead.  What do I want that picture to look like?  It will have little snips of what I had in the first 2/3, but I want to rebalance it in a way that’s MORE satisfying going forward. I don’t want it to be as good as the first 2/3”, she exclaims.  “I WANT MORE!”.  And that’s the most beautiful description of retirement that I’ve ever heard!!!

On the New vs the Old Retirement:  When our parents’ generation retired, they were following a normal path—getting that gold watch and moving on.  Today, it’s so different and we are all looking FORWARD to a whole new life of new beginnings.  For the lucky ones, we still have a lot of energy left, clearly don’t feel or look our ages (or so we think) and we want to have the time and health to enjoy ourselves during this next chapter.  We’re not wading into retirement.  But rather we will spend the time to figure out what will make us happy in this time where we can hopefully enjoy the fruits of all the hard work we’ve done during our career.  We don’t want to look backwards.  We’re looking forward!!



Stories without conclusions are…just stories.  I guess that’s why everyone I speak to about this blog keeps asking me…what are you learning?  What are people saying?  So, I figure that everyone, including me, is craving some conclusions and insights.   So…here’s some things I’ve learned from talking to people over the past 5 months…  

First of all, let’s start with THAT word:  RETIRED.  It is hardly a word with… let us say…positive connotations.  It’s a word that doesn’t role smoothly off your tongue and honestly gets sort of stuck in your throat. I mean seriously, look at the definitions of retire or retirement: “Ceasing to work”…“Withdrawal from active working life”…”to Withdraw , Go Away or Recede”.  To me, that terminology smacks of being put out to pasture with nothing to look forward to but munching on old and tired grass.  In much the same way, when people “Congratulate” you on your retirement, some give you “that look”…like the one you give to someone who has just stepped on a skunk.   I can only describe it as a look of “pity” rather than joy.  

Clearly, not everyone is on the same page with this new second chapter.  If you’re me, you look at Retirement as an exciting beginning, a transition, a metamorphosis, a new challenge, a move forward to different kinds of work.  Those are the words I’d use.  Honestly, I believe wholeheartedly that we need to come up with new Retirement terminology that’s FORWARD LOOKING, ACTIVE and POSITIVE, while trashing Retirement concepts which are passive, backward looking and seriously DEPRESSING.

Now that I’ve gotten that off my chest, here are some takeaways from my conversations about Retirement with people who have retired…partially or fully:

  • There are a whole lot of people out there who did NOT CHOOSE to retire and arguably wouldn’t have if events hadn’t gotten in their way.  Corporate actions, takeovers, new bosses and health are key culprits in derailing careers.  Unfortunately, when that happens, it’s harder to stay in the game the older you get.  In fact, many senior level people who lost jobs when they were nearing 60 just couldn’t find their way back in, and not for lack of trying.

  • There are also many people out there who would love to retire, but financially can’t do so.  A couple of people told me that they couldn’t read my blog because it was too depressing for them.  They wanted to retire or slow down, but they weren’t in a position to do so.  Clearly, I haven’t touched on this issue at all.    But it’s very real.
  • Key words that I have heard in my conversations among people who have slowed down are:  Structure and Identity:  In almost every conversation, people talked about their desire to maintain their identity in the new life life chapter they are inhabiting.    Some people who have fully retired are struggling with living without that work identity and those who’ve quasi-retired cherish having maintained it.
  • Uniformly, people talked about their perceived need to put some structure into their lives.  The conversation about doing laundry on Mondays providing some structure comes to mind here.  Coming from a life of schedules and structure to 12 hour days of “To Be Determined” isn’t something that necessarily comes easily.  It takes work to figure out how much structure you want and then to “implement” that plan.

  • It’s an open question whether the Retirement story is different for men and women.   Some women talked about the fact that their identities were not fully tied up in their career, which they felt gave them some wiggle room in moving on.  And some men do feel that their identify is defined by their careers.  But I’m not really sure if this is just the stereotype. …or actually truth.

  • Everyone I’ve spoken to admits that  if you think you’re going to morph successfully from those 8-12 hour work days to an equally satisfying and productive next chapter, think again.  It’s a challenge to define  “what makes you happy” after you’ve given up full-time paid work.  Whether you’re fully or partially retired, one of the first tasks to be addressed is: “How to be the best boss to yourself”.   This may take 6 months, it may take a year or even more.  It’s a process and overnight success and answers aren’t the norm.

  • There are chapters in retirement.  It’s a continual process of figuring out how to “carpe diem” all along the way.  It’s sort of like a moving walkway.   In many ways, that’s a plus.   You have the freedom and the luxury to keep making adjustments as you walk along the path.

Clearly, everyone’s story and everyone’s experiences are uniquely their own.  At the same time, I do think that there are things we can all learn from each other about this evolving chapter in our lives.  And I do hope that the stories told here can be instructive.  


Nothing highlights the Retirement continuum better than a conversation among businesswomen at different stages of that path.  First there’s me—with a couple of months of retirement behind me, then there’s Cathy, who retired from a successful financial services career a year and a half ago, and then there’s Helen, who is still working at the firm that bears her name.

As we all asked each other questions and shared our stories and feelings (as women will do), the differences in our current experience were incredibly stark.   (While not wanting to get off topic here, I just have to comment that I can’t imagine men sitting down to have this same kind of sharing and caring and listening conversation…but that’s not today’s subject.)

I somehow wish I could write this as a screenplay, rather than a documentary… because that would capture the immediacy of the conversation.  But I’m not sure how to do that, so I’ll try to do my best.

Helen is still working very much full time…and while she’s working, she’s looking FORWARD and wondering what Retirement or non-Retirement might mean for her.  From her current vantage point, there’s absolutely tons and tons of uncertainty and questions.  But, she’s definitely in the driver’s seat and can control her own destiny.  She sold the successful services business that she had built over the past 20 years to a much larger firm in the industry a little over a year ago.  Her contract runs out at the end of this year and she’s considering her options.  At the beginning of our conversation, she commented that the differences in working for a larger and more bureaucratic structure vs her risk taking/entrepreneurial business and the loss of control and power that she’s experienced have caused her to wonder whether she wants to stick around.  And far later in her conversation, when Cathy asked whether the sale of her firm wasn’t actually her exit strategy anyway, she demurs a bit and it’s not clear whether she effectively orchestrated her exit or bumped into an exit strategy. Guess what—treading on the shores of retirement is very definitely a slippery slope and each time you look at it, everything looks different.



I know I wrote before about the retreating and passive connotations of the word Retirement.  But I just have to revisit that conversation in light of two events that happened to me.

While I know that this comment was well-intentioned, I bristled when someone looked at me the other day with a bit of pity in his eyes commenting “I can still remember the day my father retired.”  From his tone, it sounded like he was talking about the day his father died…or at a minimum, that day was the end of his road and clearly not a new and exciting beginning.   That’s clearly not today’s mantra—far from it.    I mean, how many people today want that “gold retirement watch”…and more importantly, how many people received one?  Just as many Baby Boomers forged a new reality in our careers and work life, many are doing the same thing with retirement.   We don’t look like our parents did when they were our age and we aren’t approaching our futures in the same way that they did either.   Honestly, we aren’t our parent’s generation and we’re not sinking into “retirement oblivion” when we leave the work force!!!

And here’s the second thing that happened:  To “congratulate” me (and you’ll see why I put that word in quotes in a minute) someone sent me a massive coffee table book sized journal book titled Retirement.  In it were hundreds of pages in which you could HAND WRITE memories of your childhood, teenage years, college experiences, favorite events of your life etc etc etc.  First of all, how many people who are retiring today still hand write….rather than type into a computer.  But more importantly, is there really a Baby Boomer retiring in 2017 and beyond who wants to spend the next X years looking BACKWARDS????   No one I know…that’s for sure!



It’s that “loss of control” thing that often trips people up.  Janet’s professional development career was solid, gratifying and very productive.  She had gotten into a development and planned-giving career after her children were grown and motherhood demands were on the decline.  She found that she was very happy and productive in this career and all went along smoothly until….her husband had a serious health scare and her mother became terminally ill.  So, because of the needs of OTHERS, she decided to curtail her working life from a full time career to a 3 day a week commitment.  She doesn’t tell this story with any rancor or expressed disappointment, but I surmise that this can’t have been that easy.

And the story didn’t end there.  After her husband’s health scare, he quasi-retired and wanted to spend more time outside of NYC in both the summer and the winter.   And then, guess what he did?   He bought a winter home in Florida—and didn’t quite inform her until after the papers were signed!  To be fair, his offer was embarrassingly low and he never thought it would be accepted.  But it was.  And then, when his plans of a living room pool table surfaced, she decided that she could no longer avoid the inevitable.  She took the Retirement Plunge.



The Freshman class of Boomer-working women in the Gloria Steinem era basked in the glow of the potential of Having IT All.  Yes…we strove to achieve that mythical HAVE IT ALL status…but the critical element missing from most discussions was and still is what your definition of IT is.  (Sorry for quasi-plagiarizing Bill Clinton.)  OK…you’re  wondering where I’m going with this one?  And I admit that this blog isn’t about how I’m feeling or what I’m doing.  Instead, it’s a reaction to the the difference in the comments about my retirement from the women I worked with…vs those from the men.  

Here’s two comments that speak volumes.  After hearing about some of my retirement bucket list plans, one person said: “Susan….You’re Killin’ me”……And the other said  “You gotta keep on climbing”.   I really appreciated both and both were from good friends, who I believe really care about me.  See the difference?  And the very divergent implications?

You see…so many of the very successful financial women in my office expressed that they were “envious” or “jealous” or more humorously, “you’re killin me.”  Not that any of them wanted to retire now, because I was admittedly the Old Lady in the house…. but the thought of getting off the treadmill and slowing down and experiencing something other than 10 plus hour work days definitely had some appeal. In contrast, there wasn’t a single man who was even a teeny bit jealous of my plans …not in the least.  (Or if they were, none said it)

And  Carrie Bradshaw would say—“I started to wonder” why did the men look at this decision one way…and why the women the other????