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.

She admits that realistically she never could have seen herself retired because so much of her identity was tied up in her work, but that the last year has colored the lenses a bit.  Her next step isn’t exactly clear, and this became very clear during our conversation.  In one breath, she talked about her first grandchild, the sacrifices she’d made during her life for her career and the chance now to do all the things she never got to do when her kids were young—meaning she could stop working and revolve life around family and kids.  And then later in the conversation, she talked about the fact that “my skills are very transferrable and so I could do many things,” adding that she would do something within a year while her contacts and power base are still fresh.   And in the next breath, we talked about the virtues or non-virtues of working part time or consulting to the parent company.  “I’m not too worried about my next gig”, she summarized.  “I just have to see how much I miss working before moving ahead on anything.”  Clearly, Helen is very much in the “I’m going to figure it out” phase of thinking about her next chapter and understands that “I will have to work on a new identity.”  After all, she’s had her name on the door for 20 years.  In short…we’ll have to revisit this conversation in a year to see where Helen ends up.  She’s looking at a wonderful empty space with anticipation and excitement and clearly, she’ll figure it out.

Carol, 18 months ahead of Holly, retired over a year ago.  She talks about the wonderful year she’s spent.  Her daughter had her second child and really needed Carol’s help, which she was more than happy to provide.  “It’s totally selfish,” she comments “if your kids need your help, it’s totally selfish to focus on your own self gratification versus theirs.”  And the three of us working mothers admit again that grandkids do provide us with a bit of a do over—we weren’t there every time our children needed us when they were growing up…so we can make up for lost time now.

In addition to that, Carol talks about reveling in the lack of structure and abundance of free time over the past year and hasn’t felt the lack of her old “work identity.”  After all, she muses, she didn’t have her own company or name on the door.  Having been in a high-travel job for the past 10 years, she’s was just ecstatic not to wake up in the morning to go to an airport.  “I just savored the stupid things…like sleeping until 7:30” and then reading the paper and being in control of her own schedule.  “I’m a bit of a slug”, she admits and “you wouldn’t believe how little I could do in a day” and really enjoy it.   She’s exaggerating a little on that one, because she has been mentoring kids, sitting on a couple of non-profit boards, perfecting her golf game and doing a lot of fun traveling.

What’s most noteworthy isn’t what she’s done for the past year…but her view looking forward.  She is about to move into what really we all agreed is the second chapter of her retirement.  For the first time, she says, “I’m seeing a void and I am looking for ways to fill it!”  The blocks of time which used to be “fun” now are looking empty and she needs something “more.”  Guilt at having free time isn’t the issue…it’s more the “wasting of time.”  The problem is that all the “little stuff” can expand into your whole day, and that after a year of this, she isn’t sure that this is a “full time diet.”  This retirement gig is a “Process”, she summarizes and it’s now time to move to the next phase.  Maybe it’s time to think about that part-time job, she says or something else that provides structure, meaning and a measure of productivity into her life.

And so all three of us are what I’d call a “retirement work in progress.”   And if we get together a year from now, we’ll surely have a very different conversation.  But, we all share the exact same goal—TO MAKE OUR RETIREMENT YEARS EVEN BETTER THAN OUR WORKING ONES.  As Helen said, “I want more!”

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