By Caroline Hall
Up until the day I graduated from college, my life path was pretty linear. Kindergarten, first grade, second grade, third grade….and so on, right through college. And yes, I had to choose where to go to college, but my mom had strong opinions about this and not going to college really wasn’t an option.
(A little aside: The day I graduated from Williams College, I had a flat tire on the way to Cape Cod, where I would sing and dance the summer away in a dinner theater in Chatham, Mass. My friend William Finn—later of “Falsettos” fame on Broadway–was asleep in the backseat of my car and wasn’t mechanically minded anyway. A tough-love semi driver stopped and walked me through changing the tire all by myself, including jumping on the wrench handle in order to budge the lug nuts. I can still dazzle people with that skill, a worthy addendum to my expensive education.)
Back to the point not yet made: life until age 21 was a straight path. In June 1973, I suddenly saw an array of options radiating around me like the rays of the sun. So many possibilities! So little experience in making the “right” choice. So clueless around most of the criteria for making good choices. And totally unaware of the turning points that would signal it was time for a change. It was like being swept into boiling eddies in a skinny canoe with no paddle. Structure, please!
Lost at Sea?
So, I got married and had a baby in short order. There’s structure for you. Locking into a career took longer, but that happened, too. And then another career. And again my path became linear, with clear choices and strong guardrails. And I’m still locked in, at 65, because the thought of the vast array of choices available upon retirement feels like another careening canoe trip down life’s rapids. Fortunately, though, I have a paddle this time. After playing the warmer-warmer-colder- colder game for decades now, I can sniff out what has heart and meaning pretty easily. Even so, the prospective lack of structure, while alluring, is also daunting.
I can imagine loving unstructured time for about the length of a two-week beach idyll. After that, what will give shape to my days? How will I distinguish weekdays from weekends? Where will I contribute my skills and expertise—and do I really want to? If I don’t have to do anything, will I become a monster of selfishness and sloth? Will I devolve to a kindly wizened granny? Will I become self-absorbed and demented? What on earth will my husband and I have to talk about? …Into a vacuum of information, horribilizing rushes to fill the void.
One of the reasons I got interested in helping people think through their 
next chapter is that we Baby Boomers do have the tools and resources to make good next choices, but it takes time and thought to marshal these resources and plan next steps. Another reason is that many of us have a comfort zone called structure, and it’s too easy to jump into something willy-nilly because “I don’t know” is such an uncomfortable place to hang out. Yet “I don’t know” is the foundation of a clean-sheet approach to planning a retirement that yields joy, contribution, meaning, stimulation, and love in equal measure. These are conversations I want to hear and to have.
Caroline Hall is Co-Founder of Life Reinspired, a reset lab for successful Baby Boomers contemplating a meaningful next chapter of life. Find out more about our programs and upcoming retreats.
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