This circle of life has nothing to do with birth and death. On the contrary, it is all about life and longing. It is something that children do in common with older folks and that middle-agers avoid like the plague: wishing you were older.

Ask a toddler how old he is and he will, with great pride, tell you precisely. “I’m three and a half years old.” An older child will make sure you know she is on the cusp of the next age. “I’m almost 8”.

The summer of my 14th year I was hit with the desperate imperative to be older than I was. The cause was a realization that the staff college boys at the lodge we stayed at regularly were its best amenity. Because my birthday was in the fall, I felt I was “close enough” during the summer and 13 became 14, 14 became 15. All the time I was convinced that the ruse was working and I was as sophisticated as the college girls who were waitresses and chambermaids. I would flirt with the sous chef and never saw the irony in the clown face of blueberries he put on my pancake every morning.

Growing up, there was always one more thing you could do “when you are older” such as drive or vote. These were rites of passage that we cannot wait to achieve. Adulthood and middle age has nothing like that anticipatory excitement unless you count turning the Big 4-0 and that’s not usually met with the same excitement as, say, turning 21.

As much as we hate to have time fly, late middle age begins the cycle again. Suddenly we want to announce that extra half year of age: “I am 59 1/2 and can take withdrawals from my IRA without penalty.” This is no modest moment.

The next milestones are turning 62 when you could begin Social Security and 65 when we become Medicare eligible. The privileges of these programs take on great significance for the growing population of baby boomers who are being downsized. We are in a No Man’s Land of no health care and no income. Severance ends, unemployment benefits end, COBRA ends. Again we are faced with “when you are older.”

Those of us who are in our late 50s and early 60s face the prospect of being too young to retire and too old to be of immediate interest to employers. The circle begins to run in reverse; the 60-year-old becomes “in my late fifties.” Despite the exhortations of AARP for employers to embrace the wealth of experience that older workers represent, that is not the real world.

Younger means cheaper in many industries. The perception is that older workers are not tech savvy enough to meet the needs of sectors such as financial services. The polls still show that if an older worker does secure another job, it is often for much less than his or her prior compensation.

Reinvention and encore careers are the buzzwords du jour by necessity. The fact is that we are healthier and living longer overall and it doesn’t take a quant to figure out that there is a growing population of seniors who need to be useful. Most of the guidance on how to take advantage of this theoretically exciting phase of life focuses on self-reflection: find “your bliss” and then persevere until you create a way to make it your living or find a job doing it.

Great advice if the financial cushion is there. Read the success stories and very often the reinvented one had once been a hedge fund manager or there is a spouse mentioned in passing who is still working.

If this opportunity for re-creation comes to you voluntarily because you can afford to retire, be grateful. Doing what you love is indeed a blessing. However, if this “opportunity” comes to you via pink slip, there is not a great deal of practical advice on how to fast track the introspection, find your bliss (I know I put it here somewhere), and monetize it before your savings run out and you are still too young for Social Security.

The period before Medicare eligibility is the scariest of all. Being able to secure income to keep the roof over your head or food on the table is not impossible. Being without health and prescription coverage is potentially devastating. Who among us isn’t taking at least one pill? If you have always had an employer-paid plan, don’t ask what that pill costs if you have to pay for it yourself. Your heart can’t take it.

And so we long to be older yet again. The trouble is, neither Social Security nor Medicare is fooled by our ruse of claiming the next year up. Sixty-four and a half won’t fly. You still get clown-faced pancakes for another six months.

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