AGING WELL

At 68, I’m Still Betting on Myself

It’s a habit that’s gone on for decades

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Placing bets on oneself is important, and even more important as we age. I have made it my habit, and I share an important bet below.

My bets placed on that four-letter word: “Work”

I failed the first time I tried to write my “work story.” I think I had too much to say — sort of like a carbonated beverage that’s been shaken and is ready to explode at mere opening. So here is take two, and I will start with a seminal moment that changed my journey. It involved one simple bet.

I was working at a startup that, on a good day, was crazy but still productive. It was 2001, and except for me, the senior team was all men. I stood out, from not being invited to join in the daily lunch ritual to not ending the day with drinks at a bar. They were nice enough, but I didn’t really belong.

One afternoon, I got a call from my nanny that she couldn’t pick up the kids from school. My husband was unavailable, so I immediately left work but got stuck in a traffic jam caused by Bill Clinton's visit to Boston. I ended up being very late to retrieve my kids.

There they were, ages 11, 9, and 6, sitting happily at the school's curbside, playing word games (“20 questions” was a favorite), no worse for wear. Not so for me. I was irritated by the late call, by struggling with traffic and Boston drivers, and wondering what I got out of my job that made this complicated straddle worthwhile.

That moment gave me the push to start my own business — something I had occasionally dreamt about but previously lacked the courage to attempt. I had been on a fairly conservative and predictable path, which went something like this:

Business school, management consulting, CitiCorp, Hewlett Packard, sprinkled in 3 kids over 5 years, capped off by a few smaller, less mainstream businesses that made going solo not so scary.

Once before, I had ventured outside the conventional career path.

In 1989, after the birth of my first child, I asked Hewlett-Packard (HP) to let me work part-time. But back then, even HP's progressive culture did not have a policy to easily accommodate what seemed to me like a simple request. Just as I was preparing to strike out on my own, the HR department decided to try a 6-month pilot program with no guarantees. That pilot lasted 10 years and 4 bosses, and opened the door for many more women like me.

My view today

I am now in my 26th year of solo consulting and only a few steps away from retiring my business. I’ve sometimes asked myself whether I have regrets about the path I’ve chosen, but I always come back to “You chose right.”

I have friends who chose high-powered positions and all that came with it — bigger vacations, fancier cars, nicer clothes, and the like. If I ever caught myself looking with longing, I would remember I was blessed to be working for myself — at home — where I could see and hear my kids race to the fridge, plopping down their backpacks after a long school day. I caught the kids on their time, not mine, and it made a difference.

By changing course, I created a life with less “pressing,” and I liked being the boss of me — firm but positive, and determined to be a significant financial contributor and the mom I wanted to be.

I had the words of my deceased father ringing in my head: “My money’s on you,” which he said to remind us we would succeed at whatever we undertook. Those words, and my husband’s support, helped.

I know now that the career bet I placed was bigger than I thought. There are so many essential parts to running a successful solo venture. I had to sell and deliver on my work, rinse and repeat. I had to withstand rejection and waste no time licking my wounds, so I could get back on the horse and sell again.

I was patiently building relationships and proving myself time and time again.

All totaled, it was 26 years of betting on my ability to run a business while I worked to integrate consulting and family time. I had many vulnerable moments when my phone didn’t ring. Giving up would have been the easy choice, but I stayed with my bet, resisting occasional offers to join a client’s company. As tempted as I was, I’d still say “Thank you, but no.”

I believed that eventually the phones would ring. My faith would be tested, and my business would rebound.

Why am I thinking about this now?

At 68, I wonder what has driven my impulse. Will I continue to place bets?

I offer two glimpses that shaped me and a hope for the future.

First glimpse: My mom sent me a card in my early parenting years that still sits on my desk 25 years later. It shows a swing and a starry sky and reads, “A mother helps you push your swing so you can touch the stars.”

This card comes from a woman who worked full-time alongside my dad throughout our childhood years to help run a grocery store and provide for a family of six children. She knew about the importance of work and of helping to provide financial stability while being a mom in the deepest sense of the word. She found a way to insert her presence into our lives and lead us mightily.

Small memory: At night, at around 10 o’clock, would be the first time she could sit and quietly have her tea while reading the paper. This was when I would often sneak out of bed and hang with her. She always welcomed me.

My mom’s card to me was essentially her marching orders: I was to push the swings of my children, as she did. While we never touched the stars, my siblings and I landed quite well.

Second glimpse: My courage to venture out might have been inspired by my Bubbie (Yiddish for grandmother), who at 16 emigrated from Russia to marry her third cousin — a man she had never met. She was escaping persecution in Eastern Europe to start a new, better life in America.

My Bubbie frequently counseled me,

“I hear that in this country, girls can become a lererke (Yiddish for teachers).”

That was her way of telling me I was to build a profession, and that teaching would be a fine choice.

These two women somehow subliminally programmed me to both push a swing and drive a career. I knew at a young age that some version of a lererke would be in my future.

Looking ahead

I believe I am in the prime of life (albeit slower), and I want to stay in the habit of betting on myself. I know time has a way of eroding our spunk, if we let it.

I aim not to.

I remind myself that over the decades, I have shown myself to possess sufficient strength to remain true to my convictions. So, I ask, what bets will I look forward to in my seventies?

I suspect they will look something like this:

I will continue to write: I discovered at the start of Covid that writing fiction is hard but fun. I will continue to build out my Alfred series, which embodies all the values I hold dear with a splash of humor.

I aim to be a new and improved matriarch: My mom and Bubbie were matriarchs, and stepping into their shoes is daunting. But loyalty, smarts, and learning from the hard knocks of life tell me I’ve got what it takes. I hope to lead with humor, positivity, and open-mindedness born of curiosity.

I will build new muscles while maintaining the strength of the old ones, literally and figuratively. I play tennis and intend to play this wonderful game for as long as I can hold a racquet and kinda run. I am building a Mahjong game, which allows me to meet new people and keep my mind sharp. Maybe Bridge will be ahead — if I can convince my husband to be my Bridge partner. That will require significant sales skills, which I have.

I will learn to relax. I am no longer building a business, so I can slow my pace if I try hard.

And a particular bet that I look forward to placing over the next year?

I bet I can create a meaningful fourth book of fiction in the Alfred series. The protagonist is Lucy, a mid-thirties woman born on the wrong side of the tracks who has smarts and grit, and is in the middle of a do-over.

Lucy is placing a bet on herself, which fits perfectly with my late-sixties sensibilities.

What bets might you be placing?