Photo by Tim Foster on Unsplash

The point of no return — that mysterious moment when you fully commit—here are six people and their (mostly) true stories.

In the span of human existence, retirement is but a wink.

It’s so novel, our minds get tangled up with the concept of life after work. Making the decision to stop working goes contrary to every evolutionary fiber of our being.

It’s excruciatingly hard to commit, but sooner or later we must. Like novice skydivers, we either step out or get pushed.

That moment is profound, a point of no return.

Here are six of those moments.

The vignettes below are inspired by people I’ve met and known. Their names have been changed and details enhanced for literary effect, but the moments of their epiphanies are as close to accurate as possible.

Rocket man

A uniquely talented young man scaled the tower of success to become the CEO of a hundred-million-dollar corporation.

Jake was a wizard, turning profits every year for over two decades. When the company was sold, he walked away with a life-changing bonus the likes of which most of us will never see. As a condition of the deal, Jake was asked to stay on for a full year to manage the transition. He loved that company and the job, so he agreed immediately. He would have stayed longer.

Three-hundred-and-sixty-six days later he celebrated his 60th birthday and took a high-powered job at the venture capital firm that had brokered the sale of his company.

He was miserable. The hours and travel were crippling. The nature of that business is manipulative, backstabbing and aggressive. His ulcers flared up while his home life flared down.

The chairman called Jake into his office one day and said, “Jake, I can see you’re overwhelmed. I’d like to move you to a new position with less travel and authority. What do you say?”

Jake thought carefully about his paycheck and his savings. He lived an unusually frugal life for a man of his status and didn’t need the opulence that his co-workers worshipped.

Then he thought of 5:00 AM alarms, urgent flights, and lumpy hotel beds. He thought about blistering debates in the boardroom and demoralizing the takeover targets. He thought of his wife and the neglected tools hanging on the walls of his shop.

“No thank you,” he said. “I think I’ll retire now.”

The Reaper

It takes a powerful blow to shake some people loose from their comfortable perch.

Neville was one of those people. He had carefully constructed what many of us would consider a perfect life. He worked at a low-stress job that paid okay and owned a home with his wife in a fine neighborhood near Seattle. He plied his hobbies in the evenings while touring his motorcycle up and down the coast on warm weekends.

He planned to work six more years and retire on his 65th birthday. That’s what his late father did and it seemed like a good plan for him, as well. He would build his retirement account to a level that would provide for a wonderful future, and life would be great.

One day he woke up on the sidewalk, a dozen faces peering down at him while two uniformed men worked feverishly on his chest.

He almost died. It took ten days in the hospital to recover from the heart attack. Ten long days to ponder his unlucky genetics and the likelihood of a shortened life.

It would be tight, he thought, but the house was paid off and his wife still worked. In a few years, Social Security would soften the blow, but there would be sizable corners to cut.

He left the hospital with the euphoria of an innocent man released from prison. He tightened his belt and informed his boss that he was retiring in two weeks and then immediately got back to the task of building a new, perfect life in retirement.

Stair steps

Bartholomew is his name, but everyone calls him Buddy. He’s the most generous person you’ll ever meet but he’s a workaholic and a “playaholic.” At the age of 69 he has two jobs, two homes, six hobbies and one wife. He also has scores of friends who can’t figure out how he does it all.

Nobody, not even Buddy, understands why he still works. He doesn’t need the money anymore. Maybe the identity, the prestige. Maybe it’s just a habit he can’t shake.

“I’d be bored,” he says. But nobody believes him.

“I enjoy working,” he says. But there’s a sense of fear in those words.

After years of dogged persistence by his wife, children, and friends, Buddy has reluctantly cut back his workload by half, so now he has the equivalent of just one full-time job. In two years, he’ll quit one job completely, and he’ll phase out the other by the age of 75.

Then he’ll turn his full attention to retirement.

At least that’s what he says.

Epiphany

Grace sat in her underwear on the edge of the bed in a hotel room that looks like every other one she’s seen in her long and storied sales career.

The muted TV flashed the bright colors of a Hallmark movie while she held her head in her hands, frustrated with life. It had been a rough day with an outraged client, but she managed to set things right. That’s what she does.

She envisioned her husband back home, tossing a pesto pasta meal while enjoying a glass of Valpolicella. While she sat in the flickering darkness.

Sales was a perfect career for Grace, with her bubbly personality and cutting wit. Under a friendly guise, she was a lioness on the prowl, and she consistently closed more deals than her contemporaries. But lately, the thrill of the kill was gone. It was rote, and she was performing like an actor in a play.

“It’s time,” she declared out loud to the room. “No more hotels and petty scuffles over payment terms and service levels.”

She was energized. Grace popped up from the bed, shut down the TV, and opened her laptop.

“Dear boss — I quit.”

She dressed and went down to the lounge for a celebratory toast.

Double bogey

Looking in from the outside, retirement is an alluring fantasy. We expect it to be some version of paradise, but more than a third of us end up returning to work, disappointed with what we got.

Danny reached his milestone 65th birthday and retired like he was supposed to. He puttered around in the yard until it was neat and tidy. He cleaned the garage. Then he read some books and discovered they put him to sleep. Books were replaced with the Golf channel which was marginally less sedate, and he sat. And sat. His wife worked, so he was alone and lonely.

Six months in, he got a call from his old boss who had some questions. Dan asked if he could be of service in any way and his boss said sure.

Danny was back at work the following week. Even drudgery beats stark raving boredom.

Waffling (my personal story)

I planned my retirement for years — you should see the spreadsheets and activity lists. “Next summer,” I told my wife. She thought it was a good idea. The next summer came and I kept working. Maybe at the end of the year, I thought. December is a good time.

The paychecks kept coming and the antics at work continued to be tolerable. I was pretty good at what I did and for the most part, I was appreciated. The people were nice, and we were doing remarkable things for the company.

I was only 60 so there was no rush. I planned all the trips we’d take and ranked the home improvement projects by priority. I even started publishing articles about my plans. People read them and could see that I was on top of life, fully in charge of it all. But they could only see the words, not the person who couldn’t commit.

“Next summer,” I said to my wife. But the pandemic came and why would I retire when I can’t go out and do anything anyway? It made sense to me, and I figured I could save more for an even better retirement.

“July they give out bonuses,” I told my wife. “I think that’s when I’ll retire.” She thought it was a good idea.

I tore my hair out for a week as I struggled with the message I’d dictate to my boss. I was tormented by demons who assured me it was a stupid idea; too soon and too dangerous.

“Congratulations, I’m so happy for you!” were the first words out of his mouth when I announced the news. “When will your last day be?” he asked.

“Oh, I don’t know, sometime this summer? Whatever works for you.”