I Brought 3 Retiree Friends to Bowling. They Revealed Their Spoken [& Unspoken] Fears

The best retirement life lessons come from the people around you

I have many retiree friends.

I observe them. I ask questions. I learn. I think.

They humble me.

I assume I know what retirement is about. Have enough money. Not worrying about money. Get healthy. Stay there. Be happy. Stay there.

Easier said than done.

Everyone frets. We all do.

Kids fret over losing followers.

Corporate rats fear getting axed.

What about retirees?

My Friends in Their Retirement

Joseph, Jeremey, and Jacqueline are my LinkedIn pals and gal.

We got connected in that app and stayed in contact. We became friends. It helps that we are all in Singapore. Coffee chats are easy.

And when we do, my eyes open.

We Are In Different Stages of Our Lives

Joseph [age 64] is the classic retiree.

He is looking for good conversations, easy income, and peer respect. He is occasionally grumpy and can be very funny.

Jeremey [age 49] got retrenched multiple times as a senior marketing guy.

He joked about his identity as a frequent in-between-jobs retiree. He retired [and unretired] 3 times in 5 years.

Jacqueline [age 51]? She is a forced retiree.

She got out of cancer treatment 2 years ago and is actively looking for administrator jobs. She is still searching.

Put these 3 and me together guarantees a catch-up filled with grouses, repeat stories from their pre-retirement life, and above all else, daily worries.

An Unplanned Bowling Session. One Good Conversation.

We met for bowling last Monday.

We originally arranged to meet for dinner. Jacqueline wanted to eat and tell her life stories on repeat. I wasn’t interested. So, I countered.

“Let’s go bowling. Bring your socks.”

I was surprised. There was no resistance.

Replies were,

• “Yes!”
• “Okay. Something new!”
• “Sure. We are old. Got to think about air-con sports.”

Wow.

This is going to be a fascinating year, I muttered.

Questions, Questions, Questions.

Joseph was early that day.

I fetched him from the train station and headed for the bowling center. He bombed me with many questions.

And he needed answers.

Urgently.

• “What am I going to do with my China equities? Hold it? Sell it?”
• “I have a big position in bonds, in mutual funds. What should I do?”
• “Can you refer me to an easy job? I want to make some money.”

They are all related to investments.

And income.

It’s surprising because Joseph doesn’t need the darn money. He has cash-producing assets such as stocks, bonds, and rental apartments. Why the jitter?

This is what he said.

“I will be wiped out if all of these assets tanked. What will I live on? This worries me. I’m scared.”

Financial intelligence, maturity, and wealth do not negate our fear of money loss. Wealth woes are real.

Jacqueline arrived next.

“Is this bowling center expensive? I haven’t found a job yet. Money is tight.”

I assured her it was affordable.

“I hate to worry about money. Yet, I am. Every single f**king day.”

It was a silent grouse she muttered beneath her nose. I caught it.

It exposed me to the depth of retirement life even before I threw a single ball. It was telling.

Then, Jeremey came.

It’s playtime.

A Cocktail of Worries, Light-Heartedness, and Deep Thinking.

I dragged Jeremey aside.

“Hey, I will pay for the bowling, and you pick the tab for dinner later. Any issues?”

He listened. He complied.

“No issues. I am future-proofing my next unplanned retirement. Might be coming soon.”

Another soundbite worthy of reflection.

I smiled back. And I proposed one more idea.

“Shall we each fork out $100 and table it as a cash prize for the winner? Jac and Joseph are fretting over money. I think we can do something.”

Jeremey was feeling generous. He upped it to $200. I followed.

Our friends were happy about the cash prize. They laughed. I smiled, too.

I knew why. What can $400 do for their retirement? Nothing. But they know Jeremey and I had good intentions.

We started playing.

It was the best gathering we had in a long time. We laughed, stomped our feet when 1 pin was left standing, high-fived with a strike or spare, and made a nuisance of ourselves.

We frightened the little boy next lane.

I caught what he whispered [loudly] to his mum.

“Are these old people retirees or unemployed? How come they behave like Grandpa? They are so loud.”

It says a lot about the worldview of a 1.30-meter-tall dwarf.

And how he sees his grandpa.

It wasn’t funny.

Was it uninformed social discrimination? Maybe? I have no idea. It exists, for sure.

By now, we were almost done with 3 games. Our wrists hurt. Time to stop. There was an obvious winner. Jeremey and I handed our money to Joseph.

“I thought you guys were kidding!”

“You need it, old man. Take it.”

“Let’s bowl again tomorrow.”

I laughed and politely declined. I will be bankrupt if this continues.

Jacqueline wasn’t too pleased.

“Can we have 2 cash prizes next time? I want some easy money. I made $0 today!”

I stared at Jeremey. He just finished changing back to his cloak shoes. He had no rejections.

But he had a caveat.

“Provided I am not retrenched when we meet the next time!”

Haha. Well. Point taken.

The Close

Retirement in real life is not what we imagined it to be.

I see it in my friends.

Joseph is a classic retiree. He has money and assets. And… he frets over losing it all. Why would he not? His retirement is wiped out when that happens.

So he is jittery. He worries about money. He feels better with active income.

Jacqueline is nervous about money, just like Joseph. She is desperate to unretire herself to contribute to her family and declining bank balance.

Her 5-digit turning 4-digit bank balance is killing her daily. Trust me. It is [absolutely] horrifying.

Then, there is the seasonal retiree-retrench’ee.

Some jobs are [more] vulnerable to the economy’s booms and busts. Jeremey has been a marketing director twice. He got fired twice. And each time, he takes 12–15 months to get the next job.

It’s nerve-racking.

I observe their worries. I reflect.

At first glance, we worry about money for and during our retirement. But there is something else lurking deep in our psyche.

It’s fear.

• Fear of losing income.
• Fear of declining bank balance.
• Fear of losing that next paycheck.
• Fear of all investments going to zero.

How can we overcome that?

I have no idea.

And that is the million-dollar question I intend to ask each of them.

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