avatarAldric Chen


I Asked Toby How Retirement Has Been for Him. He Revealed Jittery Beginnings.

Spoiler — It’s not what I expect from a 57-year-old with a 7-digit investment portfolio

Confident at work, humbled by retirement. Photo by FILMon on Unsplash

Toby retired 5 years ago.

Before that, he was a senior manager in a software company. I worked under his tutelage for a couple of years. Toby is smart, witty, and enjoys a good laugh.

I had a good impression of him.

Quite naturally, I felt sad when he announced his retirement. The speech was made in a corporate townhall, and we toasted before parting ways.

“All the best to you, Toby! Enjoy your retirement!”

He smiled big.

The Unexpected Turbulent Initial Years

We met for coffee yesterday.

It was an offer I could not refuse. Toby’s text came when I was around his vicinity. I was at a client’s office just 3 streets from his apartment.

It was a no-brainer. I agreed without thinking.

We met at 2 in the afternoon. It was sweltering hot. There were many people in the café of Toby’s choice. He waved to me the moment I passed through the door.

“Hey man, how long has it been? You must have reversed aging. You look bloody good!”

He did. I thought he had more black hair than white today than 5 years ago.

Toby did not reply directly.

There was a smile and then a statement that invoked curiosity.

“The initial turbulent years are over. I am just glad. Now, I can breathe easily during retirement. Mark my words, young man. It is not easy at the start.”


I like that.

It sounds like I am about to learn something new.

“Personalities Play a Part. Never Discount That.”

I came back from the counter with 2 iced lattes.

I placed one in front of Toby before initiating the conversation.

“Is it about money? I spoke to many retirees. Their primary consideration has been a worry about depleting cash reserves or having to sell financial assets to finance daily life. I heard this millions of times.”

Toby deleted half the glass while I spoke.

He acknowledged my question, nodding his head while drinking.

Toby placed the glass down, wiped his lips, and wiped his lips before responding.

His response was surprising.

To me, it was.

“Nah, money is only 20% of the problem in retirement. If you have money problems before retirement, please don’t. It is the only thing we can solve before retirement. Non-money problems are the decimating ones.”

That’s fresh.

I had to ask what those are.

But Toby beat me to it. This mentor of mine knows me too well.

“Enjoying a peaceful retirement requires a personality fit. My wife and I retired at the same time. She could not take it. She gets upset when no one has time for her, when it is only 3 pm, or waiting for time to play tennis. She needs work.”

A problem with time. Hmm.

Toby did not stop there.

“There was something even deeper. It’s her money psychology. Although we do not worry about financial reserves depleting, having no money coming into her bank account monthly… stressed her out big time. She developed sweaty palms.”

I learned something.

Although I could not comprehend the depth of the issue [yet] — I realized this.

  • Having a salary can be a problem. We must deal with tasks or people we disagree with.
  • Not receiving a salary is [also] a problem. Our bank account shows many payments and no active income. There are many red line items with occasional greens.

I dug further.

“Toby, I am sure both of you have financial assets in your investment portfolio to keep your daily life going, right? Financial stress should be minimal…?”

He was surprised that I couldn’t comprehend.

Not for me.

I am not there yet, after all.

“No, no, that is not the issue. The banking mobile app is. We have daily expenditures and monthly credit card bills. They appear more frequently than the dividends we receive. It feels like we are leaking money.”

The story did not end there.

“She got jittery and started checking her banking app more often. It upset her. I assured her that we were good. She did not want to go out because we had to spend money. It went on for months.”

Needless to say, he was stuck with negativity for him. It chewed on him.

By now, I was lost in my thoughts.

Toby Gave Me Advice on Retirement Experimentation

The spotlight turned to me.

“Aldric, you will never know what you are made of until the salary or big-ticket business income stops coming in. You might discover a different you. Test yourself out. Oh, and test your spouse, too.”

He has a point.

I can see why he said what he said.

This is his parting statement.

“You are young, and so is your wife. Go without active income for 3 months, 6 months. See how you respond. You have years to work on an identified issue before it manifests. Don’t assume an auto-pilot!”

I didn’t have anything else to say.

I concur.

The Close

According to Toby, financial stress makes up 20% of retirement stress.

The remaining 80% are the tricky ones. They are made up of things we cannot see. We must discover our psychology, emotions, and responses toward a new way of living.

Toby is right.

We cannot assume that we know what to expect during our retirement.

We [just] don’t know.

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Oh, oh, you can buy me a cup of black too! Thank you!

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