What to do on the first day of retirement?

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21 January 2022
Some years ago, a friend who had just retired called me on his first day out of work.  He didn’t have a clue as to what to do.

What made it seem even more urgent was that he called me at 5 o’clock in the morning. He had been a director of a public company and I had always thought that he was extremely well organised. Turns out that he wasn’t.  He was completely at a loss. 

I suggested that even though it wasn’t a working day, he should make sure that he gets up early, showers, shaves, dresses up and has breakfast – all before 8h30. He kept saying, “But why?” and I said, “Because you need to establish a routine with which to live.” After three or four repeats of this interaction, I said that I needed to get up and go to Secunda, and he reluctantly put down the phone.

For that entire day, I wondered how the first day of his new life was going. So, when I got into the car to go home late that afternoon, I called him. 


“How did it go?” I asked.

“Unbelievable” he answered. “I want to have the letters YAOYO tattooed on my forehead” he said. 

“What on earth are you talking about?” I asked. 

“You are on your own” he said, “that’s what it means!” “I sat down in front of the TV at nine this morning to watch a replay of a rugby match and had just got settled when my wife walked in and said,” “Sorry, but the girls will be here in a few minutes for our morning bible study so you can’t stay here and watch TV.” “We have only one TV set so I had to move.”

“The girls made such a racket that I got into the car and went for a drive. I spotted a Mugg and Bean at a shopping centre, sat down at a table and ordered a coffee. I read the paper and when I was finished, I got up and walked out. I was stopped at the door and presented with a bill. Then things got awkward as I hadn’t thought to bring my wallet. The manager was pleasant enough, but he asked me not to come back to his shop anytime soon, and to consider the coffee that I had had as a donation to my welfare. I was mortified.”

“I went home and to my luck, the ladies were gone, so I stretched out on the couch. But that was short-lived as our domestic worker chased me out so that she could vacuum... listen to this; for my wife’s book club meeting in an hour’s time.”

“So, what did you do after that” I asked.

“I locked myself in the bedroom and tried to plan what I intend to do.”

“As a matter of interest, why didn’t you plan things earlier?” I asked.  

“I thought it would be better to just ease into it,” he said, “but clearly retirement starts with a bang and you need to be ready.” 


He couldn’t have said it better. Retirement starts with a bang. One day you have your life figured out, the next day your life has changed. I have worked with close to three thousand retirees and they all wish that they had planned earlier. It’s not even about planning better; it’s about having a plan to begin with. Knowing where you are going on the first day of your ‘new life’, as you put one foot after the other - metaphorically speaking.  Yes, plans can change, in fact plans change all the time, but having one helps a great deal.

Having a plan or an agenda from the first day of retirement puts you on a path that gives you a sense of relevance. I meet Chemical Engineers, both men and women, who are responsible for vast, complicated chemical plants and whose jobs require a great deal of preparation. They had important roles that have now gone to others and, in spite of their knack for preparation, they still feel at a complete loss when the first week of retirement starts and they aren’t as prepared as they thought they’d be.

The secret seems to lie in understanding that it will be difficult adjusting to a new way of living. If you have a skeleton of a plan, for example; times for rising and shining plus a few events loosely scheduled for the day, the trick is to follow through.

One cardinal principle that has been repeated to me by many retirees is to start a new diary that kicks off on that day. There is something about a new diary that says, “We are starting on a new journey.” Another helpful hint was that the first day of retirement should be the day in which you hold a family function to punctuate the end of your old life, and the beginning of your new one. This is over and above the party thrown by your employer, which is often a bit stiff and uncomfortable.

Of course, if your calculations show you that your accumulated retirement investments won’t be able to give you a similar living standard to the one that you had before retiring, you will retire from one job only to start another. However, the earlier in life that you do that calculation, the better.

People who manage to transition into retirement successfully usually don’t do it too quickly. They understand that you cannot just cast off one life and put on another. The aim should be to come out of the experience feeling inspired by it, rather than being embittered by it. 





D.L. Crawford CFP®

OUTvest is an authorised FSP. All investments are exposed to risk, not guaranteed and dependent on the performance of the underlying assets. Ts and Cs apply.

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