What Does a Successful Retirement Look Like?
- Jordan Defazio
- Jun 17
- 4 min read
We ask people a lot of questions about retirement.
Are you happy?
Are you having fun?
Are you keeping busy?
But we almost never use the word:
successful.
On a recent episode of More Than Money, Dave and Faisal, two financial retirement advisors, discussed this deceptively simple question.
Most people might say it’s connected to the words “Do I have enough?”
But this is only just a slice of the overall pie.
Dave Throws a Wrench
Ask Dave when he plans to retire and he’ll tell you he’s already retired (but he still works non-stop)
His framework is a stool with four legs. Pull one out and the whole thing wobbles.
Financial: The leg most people think of first.
Social: Friends, family, and close connections.
Health: Family history and your own personal situation.
Mental stimulation: The academic and intellectual side of life.

By that measure, his work feeds the mental and financial stimulation, his team and his clients feed the social one, and his frequent trips to the gym and the golf course feeds the health one.
But as he put it, he’s not exactly successfully retired; he’s more “successfully tired”.
All jokes aside, retirement is the balance of those four legs once a paycheque is no longer propping them up.
The Hole Work Leaves Behind
Here’s where Faisal sees people struggle.
For thirty, forty, even fifty hours a week, work quietly filled mental stimulation and social connection all at once.
Then one Friday, it all stops.
Replacing your paycheque with your savings gets all the attention when it’s over but the other factors rarely get brought up.
Questions like:
What will I do with my time?
Who will I talk to all day?
For a lot of new retirees, the honest answer is "I have no idea."
As Faisal said, he’s not about to become a Buddhist monk sitting in silence.
He needs people, like most of us do.
A successful retirement plan needs to factor in social changes before it appears, not after.
Where Maslow Enters a Successful Retirement
If you remember Maslow's Hierarchy of Needs, retirement maps onto it almost perfectly.
At the base is survival: food, water, shelter.
Above that is safety where health and money live, and it’s where most retirement conversations begin. "Do I have enough to support my lifestyle?" is a safety question.
Then comes love and belonging. Then esteem. Then, at the very top, self-actualization.
Here’s the part worth noticing. Money doesn’t sit on one rung. It quietly runs through all of them.
Safety: can your savings support the life you actually want?
Love and belonging: helping family, sharing an inheritance early, watching the people you love enjoy it while you are here to see it.
Esteem: setting up a foundation, backing a cause, putting your name behind something that matters to you.
Self-actualization: reaching the point where you can honestly say money was never the goal.

None of this means money buys a good family or a meaningful life. Plenty of people build both without much of it.
But financial comfort gives you the room to participate fully at every level.
Ask a 90-Year-Old
Faisal offered one more piece of advice, and it might be the most useful thing in the whole conversation.
If you want to know what a successful retirement looks like, don’t ask a 65-year-old.
Ask a 90-year-old.
A new retiree is still early in the journey but someone in their nineties has lived all of it.
The “me” phase. The “we” phase. The “them” phase.
They already know what money can do, and where it stops mattering.
That’s wisdom you can’t buy.
So, What Does Success Look Like?
A successful retirement is the balance of the four pieces: financial, social, health, and mental stimulation, held steady with purpose.
The money matters because it supports the other three, not because it replaces them.
Your mental health is as crucial as your physical health and social connections.
That’s the whole idea behind this show from the very beginning.
There is a reason we called it More Than Money.
Come Talk It Through With Us
Do you have questions about what a successful retirement looks like?
Join us at our next seminar on Tuesday, July 14th at 7 p.m., in person at the Silver Springs Golf and Country Club.
Seating is limited and you do need to register. Visit morethanmoneyradio.com or connect with us on Facebook to save your spot.
At PKAG, we help Canadians build retirement plans that account for all four pieces, not just the financial one. And we’ve retired hundreds of times with our clients, and learned what makes a retirement “successful”
If you have any questions, feel free to contact us. You can also book a meeting and we’ll go through your plan in person.
We look forward to hearing from you.
This commentary is intended to provide general information and should not be construed as tax, legal, financial, or other advice. Individual circumstances and current events are critical to sound planning; anyone wishing to act on the information presented should consult with his or her tax, legal or financial advisor.
This information, including any opinion, is based on various sources believed to be reliable, but its accuracy cannot be guaranteed and is subject to change.David Popowich, Faisal Karmali, Leanna Wachniak, Robert Gerrie are Investment Advisors with
CIBC Wood Gundy in Calgary. The views of David Popowich, Faisal Karmali, Leanna
Wachniak, Robert Gerrie do not necessarily reflect those of CIBC World Markets Inc.
CIBC Private Wealth consists of services provided by CIBC and certain of its subsidiaries, including CIBC Wood Gundy, a division of CIBC World Markets Inc.




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