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Heading toward my 59th birthday next month, I’m starting to accumulate more friends and acquaintances who are retired. They seem happy enough by all accounts.

But recently, I came across a blog post by Mike Drak, a 38-year veteran of the banking industry who confesses that he “failed in retirement.” You don’t find that kind of honesty much when people talk about their retirement.

Reading about other people’s success in retirement or in personal finance in general can definitely be instructive. But it’s equally valuable, and sometimes more relatable, to hear about someone else’s mistakes. And so, Mr. Drak’s blog post is a must read for anyone squinting into the distance to see what retirement might look like.

His mistakes aren’t money-related. He apparently saved enough. What he didn’t do was think about his expectations for retirement in terms of what he’d do with his time and how he would feel about it. He ended up falling into a trap that I have never seen mentioned before – “Believing that retiring would make all my problems go away.”

Most near-retirees mistakenly think their bad habits will vanish once they leave their job and its related stress, Mr. Drak writes. “They will magically transform into that happy person they always wanted to be. They will hit the gym daily, eat healthier, travel to exotic places, write a book, learn to play the guitar, start a business, and spend more time with family and friends.”

The lesson he takes out of his own situation is that you have to design a satisfying life in retirement. In Mr. Drak’s case, he became a financial coach, public speaker and author of a book called Retirement Heaven or Hell: 9 Principles for Designing Your Ideal Post-Career Lifestyle.

Retirement for me is way off in the future, but I did recently have our financial planner take a look at how my wife and I are doing in saving enough for the years after we stop working. I can see I have to spend some time thinking about the nonmoney side of retirement as well.

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Rob’s personal finance reading list

Have fun staying poor

In one of the best commentaries I’ve read on the current financial mood, money manager Josh Brown writes about how the old fear-and-greed dynamic has mutated into something more, well, greedy. He mentions the Twitter meme #HFSP, which stands for have fun staying poor. People, investing is not as easy as it’s seemed in the past 18 months. To quote another meme, winter is coming.

How to read a wine label

Wine’s an investment in a great meal, right? Here’s how to better understand what you’re buying.

A crash course in burger economics

A look at how the cost of McDonald’s burgers and fries compare in countries around the world, including Canada.

Online gambling’s contribution to debt stress

A credit counsellor blogs about how she’s seeing an increase in financial stress caused by iGaming, or online gambling: “Please consider that the six horsemen of the lockdown and social distancing apocalypse were drugs, alcohol, sugar, food, work, and iGaming.”

Ask Rob

Q: I got a promotional e-mail today for a Neo Savings high interest savings account provided by Concentra Bank. Add this to our HISA considerations?

A: Sure, why not? As noted on the Neo website, this savings account is backed by Concentra Bank, which is a member of Canada Deposit Insurance Corp. The current interest rate on this account is 1.3 per cent, which is subject to change without notice. It’s also one of the best rates around right now. Neo is a banking app developed by the people behind SkipTheDishes.

Do you have a question for me? Send it my way. Sorry I can't answer every one personally. Questions and answers are edited for length and clarity.

Today’s financial tool

Track Canada’s recent and historical inflation rates on the Trading Economics website.

The money-free zone

A 1970s soul classic that hasn’t aged at all: Wake Up Everybody, by Harold Melvin & the Blue Notes.

Listen to this

I had a great chat about investing, real estate and more with the Rational Reminder podcast guys.


What I’ve been writing about

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