Financial Regrets? I’ve had a few…and not too few to mention! This is my own version of ‘My Way’. To be honest, this is definitely a ‘First World Problem’. I was not lucky to make good money when I was young; I worked for every penny. I wouldn’t take back a single dollar I have ever spent on travel, wine, or dogs…but there are some spending decisions I do regret.

Dress for success?

One of my best friends had a knack for finding the diamonds in the rough at Winners. She had fabulous suits and perfectly colour-coordinated earrings, shoes and bag, all for peanuts. It took her hours of searching, but her fashion ROI was high.

I was the opposite. I hated shopping and thought my time was better spent at work. My solution was to find one perfect store and hurl my credit card at it until I had a business wardrobe. A store on Avenue Road looked perfect: “Italian womenswear luxury with the finest cashmere and bespoke tailoring. An expression of quality.”

For a decade, twice a year I dropped $10K for suits, sweaters, and so on. I calculate, using actual Canadian inflation rates and TSX total returns over the period between 1991 and 2001, that in 2019 dollars I would have had close to $400K, and if I had invested in the TSX, I would have amassed over a million dollars…enough for a nice house in the South of France for my retirement.

Did I have assured elegance of modern luxury and style…as promised by the website? I’m not sure about that, but I can tell you I haven’t worn any of it in years and tossed most of it in a recent purge. As I was putting it in bags, I noticed it was a boring wardrobe of blacks, greys, with the occasional beige for excitement.

I now know that by taking just a little more time to shop, you can spend much less and get much more interesting clothes.

Analyse this!

I was a driven woman in my 20s and 30s and while successful in my work life, I was troubled by some relationship patterns, for which I sought professional help. Hardly unique, but I became addicted to therapy! Over a decade I saw seven to ten different professionals (sometimes two in the same week). The worst parts? None were covered by insurance, and one lived in Zürich.

Mental health professionals provide an essential service in society and they are critically important for many. In hindsight, I didn’t have a genuine mental health problem – I was indulging myself in years of navel-gazing out of intellectual interest more than need. The therapy might have had a small positive effect, but I suspect I mainly just wasted a lot of time and money. The ten grand I spent on therapy annually would be worth over $500K if I had invested it in the TSX. My missing house in Provence just got bigger, and now has a pool!

Should some people seek help and get it? Yes. Looking back on it, would I derive significantly more mental health today from sipping red wine in Provence than all those hours on the couch? Also, yes.

Giving is better than receiving…or is it?

I used to be over-the-top generous about treating friends to dinner. My parents had been the opposite: paying off the mortgage, forgoing all restaurant meals, and not buying rounds for everyone else. As soon as I started making my own money, I felt free to splurge at the cool new spots in the city, and I loved the role of being the one to treat others.

My generous nature didn’t stop with dinners. When all my friends had babies, I didn’t look at the Baby Gap catalogue (pre-Internet) like a normal person. Instead, I found the most expensive store in Toronto, with a “timelessly elegant collection of baby clothes.” I would call ahead and give them my credit card number, ask for everything to be giftwrapped, drive up, usually come to a full stop, and have my favorite sales lady hand me the goods through the car window. All for a sleeper that was outgrown in a month or two.

Don’t get me wrong: Of course, I needed to buy cute outfits for babies and take turns picking up the cheque while eating out. But I am referring to silly amounts of “generosity”. I would estimate I was spending an excess of $5K annually for ten years above what I should have. Invested in the stock market, another $250K in 2019.

What are your financial regrets? And, what are you going to do differently?

Barbara Stewart, CFA is one of the world’s leading researchers on women and finance, focusing on real life financial behaviours and providing global insights into how smart women think and communicate. Barbara is an advocate for women, for diversity, and for financial education. In addition to her Rich Thinking® research, Barbara uses her proprietary research skills to work as an Executive Interviewer on a project basis for global financial institutions seeking to gain a deeper understanding of their key stakeholders, both women and men. Barbara is a frequent interview guest on TV, radio and print, both financial and general interest. She is a contributor to the CFA Institute’s Enterprising Investor website. For more information about Barbara’s research, please see