🤔 Why?

Published On: February 10th, 2023

We answer questions everyday. How are you? What are you doing Saturday? How about another Zoom meeting? If you’re like me, you’d skip the Zoom to be with friends. Kudos.

Answering other people’s questions is kinda easy. But asking yourself questions, well, that’s a lot harder.

Some of the toughest questions are about your money. Questioning yourself requires a little motivation, perhaps some discomfort, and a lot of introspection.

🧠 Today I’m sharing a mindset exercise to help you unlock your past financial experiences and reveal your present money beliefs. You may just surprise yourself.

Let’s do this!

Today’s newsletter is 491 words, 2:30 minutes.

25 Powerful Questions


🧐 The most challenging question to ask yourself is “Why”. Asking yourself “Why” can give you clarity and reveal the path towards achieving your financial goals. Your questions may start with “Why” and end with “Why not?”

I recently went down this path when MoneySense did a Q&A with me for a feature article. It took me weeks to answer every darn question – mostly because I had no idea my early experiences with money influenced me so profoundly. It was hard and I’m happy I did it.

Here’s the interview: MoneySense Q&A with Kerry K. Taylor

I want you to give it a go, too. Knowing your “Financial Why” could strengthen your money mindset and help you reframe your choices today.

You can do it!

25 Reflective Answers


Buying a pink yo-yo as a kid, graduating during a recession, and splurging on a fancy coffee machine are events that left a mark along my path. Weird, right?

What are the financial experiences that frame who you are today?

I’ll give you three of my answers to encourage you to dig deeper too. (I can’t believe I shared this with the media.)

Q. What’s the first thing you remember buying with your own money?

🪀 The first thing I bought with my own money was a pink yo-yo. I regretted it right away because my hands were too small to make it fly. This was my first foray into buyer’s remorse, and that terrible feeling has guided my spending ever since.

Q. What was the biggest money lesson you learned as an adult?

💰 I graduated university during a recession, so my financial viewpoint was that money had to be protected at all costs. With the fear of losing my savings, I invested in several GICs with interest rates of around 6% — not the worst rate, but if I had a redo, I’d put my money into a mix of equities. I had time on my side.

Q. What was your most recent splurge?

☕ I bought myself a professional coffee machine capable of freshly grinding a multitude of specialty coffees. I should now be able to save millions of dollars by making my coffee at home.

May you find the answers (and coffee) you’re looking for.

Love love love,


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