What Leaving Teaching Taught Me About Money, Family, and Freedom
This article is based on the Amplifyr Podcast episode with Calvin Van Harten. Watch the whole thing below or stream it on your favourite platform (Spotify, Apple Podcasts). Otherwise, enjoy the article.
For 12 years, I was a teacher. I loved it, and I believed it was where God had called me to be. But as my family grew, one thing became painfully clear: I was giving all of my energy to the classroom and coming home empty. My wife and kids were only getting my leftovers.
If you’re a parent, you know how wrong that feels. I wanted to give my best to the people who mattered most — and teaching simply didn’t allow it. I also wanted the ability to control my schedule, to build a career with no financial ceiling, and to stop trading all of my time for a fixed paycheck.
That’s what pushed me into financial services. And I’ll tell you this: the same lessons that made me a good teacher are the ones I use now with every client.
Lesson 1: Don’t Just Take People at Their Word — Diagnose the Real Need
In teaching, a student might say, “I don’t get math.” But often the real problem isn’t math — it’s that they never understood fractions back in grade five. If you don’t diagnose the root issue, no amount of tutoring is going to help.
Finances work the same way. People come to me saying, “I need an RRSP,” or “I want life insurance.” But often, that’s not what they truly need. My role isn’t to sell them what they asked for — it’s to uncover what will actually serve their family.
That means digging into their current policies, their debt load, their income, and their long-term goals. Sometimes I recommend a product they didn’t know existed. Sometimes I restructure their debt so they can breathe again. And sometimes I tell them: “What you already have is actually your best option. Don’t change a thing.”
Here’s the takeaway: don’t assume you know your solution before you’ve looked at the whole picture. Whether it’s your finances or anything else, diagnosis always comes before prescription.
Lesson 2: Trust Is the Real Currency
If you’ve ever taken your car to a mechanic you didn’t know, you understand the feeling: “Am I being taken for a ride here?” Most people feel the same way about financial professionals.
That’s why my first job with any client isn’t selling — it’s building trust. I do that in two ways:
Clarity. I show hard numbers, projections, and scenarios. Nothing vague, nothing fuzzy.
Honesty. If a client’s current policy is unbeatable, I tell them to keep it.
Yes, that means I sometimes walk away from money today. But here’s the truth: short-term commissions are nothing compared to long-term reputation. If you want to win in business — and in life — never sacrifice trust for a quick sale.
Lesson 3: Cash Flow Today, Growth Tomorrow
One of the biggest mistakes people make with money is focusing only on the future while ignoring the present, or only on the present while neglecting the future. The answer is both.
Your first priority should always be stability: food, shelter, emergency savings. If you don’t have those in place, investments can wait. But once your cash flow is under control, the next step is putting money to work for the long term.
And here’s the principle that surprises people most: you don’t need to start big. You just need to start. Even $10–$20 a month builds the habit and gets the compounding process working in your favor.
The earlier you start, the more powerful it becomes. Younger people should lean into higher-risk, higher-reward investments because they have time to ride out volatility. Older clients should prioritize stability and preservation. But regardless of age, waiting is always more expensive than starting small now.
Lesson 4: Play the Long Game
In real estate, I’ve learned it’s better to keep a property vacant than rush in a bad tenant. In financial advising, it’s better to turn down a client than sell them something they don’t need.
Why? Because business — like investing — is about the long game.
It takes a lifetime to build a reputation and seconds to destroy one. If you want a business that lasts, prioritize integrity. If you want wealth that lasts, prioritize patience. Quick fixes and shortcuts may look tempting, but they rarely lead anywhere good.
Lesson 5: Purpose Over Paycheque
I didn’t leave teaching just to chase a bigger paycheque. If that were my only goal, I wouldn’t have lasted long in this work.
What drives me is knowing that families are in a better position because of a conversation we had. A single mom saving $100 a month because we restructured her policy. Parents with an RESP that will actually give their kids a real shot at higher education. A couple drowning in debt who can finally breathe again.
That’s what gets me out of bed. That’s what makes the paperwork and the meetings worth it.
What I’d Tell You
If you’re in a place like I was a year ago — drained by work, feeling capped financially, or stressed about money — here’s my advice:
Get clarity on your financial reality. Don’t just guess. Look at the numbers.
Don’t self-prescribe. You might think you need one thing, but the real solution could be different.
Prioritize trust. Work with people who will tell you the truth even when it costs them.
Start investing now. However small. Waiting will cost you more than starting imperfectly.
Think long-term. Both with your money and your reputation.
That’s the playbook I live by now. It’s what I teach my clients. And it’s what I’d recommend to anyone who wants to build not just wealth, but freedom.
