Featuring Adam Chapman, Herman Chan, Steph O’Mahoney, Jennifer Strymecki and Shaun Maslyk
At Future Proof in Huntington Beach, a wealth festival held outdoors on the boardwalk, we spent a few days putting the same handful of questions to advisors and planners who have nothing to do with our firm. We weren't there to hear about products. We wanted to find out what people who do this work every day think actually matters.
Five of those conversations make up Part 1. They started from different places and kept arriving at the same question. Herman Chan put it most plainly. At the end of it all, people want to know whether they're okay, and whether they're going to be okay.
Here's what each of the five brought to that question.
Adam Chapman founded Yes Money in London, Ontario, and has spent two decades helping retirees do the thing nobody warns them about: spending their money.
People plan for a lot in retirement. What they rarely plan for is that spending turns out to be hard. After thirty years of discipline, drawing the money down feels like undoing the work. Adam thinks the industry's own language makes it worse. Advisors talk about "decumulation," which to a client sounds like we're going to make your portfolio go down.
His alternative: when you spend in retirement, you're turning money into memories. That was the point of saving it.
Our listeners are younger than Adam's clients, but this still applies to you. Chiropractors are good savers. The habits that build the nest egg don't switch off on their own when it's time to use it. It's worth knowing that about yourself now.
Herman Chan, president and co-founder of Crimson Financial in the Greater Toronto Area, works on financial health and physical health together. That will resonate with this audience, because without your health, the wealth doesn't do much for you.
His picture of a financial plan: you wouldn't set off on a thousand-kilometre road trip with your family without Google Maps. The plan tells you which route to take, then reroutes you around the traffic, the accidents and the road closures you couldn't have predicted when you left.
Which is why, in his words, financial planning isn't a one-time event. It's a journey. Something changes in almost everyone's life every year, whether it's a job, a health issue, the kids or a parent. The plan has to change with it.
He also offered advice any health professional will recognize. If you're unsure about the advice you're getting, get a second opinion.
Chris sat down with Steph O'Mahoney, who is building Vale Wealth, a firm designed for women first. Her argument is that the industry spent a century built around one kind of client, and it still shows in how advisors run the conversation.
Her fix is simple. Don't open with the portfolio. Open with the question that matters: What's keeping you up at night? Picture your 80th birthday. Who's there? What have you put in place for your family?
Steph was blunt about the basics, too. She described a friend who sat in a meeting about a significant inheritance, her own inheritance, while the advisor spoke only to her husband. Her standard for the industry is to treat every person who comes to you the way you'd want your own sister or mother treated.
For chiropractic couples, where one partner often runs the practice and the other runs much of the household, that lands close to home. Both people need to be in the room, and both need to be spoken to.
Jennifer Strymecki is a Canadian cross-border planner with Transition Financial Advisors Group, practising out of northern New Jersey. Her contrarian take was that too many conversations are about the investments. She would rather start with your life: what drives you, what makes you happy, and whether you even plan to stop working.
She pointed out that an investment account is a means to an end, and that no AI tool is going to get your plan fully right for you.
Two of her habits are worth borrowing. She tries hard to get both partners into the meeting, because the person who shows up isn't always the one who makes the decisions. And she opens every new relationship by asking how do you learn? Some people want charts. Some want the spreadsheet behind the charts. In a couple, it's often one of each.
She also raised something we think about for our own clients. Plenty of chiropractors practise in Canada for fifteen or twenty years and then look south. If that might be you one day, it's worth knowing that planning across the border is a very different exercise.
Shaun Maslyk is a financial planner in Edmonton, a positive psychology practitioner and host of the YouPotential podcast. He started by turning the question around on Scott: does money buy happiness?
Then he walked through the research, which is more interesting than the headline most of us remember. The famous finding that happiness stops rising at around $75,000 of income came from Daniel Kahneman and Angus Deaton. It measured in-the-moment emotional well-being, not the bigger question of whether your life feels meaningful when you look back on it. Later work by Matthew Killingsworth found that well-being kept rising with income well beyond that level. Killingsworth and Kahneman then teamed up to reconcile their results. Shaun's summary is that for people who already have a reasonable baseline of happiness, more money can keep helping, and for people who don't, it tends to flatten out.
So the better question may not be whether money makes you happy. It may be whether you've built the things money can then amplify: relationships, engagement, meaning, accomplishment and health. Shaun pointed to Martin Seligman's PERMA framework as one way to think about those building blocks.
Money buys security, freedom, options and experiences. What we do with those is up to us. His closing thought: people are messy, beautiful creatures, and even someone who reads all the research doesn't have it figured out. You get a little better at it one day at a time.
Five people, five practices and five different starting points, and none of them opened with returns.
They opened with spending, with the route rather than the destination, with what keeps you up at night, with how you learn and with what makes a life feel good. Each of them was answering the same question underneath: are you going to be okay?
That's a planning question, not an investment question. It's also the one worth asking before any other money decision you make this year.
The one thing: The portfolio is the easy part to get right. The real work is knowing what the money is for and whether you'll be okay.
Listen to episode 051 of The Chiro Money Show →
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