Why Are the Smartest People I Know So Lost When It Comes to Money?

It's late 2025, and I'm at a playground watching my son swing along the monkey bars. I'm there with two friends who are both physicians and have kids about the same age. It's the usual Saturday afternoon in October when the leaves are falling. While the kids run around together, we get to talking. This usually starts with small talk, but because I'm an investment professional, I usually end up being asked for financial advice. This conversation is all too familiar as these guys ask me all the time because they are daunted by everything to do with their personal finances. It's tough for me too because I'm not a financial advisor, so I'm limited in what I can say and do. It's different for each of them too. One has a good bit of cashed saved up but no clue where to start and the other has a financial advisor that he's satisfied with but knows the guy doesn't do everything he could for him. Both are good earners, but don't know what their net worth is, when they can retire or what to do when their mortgage comes up for renewal.

Why do smart, high-earning people feel lost with money?

This is a pattern. It's not just them — it's everyone. I see the same confusion showing up again and again across my personal and non-financial professional network. I'm talking about smart people with good jobs. They're not bad with money per se, but genuinely underserved. It breeds a sense of feeling lost & confused. No one has a clear picture. After enough of these conversations, I've noticed 3 main clusters: 1) somebody who has an advisor but more than half the time they're unsatisfied with this arrangement; 2) using tools built for 22-year-olds just starting out or people living paycheque-to-paycheque; or 3) or doing nothing, because nothing felt right — voluntarily opted out. This is a massive amount of the population.

What does the search for a financial advisor actually look like?

Even as an investment professional, I also feel the pain from personal experiences. My wife is physician, and we combined our finances about 6 years ago when she finished fellowship and we were expecting our son and buying a house. Up until that point, I had been doing my own thing, but I felt like there needed to be a professional in the equation that wasn't me. So, we did the tour of a bunch of advisors. It's not my first rodeo with financial advisors/planners/retail brokers…whatever you want to call them, as I've been on the institutional side of the business for a long time, but this was still an eye-opening experience. Where it got weird for me is that we were referred to a small firm through a close personal relationship. I've been working in finance long enough to have a pretty good idea who's good and who's not in Canada, but it was treated like I was being done a huge favor by these guys (it wasn't, it was a favor for them). I went to the meeting anyways, and the red flags started going off right away. It got worse the longer I listened to them talk. It was clear these guys were dishonest and incompetent. Even though there's no way we would go with them, now I'm in a pretty awkward position personally. I didn't need that.

Where do the existing tools fall short?

Then, I looked at what tech & innovation could do for us. Trust me, I looked at everything. There's a lot of budgeting apps that are great for beginners. There are robo-advisors — automated online investment services — that are competent, easy on your time but as soon as your life gets just a little more complicated than having a little money in a couple of accounts, it's not good enough. There are advisors and a good one is worth their fee, but you can't tell who those are and it's opaque, siloed and expensive. The "just Google it" approach produces noise, not clarity. For a 38-year-old couple looking at a new baby, a mortgage, no pensions and a little money starting to build up in various investment accounts — there's simply no tool that fits.

What does building your own financial strategy involve?

For my family, I pieced it together by going with an investment management firm to handle the portfolio (and at least have a person to call when you need to) as well as a tax accountant. Then I ended up handling the rest of the picture myself, which has been a ton of work. The most strenuous part was putting together a financial plan. I modelled it up myself, which took me every night for six weeks. When I was finished, I was happy with what I had done and felt a huge relief seeing the roadmap. However, I also sat in my basement thinking, 'there's got to be an easier way'.

What is YouGotThis?

That's why I created YouGotThis. YouGotThis is a personal finance platform for Canadians that puts your whole financial picture in one place. It's based on 3 pillars: 1) find out where you are now; 2) where you are going; and 3) we'll tell you how to get there. I designed it with the intention of being easy to use without being useless but also complex enough that you can make important decisions without it being too complicated to understand. It's a platform built for mass-affluent professionals — people with meaningful income and savings who sit below the minimums most private wealth managers target — who've outgrown simple tools and maybe don't want or aren't ready for an advisor. If you do want a professional at some point, we have that too. It covers net worth, investments, retirement, debt, education savings, estate planning — all in one place, with clarity and without gatekeeping. It runs through steps on where to start and what to do next. The goal: financial clarity and peace of mind.

If you're that doctor, that lawyer, that engineer — or if you advise them — I'd love to talk. We're building this for you.

Frequently asked questions

Why do high earners still feel lost with money?

The pattern described here is structural rather than a lack of ability: advisors are often unsatisfying arrangements, most tools are aimed at people just starting out, and some professionals opt out entirely because nothing fits. Without a clear full picture, even good earners may not know their net worth or when they can retire.

Are budgeting apps and robo-advisors enough once finances get more complex?

In the author's experience, budgeting apps work well for beginners, and robo-advisors — automated online investment services — are competent and easy on time. Once a household adds a mortgage, children, multiple investment accounts and no pension, those tools stop fitting, and searching online tends to produce noise rather than clarity.

What is a "mass-affluent" professional?

The term describes people with meaningful income and savings who sit below the minimums most private wealth managers target — physicians, lawyers, engineers and similar professionals. They have typically outgrown beginner tools but may not want, or be ready for, a traditional advisor relationship.

What areas of a financial picture does YouGotThis cover?

The platform covers net worth, investments, retirement, debt, education savings and estate planning in one place, organized around three pillars: where you are now, where you are going, and how to get there. It also outlines steps on where to start and what comes next.

This article is for educational purposes only and does not constitute financial, investment, tax, or legal advice. It describes the author’s personal experience and observations. Consider speaking with a qualified professional about your own situation.