Fifteen Lessons from Fifteen Years
I started my career in September of 2010 at a global investment management firm in downtown Toronto. Sounds fancy, doesn’t it? Well, I answered phones in a call centre.
My job was to fix problems for advisors: I received countless calls from angry advisors about things like incorrect tax slips, missed RESP grants, and errors in our marketing material. I was the guy who turned angry advisors into happy ones. I fixed a lot of errors along the way too.
From there, I landed my first client-facing role at a credit union back here in Victoria. You know when the teller says, “Your chequing account balance is high, you should talk to an investment person”? I was that investment person. I wasn’t a great employee (I was a know-it-all millennial who knew nothing). As a result, I didn’t get along with my boss at all. But she gave me a shot early in my career when no one else would, so I have to say thanks to her for that.
My next stop was just as short and just as rough. It was from frying pan to fire. Different office, different boss, same lessons. Still, that boss pushed me to finish my CFP designation, and I will always give him credit for that.
Then in 2014, thanks to a local investment consultant*, I joined the firm where I would spend the next decade. The early years were hard: door knocking, cold calling, awkward networking events, even pestering friends. I eventually hit my stride, met (and hired) Carey, and built a practice I was proud of.
In 2024 I started Herlaar Wealth Management. Fifteen years has flown by. Here are fifteen lessons I’ve learned along the way.
Some of these lessons were obvious in hindsight, some I learned the hard way, and a few I’m still working on (and will continue to work on). But after fifteen years, these are the ones that have stuck.
- Speak less
Communication follows the law of supply and demand: scarcity gives your words value. I can’t remember where I heard this, but it’s too true: the more you talk, the less people listen.
- Rapport is hard, follow-up is harder
Building rapport is tough, and following up without being annoying is even tougher. Get rapport right and following up is simpler.
- Spreadsheets are not financial plans (sorry, engineers)
A plan is a snapshot. Planning is a process. Life moves too quickly to think you can script the next 30 years.
- Good leadership is priceless
One call-centre supervisor taught me about rapport after I constantly said I didn’t need help (know-it-all millennial again). And my mentor at my previous firm taught me about lesson number one. It took a while and he was patient (and probably annoyed a lot too). I’ve carried their lessons into every mentorship role I’ve held.
- Behaviour beats brilliance
Your behaviour is the biggest driver of investment success. Not timing, not forecasts, not IQ.
- Work with the right people
Advisors: you cannot be all things to all people. Boundaries serve both you and the client. Don’t bring on clients that don’t fit. You’ll regret it later and that client won’t ever be happy with you.
- Taxes and estates matter more than you think
Estate planning is more than “Do you have a will?” Tax planning is more than this year’s return. Both deserve serious attention, even if you don’t think they do.
- Insurance is an expensive but necessary piece of paper
If you have a spouse or kids who would be in trouble financially if you died, you need life insurance. Critical illness and disability often matter too. Review them regularly.
- Finance and economics are social sciences (sorry again, engineers)
They’re not STEM. Human behaviour drives outcomes. Treat them that way.
- Hire the right people
The job interview I conducted with Carey was about five minutes. “I’m looking for someone who does what they say they’ll do, won’t leave me hanging, and wants to work with me until they retire.” Without a shift in body language or an ounce of hesitation Carey said, “I can do that.”
- Incentives matter, until they don’t
As Munger said: “Show me the incentive and I will show you the outcome.” Goodhart’s Law reminds us that once a measure becomes a target, it stops being useful. It’s quite the tug-of-war.
- Parkinson’s Law is real
Work expands to fill the time allowed. Nothing derails progress faster than a project with no timeline. If you’re going to procrastinate, procrastinate tomorrow.
- Financial education is overrated (sort of)
You wouldn’t have cared about investing in high school. But timely education, at the right stage of life, is priceless. Risk comes from not knowing what you’re doing. The most valuable financial education should come from your advisor, because mistakes are expensive teachers.
- Investment risk is misunderstood
Risk isn’t volatility. Volatility is discomfort. Risk is permanent loss, bad behaviour, or failing to meet your goals.
- Most financial content is garbage (pot meet kettle?)
Financial media is filled with predictions, rants, and marketing dressed up as wisdom. Nobody knows what happens next. Nobody.
Those are my fifteen lessons from fifteen years, most learned the hard way. If there’s a theme, it’s this: behaviour beats brilliance, planning beats prediction, and humility beats hubris.
*That consultant also helped me with finding that first job in Toronto. He epitomizes the term ‘salt of the earth.’ I can’t thank him enough. Even if he is Chelsea Football Club supporter.
