How I Ended Up in Retirement Planning

he somewhat indirect story of a finance book, a bad sales pitch, the military, accounting, and eventually finding the work I was actually looking for.

I have been interested in money for about as long as I can remember, although I definitely did not grow up thinking I would become a retirement planner.

Looking back now, there is a fairly obvious thread through my career. At the time, it did not feel obvious at all. There were a few changes of direction, a couple of encounters with the financial industry that made me want nothing to do with it, and quite a bit of figuring things out as I went.

The Wealthy Linesman

My dad was a blue-collar lineman for Telus. He did not work in finance, but if you looked at the bookshelf in my parents’ house, you might have thought otherwise. It was filled with the personal finance and investing books of the 1990s. Warren Buffett, Motley Fool, and all the other names that seemed to occupy that world at the time.

One day in my mid-teens, I picked up The Wealthy Barber. I do not remember exactly why that book caught my attention, other than the title sounding more interesting than most of the others. What I do remember is being surprised by how simple many of the ideas were. Save consistently. Spend less than you make. Start early. Protect yourself from the things that can really hurt you financially.

Then I would hear adults talking about money problems and wonder why there seemed to be such a large gap between knowing these relatively simple rules and actually living by them.

I did not have the language for it then, but I think that was the first time I became interested not just in money, but in how people make decisions about money.

By high school I was taking business, marketing and accounting electives and assumed I was heading toward a career somewhere in finance. The summer before university, I spoke with someone at a bank about potentially working there. At that age, I saw banks as the serious, respectable centre of the financial world, so I figured this was probably where people who understood money went to work.

My first look at the financial industry

The person I spoke with was not some random bank recruiter. She was the mother of a friend who worked at Scotia Bank, which probably made the whole conversation feel a little more real to me. I was about to start university and was genuinely interested in finance, so I asked her about what it might take to eventually work at the bank.

She told me they would not be able to hire me until I had at least a year of university behind me, but encouraged me not to worry. I was a charming young guy, she told me, and I would be very good at convincing old ladies out of their money.

I remember thinking, absolutely not.

The thing that interested me about finance was the idea that understanding money could be useful to people. The idea of using that knowledge primarily to sell something to them felt like the opposite of what I wanted to do.

So I changed my university plans that night.

A detour through political science and the military

Political science came with its own recurring question: “What are you going to do with that?”

My answer, for quite a while, was some variation of, “I have no idea.”

Eventually, that uncertainty led me into the military for a few years. It was not ultimately where I wanted to build my career, but it ended up being an important part of figuring out what came next.

One of my commanding officers had an accounting background. We talked about what I enjoyed doing and the kinds of problems I liked solving, and he suggested that I consider accounting.

That clicked.

Accounting brought me back toward business and finance, but from a completely different direction. It was analytical. There were rules. There were problems to solve. I could understand how businesses worked and how financial decisions eventually showed up in the numbers.

So I changed direction again and started working toward my CPA.

Apparently I was not quite finished testing whether the financial industry and I could get along. While I was in college, I spoke with someone from Freedom 55 Financial about what a career there might look like. They explained that the first month would largely involve cold-calling people to drum up clients.

That was enough to send me happily back toward accounting.

What accounting taught me

After earning my CPA, I worked for a few small accounting firms around Victoria. Accounting gave me a foundation that I still rely on every day. I learned tax, corporations, financial statements and how money actually moves through a business. I learned how to follow a decision through the numbers and understand where it eventually leads.

I also learned something about myself.

I did not particularly love looking backward.

Accounting, by its nature, spends a lot of time explaining what has already happened. The year ends, the transactions have occurred, and then you work out the result. How much did the business earn? What expenses were incurred? What tax is now owed?

That work matters, and I still value the training enormously. But I kept wanting to ask a different question: what should we do next?

The client who changed my direction

I was working at an accounting firm when a very successful business owner came out of a meeting in tears. She quietly grabbed her coat and left the office.

She had just been told that she owed more than $400,000 in tax.

The bigger problem was that she did not have the cash to pay it.

There were decisions she had made that contributed to the situation, but there were also professionals around her who understood her finances. We could calculate the tax perfectly. What bothered me was that we were calculating it after most of the useful opportunities to do something about it had already passed.

Eventually, we learned that she sold her house, shut down the business and moved away.

That one stayed with me.

I kept coming back to the same question. How does someone get that far before the problem becomes obvious? Why had nobody been looking ahead and asking what would happen if things continued on the same path? What could have been done a year earlier? Two years earlier? Five years earlier?

I went to one of the partners at the firm and asked whether we could do more forward-looking planning with clients. We already understood the tax and accounting. There were books, software and planning tools available. It seemed obvious to me that we could use what we knew to help people make decisions before the consequences arrived.

The answer was essentially, “We are accountants. We do not do that kind of thing.”

It was a perfectly reasonable description of the job.

I just realized it was no longer the job I wanted.

I was not at that firm much longer.

Building the work I wanted to do

After a stint working as a financial analyst with the BC government, I eventually came to a fairly simple conclusion. I could keep looking for a job that combined everything I wanted to do, or I could try to create one.

So I started Lotocky Planning and Tax.

The idea was to take what I had learned as an accountant and use it looking forward instead of only backward. Instead of just asking how much tax someone owed last year, I wanted to ask what we could do today to change the tax they might pay over the next twenty years. Instead of simply reviewing investment performance, I wanted to understand what those investments were actually supposed to accomplish. Instead of cataloguing what someone owned, I wanted to know what all of it could make possible.

That felt much closer to the work I had been trying to find.

Finding Dixon Davis

Not long after that, I crossed paths with Howard Dixon and Lenore Davis.

Dixon Davis had been doing financial planning since 1988. What interested me was not simply that the firm had been around for a long time. It was that decades of real client situations had shaped the way Howard and Lenore thought about planning.

They were asking the questions I had wanted to ask when I was an accountant.

I had the opportunity to learn from them and from a planning process that had already been shaped through decades of real decisions with real people. Eventually, I became the owner of Dixon Davis and continued refining that work.

Over time, I also became increasingly focused on retirement.

Why retirement

I have worked with people in their early twenties through to their nineties, across all kinds of financial circumstances, but retirement is the work I keep getting drawn back to.

Part of that is because retirement is technically interesting. Almost every part of someone’s financial life can collide at the same time. Tax affects income. Income affects investments. CPP and OAS decisions affect tax. Corporate assets can affect estate planning. Real estate affects cash flow. Helping your children can affect your own retirement. A decision that looks smart when viewed by itself can look very different once you see what it does to everything else.

I like solving that kind of problem.

But that is not really why I love the work.

Retirement is one of those points in life where financial decisions suddenly stop being theoretical. Someone can walk into my office asking whether they will ever be able to retire. They may have spent thirty or forty years thinking of retirement as something far off in the future, and suddenly it is right in front of them.

Then we start working through it. What do you actually spend? What income will you have? When should you take CPP? What happens with the pension? What should the investments be doing? What happens if you retire this year instead of three years from now? Can you travel more? Can you help the kids? What happens if the market falls? What are we missing?

A few months later, that same person may be handing in their notice.

I never really get tired of that.

It is always a privilege to be part of someone’s transition into retirement and watch the question change from “Can I actually do this?” to “Okay, so when am I leaving?”

I have also learned that good planning does not always mean finding something that needs fixing. Sometimes we uncover a tax issue or a better way to structure something. Sometimes the plan shows that someone can retire earlier or spend considerably more than they thought. Sometimes we challenge an assumption that has been quietly driving decisions for years.

And sometimes the most valuable thing I can say is, “I looked at it. This makes sense. I would not change it.”

That counts too.

How I think about planning

I still think like an accountant, and that probably explains a lot about how I approach planning today.

I believe the plan should drive the decisions, not the other way around. I do not think you should start with an investment product, a tax strategy or some clever financial structure and then try to fit your retirement around it. Start with the life you are trying to fund, then work backwards into what the financial pieces need to do.

I also believe complexity has to earn its place. There is almost always another strategy available, another account, another corporation, another tax idea or another investment structure. Some of those things are useful. But complicated does not automatically mean better. If the simple answer works, I would rather use the simple answer.

Most importantly, I believe the whole retirement matters more than winning any individual financial decision.

Sometimes paying more tax today produces a better lifetime result. Sometimes accepting a lower expected investment return makes the overall plan better. Sometimes giving money to your children today means leaving them a smaller estate, but creates far more value because you actually get to see what the money does for them.

That last one has become more important to me the longer I do this work. We can get so focused on preserving and optimizing that we forget to ask what the money is actually for.

The goal is not to win every calculation. It is to get more of what matters to you from the money you have.

How people actually make decisions

The longer I have done this work, the more interested I have become in something that rarely appears on a financial planning spreadsheet: human behaviour.

I have done extensive training in coaching, human behaviour and the heuristics that influence how people make decisions. That has become an important part of how I think about planning because people do not make decisions like spreadsheets.

We anchor to old assumptions. We become attached to things because we have owned them for a long time. We worry about some risks far more than others. We keep working because stopping feels uncomfortable even when the financial reason for continuing has disappeared. We can spend decades preserving an asset for our children without ever asking whether they actually want it.

I see versions of this all the time.

Someone tells me they absolutely cannot sell a property because it is for the kids. We ask the kids, and the kids do not want it.

Someone has convinced themselves that they need a particular number before they can retire, but cannot really explain where the number came from.

Someone is worried about paying a little more tax this year even though doing so could materially improve the next twenty years.

None of this means people are irrational. It means we are people. There is history, emotion and identity wrapped up in financial decisions, and pretending otherwise does not make for better planning.

Knowing the technically correct answer is only part of the job.

Being a thought partner and an outside voice

That is why I think of myself as a thought partner.

The person sitting across from me knows things I never will. They know their life, their family, their history, what matters to them and what they are afraid of losing. I bring the technical knowledge, the experience of having worked through thousands of financial plans and, often most importantly, an outside voice.

I think that outside voice is underrated.

Sometimes I agree with what someone was already thinking. Sometimes I see something they had not considered. And sometimes I challenge a belief that has been sitting there unquestioned for twenty years.

I do not need someone to agree with me. In fact, some of the best planning conversations happen when they do not.

What I want is for us to work through the decision well enough that they understand the options, understand the trade-offs and know why the path they eventually choose makes sense for them.

That, to me, is where expertise becomes useful.

It is not simply knowing a tax rule or understanding CPP or being able to build a complicated spreadsheet. Those things matter, but they are inputs.

The real expertise is knowing how to apply all of them to the decision sitting in front of you.

Back to the bookshelf

When I look back now, it is funny that so much of this started with a copy of The Wealthy Barber sitting on my dad’s bookshelf.

There were quite a few detours between that book and Dixon Davis. Political science. The military. Accounting. Government. Starting a business. Two encounters with the financial industry that mostly convinced me not to join the financial industry.

At the time, none of it felt like a particularly coherent career plan.

Now it does.

The question that interested me as a teenager is still basically the question that interests me today: what is money actually for?

For most people, the answer is not simply to accumulate as much of it as possible.

It is to retire, travel, spend time with family, help your children, work less, keep working because you genuinely enjoy it, give something away, take a risk, simplify your life, buy the property you have always wanted, or sometimes just know that you have not missed something important.

The tax matters. The investments matter. The spreadsheet matters.

But they are not the point.

The point is what all of it makes possible.