I was cleaning out my basement recently when I found a copy of one of my business school recommendation letters.
It was written by one of the traders I worked for at my first job on Wall Street.
The letter was nearly 30 years old.
As I sat there reading it, I expected to find a younger version of myself. Someone less experienced, less polished, and less mature. Instead, I found someone who was surprisingly familiar.
One section read:
"John becomes a leader by necessity. He tends to stay in the background... He always seems to know what should have been done, or has a better idea for how some task should be accomplished, but often keeps his ideas to himself for too long."
That one hit a little close to home.
I've known for most of my adult life that my instinct is to observe first, analyze second, and speak third. Under pressure, I can be decisive, but I have spent decades trying to become better at stepping forward before the pressure arrives.
I've worked on it for nearly 30 years.
And I'm still working on it. (Please, let my long suffering wife know too if you can.)
The funny thing is that I don't view that as failure anymore.
When I was younger, I believed personal growth meant eliminating weaknesses. but now I think it means understanding them. This is a subtle but important difference.
Most of us are not blank slates. We don't wake up one day and become completely different people. We can improve. We can learn. We can develop better habits and better judgment. At the same time, our fundamental wiring is remarkably persistent.
The older I get, the more I believe success comes less from changing who we are and more from understanding who we are.
That idea has shaped how I think about financial planning.
The Problem With Most Financial Plans
Many financial plans are built around an imaginary person.
The plan assumes that you'll never panic during a bear market. (Or that a hero financial advisor stops you from panicking. LOL)
The plan assumes you'll spend exactly what the budget says.
The plan assumes you'll save consistently, delay gratification, and make perfectly rational decisions for decades.
In other words, the plan assumes you'll become someone else.
The problem is that real people don't work that way.
Some people are naturally cautious.
Some are naturally optimistic.
Some need simplicity.
Some need flexibility.
Some need guardrails.
Some need permission.
Some need accountability.
The best financial plan isn't the one that looks perfect in a spreadsheet, it's the one that works for the person who has to live with it.
Why Asset Life Matching Resonates With Me
One reason I developed the concept of Asset Life Matching is because it starts with reality.
Not with market forecasts.
Not with risk questionnaires.
Not with what someone claims their risk tolerance is on a Tuesday afternoon.
Instead, it starts with the life that money is supposed to support.
A family paying college tuition next year has different needs than a retired couple funding spending twenty years from now.
A physician nearing retirement has different needs than a young entrepreneur building a business.
The time horizon of the asset matters.
The purpose of the asset matters.
And just as importantly, the personality of the person matters.
The plan has to fit both.
The Other Part of the Letter
The recommendation letter also contained praise that was gratifying to read.
The author described me as honest, frank, calming, and "a breath of fresh air" in an industry dominated by greed.
I'd like to think that part still holds up too, because the longer I do this work, the more I realize that technical knowledge is only part of the job.
Clients don't hire advisors because they can't find a tax table.
They hire advisors because major financial decisions are emotional.
Retirement is emotional.
Selling a business is emotional.
Inheriting money is emotional.
Losing a spouse is emotional.
Market declines are emotional.
Sometimes the most important thing an advisor can do is help people make a good decision while they're experiencing a very human reaction.
The recommendation letter mentioned that I had a calming effect on people.
I smiled when I read that because, whether I realized it at the time or not, that may have been the most relevant qualification for the work I do today.
The Goal Isn't To Become Someone Else
Finding that letter reminded me that I've been working on some of the same challenges for almost three decades.
I suspect I'll still be working on them ten years from now.
And that's okay.
The goal isn't to become someone else.
The goal is to know yourself well enough to build systems, habits, relationships, and plans that work with reality instead of fighting it.
That's true in life.
And it's true in financial planning.
A good financial plan should not require you to become a different person.
It should help the person you actually are make better decisions.