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What My Dad’s Death Taught Me About Personal Finance

My father was fifty-one when he died of cancer. And with the exception of a house, a mortgage, and a little life savings – he died penniless.

Dad loved to fly. He became a flight instructor to help pay for his hobby, as a way to spend more time in the sky.  He would share his love of flight with anyone. He’d charge only what he thought you could afford, but the truth is, he’d have done it for free. 

There was only one thing dad loved more than flying: His boys. He made huge sacrifices for me and my brother. He sold his airplane to help pay for college and insisted that we get our degrees. He would have liked to fly every day, but put his dreams on hold until we could finish school.

He talked about downsizing his home in order to afford an amphibious aircraft, something he could land on a lake he might call home.  He was going to start saving for retirement as soon as we were out of school. He just never got the chance.

It didn’t have to be that way.

The irony is that my father’s sacrifices provided me with the education, training and set of transferable skills that could have saved him the sacrifice in the first place. I could have readily shown him how to put his kids through school, save for the home on the lake, purchase his dream aircraft and retire comfortably. The kicker is, he might even have been able to do so without changing his standard of living or the amount of money he got to spend every month.

I do not believe people should have to struggle financially simply because they cannot throw a 98 mile-an-hour fastball or star in this years’ Academy Award winning film.  I believe that people just like my dad can send their children to college, retire early and debt free with well over a million dollars in retirement savings. And I believe they can do it on a middle income wage earner’s salary.

Most of what appears above I wrote more than 20 years ago – a few years aftermy dad passed. I never shared it, never made it public, never completed it until now. But I came across it recently and realized that what I had (merely) believed back then, I can point to now.

I have evidence.

Evidence you don’t have to struggle financially. That you can put your kids through college, retire debt-free, and become a millionaire. And evidence that those skills are indeed transferable.

I recently became a private pilot myself. And as I was going through the training I got to thinking, no one would ever think you learn to fly an airplane in your head. As if you take a class, pass a final exam, and then some bloke hands you the keys and says “okay, have at it.”

We all recognize you don’t learn to fly an airplane in your head – with knowledge, and information. You learn how to fly an airplane in your body – with skills, and with sensibilities.

Yet when it comes to personal finance, too often we often we retreat back into our heads. Traditional financial planning leans heavily on knowledge and information, relying on probability analysis and predictive algorithms to pre-determine the path to achieving ones financial life goals.

But the world doesn’t work that way. The future has always been uncertain. And the speed and complexity of today’s change is leaving many Americans behind – disoriented and struggling to cope. 

What worked in the past is no longer adequate. And knowledge and information, once stable sources of economic power, are no longer enough.

What is needed is a radical reinterpretation of financial planning

This orientation towards prediction and probability is at the root of the problem we see with traditional financial planning. In our view of financial planning, skills matter. And because new skills make available new possibility, our primary aim is to help clients cultivate the personal financial skills and sensibilities necessary not just to cope, but to thrive in a world of uncertainty.

If life were merely random there’d be no point in cultivating new skills. And no reason to engage in our brand of financial planning. Your possibilities would be defined by your probabilities. On the other hand when nothing is certain, far more is possible. It’s in this spirit of uncertain adventure that we engage with you in conversations for possibility, for co-creating your future, and for reinventing your financial reality. Call us, and let’s discover what’s possible for your unique financial situation. 

Written By

Don St. Clair, CFP®, AIF®, ChSNC®, CCFC

Don has spent his entire career helping clients turn Debt & Taxes into Savings & Investment™. His primary aim is to help clients discover new opportunities and create possibilities not previously imagined.

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Our unique approach emphasizes the integral role taxes play in personal finance, and leverages the value of tax planning by incorporating tax considerations into the entire financial planning process.

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While many of our clients are already retired, our pre-tirement planning services are specifically designed for self-employed professionals. If you’re self-employed, pay too much tax, and are looking to make work optional – we can help.




1. The time of transition from “working too much” to “making work optional.”