Doing Money Backwards: Not Saving For Retirement, Buying The House Last, Living The Semi-Retired Life

Most of how I do personal finance involves a backwards approach. Backwards to the most common strategies on budgeting, home ownership and retirement. At the very least, I have come to embrace a philosophy of living more evenly across the lifespan in all areas of life. And, like it or not, most areas of life depend—to some extent—on money.

I explain what I mean by all of this in a second. But first, I fully realize and appreciate that the traditional approach can work.

One of the things I love most about the community we’re forming with this newsletter is how diverse it is. Over the last few months, I was surprised to discover a large number of people among us who will traditionally retire, own homes they live in, own property they rent out and/or have little to no interest in working into relative old age.

Yet, they subscribe to this newsletter.

This tells me two things:

• The idea of semi-retirement resonates. Even if you’ll one day completely retire, maybe you want to be semi-retired now or during your transition. Or possibly, to some people, semi-retirement is more a mindset than an actual thing.

• You absolutely can blend approaches. You do some stuff backwards. You do other things traditionally. Maybe you switch midway through, then switch again, as circumstances dictate.

It also tells me that times have changed. No matter how old you are, you’re not your parents. Most likely, you have lived and are living a radically different experience.

That said, even my near 89-year old father and I share some similarities. He mostly took the traditional approach. However, as I noted the other day, he also had several side hustles—he was partially self-employed—before having side hustles and being self-employed were cool things to do.

One of his side hustles was—

• Helping a local sports bookmaker. A bookie. Sounds crazy. But it’s really not. At a very young age, I even helped my Dad help the bookie! I’ll tell you the story one day.

Today is that day.