To bring more structure and so you have a better idea of what to expect, I’m making a slight tweak to the Never Retire newsletter.
Going forward, I will publish a minimum of two posts per week, most weeks.
One, like today’s, will be for paid subscribers only and focuses on the theoretical aspects of my path to embracing the reality that I’ll Never Retire. With ample details from my personal experience, I detail how I deal with/have dealt with the practical and psychological elements and implications of this reality.
The theme underlying these posts—It’s not a bad thing to Never Retire.
It’s positive. A welcome, healthier alternative to the traditional retirement norm.
The other post of the week will focus on Never Retire-related research and concrete personal financial strategies, relevant to all, but specifically for those of us who will Never Retire (by choice, out of necessity, or both).
Frequently, I will intersperse additional, mostly free installments between these two.
Regardless of what resonates with you most, I encourage you to consider a paid subscription, which you can secure for 20% off on an annual membership.
With that in mind, part one of a series chronicling my journey over the last 30 years, focusing on the transition to where I am today—not just happy, but excited about Never Retiring.
I was obsessed with two things as a teenager: radio and investing.
These obsessions—supported by my working class family, who prioritized and rewarded ambition and work ethic—ensured I’d follow a traditional path through life.
And, for a solid 20 years, I did exactly that.
To situate your chronological compass, I was born in 1975. So I turned 47 this year.
In future installments of this series, we’ll look at what happened after that solid 20 years. For now, we focus on what set the stage for my lifestyle transformation.
As a teenager, I already had my sights set on traditional retirement.
I had my life all planned out:
Invest early and often.
Focus almost all my energy on my radio career.
Graduate high school and get a full-time radio job away from home (Western New York).
Become the next Howard Stern or sports radio equivalent.
Have a solid 30-year career.
Call it quits—retire traditionally—by or before age 50.
It didn’t take long for this plan to hit road bumps.
I was investing in mutual funds and individual stocks as early as 15 years old. After working in radio through junior high and high school, I got that full-time job away from home.
In 1995. As I was about to turn 20. In South Florida.
My annual salary: $26,500.
Even in 1995, $2,208 a month—before taxes—wasn’t a lot of money. Particularly if you followed convention and thought you needed a relatively big apartment and a nice car with your sights set on home ownership.
Funny side note—I can live better today on $2,208 a month (before taxes) than I was able to in 1995. This says a lot not only about how I’ve changed, but about the hysteria around inflation and the purchasing power of the dollar.
I rarely made ends meet. In fact, most months, I ran a deficit, using credit cards to keep things afloat.
At the beginning of what would become a repetitive cycle, I continued to invest regularly.
Looking back, it made absolutely zero sense. Sending money to investments at the same time as racking up credit card balances with interest rates in the teens. Not to mention the occasional cash advance good for 20%-plus interest.
If you’ve ever been in a similar situation, you know rationalization rather than logic prevails.
I was paying myself first.
I got paid on the 15th and 30th of every month. When my check hit my account, 10% of it went to my investment account.
I told myself I was doing the right thing, putting investments first.
I would soon start earning more money. At that point, I’d take care of the debt, stop using credit cards, and double up my wealth-building activities.
I was right about one thing. I did start earning significantly more money.
In part two of this series, we’ll get into what happened from there. From a financial standpoint, things got worse. While they never became dire—because I was making good money and I knew how to do the credit card dance pretty well—I should have seen the writing on the wall.
The writing on the wall.
Initially, we don’t see it. Then, when we catch a glimpse, but we ignore it. Sometimes for years. Like I did.
You become an active participant in turning your relationship with money into a struggle.
Next, I detail the writing on the wall and the long journey to not only reading it, but embracing and doing something about it.
This will include a discussion of the popular budget principle of paying yourself first and why it doesn’t always work and has never worked for me, no matter the financial position I’m in.
Even now—doing well with money—paying myself first ends up the wrong thing to do, in theory and practice.
A recent night in Los Angeles, looking north to Hollywood