Summary

Rocco Pendola, a writer and newsletter author, embarks on a journey through seven cities in Spain and France, sharing personal finance insights for those who plan to never retire, while reflecting on his own financial journey and the ongoing retirement crisis.

Abstract

Rocco Pendola is currently in Barcelona, the first stop on his month-long trip through Spain and France, where he plans to publish 16 posts in February 2024. These posts will focus on personal finance and investing, targeting individuals who embrace a semi-retired lifestyle rather than traditional retirement. His content will include urban and food photography, cost of living comparisons, and mock grocery store price comparisons between Los Angeles and the cities he visits. Pendola's work is informed by his past experiences, including his initial career in radio with a starting salary of $26,500 and his subsequent financial challenges and lifestyle inflation. He candidly discusses his early financial mistakes, such as selling investments and accruing credit card debt, and the realization in his mid-to-late thirties that he would not achieve traditional retirement. This led to a reassessment of his financial strategies and a commitment to a different path, which he now shares with his audience to help them navigate their own financial futures.

Opinions

Pendola believes in the importance of practical and psychological adjustments to deal with the reality of never retiring.
He emphasizes the value of his newsletter for those interested in living a semi-retired life and preparing for financial independence.
Pendola reflects on his past financial decisions with a sense of acceptance rather than regret, viewing his mistakes as necessary steps towards his current financial wisdom.
He suggests that had he known then what he knows now, he could have been financially independent with a seven-figure bank balance.
Pendola acknowledges that life is a learning process with financial fits and starts, and that his journey can serve as a learning experience for others.

16 Posts In February For People Who Will Never Retire

From seven cities in Spain and France

Right now, I’m in Barcelona, Spain. The first of seven cities I’ll visit on a February-long trip through Spain and — mostly — France.

In my newsletter (Medium readers can subscribe here for a nice discount), I’m doing a few things during this trip —

Publishing 10 posts on basic-to-intermediate personal finance and investing, inspired by my work at CNN and geared towards people who will Never Retire and want to Live The Semi-Retired Life.
Writing from each of the seven cites on the itinerary — Barcelona, Girona, Montpelier, Lyon, Paris, Bordeaux and Toulouse — with urban and food photography, general observations and cost of living comparisons.
Making mock (as in we don’t actually buy everything), but actual grocery store runs to compare prices between Los Angeles and a couple of these cities.

Of course, you can subscribe and go there to see that.

To get a good sense of what we do in my newsletter, I decided to dedicate February 2024 on Medium to looking back at what we did in the newsletter during February 2023’s journey to Spain and Italy.

So, this month I’ll adapt the still very relevant posts I published after 2023’s trip to address the ongoing retirement crisis we continue to deal with in 2024. It’s the way I decided to respond to this crisis that helped me grow an audience on Medium, which helped me start a successful newsletter.

This series takes you through the steps I went through as I accepted the reality that I’d Never Retire, then figured out how to deal with it — practically and psychologically. I hope you enjoy.

And I hope you’ll subscribe to receive a notification each time I publish a Medium article by going here. Then, head to my newsletter to subscribe for access to everything we’re doing not only on this trip, but in preparation for my January 2025 move to Spain.

Never Retire Checklist Item #1: Assessment Of Your Situation

In Spring of 1995, on the eve of my 20th birthday, I moved away from home.

To Miami. For my first full-time job in radio.

The gig paid $26,500 a year. Or roughly $2,208 a month, before taxes. That was not a lot of money. Not even 27 or so years ago. Especially in one of the nation’s most populated regions — South Florida.

I should have — I wish I would have — realized then that I’d Never Retire.

Of course, I didn’t. The thought wasn’t part of my vernacular.

I was following the typical trajectory: upward mobility on the way to traditional retirement.

Anything less would have been selling myself short. A failure.

Throughout my teen years — without bills to pay — I invested regularly.

Through mutual funds and dividend reinvestment plans in a handful of individual stocks, I built a decent size nest egg, especially for a kid.

However, when I got to Miami, it was incredibly difficult to make ends meet.

So the first thing I did to cover my monthly shortfalls was sell investments to raise cash. I did this until I had nothing invested. It didn’t take long.

After blowing through this savings, I turned to credit cards to help finance life.

Looking back, I did what I had to do at the time knowing what I knew at the time.

I was embarking on a career where I would move up the ladder, each job paying more than the one that came before it. For the six years I spent working full-time in radio (I had been working part-time since I was 13, so I was in the business for a total of 12 years), this actually happened.

When I moved to Pittsburgh after a year in Miami, I made $45,000, then $50,000.

Then, in Dallas, my base salary increased to $65,000 and $70,000. With incentives, I came close to $100,000 a year. In Las Vegas, I think I was making $80,000 a year.

The first job I had outside of radio — in San Francisco in 1999–2000 — brought in more than $100,000.

Sounds amazing. As if I was executing the plan.

However, there were two problems with what I was doing —

In Miami, I got into credit card debt.
Throughout my twenties, I had the attitude that I’d always increase my salary so I could continue to spend more than I made because, at some point, I’d be established in a high-paying job that would (1) eliminate the debt, (2) afford the lifestyle I had become accustomed to and felt I deserved and (3) allow me to save enough to secure a traditional retirement by 55 (or thereabouts).

I was effectively robbing Peter to pay Paul.

I was also always raising the bar.

If the $65,000 salary can accommodate a $85,000 lifestyle, the $80,000 salary could take care of a $100,000 lifestyle. And so on. It’s not like I was spending recklessly. I was living life under the guise of I’d always make more so I could spend more. Eventually, things would even themselves out.

Alongside my upward mobility/lifestyle expansion attitude, this was a good way to dig a personal financial hole for myself.

I’m sure more people than would care to admit have some variation of this history with money as it meets lifestyle.

Interestingly, if I knew then what I know now and followed the strategies and thought processes I follow now, I’d probably be fully-retired (if I wanted to be) with a solid seven figures in the bank.

But hindsight is 20/20. And very few people go through life making all of the right decisions, particularly with money.

Life isn’t neat and tidy like this. It’s a learning process full of a shitload of fits and starts and trial and error.

So I’m not kicking myself. Not at all. Because had I not made the mistakes of my twenties, I would not have searched for a better course in my thirties and committed to it in my forties.

In my mid-to-late thirties, the light bulb went off. I missed my opportunity.

I was never going to save enough money to secure a traditional retirement. And I didn’t want to keep working so hard — 40+ hours per work — to try to salvage things.

It was only at this point where I began to assess my situation.

The kind of easy part — what was I doing wrong?
The really hard part — what should I be doing instead?

It would take a little longer before I got serious about making material change.

When I would actually acknowledge my situation and begin to act.

We pick up this part of the story in my next Medium article.