I’M IN NO HURRY TO retire—but I am making sure I’m prepared. I’m age 56, and I plan to work full-time until 70 and part-time until 75. I’m an English professor, and I enjoy teaching, service and scholarship. I also enjoy having three weeks off at Christmas and two months in the summer.
I received a fairly large inheritance, which has been growing over the years and which will allow me to do some special things in the years to come.

I’M NOT A SAVVY investor, nor do I pretend to be. Some people get paid to analyze and make predictions about stocks, often for people like me. How reliable are their opinions? I’m not so sure.

Take the newsfeed about my largest single stock holding, the utility Public Service Enterprise Group (symbol: PEG), that I got late last month from my Fidelity Investments account:

“Guggenheim Downgrades Public Service Enterprise Group to Neutral From Buy,

LAST YEAR WAS OUR first full year living solely off our portfolio, with no paycheck coming in.
How did it go? It was a vast improvement from 2022, when we not only retired, but also got hit with high inflation, tumbling bond prices and a sharp stock market decline. We were looking at sequence-of-return risk—that perfect storm of rising living costs and a shrinking portfolio that can derail those early in retirement—and I can recall feeling a bit panicked.

“YOU CAN PAY ME NOW—or you can pay me later.” Years ago, that was the catch phrase, spoken by an auto mechanic working on a broken-down car, in ads for FRAM oil filters. The pitch: If you spend a modest sum on routine car maintenance, you’ll avoid far bigger bills down the road.
The same philosophy applies to retirement savings. There’s a constant tradeoff between now and later.
Faced with life’s challenges, we need to strike a balance.

THE S&P 500 INDEX just hit a new all-time high, topping 5,000 for the first time. Is it now too high? For investors concerned about market risk, this is an important question. But it isn’t an easy one to answer.
For starters, there’s no single definition of “too high.” Consider the price-to-earnings (P/E) ratio, the most common measure of market valuation. By this metric, the market does indeed look pricey. The P/E of the S&P 500 stands just a hair below 20 based on expected 12-month earnings—far above its 40-year average of 15.6.

HAVE WE GOT IT ALL wrong? “It” is our relentless, lifelong focus on socking away great wads of money, so we don’t have to worry about earning another penny once we reach our 60s.
In fact, adherents of the FIRE—financial independence-retire early—movement aim to reach this blissful state far earlier, perhaps even in their 30s. This, of course, involves saving voraciously, with all the financial sacrifice that’s entailed. Even retiring in our 60s can seem like a Herculean task,

I KISSED REBALANCING goodbye. In any case, I wasn’t consistent about rebalancing our retirement portfolio.
I’ve never attempted to maintain a specific stock-bond ratio. Whenever I did something akin to rebalancing, it was usually in response to some vague discomfort about the level of risk we were taking. Or it was based on a hunch about where the market would move in the near future—typically misguided.
This latter activity is also known as market timing.

I WAS WORRIED ABOUT what we’d be giving up when, a few years ago, we moved to a 55-plus community in Atlanta. We downsized from a large home to a small apartment, plus all our neighbors were considerably older. It was obvious we had to adjust and start enjoying our unfamiliar environment or we’d end up miserable.
My wife and I made a conscious decision to slow down, and make every effort to get to know other residents and their life stories.

ONE OF THE MOST exciting events at a track meet is the relay race. Each runner has to run his or her leg, and then hand over the baton to the next runner. If the baton gets dropped, the team usually loses.
My wife and I occupy two roles in our financial life. I save the money and my wife spends it. This arrangement works well for my wife. When she complains about my frugal nature,

“SO STEVE, WHAT BRINGS you to therapy?”
“I’ve been moody, sluggish and short-tempered lately. I think I’m depressed.”
“Any guesses what might be going on?”
“I do, but it’s so silly. My wife Alberta needs to make her first required minimum distribution in a few months. You know, when you reach that point in your 70s where they make you withdraw from your retirement accounts. I don’t think it’s about the tax liability. We’ve planned for that.”
“Then?”
“This is going to sound strange.

FANS OF PROFESSIONAL sports know the excitement and agony of watching each year’s fresh crop of rookies. These young players have to relearn a game they thought they knew.
The fact is, the strategies, tactics, intensity and winning habits of big league sports teams are tougher than those of college and minor league teams. That can leave rookies wondering what hit them when they move up to the big leagues.
That’s how I felt in December 2022,

I’VE WRITTEN BEFORE about the financial benefits of learning to cook and then preparing meals at home, rather than frequently eating out. I still heartily endorse that notion. Still, our recent decision to remodel our kitchen can’t be defended as a wise financial choice.
In fact, the consensus is that almost all remodeling jobs result in an increase in home value that’s less than the remodeling project’s cost, and that includes kitchen renovations. Instead,

SOME FOLKS SEEM HAPPY to tell the world how much they earn, how much they have in the bank and what their portfolio is worth. Not me.

If I were to share my income and net worth, I’d expect some serious consequences, and not just from local thieves. In fact, I’m so cautious I have a plan not to tell anyone, except my wife Connie, if I win the lottery.

To be sure, overt sharing often isn’t necessary.

I DIDN’T ALWAYS LIKE my retirement. After I quit my full-time job, I briefly went to work for another aerospace company. It seemed like the perfect arrangement for a retiree: just 16 hours a week, with the luxury of setting my own schedule.
But it was the same old pressure cooker environment that I’d wanted to get away from. Although I was working fewer hours, it didn’t feel like I was retired. Instead, it felt like the same old grind.

ROGER PENSKE STARTED as a race car driver, but soon found he’d be better off as a team owner. Penske’s holding company also has stakes in Penske Truck Leasing, among other businesses, as well as the Indianapolis Motor Speedway, home of the Indy 500.
One of Penske’s criteria when hiring race car drivers: select folks with a burning desire to win. Penske has said he can guide a driver’s thinking about the best way to pursue wins,