I’ve Had Terrible Timing My Whole Career – Class of 2026, Welcome to the Club

Today’s article is dedicated to the Class of 2026. My points, however, are relevant for all of us.

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You see, all my life, I’ve had terrible timing. If you’re in the Class of 2026, then you do, too.

As you know, you’re graduating into a difficult job market. Unemployment for your cohort is higher than average, and many of you will be underemployed when you do find work. Salaries for your group are where they were a decade ago. AI won’t make it any easier.

Once you get a job, you’ll quickly learn that, year after year, employees are asked to do more with less. AI will exacerbate the trend. Sorry.

I don’t mean to lessen the challenges that you will face. What I want you to know is that you aren’t alone. I’ve been there. My age group, parents to many of you, started off where you are now.

This is my story of a lifetime of bad timing.

Born during a bear market, it never got easier.

The chart says it all. There’s been a recession, or some type of economic weakness, at nearly every major educational or career milestone in my life.

The blue line is the S&P 500 (SPX), which measures the performance of the stock market and the health of the economy. Since I was born, it’s up 76x. $100 invested on the day I took my first breath would be worth around $7600 today.

The red line shows how much the S&P 500 has fallen from its prior high. Compare it to the blue line, and you can see it.

Pretty much every major educational and career milestone in my life has coincided with big drops in the stock market. Yes, I have bad timing. This is the hand that was dealt to me, and I’ve done my best with it. You will, too.

I was born into a bear market. Stocks dropped 36% before I learned to walk. Had I read the newspaper when I first became a reader, I’d have seen that the market was down 28%.

80s music was fun. The economy was less so. The year I went to middle school, stocks lost 27%. I was a college freshman during the 1987 Crash and panicked that I would have to leave school. I was spared, but graduated in 1991, during an economic recession that coincided with the Gulf War and spiking oil prices. There were few jobs to be had.

I started working on Wall Street in 1992. I found that first job through a family connection, but it was anything but a dream job. The $14,000 salary it paid barely covered the cost to commute from my grandmother’s house. Living in Manhattan was not an option.

As the market soared, I was hired to be a trader. All was well… Until I applied to business school. That was during 1998, when the literal geniuses at Long Term Capital Management got greedy and tanked the entire stock market. A 19% drop. While the tech stocks recovered, the rest of the economy was more bust than boom.

As you can guess by now, the stock market would stumble while I was at business school. From the time I entered NYU’s night school in 1999 to the time I earned my MBA in 2002, the S&P 500 would drop 49%. Tech stocks would fall even further!

Shocker, I would not find a new job for more than a year.

You get the idea. The pattern hasn’t let up. Not when I started teaching at CU Boulder in 2020 (pandemic!), and not when I began working at TheStreet Pro (Putin invaded Ukraine).

AI Took My Job

Some of you are skeptical and think it wasn’t that bad. It’s not like AI took my job.

But it did. I’ve lost at least one career to AI. When I started on Wall Street, the trading floor looked a lot like it had in 1929. When I left in 2002, computers were taking over. In fact, when I left my last job as a trader, there were around 30 of us at my firm. Within ten years, all but three had been replaced by a computer.

It’s not just me. The New York Stock Exchange used to be packed with thousands of traders and their assistants. Now, it’s a fairly empty TV set used to film the business news.

AI came for the Wall Street jobs first.

So, yeah. From a career timing perspective, I’m cursed.

I’m within a decade now of retirement, so all I can say is, you’ve been warned.

Graduating into a Tough Market

This story sounds like it’s about me, but it’s not. It’s a story of the economy, told through my experiences. I’ve left out the good stuff, though. You see, I’m an optimist. Times are tough now, but in the long run, things get better. The economy drifts higher most years because people like you and me work hard to build our lives.

If you haven’t yet, you will find a job. It may not be your dream job, but you will make the best of it, and you may even love it more than the career you thought you wanted. I never thought I would be a writer or manage a team as talented as the one I do at TheStreet Pro. I love what I do now, but it was a windy road to get here.

Words of Advice

First, economic volatility will be a part of your life. Prepare for it. I’m on my third career now and look forward to the day when I start my fourth. I have no idea when or what it will be, but it could be the best one yet!

Second, learn to write. Communication skills and your ability to think are what differentiate you from AI. Plus, you don’t really know what you think until you write it out. That’s how you learn what’s true and what isn’t.

Third, and most important, be young. Get out of your house and have fun with your friends. Make new friends, too! Be social. Make memories. Not only will your life be richer, but your career will be, too.

Finally, invest for the future. Play the long game. And that means you should invest for the long run, too. Put away a little each month, and by the time you are older, you’ll have enough to buy a house or retire.

On TheStreet Pro, Kate Stalter and I have been writing articles that we hope will help people plan and grow their wealth. It’s part of our Filthy Rich Animal series. Our Filthy Rich Animal Basics are ten articles that show you how to invest and make the case for why you need to. We discuss how you can build a portfolio using ETFs like the SPDR S&P 500 ETF (SPY) to own a wide basket of stocks, or the iShares Russell 2000 ETF (IWM) to invest in small-cap companies with lower risk. ETFs can even help you invest in bonds, like the iShares iBoxx Investment Grade Corporate Bond ETF (LQD).

One of my favorite articles is “Investing is Rigged (In Your Favor).” It shows that the market is stacked in your favor and lays out a plan for getting rich slowly.

If you’re interested in learning more and becoming an advanced investor, TheStreet Pro will be here to provide guidance.

Bottom Line

Congrats to the Class of 2026. You have terrible timing. But remain optimistic, and you’ll find ways to build a fulfilling career and grow the wealth you need to retire comfortably.

I know you can do it. I’m rooting for you.