It was inevitable, but I am starting to see comparisons made to the current market environment and other monumental periods of the past. This time, 1987 seems to be cropping up. Part of it has to do with valuations, but also because major indices continue to hit new highs, as they did in 1987.

All of this drives me crazy. It isn't because I don't have some concerns about valuations, as I am having a devil of a time finding many truly cheap stocks (but what else is new?). But the continuous quest to identify the next great pullback almost always is framed by some other pullback, a ghost from the past. Maybe that's just part of human nature or investor behavioral psychology and it makes for good controversy and draws in readers. But does it really help investors?

As we slowly approach the 30th anniversary of Black Monday, Oct. 19, 1987, and as comparisons with back then to the current market environment become more prevalent, it's time to head off at least some of the rhetoric we may be hearing in the coming months. I remember it like it was yesterday, if only because I was a senior in college who was seeking a job at the time in financial services.

The nearly 23%, 508-point drop in the Dow Jones Industrial Average that day seemed like the beginning of the end to this then-21-year-old job seeker. The beginning of the plunge was announced to us by our economics professor, free-market (Austrian school) economics guru Dr. Hans Sennholz. He was beaming as he told to the class, "The markets are crashing" in his thick German accent. For weeks, Sennholz had been warning students about the growing excesses in the markets. Indeed, several students in the Futures class that he was teaching at the time felt compelled to buy deep out-of-the-money puts on the S&P; the story at the time was that a $400 investment became $30,000, a tidy sum in 1987, especially for a college student. Years later, with access to a Bloomberg terminal, I did the analysis and the numbers were correct.

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That was a very different time. The prime rate stood at 9.25%, and there was euphoria in the air. Mutual funds were starting to go mainstream at that time, and there was very much an air of "pick a fund, any fund" and watch it rise 20% over the next year, easily. The all-time highs that markets were hitting came at a time when information was much tougher to come by then it is now. Bloomberg was in its infancy, financial news coverage was not nearly as robust as it is today (maybe a positive), and any stock-related research we did always began (and probably ended) with Value Line. Al Gore had not yet invented the Internet.

I certainly don't sense the same type of euphoria nearly 30 years later. The all-time highs the markets are hitting seem tepid, and investors, still anchored to 2008-09, seem to be fearful of what may be lurking behind them.

It's not another 1973-74, 1987, 2000, or 2008 that I fear. I'm more concerned with the $20 trillion in debt that we've managed to build, half of it in just the past eight years, and how that burden ultimately might affect the markets. I recall dear old Dr. Sennholz warning us about this 30 years ago.

This article is commentary by an independent contributor. At the time of publication, the author held TK positions in the stocks mentioned.