What Missed Opportunity Will You Regret Most?

For me, 2024 was a year of regrets; not of having them but of pondering their meaning, mostly thanks to quotes from a well-known comedian and a somewhat lesser-known private-equity billionaire.

I’m not big on regrets, though several times I’ve told my two kids, who are now both in their twenties, that if I had it to do over again upon arriving home after many a long day at the plant, I would have grabbed a ball of one sort or another and headed over to the playground with them much more often than I did. They both find this amusing and have encouraged me to let it go. Perhaps one day I will.

More family time and less time at work. I’m not the first to ponder whether or not that might have been the better route. Many have heard the adage, “Nobody on their deathbed says I wish I had spent more time working.”

Comedian Jerry Seinfeld’s take on this topic, offered last spring during his commencement address to Duke University’s class of 2024, really struck me.  

Seinfeld said, “About work, you know how they always say nobody ever looks back on their life and wishes they spent more time at the office? Well, why? Why don’t they?”

And moments later, he added, “Don’t blame work. Work is wonderful. I definitely will not be looking back on my life wishing I worked less.”

I agree. Certainly, I’ll never regret time spent on family, faith and fitness. But maybe investing a little too much time working is something to be celebrated rather than condemned. After all, as owners, leaders and managers of machining operations, we do a lot of good through our work, helping to fuel an entire economy, provide the world with the products it needs and employees with opportunities that can change lives forever. Our work has deep meaning.

Which leads me, as often happens in this column, to the game of baseball. The Wall Street Journal’s Jason Gay is one of my favorite sports columnists. We email back and forth from time to time when one of his columns hits me. In his recent interview with private-equity billionaire David Rubenstein, who in 2024 acquired his hometown baseball team and the team of his childhood, the Baltimore Orioles, poured fuel on the fire of my recent obsession on the topic of regrets.

As to the logic of Rubenstein and a small group of partners acquiring the Orioles, Rubenstein noted, “What you tend to regret the most in life are the things you didn’t do.”

What if Jerry Seinfeld is right and working a little too much isn’t a bad thing? What if David Rubenstein is right and what we’ll regret most are the things we didn’t do? What strategies and endeavors in our businesses will we regret most if we don’t do them now? To paraphrase a line from Braveheart, “And dying in our beds, many years from now, would you be willing to trade all the days, from this day to that one, for one chance, just one chance” to come back here and do something epic? Perhaps now is the time.

Perhaps now is the time to double down on your business model and genuinely pursue that acquisition you have been thinking about for years.

Perhaps now is the time to build that new plant, expand your current one or add the new machine tool, process or emerging technology that will enable you to create even more products, services and jobs.

Perhaps now is the time to mentor and promote the next generation of leaders for your company.

Perhaps now is the time to add valuable members to your sales, quality or production teams.

Perhaps now is the time to put everything into landing that huge customer you thought you never could.

Perhaps now is the time to use your business to transform the market, or the world.

Perhaps now is the time to … you fill in the blank.

Many years from today, when it comes time to hang up your cleats, the crimson sun setting on your machining career, what will you most regret not having done if you don’t do it now?