A recent epiphany was important; it was a “be careful what you wish for moment” during a discussion with a colleague over rules and policies.

On one hand, you must have rules and protocol; on the other hand, a moral code that considers “principles over rules.”

It’s a constant balance; even though there are convincing arguments that bare feet are more sanitary than shoes, it is not worth fighting the “no shoes, no service” policies in place. Sometimes it is about prudence and respect, other times “rules are made to be broken.”

There are times in my businesses where rules are broken, punishments handed out, and penitence served. One incident involved doing something for a group of children who live in tough surroundings. Even though the expense was unauthorized, it was done with purity and the cost minor. The person breaking the rule took the punishment in stride, but one could see it was hard to let go of because it was minor and because it was done for the right reason, even if the rules didn’t allow for it. Serving humanity is an example of “principles over rules.”

Breaking rules can be met with different philosophies; one, you do the crime, you do the time. Another avenue is to create teaching moments. I want the latter as I enter my twilight years.

Thinking about “how do you punish love” gave way to thinking about one of my sons and how we need to be careful what we wish for.

We want our kids to be responsible. We want them to have a good grasp of money and, of utmost importance, we want them to be good and kind people. Sometimes, being responsible and being kind clash and our kids learn where the weight of their feet lies.

One night, when all three of my boys lived in Boston, I went to visit and take them to a ballgame. One son was struggling financially, working but unable to get ahead with high Boston rent that led to a lifestyle many of us have experienced; it’s called living “day-to-day.”

After working a double shift, he had $250 in tips, enough to pay the balance of his late rent and get the “monkey off his back,” at least for three weeks. Sharing shift drinks and watching Celtic’s highlights on ESPN, the busboy asked what it was like to see a game in person. He was a kid with a lifetime of struggle in his 20s and had never been to any professional sporting event.

At home that night, my son left $150 for his roommate and went online to buy a couple of cheap seats for that evening’s Celtics game — a surprise for his co-worker — saving enough for a couple beers at the game.

This story came out as I explored, in a fatherly way, his finances, asking for detailed “money in and money out” during the last month, hoping to find a pattern that might help him figure things out.

I said nothing as the story unfolded; how do you punish love?

He didn’t ask me for the $100 rent shortage, nor did I offer. He needed to figure out his own code, and he was much closer at his age than I had been.

There is a fine line between teaching moments and punishment. The first is preferred but sometimes we learn more in our “not so proud” parent moments, reminding us how hard it is to be father, a role model, or a boss.

Teaching moments can be hardest when in the thick of it. During the early 1990s, a struggling business and three kids under 4 years old meant sleep deprivation.

One son would often come upstairs in the morning while we were sleeping in our bedroom. The warnings of not waking us had gone mostly unheeded.

One early morning, awoken again, the warning turned into a stern spanking on the bottom (hard with multiple strikes, the first and only spanking I recall on this lad). I needed to get my message across, and I did; previous yelling had not worked.

He never woke us again. He never forgot that spanking. It is one of the biggest regrets of my life.

He never woke us up because he never came into our bedroom again in the morning to snuggle up when he was scared, or because he wanted cuddling, or just because he loved his mama and daddy. I sure did teach him a lesson, but at what price?

That was almost three decades ago. I forgave myself and I have said sorry. He forgives me; luckily, my body of work as his dad speaks louder than that spanking.

How do we punish love; perhaps by embracing it and meeting people where they are while honoring their moral code and considering intent above all else.


“Love has nothing to do with what you are expecting to get — only with what you are expecting to give — which is everything.” — Katharine Hepburn