photograph by larry kuzniewski
My sister has an expression she likes to throw my way when I start griping about a decision I made or step I took that I’d like to reconsider: “Stop shoulding on yourself, Frank.” It’s an abrupt, slightly blue admonishment that happens to be very wise.
I recently discovered that the third Saturday in July has been dubbed “Toss Away the Could Haves and Should Haves Day.” Seriously. Visit nationaldaycalendar.com and you’ll find it between National Nude Day (July 14) and National Cousins Day (July 24). It’s an event I now intend to properly acknowledge. As I consider decorations, I’ll share the value of “tossing” in three primary areas where we all tend to “should” on ourselves with regularity.
Career
If you’ve held a job for as long as 12 months without a regret, you need to find a new job. The best careers require decisions on at least a daily basis, often multiple choices on the same day, one of which might erase the impact of an earlier call. Human beings don’t ace such tests, not every day. Matter of fact, we get better at making decisions with the experience of having survived poor ones.
I’ve been blessed in this area, having worked with the same small business for 33 years. I’ve explored options, though, once actually certain that another industry might be a better fit. As Al Green would put it, here I am. And the best work of my career in journalism has come after that mid-career fork in the road. Sometimes not getting what you want is the best thing that can happen to you. Those closest to me, for the record, exhaled the loudest when I chose to carry forward as a journalist. Trust your instincts with those myriad decisions, and importantly, allow the input of colleagues (and potential employers) to help in paving your path. But it’s your path.
Family
This is dangerous territory. Let me tell you, as a relatively new empty-nester, the “should haves” in raising children are enough to require an extra layer of padding in that proverbial madhouse. Maintaining a healthy marriage — never mind growing a marriage — over at least two decades of parenting would intimidate Hercules. But it can be done.
Your children and, later, grandchildren aren’t following a script. Matter of fact, they’re ripping yours in two behind your back. But that is precisely the magic of raising children. Will my daughter be able to navigate this world? Yes, but only when you surrender the captain’s deck and let her lead. (Ignore those dark clouds ahead and remember: All is temporary.)
One of my daughters graduated from high school and entered college in 2020, during the depths of a pandemic unlike any human alive had experienced before. My sister would cringe at the “should haves” and “could haves” that still dance in my head on sleepless nights or long plane flights. How does a father steer, alongside his daughter, through clouds so sinister? Well, we made it. Most significantly, Elena made it. She has suffered trials and errors over the last half-decade, but she’s emerging as a bright, compassionate force, almost entirely her own doing. More decisions to make, more corners to turn. But whatever mistakes I choose to unearth from Elena’s pandemic pivot are only keeping me awake. I did the best I could, and I relish now seeing her do the same.
Personal
This one comes down to kindness. Don’t hurt someone else. Don’t hurt animals. But most importantly, don’t hurt yourself. Similar to navigating a job, if you’ve lived as few as 10 years, you’ve crossed someone the wrong way. It’s part of being human, with interests different from others in your home, on the playground, at work. I could itemize people I’ve crossed (or those who’ve crossed me), but then what? This isn’t to say a well-timed apology can’t go a long way. If that kind of opportunity surfaces, take it. But limit the damage of conflicts now well under the dust of history.
Here in 2025, I’ve made it an objective to lift someone’s spirits every day. Can be intentional: a family member I’d like to see smile or a friend I’d like to hear laugh. It can also be random: complimenting someone’s handsome dog, or a hat worn just the right way. This makes me feel better in a time and place where kindness seems to be at a premium. I’ve also never — not once — suffered “could have” or “should have” after one of these little exchanges.
Being you is enough. Always. Decisions you’d like to reconsider. Forks in the road where you’d now rather have gone left than right. Those are mini-bombs to your gray matter that need to be silenced, and permanently. Allow regrets to be buried, to rest in peace. You’ll be better prepared for National Talk in an Elevator Day (last Friday in July). You’ve saved that compliment long enough.
