Friday Forward - Bad Choices (#527)
The price of avoiding mistakes, failure and embarrassment
Over the past few years, I’ve noticed memes and merchandise with the slogan “bad choices make good memories.” I’ve seen it on t-shirts, hats, and koozies, and it always makes me smile.
That slogan came to mind last week.
It was during a ski trip my close friends from college have taken annually for nearly 25 years. The trip has taken many different forms over the years, but this one featured a particularly large group, as we’re celebrating a milestone birthday year.
As we sat around the dinner table on the last night of the trip, the conversation turned nostalgic. We reminisced about some of the spectacularly poor decisions we had made in college. There were stories involving stitches, hospital visits, attempted cow tipping, and other displays of stupidity and carelessness that we would almost certainly chastise our own kids for today.
Many of us were in tears as we retold different versions of the same events. Details one person had forgotten were vivid for another, filling in blanks that faded over the decades. And these memories have kept us bonded for over 30 years, always invoking smiles, belly laughs, and the kind of connection that only shared experience can produce.
As the laughter died down, one thought kept entering my mind: thank God there were no smartphones.
These stories involved poor judgment, no question. But we were 18 and 19 years old, and it’s at that age that you’re supposed to make mistakes, endure the consequences, and learn from them. Those repercussions were often immediate and uncomfortable, and there was no cell phone to call a parent to get us out of trouble. We had to just figure it out.
Everyone at that dinner table is now a professional, a parent, and a genuinely good person. I’m happy to report that doing dumb things as a teenager did not derail any of our lives. In fact, given everything we learned at that age, it may have done the opposite.
Kids need to make mistakes. They need to do dumb things, suffer the consequences, recover, and learn. But today’s kids live in fear of being photographed or filmed by a nearby phone. Their parents teach them that discomfort is a form of danger, and foster perfectionism, rather than trial and error. As a result, young people live to avoid mistakes and embarrassment. Rather than experiencing the messiness of life at an age where they’re still young enough to bounce back, teens focus on projecting perfection. This then prevents people from building the muscles of resilience; as many experts have noted, shielding kids from discomfort often leaves them less equipped to handle the inevitable challenges of adulthood.
This is where a well-known leadership principle is valuable.
Great leaders understand that mistakes are necessary for growth. Instead of protecting their people from any failure, they focus on helping their team avoid what are often called “below the waterline” mistakes. The metaphor comes from a ship, which can take on a hole above the waterline and stay afloat until the damage is repaired. In contrast, a hole below the waterline may sink the ship before you can fix it. Leaders can permit the former, but they should try at all costs to avoid the latter.
This leadership framework applies effectively to parenting. Both parents and leaders should only intervene to prevent the mistakes that can cause irreparable damage: the ones involving serious danger, legal consequences, or lasting harm to others. Above-the-waterline mistakes, the ones that sting, embarrass, or inconvenience, are often the ones that teach the most valuable lessons.
Incidentally, none of the stories my college friends laughed about that night sank anyone’s ship. Instead, the literal and figurative scar tissue from those experiences helped build a group of people who are resilient, self-aware, and capable of laughing at themselves decades later.
In a world that increasingly treats every misstep as a crisis, or prevents failure entirely, it’s worth remembering that some of our best growth comes from our worst decisions. It takes a while to be grateful for those lessons, but most people are in the end. Rather than eliminating mistakes entirely, the goal should be to create an environment where people can make recoverable ones, learn from them, and come out stronger on the other side.
What above-the-waterline mistake taught you something that still serves you today? I’d love to see you share in the comments below.
Quote of the Week
“Good judgment comes from experience, and a lot of that comes from bad judgment.” – Will Rogers
Have a great weekend!
-Bob
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Oh man, I’m going down Memory Lane. I’m not proud of a lot of these moments: from beings caught drinking beer outside my school —how dumb is that?; to my biggest mistake in life as an adult that almost cost my marriage —I held a sign during the 2006 Soccer ⚽️ World Cup that said: “change wife for a tkt” —even dumber.
Now, you are on point regarding cellphones 📱 and the realities of the new generations. We didn’t have to also worry about being caught on camera.
Way back in my college days, had a summer job laying rebar on a bridge for a construction company. I was the "spoiled" college kid who got razzed every day....some of it could be nasty. One day they went too far in my mind and I walked off the job. My dad, who worked for the company, well aware of what I did when we sat down for dinner that night, asked me about my day and I gave him account. Thinking he would sympathize, of course. Well - turns out he told me to return to that job the next day, apologize to the whole crew and work twice as hard from then on. His final message - never quit when it gets too hard to take. Went in the next day and did what he told me to do and the crew was extremely respectful, believe it or not. Moral? I have NEVER quit at anything since!!!