Leadership and Regret: How Missed Opportunities Can Shape Better Leaders

Hey folks, Jim here from Toronto, where the leaves are just starting to turn and the air's got that crisp back-to-school feel. As a dad with a son hustling in Florida's social media world and a daughter grinding through nursing school at Providence College, I've been reflecting on the risks they're taking—starting businesses, pursuing tough degrees. It reminds me how easy it is to play it safe, especially in leadership. But lately, with the economy rebounding from those wild post-pandemic years, I've been thinking about a subtle trap we all fall into: fearing the mistakes we make more than the ones we miss by doing nothing.

You see, humans are wired funny. We beat ourselves up over the blunders that blow up in our faces—the bold move that flops, like promoting the wrong person or launching a project that tanks. Those sting, and we learn from them fast because they're loud and visible. But the real killers? The quiet regrets of inaction. The opportunities we let slip because we hesitated, second-guessed, or just stuck with the status quo. We call it the "asymmetry of errors," inspired by a fellow blogger's sharp take on it. We overlearn from what we do wrong, but underlearn from what we don't do at all.

Take my own career. Early on, I turned down a big promotion because it felt like a mismatch with my values (you can read about it in Chapter 6 of my book). At the time, it was scary—saying no to more money and status. But staying put let me grow in a role that fit, and it paid off big. What if I'd played it safe and taken it? I'd have wasted years in a toxic setup, draining my energy and probably getting fired anyway. That's the hidden cost: not the explosion, but the slow leak.

In leadership, this shows up everywhere. We agonize over firing a underperformer (error of commission), fearing lawsuits or morale hits. But we ignore the drag of keeping them on—the team resentment, lost productivity, and missed chances to hire a star. Or think about innovation: Kodak sat on digital photography for decades, scared to disrupt their film empire. Poof—bankruptcy. Closer to home, during the pandemic, many leaders (myself included) empathized deeply with teams working remotely. But some hesitated to rein in accountability, letting complacency creep in. The result? A tougher rebound when business roared back.

As a busy exec who's rolled up his sleeves through recessions and booms, I've learned this the hard way—and with a dash of humility. I once held onto a project too long because I didn't want to "quit" and look weak. It cost my team months of frustration. If I'd pulled the plug earlier, we could've pivoted to something game-changing. Humor me here: It's like being that dad who insists on fixing the leaky faucet himself, only to flood the kitchen. Sometimes, admitting "this isn't working" is the boldest move.

But here's the good news—we can flip this script. As leaders, our job isn't to avoid all pain; it's to spot the silent thieves stealing our potential. With empathy for ourselves and our teams, we can take small risks that build resilience. After all, I care deeply about helping you succeed, just like I do for my family and my teams.

Actionable Steps to Avoid the Trap of Inaction:

1. Audit Your "No's" Weekly: At week's end, list three opportunities you passed on— a tough conversation, a new idea pitch, or delegating a task. Ask: What did I lose by not acting? This builds awareness without overwhelming you.

2. Set a "Risk Budget": Allocate time each month for one bold move, like giving upward feedback or testing a process change. Start small to build confidence—remember, the sting of trying fades faster than regret.

3. Seek External Eyes: Talk to a mentor or peer (or even your spouse, like I do) about a hesitation. Their perspective can reveal blind spots. Bonus: It fosters genuine connections.

4. Celebrate the Attempts: Reward your team for efforts, not just wins. Share a "what we learned" story in meetings to normalize commission errors and highlight omission costs.

Leadership's about progress, not perfection. Let's not let fear of the wrong step keep us standing still. What's one risk you're taking this week? Drop a comment—I'd love to hear.

Disclaimer:  This post is mine alone and may not be the views or opinions of any others, including past or current employers, friends, or family.  You can also find me on Substack, Medium, Tumblr, Facebook, LinkedIn, and X