Trending
There’s a place on the northern edge of Lake Michigan where time seems to slow and stories settle like driftwood along the dock. It’s the kind of harbor town where fish shanties lean into the wind, seagulls wheel overhead, and generations return each summer not just for the views, but for something they can’t quite name.
I was eighteen the summer I found myself there, standing on worn wooden floors behind a weathered hostess stand, wearing borrowed sneakers and a brave face. I had just finished my first year of college and needed money for the next one. What I didn’t know was that I was about to earn something even more valuable.
Tucked among smoked fish shops and cedar-lined storefronts was a lakeside restaurant I’ll call The Anchor Inn. It was part neighborhood legend, part beautiful mess. The owner, whom I’ll refer to as Captain, ran it with a booming voice, a sharp eye, and an old-school pride that both intimidated and intrigued me.
The Anchor Inn wasn’t just a job. It was a rite of passage. And that summer, it changed me.
More Than a Job, a Training Ground
Like many young people, I expected summer work to be straightforward. Smile, serve, save. But The Anchor Inn was intense.
The pace was relentless, the systems were cryptic, and the standards were sky-high. One night, I forgot to bring out salads before the entrees. Another time, I misentered a coded order. Each menu item had its own odd nickname. The kitchen team wasn’t shy about pointing out mistakes, and neither was Captain.
He let me know when I had fallen short, with a sharp tone and no filter, often within earshot of others. It was tough to hear, but harder still was the feeling of being corrected without any real support or coaching.
I went home defeated. My mom, always practical but empathetic, said gently, “You don’t have to love the job, but if you want to earn what you came for, you’re going to have to push through this part. And you might just learn something about yourself in the process.”
She was right. That moment became a turning point.
When Leaders Don’t Step In
What shaped me most wasn’t Captain’s criticism. It was his distance.
When things got chaotic, he stayed on the edges. He never jumped in to help during a dinner rush, never grabbed a tray, never backed up a team member under pressure. He was present, but removed. Always watching, rarely contributing.
Even at eighteen, I could tell something was missing.
True leaders don’t disappear when the pressure rises. They show up. They steady the room with their presence. They lend a hand, not just their voice. The absence of that leadership taught me something essential—what not to do.
Angela Ahrendts once said, “I don’t believe in hierarchy. I believe in teams.” That line speaks deeply to me, because I’ve lived through the opposite. And I carry the memory of that disconnect into every leadership decision I make.
"I don't believe in hierarchy. I believe in teams." — Angela Ahrendts
What The Anchor Inn Really Taught Me
I stayed. I learned. And I left that summer stronger than I arrived. That job tested me in all the ways I didn’t know I needed.
The lessons I took with me have never left:
- Resilience is built under pressure. Every tough shift gave me a little more strength.
- Being present matters. Especially when things get hard. Leadership is active, not distant.
- Clarity is powerful. That confusing menu taught me to ask questions early and often.
- Feedback shapes growth. Even when it’s hard to hear, it can push you to improve.
- Empathy is everything. When you’ve felt unsupported, you learn how to truly support others.
- Details matter. It’s not just about getting things done. It’s about doing them with care. Because if the small details aren’t right, the big ones will never come together.
- Teamwork is essential. We relied on each other more than we realized.
- Mistakes are part of the process. Owning them builds trust and maturity.
- Composure is contagious. Chaos doesn’t always require volume. Sometimes, just staying calm is leadership.
- Adaptability is a lifelong skill. The Anchor Inn didn’t wait for anyone to catch up. I learned to keep pace.
What I Learned From Bad Bosses, Then and Now
A study by the University of Central Florida found that people who have worked under abusive or disengaged leaders often make a conscious choice to lead differently when it’s their turn. Instead of perpetuating the cycle, they develop stronger emotional intelligence, greater empathy, and a deeper focus on team wellbeing.
“Rather than paying the abuse forward, many employees respond by becoming exceptional leaders—more supportive, communicative, and emotionally present.” — UCF College of Business
That research gave language to what I’d felt, time and again, throughout my own journey.
Captain wasn’t the only difficult leader I’ve worked for. Over the course of my career, I’ve reported to leaders who inspired trust, and to others who ruled with fear, ego, or absence. And every one of those experiences taught me something. Some gave me a model to emulate. Others gave me a list of lessons I would never want to repeat.
And this pattern is backed by even more research. A study from the Academy of Management identified the “mirror or window” effect. Employees exposed to poor leadership either reflect those same behaviors or consciously grow beyond them. Those who grow beyond are significantly more likely to lead with ethics, presence, and care.
In many ways, the contrast between the good and the bad has shaped me more than any formal training. Because when you’ve seen what happens in cultures led by fear or silence, you’re twice as motivated to build something better.
Today, I lead with intention. I check in. I show up. I give feedback—but I also give context, encouragement, and clarity. I don’t believe in managing from a distance. I believe in walking beside my team.
That summer at The Anchor Inn gave me my first glimpse into the cost of poor leadership. And throughout the years that followed, I kept building from it—refining the kind of leader I want to be.
Because resilience doesn’t just come from overcoming difficulty. It comes from choosing, again and again, to lead differently than what you experienced.
The Other Side of the Table
Of course, not every situation ends in growth. Sometimes, despite best efforts, it becomes clear that someone simply isn’t the right fit. I’ve had to make those calls as a leader. It’s never easy, and it shouldn’t be. But part of leading with integrity is being able to separate compassion from avoidance.
Holding people accountable doesn’t mean you lack empathy. It means you are honest—with yourself, with your team, and with the business.
There are times when someone isn’t meeting expectations, and despite coaching, clarity, and opportunity, the gap remains. In those moments, the most respectful thing you can do, for them and for the rest of the team, is to move on.
Some people have blind spots. They may genuinely believe they’re contributing, even when their impact isn’t aligned with what the team needs. As a leader, it’s my responsibility to address that directly, but respectfully.
Supporting someone doesn’t mean shielding them from truth. It means offering it with clarity, care, and courage.
When someone can grow, I’ll invest. When someone won’t grow, or can’t see the issue, I owe it to the team to make a change.
Leadership is about knowing the difference.
Full Circle
When I go back to that lakeside town, I still pass The Anchor Inn. Captain is still there, keeping watch from the edges. He never remembers me. But I remember him. And I remember that summer like it was yesterday.
Not for the tips. Not for the view. But for the growth.
Here’s to the hard jobs, the hard bosses, and the hidden gifts they leave behind.
Related: Why Now Is the Moment for Small Caps: Outperformance Ahead?