Leadership is easy when things are good.
You learn who you truly are when things fall apart. When someone on your team is facing real grief, when life becomes heavier than work, and when you’re forced to decide what kind of leader, colleague, and man you’re going to be.
I learned that early in my career in a small startup with no structure, no HR, and a manager who quit suddenly. I was 29, and overnight I became the leader simply because someone had to step up.
The First Lesson: Supporting Someone Through Real Loss
One of my teammates, someone I genuinely admired, was living through a nightmare. His mother was dying of terminal cancer. He had a teenage half-brother who now depended on him completely.
At 28, he was forced into fatherhood.
I had no training for this. No guidance. No idea what the “right” managerial move was. All I had was empathy. And instinct.
So I told him:
“Don’t worry about work. Don’t worry about time off. Tell me what you can do, and we’ll take care of the rest.”
It wasn’t a formal plan. It wasn’t backed by a policy. It was simply the right human decision.
To this day, I think about him, and the weight he carried. The sacrifices he made, the maturity he showed in a moment no one is ever prepared for. It taught me more about strength and responsibility than any leadership book ever could.
The Second Lesson: The Pattern Repeats
About a year later, another direct report went through something painfully similar. His younger brother was battling serious cancer. He too was young, overwhelmed, scared, and still trying to show up for work every day.
Our company had unlimited PTO, but unlimited PTO doesn’t automatically create unlimited support. People need permission to be human.
So I gave it to him.
And again, the lesson was the same:
Leadership is about holding space for people when life overwhelms them.
It was nearly impossible to get all the work done we needed to get done with less people. This was my most productive employee too, and I just couldn’t get the work I needed out of him because he had to go take his brother to chemo multiple times a week.
Do you say no in a situation like that? How can you? How do you come back from saying no to something like that?
There were no good answers, no good results. He needed the time off so I gave it to him.
The Third Lesson: Standing Up For What’s Right Costs You Something
Not long after, I faced my own test.
A developer on my team made a coding mistake. He forgot a semi-colon in a line of code, and the application didn’t do the one thing it was designed to do. The front-end was fine, but the backend didn’t record the data. It was a catastrophic error, but it was impossibly easy to make. It was just a typo. Leadership wanted him fired.
I refused.
It wasn’t right, and I wasn’t going to be the kind of leader who sacrificed people to protect optics. Without a job he would lose his visa. I couldn’t do that to someone.
And I lost my job.
It wasn’t dramatic. It wasn’t heroic. It was simply a situation where my principles and someone else’s priorities didn’t align.
Now I was let go with a lot of other people in a large layoff. So it was shielded by that. But I knew the reason why. I’m sure there were others as well, but that was the big reason.
But here’s the part that took me years to understand:
Getting fired for doing the right thing taught me more about who I am than getting promoted ever did.
What That Company Ultimately Gave Me
I spent 3.5 years at that job. I was let go in a mass layoff. I was jaded. Burnt out. Negative. Frustrated.
But a decade later, I can say with full confidence:
I am grateful for that experience.
Not because it was easy, but because it forced me to grow.
It taught me resilience. It taught me emotional endurance. It taught me grit. It taught me what it means to protect people, not policies.
And it taught me what kind of man I actually am. I am grateful for that.
Failure Shapes You More Than Success Ever Will
It’s strange to say, but I learned more about becoming a man, about responsibility, courage, and loyalty, in those years than I have in any job since.
You grow in the fire. You find your values when someone pushes against them. You discover your strength when you’re forced to carry something heavy.
Those early experiences, supporting teammates through grief, standing up for someone who made a mistake, and facing the consequences, built the foundation of who I am today as a leader and a human being.
Looking back nine years later, I wouldn’t trade that chapter for anything.
Because sometimes, the role doesn’t work out…but the person you become makes it all worth it.
Robert Statsky 