“Smooth seas never made a skilled sailor.” I’ve heard that quote my whole life. It didn’t mean much to me until 2020 made it impossible to ignore.
I joined Steel City Pops as CEO in January 2020. Two months later, COVID shut down the world. What followed was the most compressed, demanding, and clarifying leadership experience of my career. The small business leadership lessons I took from that year have shaped everything I’ve done since.
Here’s an honest look at what that year actually taught me.
Small Business Leadership Lesson 1: Adversity Exposes Your Real Culture
Before COVID, you could paper over cultural problems with momentum. When things are growing and people are busy, dysfunction can hide. The moment things got hard at Steel City Pops, everything that had been hiding came to the surface — the communication gaps, the misaligned priorities, the places where trust hadn’t been fully built.
In Build Kickass Teams, I write that culture isn’t built by what you preach — it’s built by what you tolerate. The crisis didn’t create our problems. It revealed them. And that’s actually useful, if painful, information. The small business leadership lesson here: don’t wait for smooth seas to build the culture you need. Build it now, when it’s not urgent, so it holds when it is.
Small Business Leadership Lesson 2: Communicate More Than Feels Necessary
One of the biggest mistakes leaders make during uncertainty is going quiet. They don’t want to alarm anyone. They don’t want to communicate before they have all the answers. So they say nothing — and the team fills the silence with their worst assumptions.
At Steel City Pops during COVID, I learned that over-communication is almost always better than under-communication. Your team doesn’t need you to have everything figured out. They need to know you’re thinking, you’re moving, and you haven’t forgotten about them. In Lead With Empathy, I write that transparent communication — especially in hard moments — is one of the most powerful tools a leader has for maintaining trust. Use it, even when what you have to say is “here’s what we know and here’s what we don’t.”
Small Business Leadership Lesson 3: Pivoting Isn’t Weakness — It’s Survival
We pivoted constantly in 2020. Retail locations closed. We leaned into wholesale and B2B deals with professional sports stadiums, universities, and corporate partners. We launched new products. We rebuilt the revenue model in real time.
None of those pivots felt comfortable in the moment. Every one of them required letting go of how things had always been done and being honest that the old approach no longer fit the new reality. The small business leadership lesson: your ability to adapt is not a sign of instability. It’s a sign of leadership. Clinging to a plan that’s no longer working because you committed to it publicly is not loyalty to your vision — it’s ego.
Small Business Leadership Lesson 4: Cash Is Not Optional — It’s Your Oxygen
I’ve written about this in The Small Business Playbook, but I lived it in 2020. My CFO and I reviewed every expense and cash flow line item every single week. Not monthly. Weekly. Because in a crisis, the difference between staying open and closing can be days, not months.
Small business leaders who treat financial review as a quarterly exercise are flying blind. You need to know exactly how much runway you have, what’s coming in, what’s going out, and what’s negotiable. That clarity — uncomfortable as it can be — is what lets you make real decisions instead of hoping things improve.
The U.S. Small Business Administration identifies cash flow management as one of the top reasons small businesses fail — making financial clarity not just smart leadership, but survival.
Small Business Leadership Lesson 5: The Team You Have Is the Team You Have
In a crisis, you don’t get to rebuild your roster before the game starts. You lead the people who are there. And one of the most important small business leadership lessons I took from 2020 is that the quality of your team — the trust, the competence, the accountability — is determined long before the crisis hits.
The leaders who had invested in their people before COVID were able to lean on them when things got hard. The ones who hadn’t found themselves carrying far more than they should have been. In Build Kickass Teams, I write that great teams are built slowly through deliberate hiring, clear standards, and consistent coaching — not assembled in a panic when you need them most.
Smooth Seas and What Comes After
2020 was the hardest professional year of my life. It was also the year I became a better leader than I’d ever been before — because it demanded it.
The small business leadership lessons from that year didn’t come from a conference or a book. They came from making hard calls under real pressure with real consequences. And I’d take that education over any other.
If you want to build a business that can handle the hard years, start with what I learned about leading through crisis — or book a free fit call with Pete and let’s talk about where you are and what’s next.