There are moments in business that stay with you forever.
Some moments make you proud.
Others humble you.
And then there are the moments that remind you leadership isn’t always about growth, revenue, or celebrating wins.
Sometimes leadership hurts.
A few weeks ago, I had one of the hardest conversations I’ve had since starting Express Errands & Courier 14 years ago.
I had to call one of my drivers and tell him the two routes he had faithfully driven for more than five years were ending.
Not because he did anything wrong.
Not because he wasn’t performing.
Not because of attendance.
Not because of complaints.
Simply because our client made the decision to eliminate those routes.
As business owners, we know clients have the right to make business decisions. They have budgets, operational changes, and priorities that sometimes are completely outside of our control.
That doesn’t make the conversation any easier.
This wasn’t just another driver.
This was one of the best drivers I’ve ever worked with.
For more than five years, he showed up every single day.
He never called out.
He never complained.
He never made excuses.
He represented Express Errands & Courier exactly the way I would have represented the company myself.
He became someone I never had to worry about.
As a business owner, you know how rare that is.
Then there’s one story I’ll never forget.
His grandfather passed away.
Instead of immediately asking for time off, he scheduled the funeral services around his route so he wouldn’t miss his deliveries.
Now, before anyone misunderstands me, family should always come first.
But that moment showed me the level of commitment he had to his work, his customers, and the responsibility he felt toward the company.
That kind of loyalty is hard to find.
He wasn’t just one of my most dependable drivers.
He was also the highest-paid driver in our company because he earned it.
When I found out those routes were ending, my first thought wasn’t about replacing the work.
My first thought was about him.
How was I going to tell someone who had given me five years of loyalty that the work he’d built his schedule around was gone?
I immediately started looking for solutions.
Could I move other routes around?
Could I combine work from other drivers?
Could I piece together enough deliveries to make it work?
I wanted to.
I really did.
But the math simply didn’t add up.
The other routes were much farther from his home.
Even if I reassigned work from other drivers, it wouldn’t have come close to replacing the income he had been making.
Sometimes there isn’t a perfect answer.
That’s one of the hardest parts about being a business owner.
People often see the awards.
The growth.
The social media posts.
The new clients.
They rarely see the conversations that happen behind closed doors.
They don’t see the sleepless nights trying to solve problems that don’t have a solution.
They don’t see the weight you carry when your decisions affect someone else’s livelihood.
That phone call stayed with me long after we hung up.
As difficult as it was, it also reminded me of something every courier business owner needs to understand.
Never stop building your pipeline.
Not just for customers.
For drivers too.
One client can change your business.
But one client can also change your business overnight.
As entrepreneurs, we spend a lot of time thinking about finding reliable 1099 drivers.
But we don’t spend enough time thinking about protecting the business we’ve built.
Over the last 14 years, I’ve learned a few lessons that have become part of how I lead.
Great drivers are rare.
When you find someone dependable, invest in that relationship. Appreciate them. Communicate with them. Respect them.
Loyalty goes both ways.
When this happened, I didn’t simply tell him the routes were over and wish him luck. I looked for every possible solution because that’s what leaders do.
Clients change.
Even your best clients.
Even long-term clients.
That’s why you should never become comfortable. Continue marketing, prospecting, and building new relationships so your business isn’t dependent on one customer.
Always be recruiting.
One of the biggest mistakes I see courier companies make is waiting until they’re desperate to hire.
Recruiting should never stop.
You should always be meeting new drivers, building relationships, and creating a bench of dependable people before you actually need them.
That’s how you reduce turnover.
That’s how you build stability.
Most importantly, remember that your drivers aren’t just names on a dispatch screen.
They’re people.
They’re parents.
They’re sons and daughters.
They’re providers.
They’re trying to build a life just like you are.
How you lead them matters.
To the driver who gave Express Errands & Courier more than five years of loyalty, thank you.
Thank you for every early morning.
Thank you for every late afternoon.
Thank you for representing my company with excellence.
Thank you for reminding me that truly dependable people still exist.
You’ll always have my respect.
If you’re reading this as a courier business owner, I hope this story reminds you that building a successful company isn’t just about landing clients.
It’s about building relationships—with your customers and with the people who help you deliver on your promises every single day.
And sometimes, being a CEO means making decisions that break your own heart.
If you’re struggling to find reliable 1099 drivers or you’re tired of constantly replacing drivers, I want to invite you to my free workshop, How to Find Reliable 1099 Drivers Without Constant Turnover.
I’ll share the recruiting, interviewing, onboarding, and retention strategies I’ve developed over the last 14 years of building Express Errands & Courier.
Because finding reliable drivers is one thing.
Building a team that stays with you is what truly changes your business.
RE
