5 Lessons I Learned from Being a Paperboy (That Still Shape Me Today)

When I was 12 years old, I took my first real job: delivering newspapers.

It wasn’t glamorous. It wasn’t easy. And to be honest, most days, it wasn’t even fun. But looking back now, I realize that being a paperboy taught me some of the most important business (and life) lessons I still live by today.

This reflection was actually spurred by a great article my friend Sheri Fitts recently wrote about how personal branding is a lot like knocking on doors. Her story brought me right back to those early mornings on my bike, bag full of newspapers slung over my shoulder, learning lessons I didn’t even know I was learning yet.

So today, I wanted to share five lessons from my time as a paperboy — lessons that still guide me as an entrepreneur and business owner all these years later.

1. Reliability Isn't Optional — It's the Whole Game

When you're 12 and carrying 50 newspapers before school, rain, snow, or stomach flu, you learn something fast: nobody cares about your excuses.

The paper had to get there.
Whether I was tired. Whether I was sick. Whether it was 10 degrees outside and sleeting sideways.

Reliability wasn’t a nice-to-have — it was the entire job.

Today, I wake up at 5 a.m. every morning whether the alarm goes off or not. That instinct to show up—no matter what—started on those dark, freezing mornings when the only other creatures awake were me and a few squirrels.

In business (and life), it’s still true: being reliable is one of your biggest competitive advantages. Lots of people have talent. Far fewer can be counted on.

2. Discipline Becomes Habit (And Habits Shape Your Life)

Waking up before the sun rises isn't natural for most 12-year-olds. It wasn’t for me, either. At first, it was brutal. But over time, it just became normal.

Discipline turned into habit. Habit turned into identity.

These days, my mornings are my most productive hours — writing, thinking, strategizing. And it’s because that little discipline muscle got built early.

If you want long-term success, you don't need to be “motivated.” You need to be disciplined enough that you don’t have to think about it anymore. The hardest part isn’t doing the work — it’s doing it when nobody else is watching.

3. Asking for Money is Awkward — But Necessary

One part of the job I absolutely dreaded? Collecting payments.

Back then, you didn’t just deliver the paper — you had to physically knock on doors and ask people for their subscription money.
Imagine being a chubby, introverted kid, trying to collect $6.50 from grown adults who sometimes hid behind their curtains to avoid paying you.

It was miserable... at first.

But it taught me something incredibly valuable: if you provide a service, you have to be willing to ask to be paid.

Even today, whether it's quoting a project, closing a deal, or sending an invoice, that early discomfort reminds me: if you're creating real value, there’s no shame in asking for fair compensation. It’s part of the exchange.

4. You’re Running a Business (Even If You Don’t Realize It)

Looking back, I wasn’t just "working a job." I was running a little microbusiness.

I had to collect the money. I had to track who owed what.
I had to pay the newspaper company — whether my customers paid me or not.
If I didn’t collect, I was on the hook. There were no extensions, no grace periods.

Managing cash flow, tracking accounts receivable, dealing with “clients” — it was all there.
The stakes were small, but the principles were massive.

Every entrepreneur has to learn this at some point: revenue doesn’t matter if you don't get paid. Collections, cash management, and honoring your financial obligations are core to staying alive in business.

5. You Have to Knock (Even When You’re Scared)

There were some houses on my route I dreaded visiting.
Maybe the dog barked like crazy.
Maybe the owner was grumpy.
Maybe I just didn’t feel like getting rejected that day.

But the job required me to knock anyway.

There’s a lot of power in learning early that fear doesn’t mean stop.
Fear just means you’re doing something important.

Even today, there are still “doors” I don’t want to knock on — conversations that feel awkward, risks that feel scary, opportunities that feel intimidating.
But every great opportunity I’ve ever had in life and business came from knocking anyway.

Full Circle Moment

It’s funny — when you’re 12, riding a rickety bike with a bag full of newspapers, you’re not thinking about personal development or business strategy. You’re just trying to get the job done and maybe make enough money to buy a new baseball glove.

But looking back, that little paper route was one of the best "business schools" I could have ever attended.

It taught me lessons that fancy degrees and motivational speeches can’t:

• Show up.

• Be dependable.

• Ask for the sale.

• Manage your money.

• Push through fear.

I owe a lot to that kid with the bag of papers slung over his shoulder.

And I owe a huge thank you to Sheri Fitts for sparking this trip down memory lane.

💬 Now I’d Love to Hear From You:

What was your first job — and what’s one lesson you still carry with you today?
Drop it in the comments! I’d love to hear your story.