Newspaper Deliver and Babysitting Taught Me the Secrets of Success

Do you remember your very first job? The one that started your journey to making money and perhaps planted the first seeds of your entrepreneurial spirit?

I do, like it was yesterday. There were actually two jobs for me—delivering newspapers and babysitting. I was saving for something big (though I can’t quite remember what now), and one job wasn’t enough.

Growing up, we knew that if you wanted something that wasn’t a life necessity, you had to find a way to earn it yourself.

I can still remember the crisp air of early mornings and the weight of responsibility as I loaded the newspapers in the sack to be delivered while riding my Schwinn bike—it was both exciting and challenging.

“Go-getting,” my dad called it.

For me, that mindset was the beginning of my entrepreneurial journey, though I didn’t realize it at the time. Back then, I was just out to make a buck.

The funny thing is, there was no overthinking or worrying about sleazy sales tactics—just the simple, straightforward problem-solving of figuring out what needed to be done and getting it done.

Things felt so much simpler when you’re a young teen. But looking back, those jobs taught me the foundational skills needed to succeed in business: selling and providing great service.

For the newspapers, the Pittsburgh Press (our local paper at the time) handled the sales end. My job was to deliver on my promise—literally. Rain, snow, or shine, I had to make sure that paper landed on every doorstep. It was all about reliability.

Babysitting, however, was a different beast. I had to find the families myself, which was easier back then because everyone knew everyone (and all their business). To earn trust, I had to show that I was responsible, capable, and willing to put in the effort.

I had goals: make money but still leave time for fun.

This balance taught me early on that managing priorities and setting boundaries could make work more rewarding without sacrificing the fun, a lesson I carry even today.

Hanging out with friends and enjoying whatever outdoor activities the weather allowed were non-negotiable for me. Balancing work and play meant I had to get good at planning. Who knew you could be ultra-productive at 14?

So, as we step into another year and get inundated with messages about goals, resolutions, planning, and prepping, let’s remember this: sometimes, it’s as simple as channeling that 14-year-old version of ourselves—balancing work and play, showing up reliably, and making space for what truly matters.

Sometimes, it’s about going back to the basics—being reliable, putting in the effort, and making space for what truly matters.