I mowed a lot of lawns and cleaned a lot of gutters as a kid, but my first consistent job was delivering newspapers. Today that sounds quaint, but it was a rite of passage back in the day.
I grew up in Chevy Chase, Maryland, just outside Washington, D.C., raised primarily by my mom and in the most modest house of anyone I knew. She used to say we were never poor– we just didn’t have a lot of money. So at age 15 when I heard that a Washington Post delivery route paid $100/month, I jumped at the chance.
This was the Post in its prime, not long after its reporting on the Watergate scandal made the paper famous. Every home in the area had a subscription. Politicians, lawyers, lobbyists, staffers – they all woke up and reached for the same paper, expecting to be on their porch by 6:30am. And even if I was just the kid making sure it landed there, it felt important.
So at 5:30am seven days a week, I was out the door, ready to fill the bag slung over my shoulder and walk porch to porch. There’s something clarifying about that hour. No one is asking anything of you– it’s just the work in front of you and the responsibility to get it done. I loved it.
Except Wednesdays. Wednesdays were brutal. Coupon inserts from Safeway and Giant turned what was already a heavy bag into something you felt in your shoulders for days. And it was doubly brutal if it rained that day. But people were counting on the Post showing up. Someone was going to pour their coffee, sit down at the kitchen table, and reach for it, rain or shine. Coupon day, or not.
Looking back, what that job really taught me wasn’t just about showing up on time, though it was that, too. It was about understanding that reliability is a form of respect. Everyone wants to be seen. When you commit to being there for someone – and you follow through – you’re telling that person: I see you. You matter.
That sits at the center of what we do at Lyft. Every ride is a commitment. A driver heading out at 5 a.m. (and there are a lot of them) is honoring the same promise I made on that paper route: I’ll be there. They’re getting to the airport, to the hospital, to a job interview.
The stakes are higher than a twelve-year-old delivering a Wednesday newspaper. But my commitment is the same, seven days a week, 24 hours a day, a billion times a year.
It’s a valuable lesson no matter what you do.
My First Job is a recurring series in which prominent business leaders share what their first job was and what they learned from it.



