I started delivering newspapers when I was nine years old, and did it until our local paper changed from afternoons to mornings, when I was 14. Every day after school I would ride my bike and deliver 40-50 papers. On Sunday mornings, I would deliver about 120 papers, which were about 3 times the size of the weekday papers, with the extra sections, plus all the comics, coupons, and advertisements. Which meant that I used a wheeled garden cart to haul the papers, and Toby would walk with me.
Toby never needed to be on a leash. He always stayed close by. When I went into apartment buildings, he would wait for me by the door. And he was so smart that he learned the route. He knew which houses we delivered to, and which ones we skipped. I didn’t know that he knew that route until the first time a customer cancelled their delivery. I was walking past their house, but Toby turned up their driveway. He knew that we normally delivered there. I called him back, and laughed out loud at how smart that dog was. He remembered the next week. When we got to that house, he just walked past.