Work-week Interview #4: Joe Cassidy

What was your first job ever?

I was a paperboy for what used to be called the Milwaukee Journal. I, along with dozens of my friends, delivered papers seven days a week for a couple of years leading up to high school. My route, which was between fifty and sixty customers, depending on the week, was just a couple of blocks from where I lived. But, I still had to [bike] the stacks of papers from where they were dropped off by the Journal at the little shack across from my grade school, which was a mile or so away. I either lost to the wind or dumped several stacks over the years, as I lugged them back on my bike handlebars or pulled them on the wobbly red wagon behind me. A fun part of the job was what they called ‘subbing’ — putting the coupons and special sections into each day’s paper. We had major competitions daily among the guys to see who was the fastest. If you had those little rubber do-dads on your fingertips, instead of just having to lick them, you were a real pro.

Were you good at it?

No, I was rather terrible. Sunday morning at 4:30 a.m. comes very early, especially in the oh-so-pleasant winter months in Wisconsin. It was almost always my dad and I, but my poor big sister — God bless her — frequently got stuck with having to help deliver them with me a lot of Sundays too…We got lots of early phone calls on most of those Sunday mornings, usually from hard-of-hearing retirees, wondering why they didn’t get a paper that day. My Dad would also make us go to 6:30 a.m. Mass afterward. It was usually packed with fellow bleary-eyed dads and their equally zombie-d sons getting in that Sunday obligation, post-deliveries. Back then as a paperboy, you also had to collect the subscription fees directly from the customers, and you did this by going door to door. I had zero money management skills then and was not good at getting people to pay on-time. [I] was almost always late in getting the weekly bill paid and nearly got fired numerous times. Our manager Ed thought I was a meathead, but found my wild and elaborate excuses funny. Plus, I think my dad intervened a few of those times and saved my neck.

What did your parents do for a living when you were growing up?

My Dad was an attorney with his own practice specializing in family law, and my mom was a librarian at a K-6th grade public elementary school. They both worked most of my life growing up, and yet I feel really lucky that they always made it to the important life events, as well as to so many of our schools’ sports events. My dad died way too young at 55, but was at the top of his game when he passed and left a wonderful legacy as a highly-respected attorney in one of the more demanding and stressful fields of law. Both my parents’ jobs, in large part, defined who they were and are. My mom is an avid reader and still a staunch defender of teachers – not always an easy task in my home state these days!

What was the worst job you’ve ever had and why?

I was a dishwasher-slash-sometimes-short-order-cook at a small diner-style restaurant called John’s Sandwich shop in Wauwatosa, Wisconsin. A very popular little place for breakfast, burgers and malteds. It wasn’t inherently the worst job in the world, I just couldn’t keep up with the pace of it all, so I was constantly stressing. And to boot, I got Salmonella while I was there and landed in the hospital for over a week. I did lose 15 pounds though…

Who is the hardest working person you know and why?

All of my sisters, but specifically, my big sister. She is raising two great kids, one with special needs, and works for the Wisconsin Heart Association, often having to travel among several Midwestern states. Among other concurrent struggles, she did all of this whilst battling — and beating! — cancer over the last four-plus years. I marvel at that kind of strength and grace.