7 Lessons Learned From Working Over 40 Jobs

What delivering newspapers, waiting tables, and practicing law taught me about the dignity of work

President Ronald Reagan famously said, “A job is the best social program there is.” I think about that line every Labor Day.

It’s hard to believe that just five years ago, at the height of the pandemic, unemployment in America hit 14.8%—the highest level since the government started collecting data in 1948. As the virus started spreading, ten million jobs disappeared almost overnight, and the idea of full-time employment fell out of reach for many. Eventually, though, things turned around. Today, America enjoys one of the lowest unemployment rates of any industrialized nation at 4.2%.

For perspective: the U.K. is at 4.7%, and France is around 7%. Germany, though, has us beat at 3.7%. In other words, America—despite all its flaws—remains one of the best places on Earth to find work.

Having a job is about more than just work, though. It’s about dignity. And the dignity of work is something we should never take for granted.

I’ve been blessed to have had a strong work ethic instilled in me since I was 9, first delivering papers for The Carrier Pigeon (yes, that’s a real publication advertising local businesses) and then for the Philadelphia Inquirer. My older brother JJ and I had 84 heavy Sunday editions to haul around. Instead of breaking our backs lugging them around, we got creative. We stacked the papers in a shopping cart we borrowed from the local Acme, laced up our roller skates, and pushed the carts down each city block as we divided and conquered.

That was my first lesson in efficiency: work smarter, not harder.

Lesson #2 Embrace the Suck

I discovered pretty quickly that being in front of people came naturally to me—a skill that would later serve me well when I ran for office. I started in the food industry as a cook and dishwasher at the local Pizza Hut in the Philadelphia Mills mall. It was a fine job for a fifteen-year-old, provided you didn’t mind smelling like pepperoni all day. But the real thrill came when I moved up to busboy at the local Italian Bistro. Suddenly, there were tips. The more I hustled, the more I made. The idea of earning tips for my work was highly motivating.

The tips got even better the following year when I took on the “graveyard shift” of waiting tables, 11 p.m. to 6 a.m., for the Perkins family restaurant.

That job taught me to “embrace the suck.”

An overnight shift serving pancakes to intoxicated customers is one kind of suck; a month of 130-degree heat without proper plumbing in Iraq during the “Fire Month” of August 2003 is another. Both teach you how to grit your teeth, tough it out, and keep moving forward with a smile but stern look when needed.

Lesson #3 The Subtle Art of Suggestion

By the time I landed at Olive Garden years later, I thought I’d seen all the restaurant world had to offer. But Olive Garden had its own peculiar system, complete with a ranked system of employee performance. Waiters were ranked not just on service, but on “add-ons”—the appetizers, bottles of wine, and desserts we could tack on to an order.

The trick was never to ask, “Do you want dessert?” No one wants to be the person who raises their hand for cheesecake after having pasta and never-ending breadsticks. Instead, you brought over the tray of sweets, including chocolate cake, lemon meringue, tiramisu—an entire pageant of sugary treats. Faced with this glossy display, at least one person at the table would always surrender to their sweet tooth. It was less a sales pitch than a Jedi mind trick.

I mastered the subtle art of suggestion through showing, not telling.

It may seem trivial in the grand picture of my life, but being ranked number one at the Olive Garden out of dozens of other waiters is something I’ll always be proud of. 

The lesson here (#4): treat all work with the respect it deserves.

It doesn’t matter how big or small the task is. 

When I was 18, my parents moved to Hershey, PA, and I worked yet another graveyard shift at the Hershey Reese’s factory. They offered fifty cents more an hour for overnight work, and to me, that was a no-brainer. I could pull all-nighters at the factory and still lifeguard during the day that summer before I joined Army ROTC later that fall.

It was hard, exhausting work, but it was also phenomenal. I was surrounded by people who were salt of the Earth folks and as good as the peanut butter cups we packed and the KitKats we baked. I was basically Willy Wonka that summer.

Lesson #5 Stay Humble

Eventually, I moved on to more buttoned-up work. When I earned my J.D., being proactive instead of reactive was something I learned early on in the law. In America, we don’t really have one justice system—we have two. One for people who can afford lawyers, and another for those just trying to get by without one. That’s why I was proud to serve on the board of the Legal Services Corporation, which funds more than 200 legal aid clinics across the country.

But my start was humble. I didn’t attend a prestigious law school that earns you a Supreme Court clerkship or plush job in Manhattan or DC. I attended Widener Commonwealth University School of Law in Harrisburg, Pennsylvania—a school most of you probably haven’t heard of. It wasn’t fancy, but I earned a great education. While there, I became the student clinic leader at the Harrisburg Civil Law Clinic under Professor Palmer Lockard. Our ragtag team of law students helped anyone who walked through the door: a single mom who needed a will, a retiree fighting off a fraudulent lawsuit, someone who just needed help filling out a job application.

At the same time, I was president of the St. Thomas More Society, which volunteered at the St. Francis soup kitchen. What struck me most was how often the people we served hot meals to were the very same people who needed legal help, but had no idea the law clinic even existed a few miles away.

So we brought the law to them. Once a month, we set up a table in the soup kitchen and offered legal services right there. It was one of the most gratifying experiences of my career. To sit across from someone, look them in the eyes, and give them even the smallest measure of hope—hope that someone was willing to fight for them—was the kind of job that stays with you.

Lesson #6 Bigger isn’t Always Better

If you’re someone who attends one of the elite Law Schools, first of all, congrats. Chances are, you are considering a career in Big Law, which is understandable since the starting salary for a first-year associate is over $200k in the major markets. But beware that Big Law is not nearly as glamorous as people think. There are more than 50,000 law firms in America, but the top 100—the so-called Am Law 100—are treated like a league of their own. (They’re called “white-shoe firms,” a term so pretentious it needed its own vocabulary.)

I know from experience. I’ve worked at two of them. 

After five years of active duty in the JAG Corps, where I tried cases before federal court and military martials, I knew I was ready for the big leagues.

After months of interviews and being unemployed (having turned down the first job I was offered), I joined Cozen O’Connor, a first-generation mid-size Big Law firm co-founded by Patrick O’Connor, a fellow King’s College graduate. The O’Connor family was practically its own legal dynasty. I had worked for Michael O’Connor as a messenger when I was 14, and for Tom O’Connor—who later became a judge—while I was at King’s College. To finally work for Pat, one of the true legal titans of his generation, felt like a full-circle moment.

The reality was less glamorous. There were nights I literally slept in the office and shaved in the bathroom with razors I picked up at the local 7-Eleven. It wasn’t what I pictured when I imagined practicing at a major firm. But I was home, back in Philadelphia after years away, and working alongside some of the best lawyers in the country was truly an honor. I also met the mother of my children there.

For a skinny kid from Northeast Philly who started full-time at community college, it was an opportunity I’ll never forget, and one I’ll always be grateful the O’Connor brothers gave me.

Lesson #7 The Best Jobs Aren’t Jobs At All

The greatest job I’ll ever have is being a dad. It’s cliché, but true. If you read my piece This #GirlDad Says Goodbye, you know how emotional I was about my daughter Maggie starting college at Clemson and joining ROTC. That’s how close we are. And I’m just as close to my 15-year-old son, Jack. 

Being a parent is a never-ending job that involves sacrifice. But it’s always worth it.

There were jobs and opportunities I turned down so I could coach Jack in hockey year after year. I’ll never forget leaving the Pentagon late at night, driving straight through until morning just to make one of his tournaments in Canada. Maggie, meanwhile, was a competitive dancer for over a decade before switching to high school volleyball. I made it to almost every recital and every game. I don’t regret a single missed professional opportunity I turned down for them.

But the best part of all those years wasn’t the tournaments or the recitals, it was the rides to and from practice. The rule was simple: whoever sat in the front seat couldn’t be on their phone. We had to talk. Those conversations are what I’ll treasure most. Letting them DJ the music, on the other hand, is one thing I don’t. 

I know as those rides become few and far between, the bond will carry on for decades. Those were some of our most heartfelt conversations.

I’ve had so many jobs over the years, it’s hard to keep track. But what they all have in common is this: a job is never just a job. It’s a story and a lesson. Sometimes it’s humiliation, sometimes it’s a small triumph. Sometimes a huge, legacy-defining triumph. But whatever it is, every job reveals something deeper about yourself that you carry with you into the next chapter of your life.

So, as people go back to school or return to work from summer vacation, remember your job doesn’t solely define you. But the sum of your experiences do shape who you are. Each experience deserves its own measure of pride.

And yes, not to be overly sentimental, but being a dad is the greatest job I’ve ever had and the title I’ll always be proudest to hold.

— Patrick