The Toughest Job I Ever Had (and What It Taught Me)

The Toughest Job I Ever Had (and What It Taught Me)

Jeff Wolf, President, RCC

Time to read: 2 minutes.

During my college summers, I was fortunate to land a well-paying, union job as a summer replacement janitor at a sprawling suburban apartment complex just outside Chicago. It was one of the toughest and most eye-opening jobs I’ve ever had, leaving a lasting imprint on how I think about work.

My role was to fill in for the full-time janitors while they took their vacations—a position that taught me lessons I still carry with me today.

The complex was massive: over two hundred apartments spread across two-story buildings, all surrounding a large swimming pool that served as the center of community life. It looked serene on the surface, but behind the scenes was an entirely different story, especially during a Chicago summer, when the humidity clings to you like a second skin.

Our uniforms? Thick khaki pants and matching long-sleeve shirts, great for protection, not so great for comfort in 90+ degree heat.

It was easily the dirtiest, grittiest job I’ve ever done.

Each morning, we arrived at 8:00 a.m. and got right to work on the most grueling task of the day: “pulling garbage.” From 8:00 to noon, we moved from building to building, collecting trash from each basement.

It started by grabbing a six-foot canvas bag and hooking it onto the bottom of the trash chute. The chute door was spring-loaded for safety. It stayed closed in case the latch failed, so to keep it open, we’d prop it with our heads while using both hands to pull out bags of garbage. (Yes, we wore hats for all the good it did.)

We were always listening for the sound of someone upstairs throwing trash down the chute while we were working. If we heard that familiar thud or rustle, we had to move fast, slamming the chute shut in a split second or risk getting covered in garbage. Quick reflexes weren’t just helpful, they were necessary.

Then we’d sling the heavy, often leaking bags—sometimes weighing over 100 pounds—over our shoulders, climb a flight of stairs, walk to another building, go down into its furnace room, and dump the trash onto the concrete floor.

That’s where things got even messier. This was before recycling existed, so we had to manually rip open each bag and sort through the trash to pull out cans, especially aerosol cans. We had to be incredibly careful. If even one aerosol can made it into the fire, it could explode like a cannon—loud enough to leave your ears ringing and your heart racing.

The furnace roared constantly, and the air in the room easily climbed above 130 degrees. You could feel the heat radiating from several feet away, and that was before we even started sorting through the trash.

After hauling garbage building after building, we were drenched in sweat and soot by lunch. If someone fell behind, the others jumped in without being asked. No questions, no complaints. That’s just how it worked.

After a quick lunch, we moved on to our afternoon assignments: mowing the large stretches of community grass, polishing the silver mailboxes in every hallway, sweeping and mopping basement laundry rooms, washing hallway windows, and vacuuming stairwells.

The next day? Do it all over again.

On weekends, one of us worked solo, “pulling garbage” across the entire complex—every building, every basement. Alone.

What did I learn from those summers?

More than I could have imagined.

  • The value of hard, physical labor. There’s something grounding about work that demands effort and grit.
  • Humility. There’s nothing glamorous about sorting trash in 130-degree heat.
  • Respect for behind-the-scenes work. I gained deep appreciation for the people whose efforts often go unnoticed, but who keep the world running.
  • Discipline. There were no shortcuts. You showed up, did the work, and earned every dollar.
  • Teamwork. Everyone pulled their weight, or someone else had to pick up the slack.
  • Work ethic. Even the dirtiest jobs deserve your best—how you do anything is how you do everything.

That mindset stuck with me as I stepped into roles as a CEO, executive coach, and consultant. It reminds me that respect, commitment, and work ethic matter—regardless of title or role.

Those summers didn’t just change how I view work; they defined how I lead, coach, and show up every day.

Want leadership insights rooted in real-world experience? Follow me on LinkedIn where I share fresh perspectives and practical strategies every week.

Here are three of the most popular newsletters from the past few months you may have missed:

Leaders: Balance Your Work and Personal Life

Leadership That Inspires: 7 Practical Traits for Making a Real Impact

25 Years and 25 Observations, Insights, and Reflections on Leadership (9-12)

QUESTIONS FOR THE AUTHOR?

REAL ANSWERS, REAL RESULTS

Leadership insights in your inbox.

Nationally acclaimed speaker

International bestselling author Jeff Wolf is now available for your next meeting, conference or convention to provide a high-energy presentation filled with strategies and techniques attendees can immediately apply to improve their skills.