BL&T No. 180: Turning an Early Career Challenge into a Stepping Stone

Agency Leadership

This post originally appeared in my newsletter, Borrowed, Learned, & Thought. BL&T is sent weekly on Mondays. In every edition, I share lessons learned in agency leadership, life, and e-commerce. This post does not include all the details shared in the newsletter sent via email. Subscribe here.


"When I first started managing, I made the mistake of thinking my job was to always “make it work.” I reasoned that if two smart, well-intentioned individuals couldn’t agree, then surely it must be the result of some misunderstanding. My job, therefore, was to shed clarity on the matter and get everyone to shake hands and sing campfire songs together again."

From "The Making of a Manager" by Julie Zhuo [Book]


Last week, I shared a turning point in my career on LinkedIn, which got me reminiscing about my early days in NYC.

In my first job out of school, I remember feeling trapped in my job. I had taken on a new role at a startup within a larger company, and as exciting as it seemed, they had no idea what to do with me. I'd try to create value and stay occupied, but the situation wasn't improving. Fear of the unknown, especially being new to New York with rent to pay, kept me from quitting without another job lined up.

About a year into the job, my manager and I sat down for a chat. I learned that she had also been struggling with what to do. She appreciated my initiative but realized that my skill set didn't align with the company's needs, which leaned more toward industrial design. Our conversation led to a decision to part ways—a layoff of sorts. It wasn't a firing, nor a resignation; it was an acknowledgment that it wasn't working out.

I couldn't believe I was about to collect unemployment this early in my career.

During the subsequent job search and period of unemployment, I longed for an opportunity at a tight-knit agency in downtown NYC. They said they weren't actively hiring but interviewed me and said they'd stay in touch.

Then, the day came.

I was in the computer lab at Tyler School of Art with Dana, my then-girlfriend-now-wife, who was working on her senior portfolio. I checked my email and BOOM. My memory of that moment looks like a kid waiting for their college acceptance letter from their top school. They open the mailbox, eyes wide, and they run into the kitchen to show the envelope to their family. Only for me, it was a reply to an email. My finger hovered over the mouse.

The email came from Peter, co-founder of Barrel, offering me a 3-month freelance designer role. I pushed back in my chair and nearly shouted with joy. The uncertainty of freelance was unsettling, but I loved everything about Barrel, so I didn't pass it up and knew I'd do my best.

As I wrote on LinkedIn, the rest is history.

Reflecting on that time, I realize how stuck and miserable I felt in that initial job, yet I persisted, hoping for improvement.

Years later, as a manager, I've faced the difficult task of letting employees go. It never gets easier. It's like an out-of-body experience where my lips are moving, but I feel like I'm floating above the scene, watching it all play out. While challenging at the moment, I've learned such separations are often the best for everyone in the long run.

The first person I had to let go of is a vivid memory. Despite numerous challenging conversations, their shock and disappointment were tough to witness. However, this individual went on to thrive, choosing a path that suited them well—becoming a successful manager and leader.

I wonder if they, too, might view their time at Barrel as I view my first job—a difficult period that, in hindsight, was a stepping stone to greater success.

Navigating the decision to let an employee go is difficult and complex, yet it often marks the beginning of a more positive path for both the individual and the organization. While inaction might feel better in the short term, it tends to lead to prolonged challenges for everyone involved.

Whether dealing with an employee's underperformance, or a personal challenge, I try to remind myself it's often the toughest decisions that pave the way for opportunities and growth.


What challenges have I faced that I later found were actually opportunities in disguise?

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