What do I really need?

It is such a simple question, yet sometimes it takes decades to discover the answer.

For me, that question began around 1999.

Several evenings each week, after work, I would ride the 7 train into Grand Central and transfer to the downtown 6 train on my way to Baruch College. My employer had enrolled me in a Project Management certification program, and I was determined to succeed. At that point in my life, I was completely in career mode. I believed that every certification, every class, and every accomplishment would move me closer to the life I wanted.

Like so many New Yorkers, I escaped the noise of the subway by putting on my headphones. Back then I carried a bright yellow Sony Sports Walkman, the splash resistant cassette player that seemed to go everywhere with me. I loved that little Walkman. As the train rattled through the tunnels beneath Manhattan, I would press play, shutting out the screech of the rails, the station announcements, and the endless rhythm of the city. One song seemed to accompany me on almost every ride: All I Need by Matchbox Twenty.

As I listened, I found myself asking a question that I could never quite answer.

What do I really need?

At the time, I believed the answer was simple. I needed more education, another certification, more experience, and a better career. I believed that if I kept climbing, eventually I would arrive somewhere that felt complete.

One evening during class, our professor asked a question that has stayed with me ever since.

“What does a project need in order to be successful?”

My classmates talked about planning, budgets, schedules, communication, stakeholders, and deliverables. Every answer was technically correct.

Then it was my turn.

I remember saying that before any project could truly be successful, it first had to satisfy the needs of the individual managing it.

Several classmates disagreed. They argued that the purpose of a project is to satisfy the stakeholders, not the project manager. Looking back, I understand why they challenged me. The truth is that I could not fully explain what I meant either.

I only knew it felt true.

What I wanted to say, but did not yet have the words for, was that if the person leading the project is disconnected from themselves, no amount of planning will ever create a meaningful life. You can complete the project, deliver it on time, stay within budget, and receive recognition, and still feel that something is missing.

At the time, I could not explain it.

Today, almost three decades later, I finally can.

I completed the certification. I passed the exam. I became a certified project manager. For years I managed successful projects. They were completed on schedule, within budget, and according to plan. From the outside, everything looked successful.

Inside, however, something felt deeply out of place.

It was not because I disliked the work, and it was not because I was not good at it. It was because I felt trapped. I was living inside a system that rewarded results but rarely asked whether the person producing those results was truly alive inside.

Little by little, I realized that what I had been searching for on those subway rides was not another credential. It was not another promotion. It was not another title.

What I was searching for was freedom.

Freedom to make decisions that reflected my own values.

Freedom to create instead of simply execute.

Freedom to explore questions that fascinated me instead of only solving problems that belonged to someone else.

Freedom to build a life instead of merely building a career.

Looking back, I realize that the young woman sitting on that subway was not really asking, “What career do I want?”

She was asking a much deeper question.

“What kind of life do I want?”

The answer had been quietly following me all along, hidden inside a song playing through that bright yellow Sony Sports Walkman.

Today, when I ask myself the same question that I asked on those subway rides so many years ago, the answer is finally clear.

What do I really need?

Freedom.

Not freedom from responsibility.

Not freedom from work.

But the freedom to live according to my own beliefs, to continue learning, to continue creating, and to wake up each morning knowing that the life I am living is truly my own.

It took years, mistakes, careers, successes, disappointments, and countless rides through New York City to understand that.

Sometimes the greatest project we will ever manage is not the one assigned to us by an employer.

It is the lifelong project of discovering who we really are.