6 AM meant it was time to check voicemails. 11 PM meant it was time to check voicemails again. Every second in between reserved for cranking and putting out the many fires guaranteed to crop up that day.

That was my life as a Goldman Sachs VP, and despite what you might assume, I didn’t hate it.

I didn’t get there by accident. I’d worked that hard since my first job at KFC to get where I thought I should want to be, and by all accounts I was crushing my goals.

Except they weren’t my goals. Despite my success, despite the deep friendships I’d made at Goldman, I could never shake the sense that I was living someone else’s idea of success.

At a certain point, it was time to leave.

Why It Took Me This Long To Walk Away

A lot of people feel trapped in their jobs for various reasons:

They’re afraid of losing the money.

They’ve grown too comfortable.

They think they don’t deserve something more.

But none of those applied to me.

I lived well below my means on Wall Street and had a little money stashed away to feel comfortable taking the risk. I didn’t know where it would lead me, but I knew I would figure it out.

I hadn’t grown too comfortable in one position—in fact I’d changed my job four times at Goldman already.

And I most certainly did not fall into the third trap. Too many people confuse their unhappiness with ungratefulness, and feel ashamed for wanting something more than what other people think they should want. On a base level, I always knew this shame was self-defeating and rejected it.

What had held me back, however, was the question that had baffled me since I began transforming my career and life, What Do I Want?

After all these years, job changes, moving countries, and cities, reading thousands of books and writing thousands of pages of ideas, I still didn’t know what I wanted.

Whereas years earlier I was certain that I wanted to be at Goldman for the rest of my life, I couldn’t point at something and say, “I am 100% certain that I want to do this for the rest of my life.”

I could, however, do something else. Looking at my current job, I could say, I am 100% certain that I do not want to do this for the rest of my life.”

So I quit.

How I Quit A Job People Would Kill For

If it seems like I was jumping out of a plane without a parachute, it’s only because I was.

In fact, it had been building up in me for so long, that a week before bonuses were paid (when you should do nothing more than keep your head down), I headed into the corner office and blurted out that I wanted to resign.

Many people have anxiety about this conversation, but if you have honest and compassionate relationships with your bosses, their reaction to you quitting will be honest and compassionate.

No one was angry with me, they just wanted to understand. They wanted me to explain what I was leaving to do, which was difficult for me, as I had no idea.

It was easier to stay. But, after many years of figuring out what I wanted, I simply knew it was time to leave. Still, that was hard to do.

I felt sure it was what I must do, and I put on a good poker face, but I was terrified to leave.

Hoping to find a way to keep me, from the day I quit in January till the end of April, I tried on different hats within Goldman Sachs. The whole time, I knew none of them would fit.

In my final conversation with one of my bosses, he said to me, “I understand why you would leave, but I still don’t know why would you leave to do nothing.”

I wasn’t leaving to do nothing. I was leaving to do everything.

Why Being Unemployed Was My Best Career Move

The day I left Goldman, I pulled out of the parking lot on Century Boulevard, dropped my silver sports car back into 2nd, and sped away.

At the first light, reaching over and picking up my Blackberry, I scrolled to the Goldman Sachs voicemail number I had dialed for many years, and hit delete.

6 AM meant I was still asleep. 11 PM meant I was doing something worth doing. Every second in between was dedicated to exploring what I wanted.

Over the next 18 months I would travel the world, read tons more books, have new adventures (like training MMA non-stop for a year), and make friends who I treasure to this day. All of this in search of what I wanted to do with the rest of my life.

What I didn’t realize is that, not only was I figuring out what I wanted, but through trial and error I was creating and fine-tuning a system for living the life that you truly want.

The Answer Never Ends

Many of us in life are looking for meaning we can state in a sentence. We want to say, “I want to do this for the rest of my life. Full stop.”

But in life the only full stop is death, and until then we are in motion. By constantly asking myself the question, “What do I want right now?” and figuring out what moves the needle on that goal, I was journeying to the place I am today.

In leaving Goldman I realized that I wasn’t seeking that mythical beach to sit on, but to keep moving towards a career and life of great purpose and meaning. I didn’t know what that was, but I knew I had to keep exploring to figure it out.

Today I spend my time working directly with others, in their businesses, in their lives driving more of what they want each day.

I didn’t build a system that gets you from point a to point b. I built a system that is point b, that keeps you in constant motion, perpetually discovering and rediscovering what it is you want and helping you develop the process and skills to get it.



I left Goldman Sachs because I had a question I needed to answer. What I built was the system that I wish someone had given me.

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P.P.S. Here you can listen to previously published tracks from the Masterclass for Rainmaking Bankers.