The Question (And Answer) That Changed Everything For Me

“Once in a while it really hits people that they don’t have to experience the world in the way they have been told to.” — Alan Keightley

For me one thing is for sure: the times in my life that I’ve been most disappointed in myself haven’t been when I’ve screwed up or when I’ve failed. They’ve been when I didn’t follow my heart and instead did what I was “supposed” to do, or what everyone else was doing, either out of fear, jealousy or a desire to fit in. And when I looked back, I was disappointed in myself. I’ve decided not to do that anymore.

Four years ago, I took my first big step off the normal path, and started trying to figure out what I really wanted out of life. I quit a comfortable job in private equity, grabbed a backpack and headed to Latin America without much of a plan. It was hard to explain but I just knew I didn’t like the path I was on, and I wanted to see more of the world. I was too scared to tell people that I didn’t really know what I wanted, so sometimes I made it sound like I had a plan. I didn’t.

A few weeks later, sitting on a cramped bus somewhere along the pacific coast of Costa Rica, I found myself doing some deep thinking. I started probing a lot of assumptions I’d made about life and I stumbled upon a question that changed everything for me:

“What is success to me?”

It sounds like a simple question. But I didn’t have an answer at first. At least not a good one. My view of the world, and myself, was still so obscured by the filter of the New York finance world.

It was the first time I realized I needed to throw out a lot of what I’d been told and a lot of what I’d seen others do — many of whom I very much respected — and answer the question for myself.

If I am making it sound like my entire life plan crystalized at that immediate moment, I assure you it did not. It was just the first time I really challenged every initial response with “Why?”

Sitting on that bus in Costa Rica my mind bounced along:

So what do you want?

Well when I go back to the US, I think I want to be a partner at a top-tier real estate private-equity fund. (Why?)

To make more money. (Why?)

To earn the respect of my friends and to buy lots of cool stuff. (Why?)

Because owning lots of cool stuff is fun. (You sure about that? You’re having fun right now and all you have is a backpack full of clothes.)

And making money means I’m good at what I do. (Yeah but is this the only way for you to do that? And why do you want more money anyway?)

Because I want people to think of me as being successful. (That’s really what this comes down to isn’t it? You’re going to live your entire life doing something you don’t want to do, just to prove something to other people?)

In the beginning, I had more questions than answers. It was confusing. It was difficult to acknowledge that I had somehow ended up on the wrong track. I had been working so hard, and I had been doing so for something that I really didn’t want at all. For a while I thought maybe it would just be easier to avoid the question all together and go on believing that I was on the right track.


If we’ve ever worked together you’ll know that I am very competitive. I like to move fast. I want to win. I can definitely be accused of being impatient.

I’ve figured out that I have to constantly make sure I’m not trying to be the best at something I don’t even want. My guess is that I’m not the only one that happens to.

Have you ever questioned the track you’re “supposed” to be on? Really, really questioned it? Over the past few years I have.

So, today, how do I define professional success? (Personal success is another thing entirely — and a story for another time.)

I think I’ve finally come up with something that works for me. A definition and a goal that I believe will bring me fulfillment:

To build something meaningful.

Two parts.

Build. Something meaningful.

I love the idea of creating something that should exist, but doesn’t yet. It’s just really hard. It’s much easier to buy something than build it. It’s much easier to critique something than to do it. But I love the creative process of making things. Occasionally I’m even good at it. I’ve decided that for me its worth doing even if it means failing. It’s just too much fun.

As for the second part, it kills me to waste time working on something I don’t find meaningful and that won’t have a positive impact on others. Of course, “meaningful” is subjective and can mean different things to different people. For me, it is about finding a group of people that I want to serve and making something that they want.

That’s my definition of professional success. That’s it. I believe the rest (i.e. money) will work itself out.

Your definition could be completely different and that’s OK. In fact, that’s my entire point. It should be your own.

So why do I believe that defining your own success is so important? Well, in the long run it will give you a better chance to lead a more purposeful life. But it helps in the short run too.

When I have a hard day, or when I find myself getting jealous of others, I take a deep breath and remind myself of my goal. Usually when I do I realize that — much to my surprise — I am pretty much on track. The track that is right for me. I have to remind myself that my definition of success is my own and to compare myself to anyone else is just wrong.

I encourage you to ask yourself tough questions and then keeping asking why. Have the courage to listen to your instincts and be yourself. I think when you find the right answers, you’ll develop the conviction you need to act on them.

There’s an awesome TED Talk by Alain de Botton who ends his extremely entertaining talk by putting it this way:

Because it’s bad enough, not getting what you want, but it’s even worse to have an idea of what it is you want and find out at the end of a journey, that it isn’t, in fact, what you wanted all along.

So what’s your definition of success? Are you on track? And if not, what are you going to do about it?