From 45 to Humility

I turned 45 yesterday.

I’ve always said that I would live until I am 90, so hopefully this is the halfway point.

I’ve had a fortunate half-life.

I have a great, supportive, loving family and hundreds of kind friends around the world.

I’ve already had quite an incredible professional career that I feel lucky and thankful for. In my 20’s I hustled my way to an intense position in the Clinton White House and I experienced and grew so much at an early age. In my 30’s and 40’s I had some success in business, and also some high-profile setbacks. I’m the type of person who bounces right back after taking a punch, and I’m still at it.

It’s been a thrilling, rewarding journey.

As I get older I try to become a better person, a better friend, a better colleague, a better mentor, a better pupil. It’s a continuous process, a perpetual beta. I take more risks than most people, which means more mistakes, and there’s always room for improvement.

20 years ago the one word others would most use to describe me was: indefatigable.

15 years ago: ambitious.

10 years ago: intense.

8 years ago: confident.

5 years ago: fast.

At 45, I’m still all of those things, but I’ve also embraced a new tool in my toolkit.

Last week, a venture capitalist made a point of telling me at the conclusion of our meeting: “you’re a lot more ‘humble’ than I expected.”

Today: Humble — a very different word than the ones above.

That’s on purpose. I’ve been working on that. I have come to learn and appreciate that humility is one of the most valuable traits for any person, and especially for a leader. I’ve come to appreciate that it’s normal to have flaws, that we’re all growth projects, and that you gain more energy through supporting others than you can ever force all on your own. I’ve come to understand that you can take more and better risks when you embrace what you don’t know vs. when you convince yourself that you know everything from the start. You’re never too old or too wise to ask for advice. You’re never too old to learn — and you learn more from listening than by talking. You deserve most of the blame for your setbacks and failures, and only some of the credit for your successes.

My overarching philosophy on life has changed a lot the past couple of years. I used to always be going places, always looking around the next corner. Now, I live in the moment and focus on the here and now. I used to scowl a lot. Now, I’m all smiles. I used to demand. Now, I try to coach, and I let myself be coached. I used to have a short temper and little tolerance for avoidable mistakes. Now, I let a lot go, knowing that most everything is fixable, and if not, it becomes a teaching moment on our collective journey. While I’ve always been in a hurry, I’ve become more patient. I used to believe that being fast and achieving results was an excuse for not being nice, and that we’d make-nice during the post mortem. Now, I live for the journey.

I’d like to think I’ve calmed and gained perspective.

From 1998 to 2014 I moved cities 10 times and lived in more than 15 homes. Today I can’t imagine moving anywhere; Chris and I have found home in Berlin and I attribute a lot of my happiness there to it being the least pretentious and the most just-be-yourself place in the world.

Above all, at age 45, I can say with confidence that I know myself today more than ever. I’m comfortable and self-aware with myself and who I am, what I’m good at and where I have flaws.

The addition of humility makes me feel stronger and more capable than ever.

Why am I sharing all this?

Partly because most people don’t — especially not tech entrepreneurs. I was quoted recently saying that “tech doesn’t need to be so douchey.” I truly believe that, and I have definitely contributed my share of douchey moments in the past.

Partly because we have a President in the White House who is perhaps the least humble person on earth. The world could use some embracing of humility right now.

And, largely because I wish I could have had this chat with my younger self long ago. You can be all those things that make a strong entrepreneur: indefatigable, ambitious, intense, confident and fast, but until you are humble about it and self-aware, you’re not playing with a full deck. Sure, there are some high profile examples of successful entrepreneurs who seem to lack the empathy gene but don’t model yourself off of them: model yourself off the most gracious you that you can be. This may sound counterintuitive but it’s true: A humble leader is a more confident leader — as you are more aware of who you are and what you do.

p.s. I’m well aware that writing about being humble can be perceived as not-humble. I humbly ask for your understanding.