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Chasing Happiness?

A few weeks ago, I received a surprising email. Here's a short snippet:

"I am one of the co-chairs of the Tuck Media & Entertainment club.  We are currently planning the 3rd annual Tuck Media & Entertainment Symposium and would be honored if you would come speak and present your web series "The Consultants"."
(Tuck, by the way, is Dartmouth's business school.)
So that's what I'm going to do next week -- apparently go speak at Dartmouth about me and "The Consultants"! Here's the webpage for my talk. [link]
I've been thinking about what I'd like to talk about because they've asked me to talk a little about my journey from to Google to somehow end up making a web series. This blog post is an attempt by me to organize my thoughts around it.
Google was amazing to me on many levels. I can't necessarily say that I always enjoyed my time there, but it was a life changing event on many levels and I'm extremely grateful for my time there, the opportunity, and how it's subsequently impacted my life. The key thing that confronted me towards the end of my tenure at Google was this: I no longer need to work for money, so why do I work at all?
Growing up, I was the business guy in the family -- or at least the one that was looked at who would have a bright future in business. I gravitated towards it naturally and my grandfather (who was a very successful entrepreneur in real estate and banking) nurtured this passion in me. I still remember when he bought me ValueLine when I was only 7. For those of you who don't know, ValueLine was this rather technical stock publication which had all sorts of financial data about companies -- pretty useful stuff before the Internet came around. I can't really say that I understood much of it, but the act of just having it made me feel... serious I suppose, serious about business.
I was always in a hurry with business. When I was in college, I couldn't wait to be working -- for that and other reasons, I even graduated in 3 years just so I could get working sooner. It was June of 2000 -- I graduated on a Thursday, flew out to Seattle on Friday, and started my job at on a Monday. When people ask me if I liked Princeton, my unfortunate answer is no. I was working all the time so I was unable to enjoy it on any level. 
I don't regret many things. In fact, I rarely even think of the past. However, while I wouldn't say I regret leaving because I ended up at Google -- I do regret it in a theoretical way I suppose. I loved my time at very much -- I think there's so many things screwed up about it but it's wonderful in ways remarkable. I look at all the amazing things they've launched since I left -- Amazon Prime, Amazon Web Services, Kindle -- I just can't speak highly enough about how innovative they are and I remain a very loyal and enthusiastic customer. I do look back and kind of wished I worked on some of those products though. I wish I wasn't in such a rush.
But I wasn't happy at -- I had great friends, huge amounts of freedom in terms of what I worked on, and even multiple teams within the company that offered me positions within their groups. I know this sounds strange, but I think I wasn't happy because I just wanted more. I was tired of some of the internal dynamics, I wanted to be accomplishing more -- and I thought that I could do more on my own. I was wrong. 
I've been unemployed twice in my life -- the first time after I quit and the second time after I quit Google. The first month or so is amazing. Absolutely amazing. I would call my friends at 11am from Wal-Mart and say, "Guess where I am? Wal-Mart! I'm buying detergent!" They would proceed to curse me out before heading off to a meeting. However, after a month or so, I found myself kind of sad. I didn't realize how much of my identity was wrapped up in where I worked. How much, in some sense, of my own sense of value and worth. I sort of was floating around with a, "What exactly do I do? What's my purpose?" I hope this doesn't sound very airy and fluffy -- but I wondered that. 
I realized something a number of years ago. I remember that the CEO, I think of Proctor & Gamble or someplace equivalent, retired and I was reading a recap of his career. This was the CEO of one of the largest and most respected companies in the world. He was essentially what I had dreamed about being when I was a little kid. And I realized that I would've been unhappy if I lived his life -- his life wasn't enough for me. That what I thought I wanted wasn't what I wanted. Looking back, I think I wanted that life for the wrong reasons -- prestige, power, and accomplishment in the eyes of others.
So I set about to figure out what kind of life I did want.
This journey has been very difficult. I've had a lot of dark nights. A lot of nights where I questioned who I was, what I was doing, and really questioned my own sense of worth. I've had many nights I've wanted to throw in the towel, give in to all the criticisms -- both spoken and unspoken, and just find a way out. I didn't, and for me, this has been the most rewarding thing I've done.
I don't write this blog post from the perch of success. I'm at best an outsider in the entertainment industry. At worst, I'm a wanna-be, a pretender, a dilettante. And that's ok. I have more fun in a day than I used to have in a month. Every day, I try to take on a little more risk, to try something new, and to push myself creatively. I try to grow as a person, pursue my passions, and figure out what gets me excited.
Looking back, I think I was deeply unhappy with my life. I didn't like the life I made for myself, the career I was building, even the person I was becoming. I don't know if I was aware of it at the time -- but I think I set about to chase happiness. I wanted to be happy and in the process figure out who I was and what I wanted out of the time I had.
I don't know if I even know that today. I do know this though. I like what I'm doing. I like the fact that I'm a person that puts myself out there. That's willing to fail. That's willing to try new things. That's willing to take in feedback and that's also willing to ignore other people's opinion of me. I don't do all these things well -- some I probably do badly -- but all I do more than I did before and I struggle every day to improve myself. Some days go better than others :)
I'm obviously in a very fortuitous position, even to be able to undertake this, because of Google. I'm very grateful. I'm very grateful even to the people who I didn't get along with at Google because they played a part in making my current life possible. I want to get the most out of my life. I want to do good things in this world, and I'd like to be happy. I'm willing to work for this and I try every day to build this.
So what do I do? Why do I have a month's worth of happiness in a day? I do things like "The Consultants". When my friend Adrienne told me about her summer internship -- I thought, "Hey -- that sounds like fun! I can make a web series out of it and act in it." So I went about doing it. It was brutal and I was an arrogant buffoon thinking that my experience as a product manager would make it easy to produce it. But I met some great people along the way who helped immeasurably -- from writing to producing to a wonderful cast and crew -- and we got it done. And because of that, I'm going to be speaking at Dartmouth's business school. I don't say that in any bragging sense -- just more a sense of amazement of, "Hey -- if you put yourself out there and try things, sometimes cool things happen. Sometimes they don't -- but they definitely don't happen if you just do nothing."
When I was hanging out at the Magic Castle and a magician relayed the story of what people say when he tells them he's a magician -- they say, "That's fantastic! [pause] So what is it you actually do?" I heard that and thought, "How do magicians make a living?" -- and set about making a documentary on the business side of being a magician.
Even in tech, after I left, I've had the most rewarding professional experience of my life. A friend of mine is a partner at Google Ventures and frankly, saw in me something others did not. He thought I could help startups as an advisor -- so he went about and brokered a couple of introductions. I have never enjoyed anything I've done in business more and the great irony is this happened after I left tech.
These days, I try and do 3 things.
1. Keep an open mind to anything, everything, and new opportunities. Try to find ways to say yes.
2. Work hard. Try to get a little better every day.
3. Make new friends.
If you knew me before, I think I probably worked actively to say no to things and didn't care about making new friends. I think it's fair to say I've always tried to work hard. I hope I'm on the path to becoming the person I'd like to become. I hope I do do good things in this world and have a positive impact. And I hope to have a lot of fun doing it.