Never settle. Keep looking. Be hungry.

Last week, I resigned to go co-found a startup that tackles local search. We believe that it’s done badly and we intend to do better. We will bootstrap, live on savings for a bit and build prototypes that hopefully can attract angel investors while treading above a real and striking possibility that we will fail. 

About a year and half ago, I was asked to lead two things at Hill Holliday; the mobile practice and the emerging media practice in gaming. Last week, we won Adweek’s 2012 Media Plan of the Year for Branded Entertainment (a social gaming integration) and it spectacularly complemented our win last year for Adweek’s 2011 Media Plan of the Year for Mobile. While winning one national award is tough, the same team winning back-to-back across different categories is unprecedented. 

But despite winning a second Media Plan of the Year, I also couldn’t get promoted and I now realize that even if I did, it wouldn’t have changed anything. I wouldn’t be richer, or smarter or better off, I just would have continued the same course for another round. 

We are in the middle of a revolution with how we work, how we think, how we communicate and in a few years, what we did in the past will be unrecognizable. Like what the first telephone or the first television set meant to society; social media, the iPad, cloud computing, big-data and smartphones are all just the beginning. I am wildly optimistic about this future and I have always believed that the future was filled with opportunities to do things that might have seemed impossible in the past. 

Our time is limited and my bitter disappointment has been a moment of clairvoyance that I have the best opportunity to escape from the known possibilities like the next promotion, the bigger office and more awards for something infinite and unknown. Jumping straight into the unforeseen let’s you dream that not only anything is potentially possible but literally you believe in your soul that anything can be possible. At this point you start sprinting into the unknown because it’s all you want to taste, breathe and smell and nothing you’ve ever been familiar with in your life feels important at all. 

I do not know whether I will succeed or fail but I intend on obsessing on never settling since the possibilities are spectacularly unlimited. If you’re reading this and you feel unsettled with your finite possibilities, I suggest shaking things up. 

Addendum 8/21

It was not my intention to get press for what I wrote (BI, MediaPost) nor was it my intention to embarrass anyone. I write things here to clarify my thoughts and express with conviction for the things I personally believe in. When I share my personal disappointments here, it’s because I think being candid is helpful and maybe someone in a similar situation can do better. 

Fun facts: 

— When I meant I was leading the mobile practice & emerging media practice in gaming at Hill Holliday and that it was unprecedented for a team to win back to back, I left out that I was a team of one. I was fortunate to work across lots of talented different groups within the agency but my equation was based on national prestige in proportion to resources. Without a doubt, it was an incredibly entrepreneurial experience.

— I’m thrilled Business Insider, the proud publication behind 50 sexiest ad-execs (I’m not on this list?!), could put together a story using the very best of what I’ve published on social media over the years. I am reminded that I have not had any Hello Kitty candy in years.

— After I resigned & gave my two week notice, and well before I had written anything that the press could even read, I was immediately cut off. This has compounded my disappointment but I know now exactly what kind of culture matters to build a great & interesting company. 

— I’ve gotten dozens and dozens of incredibly supportive and inspiring emails, tweets, calls, messages, txts and more. I’ll say it again, if you feel like you’re dying a little everyday then you have a responsibility to yourself to shake it up. Hit me up anytime and I’ll convince you. Or be docile with your happiness and let me know how that goes. 

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