Hungry? Have Some Humble Pie

I graduated college in 2005 with an insane amount of ambition. I always opted for the internship vs. the study abroad program. I was obsessed with getting a job before I graduated. I wanted to be one of the few, the proud, the employed upon receiving my degree. 

I got my wish when I was hired by a start-up staffing firm in the middle of my senior year of college. I was so excited. I was a man. I had gotten a job. To hell with backpacking tours of Europe or stints as a captain on Royal Carribbean cruise line. I was ready to go do some WORK, despite my elders advice that “you’re only young once — take advantage of it.” 

I started working a week after I graduated. I was so excited that I had “options” as part of my package – thought I was a real bigshot. A year and a half later, I was kind of tired of the staffing game, so I moved into corporate recruiting at a consumer health company led by some pretty prominent people. Their prominence led me to believe that I was joining something special, something revolutionary, something game changing. And while I met a ton of people I loved/still love working in that energetic, adrenaline filled environment, I realize that part of my infatuation with the place was the panache of working for the “next big thing.” 

Eventually, the “next big thing” got acquired and I got laid off after several rounds of downsizing. Some friends of mine had started a company and invited me to join them as an intern/consultant. I did so, and that ride wound up being wilder than I ever could have imagined. 15 employees to 4000. Then down to 1500. Throughout my time at this company, I had the naïveté/audacity to think I was going to be a millionaire. I thought, “this is incredible! I’m so lucky! I’m going to be rich!” I was pricing Maserati’s & boats. And then things took a turn for the worse, and rich was the furthest thing from reality I could imagine.

I eventually left that place and moved on to another. My motivation for doing so was: “If I stay here much longer, people will start to question why I spent so long here” and “I want to get back to my start-up roots. I want to grow something from the bottom up again.” So I tried my hand at two start-ups based in San Francisco that were sexy, had funding, cool technology, and a host of other reasons for me to be excited. Unfortunately, neither of them was the right fit for me.

So here I am. Out on my own. Trying to figure out my next chess move. Do I join another start-up as a “get shit done/swiss army knife” guy? Do I work at a more established company that will acknowledge my management experience and bring me in to help them scale? Do I start my own thing and see how that goes?

I don’t know the answer to these questions (yet), but I do know this: for 12 years I spent all my time thinking about a) how far ahead will what I do now would get me in the future; and b) How green the grass is on the other side? c) What will others think of X, Y, Z? 

If there’s anything I’ve learned in the last 10 months, it’s that a) focusing on what you love NOW is the only way to guarantee success in the future; b) green grass is rare, so stop seeking it out so damn much; c) What others think doesn’t matter. It’s what YOU think that counts. 

This week I started driving with Uber. I didn’t have to from a financial perspective, but I’ve always wanted to give it a try because I love the concept, it’s easy money, I like driving, enjoy meeting new people, and if nothing else, it pays for our car. It’s also an interesting test of one’s ego…

Did I ever in 1 million years think I’d “drive an uber”? Absolutely not. 

Would I be embarrassed if someone I knew got into my car after requesting an Uber? Maybe at first, yeah. Should I be? Hell no. 

In the last 10 months, I’ve realized: “YOU ARE NOT WHAT YOU DO OR WHO YOU WORK FOR. YOU ARE [your name]. SOMEONE WITH TREMENDOUS TALENTS THAT A LOT OF VERY SMART, HARD-WORKING PEOPLE WILL VOUCH FOR. WHAT YOU DO AND WHAT COMPANY YOU DO IT FOR DOES NOT DEFINE YOU AND DOES NOT MATTER IF YOU DON’T KNOW WHO YOU ARE. YOU ARE [your name], AND YOU ARE AMAZING AT WHATEVER LIGHTS YOU UP. GO FIND IT.” 

I think it’s pretty easy for people to get caught up in what they do and what company they do it for, so much so that they forget the crucial message that who they are is separate from both of those things. I’m learning that now, and I hope that others will take time to reflect on that as well. In the meantime, see you in the Uber! 🙂

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