10 years ago tonight Jack Shephard laid down in the bamboo and closed his eyes. 10 years since I sat stunned in my TV chair thinking that’s it? Really??? It was about their journey??? I was not happy.
Little did I know on Sunday, May 23, 2010, the events that would affect the course of my journey were already in motion.
The next morning my bus broke down, which had never happened in the six prior years of my #buslife. Then our replacement bus broke down. 2-for-2. Did everything fall apart when Desmond pulled the plug??? When the third bus finally picked us up I half expected to see Hugo Reyes behind the wheel of my trusted route 53. Wouldn’t that have been a hoot.
I finally got to work at my job leading comms for the Republican caucus in the Minnesota House of Representatives. The legislative session ended the week prior with a budget stalemate and a brewing electoral battle over Obamacare. We intended that to shape the coming campaign season, and boy did it ever.
We rode a wave to historic electoral success in the Legislature but fell just short of claiming the governor’s race. Had we done so, the next two years would have been an incredible high. Instead they were probably the most challenging, frustrating years of my career. Halfway through the next election—2012—I knew I was ready to walk away.
Maybe I would have stayed if things went our way that year. But as Miles Straume said, “Whatever happened, happened.” We got our asses kicked. My time was up. A new chapter of my journey was about to begin, 899 days after the Lost finale.
Other than not politics I really didn’t know what I wanted to do with my career then. I never wanted to be a political lifer and with nothing but political experience on my resume at age 32 I knew the longer I stayed in the harder it would be to break out. I can only wonder how different my life would be today if I’d taken any of the opportunities I had over the next few months to stay in that world.
To be honest with you, I was not very good at being unemployed. Public relations and communications was the logical next step, so I spent months doing the lazy thing and applying for online listings at companies or industries I thought would be fun. Sports, aviation, business. PR agencies didn’t really strike my interest, but most of the locals had something I applied for at some point. Online listings funnel your resume into a soulless void of online tracking systems. I’m not sure anyone has ever gotten a job that way. The real way to find a job is to network. I am terrible at networking. In fact, I basically don’t do it. People. Ugh.
Except at some point in the mid-2000s I fell in love with online communities. There I could network my ass off from the place I was most comfortable: Behind the keyboard. Everyone else was behind the keyboard, too, so I didn’t have to feign interest in small talk. Or talk at all. I was here for it when social media emerged, and I joined Twitter on September 25, 2007, some 972 days before the Lost finale.
That one little act, so insignificant at the time, altered my journey perhaps more than any other.
Twitter and I fit hand and glove. You couldn’t write more than two sentences in a tweet and most of my thoughts aren’t more than two sentences long anyway. Social media’s rise coincided with my rising position within the caucus. By the time Lost ended I was not only the caucus media director, my tweeting was getting me interviewed on TV and invited to speak on panels. My stupid little profile icon even got me recognized when one lawmaker ran up to me in the Retiring Room to ask, “Are you Kwatt from Twitter?”
Sure am. Do you remember the campaign brochure that popped up in your district, the one designed to look exactly like your local newspaper but was full of reasons to vote against you? That was me, too. Turns out I sort of invented fake news. Sorry. But I digress…
By the fall of 2013 I wasn’t sure I’d ever work again. Then one afternoon an email popped up from a Twitter friend who was writing a story profiling prominent local Twitter users. She wanted to include me. Sure! That’d be pretty cool. So she sent me her list of questions.
I was doing some light freelance work at the time and found myself in the southeast corner of Minnesota one Tuesday. With a few hours to kill between meetings I set up in a local coffee shop and started on my responses for the article. When it came to “What do you do for work?” I paused.
Should I put that I don’t have a job? Naw, that would be cheeky. Wait. You idiot. This is going to get published. Treat it like an advertisement—for yourself. Yeah! So that’s exactly what I did. “Kevin Watterson, age 32, currently looking for a PR job. Previously did PR and communications in the state Legislature.”
Months passed and I forgot about the article. It finally appeared on January 1, 2014. A few weeks later, Kathy Jalivay came across it. Kathy was the head of PR at a marketing agency in St. Paul and just so happened to be looking for someone looking for a PR job. On February 12, 2014, I joined her at Aimclear. I was unknowingly familiar with the office: I stood outside of it every night for the last six years waiting for the route 53 bus to take me home. It was 1,362 days after the Lost finale.
My journey through Aimclear was fantastic. I met awesome people and learned more than I could have ever hoped. At one point I was the Twitter voice of Firestone auto care, handing out coupons for a discount oil change to people who posted the best #roadtrip pics and making the best tire puns. Clients came, clients went. Some were more fun than others. Such is agency life.
My journey rolled on outside of work for those five years, too. I became an uncle. I got some things right, I messed up others. I traveled. Even took my first winter vacation, having been tied to the Legislature from January through May for all those years.
Then in January 2018, Uber called. They needed someone to cover social media while one of their OGs was on sabbatical. They already had one Aimclearian and wanted another. I landed in San Francisco and walked in the door at Uber for the first time on February 13, 2018. It was 2,824 days after the Lost finale.
They must have liked what they saw because by June 1 I was living in San Francisco full-time (2,932 days) and on March 4, 2019, I badged in as an official Uber employee (3,208). My longtime goal of moving to California was complete.
I can’t predict where my journey will go from here anymore than I could have predicted it would lead me here. Maybe in another 10 years I’ll be somewhere else, making 39-year-old Kevin insanely jealous.
It has been 3,654 days since the Lost finale. I get it now.