The Merry Stormtrooper

“I work at Microsoft,” I said.

It was SXSW 2009, and I’d just bumped into someone I dated in college. This was the first time we’d seen each other since our breakup. As often happens in such situations, the uncomfortable exchange had come down to one question: whose life was better?

My reptilian brain went into overdrive as I sensed her move in for the kill.

“Oh? Ha,” she said. Knife. Twist. It was over.

In today’s tech culture, Microsoft is like the guy wearing the bluetooth headset: uncool by default. I joined the Death Star shortly after the iPhone was announced in 2007. I left earlier this year, shortly after the launch of the Surface RT, and a few months after my five-year anniversary at the company. My area of focus was the web community, a place where relations were strained to say the least. And for a brief period of time during my tenure, my job was to get the web community to love Internet Explorer again.

Sad Yoda.

At the time, Internet Explorer was any web evangelist’s worst nightmare. In the years leading up to my start at Microsoft, it had become a product that we (excluding our moms, maybe) had grown to love to hate. Try to imagine charts like this, even if made in jest, being created for your product. IE-hating is so much of a cliché that the IE marketing team even released an ad based on the very cliché of trolling IE.

Despite the incessant animosity, I loved my job. With the exception here or there, I liked my coworkers, respected my direct management chain, loved what I worked on, and delivered some work worthy of real-world pride. I was a happy Stormtrooper, and one of the things I frequently repeated to my peers and friends while at Microsoft was, “If I quit, it’s going to be to work for myself. It’s going to be really hard to beat this gig.” That is, in fact, what I did earlier this year.

But, under the predominantly #firstworldproblems lens for evaluating job quality, most people considered my job, pardon my French, shitty. Dan Ariely sheds some light on this in his first book: “We are always looking at the things around us in relation to others. We can’t help it.” Humans derive the value of Item A by subconscious comparisons to similar items B and C. And as compared to working at a “cool” Microsoft competitor or a “hot” Silicon Valley startup, I had a shitty job. So, let’s just go with that.

On the upside, though, this does uniquely qualify me to answer a profound question for you: how can you be happy in a shitty job?

Ashton Kutcher—yes, that Ashton Kutcher—provides some sound career advice in his speech at the recent Teen Choice Awards. “I’ve never had a job in my life that I was better than. I was always just lucky to have a job,” said Ashton to a sea of screaming teenagers. Comedian Louis C.K. echoes Kutcher’s refreshing eloquence with his characteristic bluntness in a hilarious routine where he says, “You think you’re too interesting a person to have a shitty job!?” But I suspect telling you that you have to get over yourself, appreciate opportunity and work hard isn’t very helpful advice. So let me borrow the thoughts of another mind whose work has influenced me greatly over the years, Mihaly Csikszentmihalyi.

Csikszentmihalyi gets credited with introducing the concept of flow: the state in which people are so involved in an activity that nothing else seems to matter; the experience itself is so enjoyable that people will do it even at great cost, for the sheer sake of doing it. But Csikszentmihalyi’s greatest contribution wasn’t the concept of flow but his insights into how you can achieve flow in any situation in life. In other words, Csikszentmihalyi cracked the code for the secret to happiness. And miraculously, he achieved this without having to resort to theoretical clichés and platitudes. He actually did it scientifically.

At the risk of unfairly summarizing Flow, Csikszentmihalyi’s recipe for eternal happiness is based on a counterintuitive idea that unachievable goals, those proverbial big dreams of fame and fortune if you will, are the root of most unhappiness. This is not to say that he is against achieving great successes in life. After all, much of his findings come from examining how the highest achievers in the world, from Olympic triathletes to concert soloists, find flow. Csikszentmihalyi’s research has found that you pretty much write off any chance you may have of achieving flow (happiness) by setting goals that are obviously out of your reach. In my experience, you also greatly lower your chances of stratospheric levels of success by explicitly setting goals that are obviously out of your reach. It’s a lose-lose.

The secret, as Mihaly discovered by studying all types of people in the flow state, lies in setting achievable goals that are just a wee bit out of reach. The kind of goals that will require you to stretch yourself and grow in order to achieve them. And when you meet them? Raise the stakes, and repeat. That’s it.

This is a profoundly simple concept in theory. But as the saying goes, “In theory, theory and practice are the same. In practice, they are different.” And it’s because it’s always easier said than done.

Leading up to IE9, I believed that getting the community to love IE again had two prerequisites: (a) IE had to become a product deserving of love again, (b) The community needed to let go of the legacy hatred. Even though I helped loop community feedback into product features, I wasn’t on the engineering team, and thus, I was limited in my ability to directly influence (a). Instead, along with a handful of my peers, I turned my focus on (b): reducing all the hatred for IE.

Eliminating hatred is no small feat. But from Mihaly’s perspective of flow, it is an achievable one, i.e. it’s relatively easier to get someone to stop hating something than it is to get them to go directly from hating to loving it. It requires humility, discipline, patience, a strategy, and admittedly, a pinch of masochism. Most of my work in and around the IE9 timeframe focused heavily on regaining community trust. Projects I was involved in, like 10K Apart and Lost World’s Fairs, were all part of an effort to show IE9 in its true light. It took a year’s worth of hard work and more than a few tomatoes to the face, but the negative sentiment around Internet Explorer reduced surely and steadily. Feedback became meaningful, conversations become constructive. The engineering team had created a good browser, and by the time it launched, the hate wasn’t canceling out that fact. Even you partook in the rare public display of affection for IE9.

Influencing sentiment in any domain is a challenging problem. But freed from my idealistic shackles, I was able to approach the problem without the surrounding negativity bringing me down. I flexed new brain cells, learned to truly strategize and measure in long-term units, reevaluated beliefs about right and wrong (a discussion for another day), and grew in all sorts of previously unimaginable ways. And, as Mihaly predicted, this led to a tremendous amount of flow. For such a “shitty” job, it was one of my happiest times not only at Microsoft, but in my career.

The beauty of Mihaly’s approach is its micro-versatility. It can be applied to almost anything in life, both at work and at play, from attitudes and behaviors to career and life goals. Having difficulty losing fifteen pounds? Maybe you should focus on losing five pounds first. Is your business not making enough money? Maybe you’re boiling the ocean, and need better focus. Unable to successfully give your sister some career advice? Maybe you should work on being a good listener first. Whatever the problem, it can be framed in such a way that you are working toward the long-term goal by setting a realistic initial goal before you raise the bar and repeat. As it turns out, the essence of aphorisms like, “He who ships, wins,” or “The secret to getting ahead is getting started,” live in Mihaly’s elegant recipe for flow.

But try to tell that to your inner critic and you’ll feel an instant backhand slap across your cheek. The inner critic sees realistic goals as the doorway to mediocrity. It will taunt you, and call you a loser for setting a “lesser” goal. It will attack you with Vince Lombardi’s infamous words that forever tipped the scale in favor of our runaway aspirations, “Winners never quit, and quitters never win.” But as Seth Godin counters in his pocket reference, The Dip, “Winners quit all the time. They just quit the right stuff at the right time.” What your critical mind dubs a lesser goal is, in fact, a smarter goal. And it is your only path towards getting the big, even if currently unachievable, prize.

In closing, I encourage you to revisit that recurring shitty situation. It could be related to your relationships, your finances, your health, your job, or something else entirely. The realm is irrelevant. What is relevant is your approach. And while there’s a limited amount I can do to help you through the internet, I urge you to dedicate some attention to the finer details. Happiness is a goal, and an achievable one if you are to believe Mihaly when he writes, “A person can make himself happy, or miserable, regardless of what is actually happening ‘outside.’”

May the force be with you.