Being called an opportunist is hard to mistake for a compliment, but maybe it’s just gotten an unfair rap. It’s really a matter of principle. Pursuing opportunities at all costs has never been a good look, but assuming one’s intentions are ethically sound, approaching whatever possibilities the universe might present with openness and equanimity seems like a pretty solid modus operandi. At least this is what I’ve been telling myself all these years. …

Who can say for certain whether people actually do have clear pictures of their imagined or aspirational futures, but long-term envisioning is a one of the more popular psychological games we play with ourselves. Where do you see yourself in five, ten, twenty years? At the very least, it’s an activity that could help us crystallize our goal-setting, giving us the impression that we’re pointing our aims towards a tangible-seeming target.

But instead of a vision board, sometimes it seems like I’m staring at a memory board. Literally–the large blank canvas I have perched on my desk is filled with…

I was just running the numbers, (you know, as you do) and it turns out that this week marks my thirtieth move since kicking off this unpredictably itinerant life at the age of seventeen. I just turned forty-three this weekend, so that averages out to packing and unpacking nearly once a year for the past twenty-six years. With every move, the quips feel like a running gag: I can’t keep up with you! How do you do it?, or, This’ll be the last time, right?

There’s a line from a song by The National that I think about a lot…

If you haven’t already, I bet you’ve been thinking about quitting your day job to follow your passion. Am I right? I’m not judging. In fact, I did it myself. Actually, I did it twice. The first time didn’t stick, and do you want to know why? Here, I’ll tell you all about it. But if you just want the short story, it’s because following my passion turned out to completely lack direction. I followed it straight off a cliff of failure and disappointment, and guess what?
I was not alone down there.

Maybe I’m being a little dramatic, but…

A few months ago, I took a short business trip to Switzerland. Just one night in Basel, a day of meetings, and then a 90-minute prop-jet flight into London City, and I was home by 7pm. No big deal, really. Still, it was the cap on an exhausting and chaotic week. I spent the next two days catching up on life, getting organized for the week ahead, and also just quietly relaxing. I blithely forgot about the tentative plans I’d made to get together with a dear girlfriend whom I hadn’t seen for some time. …

Ok, can I tell you a secret? I know I seem cool and edgy, with a devil-may-care attitude today, but if you can believe it, I was an over-achieving nerd when I was a kid. Like a volunteer for extra credit, clean the blackboards and sweep the classroom, get asked by the teacher to help others with their homework, choir-singing nerd.

Trigger warning for whom the mentions of “grad school thesis” and “theories of behavior change” induce aggressive eye-rolling.
(Updated March 6, 2021)

Since I’ve spent (and continue to spend) plenty of time thinking about my lack of consistency in practice, I thought the topic could use a fresh angle. In writing about my so-called “lazy perfectionism,” I considered the usefulness but ultimate limitation of extrinsic rewards like receiving high marks or praise, or even mo’ money. And while I recognized in myself a serious sense of drive, I couldn’t help but wonder… what was under the hood? …

Back in 1992, MTV, which was very culturally relevant and very much a part of my teenage life, played an integral role in the election of Bill Clinton. Clinton had recently donned some shades and played his sax on the Arsenio Hall show, launching himself as the “cool” candidate and appealing to a new wave of GenX voters. MTV harnessed this energy to tremendous success in partnering with Rock the Vote, inviting Clinton to appear for an audience Q&A and to be interviewed by MTV News reporter Tabitha Soren, who was the face of their “Choose or Lose” voter registration…