The office retreat done right

Today’s a day for breaking rules. Not the federal kind (ahem, Michael Vick), but those unwritten rules of the office that keep us from revealing the workplace machinations other people might actually find amusing. Today, though, I am sharing. Why? Because sometimes it’s good to explore how silly we can be.

So the story goes, it’s a regular Wednesday afternoon in early July, and an e-mail goes out to the staff inviting us to the Fortune summer picnic in a few weeks. For those of us who joined the staff in recent years, this is assumed to mean a few afternoon hours in Central Park meeting people’s families and playing games of (not too much) skill. Usually, the day starts with that uncomfortable question, “Shorts?” and ends with a sweaty walk back to the office, where piles of work still await.

And for the most part, we’ve been fine with that. (So sad.) But this year’s picnic link heralded something different — an all-day mountain-biking, pool-swimming, band-playing, and even beer-drinking extravaganza at an estate an hour and a half away. (Meaning, it should be noted, that 1) there was also going to be lots of group bus-riding, and 2) there was not going to be much stealth-escaping.)

There were whoops of joy and murmurs of excitement, for sure, but it must be said that more than a few moans of resignation also rang through the halls. And many were coming from us. In our defense, “retreats” generally combine the very worst of family reunions and corporate off-sites — trust falls and drunk uncles, a Wedding Singer-esque cover band, hula-hoops. “Shorts?”becomes the infinitely more confounding, “Bathing suits?” Plus, it’s not uncommon to find yourself wondering how you’ll ever look at your boss the same way now that you’ve seen him annihilated at 3 p.m. dancing to Gloria Gaynor in bobby socks. And clearly we were more likely to feel this way than our older counterparts; many of them had known each other much longer, and therefore had already seen each other in bobby socks.

But by the time we eventually got on the bus last week — our first date was rained out, and I think we felt so ridiculous walking around the office the whole day in our playtime clothes that we were happy the next day just to be going — there was a little buzz of anticipation. Jokes were made, newspapers put to the side, and that age-old ritual of backseat bus-driving honored.

When we reached our destination, the hors d’oeuvres were already underway, and with that, a glass of wine, and the bright summer sun, the day festivities commenced. And of course, they were great. Nobody got trashed, though that was almost disappointing in retrospect. (Our deputy managing editor, Hank Gilman, says they read our drinking post ;o). A few Advil had to be consumed with all the sportiness, but that never hurt anyone. And the band was phenomenal. (Check them out — The Jonah Smith Band.)

It shouldn’t have been surprising, since our event coordinator and overall office guru, Wendy (a singer in her own right —, is just about the coolest person around. But I don’t think that initial reaction was as much to the activities — though had trust falls been on the real agenda, I might have been less than stoked — as to the thought of spending the day with the grown-ups, people we work with and for, but still often put in the same mental box as our parents or older siblings.

Truth is, though, sometimes that’s the best way to think about your colleagues, especially your superiors, because they are family. And yes, it’s sentimental enough to make you gag, but let’s be honest, seeing them this way forces you to acknowledge that they do mean a lot to you. Just like family, your relationship with each one is different, and some are better than others, but you wouldn’t (for the most part…) trade any of them in even if you could. And the best bosses know that being reminded of that every once in a while can be just the thing we need to keep us coming back every day.

But what about you? Are these events your idea of great cross-generational team-building, too, or is the heat just getting to me?

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