Standup paddling is such a new sport that we're all beginners, really—no one has gotten old SUPing. And yet most of us hate being considered a beginner. I can't count the times surfing buddies have told me that while standup paddling might look inviting they just can't stand the idea of being a beginner again. Never mind that SUP's learning curve is as steep as a Teahupoo drop; fear of the kook-move runs deep. And I must admit that when it comes to kook-moves, standup paddling dishes out its share, even to those of us who've put in our time on board.

I recently went surfing with a good friend who belongs to the Elks Lodge in Honolulu, the venerable private club perched on the Pacific where the iconic crater we call Diamond Head dips its foot into the sea. For those unfamiliar with the Elks Lodge, suffice it to say that it's a more prosaic (read: blue collar) version of the very plush—and equally venerable—Outrigger Canoe Club right next door. While the Elks Lodge tends to host what seems like Oahu's entire legion of retired haole insurance salesmen—a slice of the Midwest set down here in paradise—the Outrigger has been the epicenter of all things hoe for over a century now, and standup is no exception. This is where Todd Bradley grew up and eventually innovated many of the SUP techniques and equipment we all take for granted. With its sumptuous facilities, restaurant, gym and board lockers, the Outrigger is the most glamorous paddle/surf club on any shore, and Old Man's, the accommodating reef break directly out in front, provides a relatively private wave-riding resource for watercraft of all types.

On this particular day, a sunny, windy Tuesday afternoon, with the afternoon northeast trades whipping around the southern tip of Le'ahi (Diamond Head's real name) and pushing a shimmering cross-chop through the Old Man's lineup, I had resigned myself to a conventional lay-down session, having no standup equipment with me. As luck would have it, I ran into fellow Elks Lodge member Edmund Pestana, for over 30 years one of Hawaii's top paddlers and now one of the Island's best standup surfers.

"Sure, I got a board you can borrow," Edmund said, pulling from his truck a 9-foot Naish shaped by Harold Iggy: a racy semi-gun with about half the volume of the board I normally ride. Considering its pulled-in nose and narrow pintail I actually gulped. I hadn't felt this sort of apprehension since my earliest days with a paddle. In fact this might have been worse—dread of the kook-move can loom heaviest over the veteran.

But c'mon, you've been riding SUP for years, I told myself. You can handle Old Man's on a board this size. Of course it didn't help to see what Edmund was riding, a 7'11" or something ridiculous like that.

We paddled out from the seawall which seemed to enjoy setting up a nice bit of backwash to go with the afternoon chop, and for the first time in a long time I experienced that shaky, leg-wobbling, newborn baby wildebeest stance; I chopped at the water like I was splitting a cord of hardwood. None of this boded well for someone who—sure, I'll admit it—prided himself on his all-around SUP abilities.

It's not like I hadn't made plenty of kook-moves in the past. I remember the first time I ever tried standup, the day after Laird Hamilton's flag-waving Malibu debut in 2002. But for some reason my eyes were only for his giant board; I must've looked like a complete idiot stroking out at San Onofre on my 12-foot Terry Martin tandem, squatting down like a chimp trying to wield my tiny outrigger canoe paddle. I thought they stared because they were so impressed.

I did my first SUP race at Dana Point on an enormous stock 12'1" Laird Surftech, figuring, having never seen an SUP event before, the bigger the better. When I got there and saw Jimmy Terrell's narrow, speedy Ron House-shaped javelin, I felt over-dressed; when I got passed by Hobie shaper Gary Larson, who was paddling on what looked like a regular longboard, I felt foolish, like I was running a 10K in ski boots.

Then there was the time I decided to paddle into the very private Hollister Ranch, figuring to tow my short board, loaded with wetsuits, food and water, behind my 12-foot Muñoz like a faithful pack mule. That worked fine until I hit the offshores and high-tide refraction waves bouncing off the cliffs. Then my three-fin pack mule sat back on its haunches, tugging me off balance every time I lifted my blade from the water. If a benevolent boater hadn't shipped my gear back to the pier for me on the way home, I might have had to abandon it. Yes, the next time I lashed my stuff to the deck like any sensible touring paddler would.

So yeah, I'd paid my dues. But that was years ago and wouldn't you think that almost a decade of standup time would've earned me sufficient acumen to ride Old Man's on a board just a bit too small for me? Yet there I stood, fighting for balance, crouched, knees bent, holding the paddle out like some Flying Wallenda, when a cute local surfer girl, who sat easily on her longboard waiting for a set, looked over and smiled.

"Not so easy when you're just learning," she said and naturally right at that moment, before I could assert any claims to my perceived expertise on equipment of my own choosing, a nasty little cross-chop caught my rail and dumped me on my ass. When I came up, the cute local surfer girl's smile was now tinged with pity.

"Hard to be a beginner again, yeah?" she said. "But you keep trying."

That's good advice, not only to those taking up the paddle for the first time, but to all of us beginners out there.

Sam George

This originally ran in our Spring 2012 issue.