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Robby Naish doesn’t know what he’s going to do today. The 56-year-old might grab his shortboard and find a lonely break off Maui’s��Honolua Bay. He might hook up the kiteboard and search for strong wind or windsurf Hookipa Beach. It all depends on the swell, the��wind, the weather. The��important thing is that Robby Naish——has options.

The first professional windsurfer, Naish��dominated the sport for two solid decades beginning in the late seventies.��He then transitioned into kiteboarding and quickly rose to the top of that field, too. Later��he helped pioneer stand-up paddleboarding, becoming one of the first people to surf Maui’s��Jaws��on one. Along the way, he earned 30 world-championship titles, started his company,��Naish Sails, in 1998, and helped define what it means to be a��waterman. But his ability to evolve is what’s��most impressive, the way he moves��effortlessly between disciplines, always an early adopter of the next wave of board sports. “I want to surf my whole life,” Naish says. “There will be some point where my body or mind won’t allow me.��Until then, this is what I’ll do.”

Today, it’s not unusual for a watersports athlete to be proficient in a variety of activities;��, Naish’s protégé, is skilled at SUPing, big-wave surfing, and kiteboarding. But when Naish, inspired by new challenges and innovative technology, started picking up new skills in the eighties��and nineties, he was an oddity. “All my contemporaries thought I was crazy when I got into kiteboarding, but it’s been fun to reinvent myself and be involved with these sports on the ground level,” Naish says. “Kiteboarding was a complement��to windsurfing, and so was SUP. You’re riding waves a little different, sure, but you’re still riding waves.”

This preternatural ability to evolve could be exactly why Naish’s career has lasted so long. Not only has he been able to stay in the thick of things competitively (he’s been sponsored by Quicksilver since 1982 and ), but he’s managed to avoid some of the physical and mental burnout that’s often associated with purists sticking to one sport. “Athletes will get to a certain point where they’re over it. They get disinterested and no longer put in the time to be competitive,” he��says. “For me��there’s no way to get bored, because the environment is always changing, and the equipment is always changing.”

To stay in shape for this shifting landscape, Naish��adheres to the same fitness principles he developed as a teenager. “The modern approach to fitness is different than what I’m used to. I’ve never had a trainer and never really had a set plan. I’m not into yoga,” Naish says. “I don’t want to go to the gym, but I make sure I do certain things throughout the day.” This includes��several hundred push-ups, pull-ups, and sit-ups,��broken into five-minute sets wherever he has the time, whether that’s��in his office or hotel room. “And I’ll curl whatever desk chair is near me,” he says. With some TRX work and jump-rope for cardio, Naish’s routine keeps him fit for long days on the water, regardless of what board he’s using at the time. “It’s created a balance between the power of wind sports and the endurance of SUP. I’m probably in better shape now than when I was in my twenties��because of it,” Naish says.

The latest piece of equipment to catch his��eye is the hydrofoil, a blade at the bottom of a board that raises it above the surface of the water.��The technology was first developed for the Navy in the fifties��and then adopted by competitive sailors in the seventies��and eighties, but Naish Sails and other brands are��finding new��applications for the blades, using them as a way to go faster and longer on SUPs and surfboards. Naish is most excited about the opportunity these blades present to recreational athletes. “We’ve been focused on making that gear as accessible as possible,” he��says. “It’s surprising. You’ll see guys that can’t surf their way out of a paper bag get on a foil and just rip.”

Almost 40 years after he jumped on a board, Naish is still innovating—without a��hint��of slowing down. “I turned pro when I was 18��and didn’t know if it would last six months,” Naish says. “I deferred admissions to college and hoped I would get a solid year out of windsurfing. The first year ended, and I hoped I’d get another year. It’s still going like that.”