There’s always some guy. Every now and then you find yourself in the room with him, a guy who’s way happier than you are, the one who sits square in the middle of his life and just eats it up. Then he leaves, taking his twinkle with him, and you’re left feeling vaguely troubled. What’s his secret? How does he do it? Not being a total sad sack, you rouse yourself and hit the gym. The blood pumps, the sweat pours and some level of wellbeing is restored. Still, he nags at you – that guy, that f***ing guy!

Nick Southwick-Hall is one of those guys and if I were any less interested in how he pulls it off, I’d probably want to smack him. This is doubly true given Nick’s relative youth and swagger. With close cropped blond hair and the rocksteady stride of a serious lifter, the 26-year-old has a greater air of command than men twice his age.

Yet he wears his confidence lightly, with an easy manner and a ready joke. An encounter with Nick can be startling, like bumping into an old friend. We’re not accustomed to such guilelessness. The lives we live seem to call for a certain tactical hesitancy, a prudent wariness or distrust. But Nick defies this impulse. Wherever he is, whatever he’s doing, he never holds back.

Take the story he’s telling now, about watching sport and bonding with his ailing grandfather. The story would be considered revealing by any measure, but the way Nick is telling it, at top volume from the swaying crown of a tree, the whole neighbourhood can hear. It’s all the same to Nick. I guess to someone that centred, the opinions of others don’t really matter.

Of course, when you spend your days handling chainsaws, you have to be centred. One slip and you lose a limb.

“What do you think, Steve?” Nick yells down to his ground man. “If I cut myself up here, would you come up and get me? Or cut down the tree with me in it and hope for the best?” “I’d go get coffee and think about it,” comes the reply.

“Steve doesn’t think too good without coffee,” Nick observes. “I don’t take it personally.” I met Nick a few months ago, when I hired him to escort a few spindly oaks from my garden. Then I kept bumping into him around town. My first thought about Nick was that his mojo probably owed less to some prize piece of personal wisdom than to the prankish thrill of climbing around in trees for a living. Unlike the rest of us chair-bound bastards, Nick works outdoors, well away from the zonk of computer monitors and the stale drift of office air. Even in an industry known for its outdoorsy types, he’s a bit of an outlier, preferring a climbing rig and a pair of old fashioned foot spikes to the usual lawn-chewing bucket truck. Nick’s in it for the sport.

“You should ride along with me sometime and check it out,” Nick said. I dismissed the invitation at first. But the more I thought about it, the more it seemed like the perfect opportunity to finally settle that nagging question: why is this f***ing guy so happy?

Let’s start with this: everyone is on the run from something – money worries, status anxiety, an older sibling who did better in life. Some wearying hang-up is always putting you on defence and keeping you from being your best self. The irony is that only your best self can open the doors to the life you really want.

Now, it’s possible that Nick’s just a weirdo and that the secret to his happiness is nothing more than sheer weirdo power. In which case, good for him, I guess. But there’s more to the story. After observing the technique by which one fells a two-ton tree – without, ideally, sending it through the lounge window of the guy who’s paying you to remove it – I’m invited to stick around for Nick’s next act.

“I gotta go talk to these two guys,” he says, as we jump into his truck and head into town. We pick up the two guys on the side of the road a few minutes later. Paul looks about 35, gaunt and thinly bearded, with tattoos peeking from under his sleeves as he sits nervously fiddling with a snuffed cigarette. Billy is younger, maybe 20.

“So,” Nick says, “what’s your plan? What’s your head telling you, anyways?”

And just like that, a day of felling two-ton trees morphs into a mobile rehab session. When Nick isn’t taking trees down, or keeping up with the hockey team he started recently, or hitting the gym to keep his lumberjack muscles jacked, or being a father to his five year- old son, he’s operating two sober houses to help down-and-out drunks get their lives back on track. One of these houses was where Paul and Billy lived – that is, until last night, when they broke the house’s cardinal rule.

Nick tells them they’re going to have to learn to stand on their own two feet if they ever hope to look the world in the eye again. He tells them that true change doesn’t happen overnight. He tells them all the things they need to hear but probably can’t – not yet, anyway.

At several points his spiel is interrupted by a phone call: client, guy calling from prison looking for a place to live (Nick has no idea how these guys end up with his phone number), girlfriend, office manager, girlfriend again. He fields the calls and then picks up with Paul and Billy right where he left off, in full-on executive mode, casually plumbing the depths of their souls as he puffs on an electronic cigarette and spins the huge truck through traffic.

This is what happens when you step all the way into life: instead of hustling to keep up with the world, the world hustles to keep up with you. Nick seems to be surrounded by people who instinctively turn to him for leadership. The truck is brimming with them – myself and Steve included. Beyond us is a vast network of others, many of whom Nick doesn’t even know. It’s not that he’s fundamentally different from any of these people – we’re all human. It’s just that somehow he has figured out how to never let anything hold him back.

Later Nick tells me a story about helping some girl relocate to one of his sober houses. On the way, they had to stop at a train crossing, which provoked a long round of “poor me’s” from the girl. Instead of arguing, Nick suggested that they pull up to the car in front and see if they could make the driver laugh. The old lady in the car seemed like a tough nut, but by the time the train had passed, she was in stitches – and she later rented Nick a place for another sober house.

“What exactly did you tell her?” I ask. Nick shrugs. “I told her I liked her shirt.” F***ing guy!

The worst are the smilers and the hand pumpers, the amped-up phonies who rattle through a room and then go home and kick the dog. There’s no depth to them, no history or foundation. I was pretty sure Nick was not of this ilk, but the full story didn’t emerge until later. As commanding a figure as he seems now, Nick too was on the run at one point.

“By the time I got caught, I had 18 warrants of arrest out for me,” he says.

In those days, he continues, he was living on the street, burgling 30 jars of baby formula a day and reselling them to local corner cafés. The proceeds went up the hole in his arm. This is never a happy existence, but you know you’ve reached a particularly low point when you find someone holding a gun in your mouth.

Nick had gone to buy drugs at a place called the Hallway, where each door opened to a different high. Maybe it’s because he went in alone or maybe it was the way he carried himself, but something about Nick made the dealer think he was a cop. He threw Nick into a chair and fed him the gun. There was only one way to prove his innocence: tie off and shoot up. The problem was that Nick had never self-administered before. He had always asked a friend.

“I just kinda dug around in my arm until the mushroom of blood came back out,” he recalls. “Then I pushed the plunger down.”

Only then did the dealer put the gun away and start lecturing Nick about how he needed to slow down. But Nick was running too hard and too fast to hear. Even today he doesn’t know what he was running from. A deadbeat father who split when he was young. Or else his own early screw-ups, which he lacked the strength to put right. Or just some built-in discomfort with a world in which he never felt quite at home.

But there has to be an end to it. A moment when you stop running and turn to face whatever it is that’s chasing you. Maybe it’s courage, or just exhaustion, that makes that final realisation possible, that a life on the run isn’t worth living. Nick’s moment came at the local jail, after his arrest. They put him in a holding cell with maybe 20 others, including a gangster whose girlfriend Nick had shagged while the man was serving time. Nick wasn’t too surprised when the guy started telling everyone he was a snitch.

“Basically he just wanted to get my ass kicked,” Nick says.

Thankfully, the cops pulled him out before that could happen. Then they pulled the gangster out and shackled him to Nick. It was then that the running ended, when Nick found himself locked in the back of a police van, sharing shackles with a guy who wanted him dead. In a way, Nick almost welcomed the beating.

“I knew I was going to have to pay the piper at some point and own up to the guy I was,” he says.

Which maybe explains what he ended up saying to the guy as their paddy wagon pulled away.

“I’m the biggest loser that I’ve ever met,” Nick said. “I just came off a cocaine run and if you want to hurt me you totally could because there’s no way I can defend myself.

“I didn’t mean any disrespect,” Nick went on. “I was horny and lonely and so I slept with her. It’s that simple.”

He waited for the beating to start. But it never happened. “I want to kill you,” the guy said, “but I won’t, because I understand.”

Well, damn, Nick thought.

From that moment, everything began to change. First he avoided jail time by detoxing and going to a sober house. He cleaned up, got a job and met the future mother of his son. A year after moving out, realising that wage labour couldn’t support his young family, he put ads online, hired two guys from the power company and started a tree business from the back of a trailer. Today that business brings in several hundreds of thousands a year and is expanding to include landscaping, home improvement and real-estate development. The sober houses, meanwhile, provide a willing labour pool and keep Nick connected to his past.

And it all began when Nick raised his chin to the gang member and invited him to hit it. When the hit never came, the moment never ended. It just got longer and longer until it became his whole life. Which is why, to this day, Nick carries himself in exactly the same way he did then, chin up, hiding nothing. Curiously, it’s this very lack of guardedness that has made him untouchable.

“Now I fear nothing,” Nick says, “because I know that I’m a valuable resource to the people around me and humanity as a whole. How could you not get confidence from that?”

True, some part of me still wants to smack that f***ing guy, to take the swing the shackled con passed up. But ultimately this says more about me than it does about Nick. It’s not just that I envy his confidence and happiness; it’s that his story raises a serious question that some part of me would much rather have avoided. What if, for instance, life and luck have spared you that defining moment, when you stand toe-to-toe with destruction? Are you therefore doomed to a life of mediocrity? Or can you still claim a moment of your own, somehow, and live the life that you want?

By Oliver Broudy