While Clitsome's retirement from the NHL on June 1, 2016 came earlier than he anticipated, the plan he had in place made sure he was set up for success whenever that day came.
Now 34, he works as the Director of Career Transition at ONE Sports + Entertainment, the sports division of ONE Capital Management - a wealth management company founded by a Winnipeg product, Donald McDonald.
That's not the only connection Winnipeg has to Clitsome's life after hockey, but more on that later.
The opportunity to work with ONE Sports came as a result of a conversation with Clitsome's current financial advisor - and now co-worker - Chris Moynes.
"I met Chris as a teammate's wedding actually," Clitsome said. "We were chatting and that's when he explained to me what he does. We followed that up with a real meeting and he explained the Pro's Process and what he does with his athletes and how he really specializes in athletes."
The conversation left an impression on Clitsome, who said Moynes stressed the importance of fiscal responsibility for the simple fact athletes make the majority of their income in a short amount of time.
"To make a proper plan for that to give you stability for the rest of your life is important," said Clitsome. "It's easy to get caught up in a certain lifestyle when you're playing, but when those pay cheques stop, it quickly changes. You have to be able to adapt and have the plan in place to help you through that."
So, when Clitsome's career-ending back injury forced his retirement after eight NHL seasons (four of those with the Jets), he was as ready as he could be.
His 205 NHL games help give him a perspective that fellow athletes can relate to, making his addition to the ONE Sports team valuable.
"We thought it would be a valuable service for the One Sports clients to have a dedicated resource in place to help guide them through that transition," Clitsome said. "Somebody who has gone through it firsthand, had that experience, and be able to plug them into the appropriate resources to help them make a successful transition."
Clitsome's transition to retirement has arguably been just as fast-paced as every night on the ice. In fact, he has far more on his plate - or rather, in his glass - than helping athletes.
The Ontario native has always had an interest in business and wine. While playing hockey for the NCAA's Clarkson University from 2004 through 2008, Clitsome earned his undergrad in business. When his career ended in 2016, he knew the next step was earning his Master of Business Administration.
His motivation for getting that MBA is a story that begins in - you guessed it - Winnipeg. It was also the best way to combine his passion and his family.
First, Clitsome took a class on wine at Banville & Jones Wine Company in Winnipeg during his playing career. Then after he retired, he continued his studies by getting his Level 3 Wine and Spirit Education Trust Certificate, followed by the sommelier program in Ottawa.
"My dad actually did the sommelier program in Ottawa before me," Clitsome said. "That also got me interested in it. Then it was really just a case of having time on my hands, not wanting to sit still, and making sure that I was staying mentally active.
"That's really what it boils down to: a love of wine and curiosity."
He admits the process of becoming a sommelier wasn't always easy. In fact, identifying scents and tastes from different wines was more challenging than he anticipated.
"You're tasting and you hear people saying 'I get mango, I get pineapple and peach' and I'm thinking to myself 'I'm not getting any of that," he laughed.
"What helped me too is outside of actual wine tasting was smelling everything. The foods you eat, smelling it before you eat it, being able to associate the smells with the words. So that was the biggest thing for me.
"The more you practice the better you get."
During the sommelier program, Clitsome didn't focus only on wine. He had courses on various whiskies and beers, as well as grape varietals and wine tasting. After a year of honing his palate and his nose, he put that training to good use.
"I started a family cidery making apple cider. We have a family property just outside of Quebec City, my father-in-law's property, where he has a big apple orchard," said Clitsome. "That was in the middle of the sommelier thing. One thing led to the next and we decided 'why don't we start making cider?'"
The decision was made. Clitsome flew to England to take cider making courses and talked with experts before searching for equipment. Slowly, 'Cidrerie Le Domaine des Sorciers' in Saint-Famille, QC began to take shape.
Perfecting their cider though, took some time.
"It started with the first trial year where we just tried our hand at making it. It actually came out that it was somewhat drinkable, so we thought 'let's try this again,'" Clitsome laughed. "The next year we refined it, it got even better, and we opened a store on the property.
"We have a small little store, it's really nice. It faces the St. Lawrence River, has a nice patio, it's a big tourist destination."
At this point, Clitsome knew he'd have to build on his education to take his cidery-making hobby to the next level.
He enrolled at Queen's University and finished off his MBA in May of 2019.
The last three years have been a whirlwind, but he wouldn't change anything about them. Although, he's pretty sure he won't be found in a classroom any time soon.
"I was convinced that once the MBA was over, I'm like 'that's it, I'm not doing any more and I've had enough school.' But sure enough you fill your time with other stuff," he said.
"I'm big on learning. I like to keep broadening my horizons and learning new things."