From retirement to CEO: Craig Aitchison’s True Patriot Love Journey

From Maritime retirement to a mountainside expedition

Straight out of the gate in February after a very comprehensive handover from Nick, Craig was on the move, flying from his home in rural New Brunswick to take part in the training camp for True Patriot Love’s Expedition to Mount Waddington in British Columbia. Then, in June, Craig travelled back to British Columbia to join the team of six civilian business leaders and eight Veterans on one of the foundation’s signature programs.

True Patriot Love expeditions are powerful tools for personal growth for Veterans and service members in transition as well as fundraisers that unite Canadians. The Waddington Expedition has raised more than $694,000 to date in support of programs across Canada for Veterans, service members and their families.

But before and after the Mount Waddington Expedition, Craig’s schedule was packed with meetings with a range of the Foundation’s partners and stakeholders; donors, ministers, and charities that support the military community. He watched True Patriot Love launch the National Veteran Volunteerism Action Plan in Ottawa, attended a donor event at HMCS York in Toronto, 2026’s Goddard Leadership Series events, and many management team meetings.

As Craig was ending his time as interim CEO, we spoke to him about his role at True Patriot Love, his “failed” retirement, and what he’s learned about the transition to civilian life, on and off the mountain.

Q: What appealed to you about taking on the responsibility of interim CEO?

The Veteran community is very near and dear to my heart because I come from a military family, and I have thousands of acquaintances and close friends that serve.

It was very daunting at the beginning. Before I retired, I had only ever had two jobs: I worked on our family farm, and I was in the Army. I had never worked in an organization that had a responsibility to raise funds because I grew up in a publicly funded organization. So that alone was a huge shift.

But one of the things I felt I could bring was executive leadership: how to lead an organization and how to support decision-making. I don't necessarily know all the issues, but I can be briefed on issues and given recommendations and be made smart to help contribute to decision-making. That's where I knew I was going to be able to provide value, and of course, with the relationship with the uniformed part of the ecosystem that True Patriot Love interacts with. It also became very clear, very quickly that True Patriot Love’s team was very committed, hardworking and experts at what they do.

Q: On a personal level, what did the Mount Waddington expedition mean to you?

My expedition was different than everybody else's for a bunch of reasons. I'm at a different point in my life than some of the other Veterans are. I was not just there as a participant. [As interim CEO,] I had leadership responsibility and some decision-making responsibilities while we were there. Just to be present as opposed to being distracted by all the decisions that had to be taken day-to-day was what I appreciated and what I took away from this trip.

The physical demands of the expedition were real, and the long, hard climbs were long and hard. The conditions that we were operating under were not easy. There was a lot of wet, slushy snow, and it was the end of June, so we went from summer to winter at the snap of your fingers. But it was considerably hotter than I think anyone anticipated it being. I'm so glad I threw a T-shirt into my rucksack because I wore that for six of the eight days that we were out there!

We had two days when we were rained out, so we gathered under the two big tents that stored equipment and food. When you're cold and wet and hungry and have nothing else to do, there's a level of bonding that happens.

By far the best part of it was the human interaction with this wonderful group with a common purpose. It was really fascinating to watch the senior people from corporate Canada interacting with people that served in the infantry and in combat who are in a different phase now in their lives, then watching the Veterans tell stories of the most ludicrous situations they've ever been in, whether it was in Afghanistan or in Wainright. There's a lot of ridiculousness in the military. It was the humour that came with it and watching the relationships form through storytelling was really special.

Q: What would your elevator pitch be about the value of True Patriot Love’s expeditions?

There’s a magic that gets created because of the conditions established by those that plan and execute these expeditions. That has a very clear impact on both the people and the purposes of the expeditions, which is partly to connect people and help people as they transition, but obviously to raise funds for the program partners we work with to help the community that we support.

I think the phrase that would sum up this expedition would be “life changing.” We take people and put them far away from support, from civilization, and we give them a difficult task, and then we watch it all come together, and each person has a role. I think everybody walked away from those experiences feeling different and better.

And then there are those connections that I was talking about between these very successful civilians and these Veterans who are very successful in their own rights. The youngest Veteran was in his mid-30s; the relationships that he built during the expedition will no doubt impact his life going forward.

Q: Going back to the very beginning, what were some of your motivations for starting a career in the Canadian Armed Forces? 

We moved to New Brunswick in 1983, when I was 15. My dad was serving at that time; he was just taking over as the commanding officer of the infantry battalion here in Gagetown.

My older brother was 17, and he joined the reserves when we moved here. We went to the same high school, so our social circles overlapped; a lot of his friends were my friends, and a lot of his friends were in the reserves.

I didn't see much of my dad growing up because he was busy doing what he was doing. But I saw how much he enjoyed what he did and how good he was at it. He was a people person and the people that he was responsible for just loved him. We saw that when he retired and when he died: the outpouring of love was incredible.

When I became old enough, I joined the reserves. I spent two-and-a-half years as a reserve soldier here in Fredericton, did lots of cool stuff, including some full-time employment on base at Infantry School and some royal family stuff and some fun stuff. Those were probably the two biggest things that caused me to then transfer to the Regular Force at 19. It was something that appealed to me, but it was reinforced by that experience from my brother, my father, and growing up in that environment.

Q: Supporting military members while they are in uniform and when they transition to civilian life is a priority for True Patriot Love. As a recently retired Veteran yourself, what is your perspective on transition?

Transition is different for everybody. My brother served for 33 years. He retired as a Master Warrant Officer on a Friday, and on Monday went to work as a security guard. He's moved into a supervisor role, but he's still working full time.

I knew 10 years before I was going to retire that I was going to retire in the summer of 2023. I joined at 16. I was leaving at 55 because 55 was the age for compulsory retirement when I joined, though it's now changed to 65. My plan was that I was going to go to culinary school, and I was going to open a food truck. That plan barely survived contact with life.

I still haven't figured it out. When people ask me how retirement is, I tell them I'm failing at retirement.

Q: From your perspective, what are some of the key issues for people leaving the Forces?

The military is really good at taking you from point A to point B and saying, “Okay, welcome to this new organization. We will integrate you.” But nobody's going to integrate you into retirement. You're on your own.

As you get closer to that transition out of uniform, you also need to start really thinking about your health. Being in the combat arms is a physically demanding profession. Jumping out of airplanes hurts every single time; it doesn't matter how soft your landing is, you're going to walk away hurt. While you're still in the system, you've got access to better health care than you will when you leave.

You have to make sure that when you stop getting a paycheque from the crown, you either have enough money to stop working or a plan to supplement that retirement income to be able to live the lifestyle you want.

Identity is also an incredibly complicated thing, particularly for people that serve publicly, and I include first responders across the board in that. You go from being a police officer to being not a police officer, or from being a soldier to not being a soldier. There's a lot tied up with that.

Start thinking about volunteerism before you retire, because it helps with that transition in a number of ways, which is, who are you and who do you want to be? It comes back to what we learned in the Veteran Volunteerism Initiative, which is that purpose, commitment, social belonging, and community connectedness are all really important when you retire.

Q: We loved having you on the team! How will you be staying connected to True Patriot Love?

Once you see what this Foundation is and does and how they affect and impact lives, I don't know anybody that could walk away from it.

I’ve volunteered to be on the Risk Management Committee, particularly looking at expeditions. I’ve been invited to be part of the Vimy 110 events as the military representative, which is a little bit intimidating to be honest. But what a way to connect Canadians to our history and the foundation and be able to give back.

And in the end, it's about people: looking after people, making sure that they're supported and have what they need, whatever that looks like. There's a significant amount of satisfaction knowing that you can be a positive force in somebody’s life and help them achieve their potential. It's always about people.

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