10 lessons from Jon, a man running the Boston Marathon

With an easy smile, self-disparaging humour, and fondness for casting the spotlight away from himself and onto others, Jon might trick you into believing he’s just your average guy.

But average guys don’t qualify for the legendary Boston Marathon. 

If you’re not aware, running in the Boston Marathon is a pretty big deal. Like a once-in-a-lifetime, some-people-train-their-entire-lives-to-run-it kind of deal. It’s incredibly hard to qualify, even for elite runners, which is why for many, it’s a bucket list item. It’s a dream, an honour, and a privilege, and one that clearly isn’t lost on Jon. 

To be clear, running 26.2 miles in a hair over three hours is awesome. Having the discipline and mental toughness required to put down a time like that is far beyond what most of us mere mortals will ever or could ever do. 

So when I sat down to talk to Jon about running in Boston on Monday, I knew there was a story to be told and valuable lessons to be learned. Always humble, he would be the first to tell you that he’s just a guy that’s good at running. But when I dug a little deeper, the wisdom I uncovered was as inspiring as it was surprising. 

The way he tells it, the whole Boston thing started just six yeas ago. That’s where the wisdom begins:

Lesson #1: Look for opportunities at unlikely times.

Jon’s journey to Boston started with divorce. An odd starting place perhaps, but that’s what happens when you look for opportunities in unlikely circumstances. Six years ago, Jon was newly single and, with shared custody of his daughter, suddenly found himself with more free time on his hands than he was used to.

Now, it would’ve been easy for him to fill that time with cold beer and a couch, but according to him, that wasn’t an option. “I knew I couldn’t just sit at home and watch sports all night.”

Instead, he started running again. He’d been an athlete in high school and dabbled in rec league sports for the prior decade, but for the first time found himself training for a half-marathon with a buddy, which leads to:

Lesson #2: Find a friend who motivates you.

This is a classic fitness tip for a reason—it works. “On days you don’t feel like running, buddies hold you accountable. I knew he was waiting for me,” said Jon. I was both surprised and relieved to hear that even a marathon runner like Jon has days he doesn’t feel like going. 

But with the support of a friend, he ran a half-marathon in 2012. After finishing he decided “that wasn’t too bad” and thought “I’d like to try a full.” 

He trained through the winter and ran his first full marathon in May of 2013. But this time it wasn’t such a breeze. “It was awful. Like really bad. I walked the last 5 or 6 kilometres. My time was atrocious. Everything hurt. It sucked.” 

He said to himself that day, “I’m never doing that again.” But then he hit upon: 

Lesson #3: Get competitive. 

We like to think that some people are competitive and other people aren’t, but when you really get down to it, everyone is competitive in some way or another. It’s about finding the kind of competition, whether with yourself or with someone else, that works for you and drives you forward. 

That’s what Jon did. Instead of giving up or giving in, he got competitive. “I knew I could do way better than that,” he told himself. By August, he was back to training, and in October, ran his second marathon in Toronto in just under three and a half hours, which he was “quite happy with.” 

If that sounds like a lot of running in a short period of time, it’s because it is. When asked about how he managed to get up to speed so fast, Jon had one answer: 

Lesson #4: Make a plan.

Jon is big on planning. He doesn’t think he ever would’ve gotten this far if he wasn’t so organized. 

When he started running he "used the ‘Google machine’ to look up some programs, tweaked and changed one to fit [his] schedule, and made it more realistic and enjoyable.” To stick to the plan, he started marking down his runs on a calendar that he keeps at his desk at work. 

Whenever he misses a run, he marks it with a giant red circle so that he has to look at it for the whole month. “For me, it works,” he concluded simply. He doesn’t miss many runs.

At this point, though he had completed two full marathons in a year, and put up some respectable times, it still hadn’t even occurred to him that Boston was a possibility, but something else had: 

Lesson #5: If you get moving, you go places. 

Jon realized that running a marathon in a new place could make for a cool trip, so he planned to go to Halifax in 2014 to run a marathon with his two buddies. It was there that he realized that he might be “okay at this.” 

Because Jon had trained with his friend, they had planned to run the race together, but halfway through, his buddy started to labour while Jon was ready to push faster. 

His friend urged him to race ahead, but Jon politely declined. And then again, his friend urged him to go ahead, and he refused. And then finally, on the third time, with three or four kilometres to go, Jon took off. 

He ended up beating his friend by 10 minutes, and finishing in three hours and twenty-five minutes. He wasn’t sure if it was lung type, or body type, or stamina, but for whatever reason, he started to suspect that he could be a pretty good runner. 

It wasn’t until the following year, at yet another marathon, this time in Kentucky, that he finally realized Boston could be a possibility. The fact that he hadn’t realized this, brings us to: 

Lesson #6: If you don’t go, you’ll never know. 

Perhaps Jon’s feet move a little faster than his head, but the fact that he didn’t even think running in Boston was a possibility until after he finished four marathons, shows just how blind we can be to our own potential sometimes. 

We constantly underestimate ourselves. We assume we aren’t good enough before we even try. Jon’s story shows why that’s such a shame. 

As fate would have it, Jon happened to be blessed with some otherworldly running skills, but even he, an athletic guy, had no idea just how fast he could be.

It finally sank in at that race in Kentucky, which went right through Churchill Downs the week before the Derby. 

The conditions were terrible that day. “It was pissing rain. Not fun,” he recalled. But somehow he still managed to finish in three hours and thirteen minutes. That’s when he knew he had a chance to qualify for Boston. Which takes us to: 

Lesson #7: Make a plan. 

You may remember this lesson from #4, but it bears repeating. Once Jon realized that he might have a chance to qualify for Boston, he did some research on what kind of time he would need and found a good qualifying race in Mississauga.

Then, he made a plan to get there. 

But things didn’t go to plan. The day of the race turned out to be horrible. “10 degrees, pissing rain, wet and windy, just awful,” he recounted with a scowl. Yet three quarters into the race, he was on pace to come in at 2:55—a time that would definitely be good enough to get him to Boston—until he started heading back into the wind.

“The wind was bad. I knew I was making excuses, but I couldn’t do it. I checked out and started walking,” said Jon. 

As he walked, he started thinking about the months of training and began to jog again. But his feet were dying. Walk. Run. Walk. Run. He went back and forth. “It’s a head game. I finally got to the point that I didn’t care. I was walking in. It was fine. People wouldn’t be mad. They know it’s hard.” 

Then came: 

Lesson #8: Sometimes one punch can change history. 

As Jon continued to walk and run, walk and run, he kept passing two dudes. Of course, at that point into the race, at that pace, all the runners knew that the others were trying to qualify for Boston. 

And that’s when it happened. As the one dude ran past Jon, he punched him in the arm. “Just a random guy, a complete stranger. And he didn’t say a word. Just gave me a shot in the arm. And that’s all it took. I started running again, limpy and slow, but running. I knew I could finish what I had started.” 

He finished the race in 3:04:53—“every runner remembers the exact time.” He was crying so much his girlfriend thought he had missed the cut. He was overjoyed to inform her that, “no, I got in.” 

Of course, accomplishing such a feat took a tremendous amount of discipline, training, talent, and hard work, but Jon is quick to admit: “Without that punch, I wouldn’t have qualified for Boston.” 

Life works out in weird ways sometimes. If you put yourself in a position to succeed, you never know when you might get a punch in the arm. 

And that’s how Jon qualified to run in the Boston marathon this Monday. Six years, five marathons, a lot of planning and hard work, and a punch in the arm. It really is an awesome story. 

And it’s even more awesome because it’s not just about running an elite marathon, it’s about: 

Lesson #9: Find something that brings you peace. 

Jon loves running because it’s time for himself. “Short or long, I know that’s time that I have to sort through my thoughts. Peaceful and quiet dedicated alone time. No phone, no screen, no Twitter, no Instagram. The time I spend out running is the most peaceful time that I have,” he says.

It’s hard to say something is life-changing without it seeming cliché, but you can tell that’s exactly what running has done for Jon. It’s changed his life. “It was my therapy. I could think through things and figure out all my problems,” he says. 

Luckily for us non-marathon runners, Jon’s quick to point out that it doesn’t have to be running. You just have to find something that gives you that same sense of peace. “Whether it’s going for an hour long walk with music, going to the park and sitting on the bench, or reading for an hour, everyone needs their own space and time in life. You can choose to do whatever you want during this time. And I’ve chosen running. For other people, it’s other things.” 

That leads to the final lesson: 

Lesson #10: You can do it.

“Any goal that anyone wants to achieve—it’s achievable. If you actually put your mind to it and have the discipline and you want it, you’ll be able to do it. You just have to put a plan in place.” 

It’s funny how easy it is to assume you can’t. Before talking to Jon, I would’ve said running a marathon was impossible. But he made everything simple. 

Set a goal, make a plan, and stick to it. Look for opportunities, get support from friends, and life will give you a shot in the arm to keep you on track. Get up and you’ll go places. 

Now, Jon realizes that most people will never run a marathon, let alone compete in Boston, but that’s not the point. 

For me, the point was that Jon could’ve easily spent the past six years on the couch, drinking beer and watching sports. No one would’ve held it against him. 

But instead, he got up and did things. He stumbled upon a tremendous talent he didn’t know he had. He’s run five marathons, in Toronto, Halifax and Louisville. He’s become an awesome role model for his daughter. He’s found peace.  

For me that’s a lesson that’s going to take a while to truly sink in. Because when I look at the next six years of my life, I know how easy it will be to spend too many hours sitting at home, and how hard it will be to spend more of them chasing after my dreams. 

But thanks to Jon, it somehow seems more possible. I’ve already started making plans.