A Boston-based financial analyst decides to make his first race ever a 50k trail run in Colorado….and meets his inspiration on the trail.
On a perfect late September Saturday, a certain frustrated, overburdened public school teacher with dreams of being a writer was stewing in his own self-pity as he mindlessly drove south towards Buena Vista, Colorado in a train of cars going 72 mph. Ascending the one uphill before the small, bustling Chaffee County community, an approaching truck hauling a skid-steer suddenly jackknifed. Vehicles converging upon the ensuing disaster had just enough time to brake, slowing to a stop a mere 20 yards from the out of control, twisting load. If everyone had elected to leave their homes 3.5 seconds sooner, it might have been different.
Fortunately, the truck was able to over-correct twice without flipping. The driver hopped out, unharmed, and began directing cars around his vehicle, which sat perpendicular to the flow of traffic. With a newborn at home, it was one of those, “Life is precious moments,” for this teacher …er, writer. Considering the day up to that point – sacrificing a weekend to make $50 writing a piece maybe a hundred people would read, all to advance a dream still hankering for a big break, while a mountain of papers waited to be graded at home – made it a “Give thanks for all things, and make the most of your opportunities,” kind of moment.
Little did I know that in the race I was about to cover, the real ‘story within the story,’ wouldn’t be about the headliner – recent Ultra-Trail du Mont-Blanc (the Super Bowl of ultra running) back-to-back champion, 2018 Western States (the World Series of ultra running) champion, and 2017 Moab 240 champion (a race in which she defeated all of the boys, too), Courteny Dauwalter. Rather, it would be about a Boston man who finished 11 minutes outside of the race time cut-off. Brand new runner Paul Omar was listening to a podcast Dauwalter appeared on this past April when he felt compelled to register for his first running race ever. He signed up for September’s inaugural West Line Winder 50k, part of Buena Vista’s 14erFest. The longest he had run at that point in his life was five miles.

His story – my first feature in my new role at the Vail Daily – needs no Seder-Skier insertions, though I’m hopeful my thematic angle, which parallels my writing journey, even only slightly, is edifying to you readers. And so, in lieu of hijacking more than the hopefully attention-getting introduction, here is to saying “Hello,” from yours truly, the new sports and outdoors reporter. Unlike Mr. Omar, I’ve been dreaming of this for more than a few months.
I recall being a homeschooled 2nd grader, waking up early on the last day of the week to print and distribute the early edition of South Branch News, a 15-page school newspaper complete with breaking news, editorials, and of course, an ever expanding sports section, to the student body – my twin brother. It didn’t matter what I had to work with – I always found the narrative. While serving this community, I promise to give 100% effort to be the best writer I can be. I’ll apply my John Woodenesque philosophy to promoting the people and passions of this valley with truth, discernment, and joy.
While it would be false to say my writing career started in the exact same manner as Paul Omar’s running life, that isn’t the point.
Looking back, I realized his story is one of shedding the unnecessary weight of fear which so often entangles and prevents us from venturing down the path we were destined for. It isn’t a perfect parallel to my career path, but it’s a worthy message we all perhaps ought to consider, and I’m grateful to make it my first feature.
Paul Omar attended high school in Port of Spain, the capital of Trindad and Tobago. His coming to America didn’t involve a life or death escape. Pump the brakes – the inspiration is coming. “I didn’t think that the environment I was in back home was conducive to learning for me,” he said about his past. His friends, as great as they were, fed his undisciplined habits. “I get distracted very easily,” Omar admitted. Sensing the potential for waywardness if he remained in the Caribbean, he opted to attend Northeastern University in Boston, where he studied economics.
This spring, he found himself working as a financial analyst for a CPA in New Jersey. Working remotely from his Roxberry neighborhood apartment, the combination of the ongoing pandemic, Boston’s strict stay-at-home orders, and tax season, took an emotional toll on the 26-year old. “I was at a really low point in my life in April,” remembered Omar. “I was really stressed out. I had a lot of anxiety. It got to the point where I couldn’t step outside without feeling really flustered. It was really bad.”
One day, his thumb stopped mid-Instagram scroll. A paragraph written by a new-to-running friend, detailing the impact of the sport on his life, stared at him. Omar ignored it. Two days later, the same user uploaded a simple photo of his running shoes, and this time, Omar was triggered.
He said to himself, “Listen I just need to pick myself up – get out of this mood I’m in.” Not ready for a leap of faith, he thought “I’m going to go outside and not necessarily run, but just go for a walk.” He decided to leave the house, go to the top of Mission Hill, and come back.
The first week of his running career was made up of three such jaunts, which were more like walks. At the start of week two, a Sunday in early April, he decided to start jogging at the top of the hill. He ran the remaining 1.7 mile loop back down to his house. Then, a pivotal thought, one which would set a pattern of positive self-talk throughout many much longer, harder challenges, came into his head.
What if he did five miles?
“It really started with me thinking, ‘how cool would it be if I did this,’” he recalled.
He did.
“Holy crap, I just did five miles,” Omar recalled telling himself afterwards. While his excitement betrayed the magnitude of the moment for a seasoned runner, for this man, someone who bridges the gap between Dean Karnazas and the everyday Joe-bag-of-donuts, the moment was perfectly transcendent.
“Who knew I could have done this?! I could have been doing this for years,” Omar said, echoing what all of us ought to be saying, too, even if our this has nothing to do with sports. Omar’s running career had been launched, empowered by a trait sport psychologists identify in high-level performers: being your best friend.
After the first of many turning points, though, his curiosity remained unsatiated.
“Paul, you still have some gas in you,” he said as he crawled into bed that night.
His last words before closing his eyes presciently claimed the next day, too. “Let’s go back tomorrow and see what you really have in you.”
The next evening, he sat out with a plan to complete two 5-mile loops. Unknowingly, his method would train his mental game as much as his physical. “Every time I make this lap and go by my house, I’m leaving my comfort zone,” he recalled regarding his strategy. “I’m leaving the option to go back in my house and call it a day. I’m leaving that to go back up the hill.”
It took five hours. “It hurt more than the ultra marathon, to be honest,” he recollected. He had doubled his distance record. If the sweatpants-wearing, whatever-shoes-are-in-my-closet donning rookie to the running world was cutting against the grain of proverbial training wisdom, he continued to demonstrate his above average psychological intelligence. Satisfied, the voice inside his head charmed, “Oh my God! I just did 10 miles!”
Omar fondly remembers saying to himself that day, “What have I been leaving on this table? I didn’t even know I could have done 10 miles.”
The message: there is something inside of us we’ll never discover if we don’t step out of our comfort zones.
For Paul, the entry point may have had more to do with closing his eyes than opening them. “When I run, I don’t wear glasses,” he said one hour into our interview, noting this as a key detail and apologizing for not mentioning it earlier. For someone who had been struggling with the weight of anxiety, not being able to see things was what he needed to get out the door. “It was more like a therapy session than a running session,” he said about those early Mission Hill repetitions. “The less stimulant I received from the outside, I felt a little bit more calm. Just being outside for that long got me feeling comfortable being outside again, too.”
Of course, no quest comes without cost – or failure, and for Omar, his first taste came early. After the 10 mile day, his innocent approach bit him in the back. He set out to reenact the prior night’s exploits, saying to himself, “If it was nice, let me do it twice.” When he reached the house 7.5 miles in, he was done. He quit, showered, and immediately felt the yoke of guilt attached to his premature escape from pain. “It was the first time I understood how much the mental aspect plays into this.”
It bothered him to not have reached his goal. The next day, he did not run, instead focusing on resetting his mind. By the end of the week, he had decided, for good, that a key part of his identity, from here on out, would be that he was a runner. “I want to be a person who runs,” he said, noting that distance and time were irrelevant, and that to him, the decision was more about ingraining good habits. Also, running was the vehicle he used to clear his mind.
To prove it to himself, he made it a goal to run everyday. When he accomplished that, he set out to run a half marathon. His inner words never wavered from that first 5-miler. “How cool would that be!?” was the mantra before the run. Afterwards, it was, “Oh my god, I just did a half marathon. What else is really possible?”
A thirst to find his limit drove him. “It really was just me seeing how far I could go,” he said. “That’s what drove me.” He had been running for two weeks and already was researching the viability of completing a full marathon. “Oh….that’s long,” he said to himself after a quick google search, discovering the distance for the first time. “I didn’t think it was impossible. I just thought I didn’t have the time to do it.”
The morning after a midnight conversation with a buddy, Omar sporadically decided to dedicate a random Saturday – literally 8 a.m to 5 p.m. – to complete the 26.2 miles … on a treadmill. Powered by podcasts and Pepperidge Farm cinnamon bread, he broke the distance into 5-mile sections, after which he would sip water, eat a slice of bread, and mentally hunker down for the next bout. When he arrived at 20 miles, he experienced what most marathoners do – hitting the wall. “I was done, I was dead, I was gone,” he said about that moment.
The gym closed in 90 minutes, he had set a new distance record, and he was ready to call it a day. His positive self-talk habits came through in the clutch, however, spurning him on yet again. “That was so cool! You made a new personal record,” was the preamble. “If you stay here for 90 more minutes and just do walking pace, you can get a full marathon,” was the clinching comment. Back on the treadmill, he reached his goal.
During the long run, a certain Joe Rogan guest gave a message Omar especially connected with. Her name was Courtney Dawaulter. The Leadville, Colorado resident is one of the premier ultra runners in history, but it was her apparent lack of strictness that lured in the new runner. “This girl just seems so nonchalant,” he said, remembering the episode. ““It didn’t seem like she was grinding to do this. It seemed like she was just having fun while doing it. Like she just enjoyed it.”
Part way through the West Line Winder 50k, Omar nearly lost his footing as a runner from the lead pack, looping back on the slower runners, came upon him. It was Dawaulter, the eventual overall – male and female – winner. “Yo!” Was all Omar could say to his inspiration, who would defeat all comers in the next day’s Sawatch Ascent 50k in Nathrop as well. Even though Omar was embarrassed for not having more to say, if you slice it a different way, perhaps Dawaulter is the one who should have been awestruck by Omar.
“At the end of the day, it’s runners like Paul that, for me, make the work all worthwhile,” race director Kelsey Banaszynski wrote in an email after the race. “We are so excited to create an event that makes folks from all walks of life and new to the trails feel welcome.”
Paul would be the first to declare that his life has been shaped by a willingness to simply try. “I would play futbol with my friends,” he remembered of his childhood. If they needed someone to fill a spot, he would play. “I would awkwardly fail at all these different sports,” he said.
But, he was ok putting himself out there.
“I didn’t really think, like ‘oh, I’m not really meant for this.’ I just thought, “Oh that looks fun – let me just try it.”
“I try. I think that’s the main thing.”
As he crossed the finish line in Buena Vista, the boisterous vocal support from onlookers disregarding his having missed the 11-minute cutoff, Paul’s plain white t-shirt stood out. A single sentence written across the chest in a small, basic font read:
“Anybody can do what I do.”
“I bought this shirt with the intention of finishing the ultra marathon with this shirt so I could show my parents, friends, and anyone in general that you don’t have to come from a running background,” he said.
“It’s never too late to just get out there and do these things.”
In this climate of “safe spaces’ and safety nets, it’s easy to lose sight of what life’s real challenges are, and how they move us forward. At a time when bravery is all too frequently attributed to affluent people who proclaim victimhood status, Omar reminds us of what real courage is.
“I just want to show people: You don’t have to be the fastest, the strongest, the smartest, to do these great things,” he exclaimed when talking about his message. “You can just get out there and just go for it!”
Whether it is competing in a new race next year or establishing a new habit for life, Omar has advice for those of us feeling too timid to shake things up.
“Just get out there and try. That’s the most important thing.”
Check out A22-23 for how this story appeared in the Vail Daily
What a great message to put out there. Trying is an underrated thing we can do in our lives. Thanks for this post!
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