The Late Bloomers: Jonathan’s Journey From Brooklyn to Boston


    Over the next few months, we’re interested in telling the stories of those who came to running after the age of 40 and what they’ve learned and accomplished in the process. If you’re interested in participating, tweet Ravi and introduce yourself. We’re starting with Jonathan Greenwald, who you can follow on Instagram (Runthesix) and on his blog “Brooklyn 2 Boston.

    Though he hails from Brooklyn, Toronto has been the site of many life changing milestones for Jonathan Greenwald, having moved north after meeting his Canadian wife in 2005. Shortly after, he became a dad to his now seven year old son and the family have called Toronto home ever since.

    Toronto is also where Jonathan kindled his obsession with running in June of 2013, just four months after turning 40, which makes his Instagram handle (Runthesix) so appropriate.

    As is the case for many who turn to running later in life, it began as a preventative health measure and only became a passion over time. According to Jonathan, at the time of that first foray into running, “I was 183 pounds, the most I ever weighed in my life. I decided I needed to make a few changes and a couple of friends invited me to start running with them.”

    “My goal was to not die,” Jonathan remembers. Like many new runners, Jonathan had no idea how his body was going to react to running. He’d been active throughout his youth playing tackle football and hockey, but running was never really in the picture. Much of that activity had also stopped after his teens and it wasn’t until moving to Canada all those years later that Jonathan decided to become active again.

    While the first run was a success in that Jonathan didn’t meet his mortal end, it still served as a rude awakening. Jonathan recalls, “I wasn’t obese, but after my first runs, it was clear I was out of shape.”

    At the very least, Jonathan hoped he could at least stick with running long enough to lose a few pounds and maybe come to actually enjoy it.

    There was also the matter of justifying all the running related purchases he made before that first run. “I purchased a running watch, shorts, a top, and running shoes,” Jonathan says. “What scared me the most was that I wouldn’t enjoy running and would have to explain to my wife that I purchased all of these items and wasn’t going to use them!”

    In the subsequent years, Jonathan has certainly justified those purchases, and the many that surely followed, as he took running from a hopeful experiment that might lead to better health to a full on obsession (Seriously, check out his Instagram!). He stays consistent, cranks out high volume, and is never quite ready to settle. Accomplishing one goal just means it’s time to chase another.

    2016 was Jonathan’s marquee year, with PBs posted at the 10K, half marathon, and 30K distances. The last one resulted in a silver finisher’s medal at the classic Around the Bay race in Hamilton, which requires a sub-2:15 finish. There was also the crowning achievement of Jonathan’s running life, racking a BQ (Boston Qualifier) “…with a time I never would have dreamed I could obtain.”

    The only drawback was that his BQ was ultimately 51 seconds off the final cutoff time. Nonetheless, it’s quite a remarkable list of achievements considering that Jonathan spent most of 2014/15 learning to keep himself from being constantly injured.

    Reflecting on those incredible accomplishments, Jonathan says the biggest lesson he’s learned about himself running is “…to never underestimate the power of determination and perseverance. I am a firm believer of the saying, ‘Don’t just wish for it, work for it!'”

    At the same time, the experience of chasing those goals has fostered a sense of maturity that allows Jonathan to accept results that may not necessarily reflect his greatest potential despite what he acknowledges to be his very competitive nature. Enough races presenting varying conditions and results have brought about the realization that, “There are so many factors you can’t control and you just have to accept it. I still get disappointed when I don’t meet a goal or have a bad day, but I quickly brush it off and move on.”

    Jonathan has put that lesson into action by continuing to chase after Boston with hopes of finding himself at the start line in 2018.

    “…the running community is the most supportive community I know.”

    There are many keys to Jonathan’s growth as a runner, but he emphasizes that your fellow runners might be your greatest resource for knowledge and inspiration. Jonathan urges new runners to, “Research run groups in your area. You will learn so much more running with your peers than trying to learn on your own and the running community is the most supportive community I know.” In addition, he adds, get to a local running store and have the friendly staff fit you with a pair of shoes that works for you so as to save you the agony of discomfort and potential injury.

    Beyond the practical lessons that other runners offer, Jonathan adds, “All accomplishments aside, the friendships I’ve made through running is something I will always cherish. If I never get to Boston or never beat any of my previous finishing times, I will always love running because of the friends I made.”

    And he doesn’t seem ready to slow down despite the challenges that come with potential injury and balancing running with other commitments, which often means he has to fit in runs at varying times of the day and at times where he may not necessarily be eager to get out the door. These, however, are mere inconveniences and don’t seem to make him question his commitment to goals and to running. “Nothing has made me want to quit running,” Jonathan proclaims, “I’m addicted!”

    • Ravi Singh


    1. I’m floored Ravi. This is absolutely brilliant and reading it resulted in a wave of emotion. I don’t think I ever sat down and thought about what I’ve accomplished in such a short period of time, nor truly considered how fortunate I am to be able to run. I’ll truly cherish what you’ve done for me here. Thank you, my friend.

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