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Failing Forward: My Step-by-Step Guide On How to Lose… And Love It

In fitness, especially elite high-intensity fitness, we like to say that iron sharpens iron.

It’s an old Biblical reference. And so, according to Proverbs, “a man sharpens the countenance of his friend.” And we do. We are made tougher by tough love. We are made harder by the hard situations we face. We are made better by adversity. Without suffering, we’d never know the true joy of success, without bitter losses — and the pain that shadows them — glory wouldn’t shine so bright and pleasure might not taste so savoury. That’s simple semiotics – we understand the selfsame more fully by its opposition the other. But what we don’t often tell you in fitness is that it’s ok to fail. We talk about winning. A lot. What it takes to win, what if feels like to be a winner. We rarely shed light on the losers.

Well, I’m a loser. Here’s my guide on how to crash and burn just a little, even if just to test the warmth of the fire.

STEP 1. Realize You Suck at Something

While I regret some of my losses, mostly those I couldn’t control, I’m eternally, existentially, grateful for the losses I’ve created by my own hand.

I left Toronto in 2012 a wide-eyed U of T law grad in a light blue oxford collar, about to start a career at an elite law firm in New York. I came back in 2017 a horse-voiced fitness coach in a sweaty tank top with no doubt about finding my place in life.

People love to ask me about what happened along the way, how I made the change, and I wish I had some cool answer about my exacting plan and stealth execution; but the truth is, I failed. I failed to find meaning in law. I grew up poor, working construction and landscaping jobs since I was 14 years old. I loved the end of the day when you could see what you built with your own hands. But everyone told me, “You’re too bright for that.” I got straight A’s in school and people kept giving me scholarships and bursaries based on financial need in my family and all roads pointed to law. “You’ll make more money in law” was the only thought in my head, but I failed to find purpose.

I started boxing for more hours than I spent researching. I lost that tactile connection I had valued in manual labour. I found it back in boxing after hours. In law, you don’t touch your opponents the way my coaches told me to touch my counterparts in the ring. Touch and be touched. “Touch him first, Chris!” they used to yell at me (code for land the first punch to set the tone and maybe hurt him a little bit.) I liked to move around; I liked to dodge a punch, I even liked to get hit. They started calling me the “Cuddly Canadian” because I didn’t love hitting people back that much. I would even apologize under my breath any time I landed a big right. But I LOVED the ring, the craft, the comradery, the touch and feel of it, the humanity of it. You’re never more drenched in pride than when you’ve earned a win through your own sweat. And a loss written in your blood on the canvas beneath your feet, that’s a story you’ll read again and again in your head. You’ll never really forget. It means something. It was tangible: it made me feel something I hadn’t felt in a long time, struggle. I’d been missing that.

I couldn’t feel a million-dollar loss for a fortune-500 company the same way I could feel the cartilage getting broken in my nose by a bigger guy I had to spar because we couldn’t find anybody my size that late at night at the gym. I couldn’t feel my knees go weak before a big trial the way they got weak when I saw the look in a man’s eyes, who was more intent on hurting me than I was him. And I didn’t feel like I earned the steak dinner a partner would buy me after a favourable settlement, the same way I earned my tequila shots with my trainers after a messy win.

It was those touch-points with adversity early on that helped me reckon who I am. And I started to feel them again the further I got from my ivory tower in law, and the more underground I went at my sweaty Mexican fight gym in midtown – Mendez Boxing (amen). At the end of the day, I think that’s something a lot of us don’t realize: life is hard. And we find out who we are in the way we react to the hardest parts. Truth is, I didn’t find law to be all that hard. If you showed up, did your research, gave it to the partner on time, that was it. You loosen your tie at 5, or 7 or 9; you go drinking with your buddies, wake up and do it again (and in New York, if you show up after 10 am, no one’s keeping score). There was never a moment, even amid the hardest cases, smartest opposing counsels, sleeping on my office floor for days at a time during trials that I felt I had gone to war with my colleagues and that we had undergone something meaningful together.  I was never pushed to my limits, so I started to forget where they were, I never helped another person be pushed to theirs. I failed to find my place in the corporate world at the highest level because I just couldn’t squeeze a drop of sweat or blood, or truth, out of the silk ties and abstract marching orders. And that’s not to say that others can’t; law is a noble calling if it moves you if it touches you. However, it just didn’t touch me in a meaningful way.

STEP 2. Realize It’s Not Worth Sucking at Something for Your Whole Life

Even though I was losing at my career in law (at least from a personal growth standpoint), it wasn’t enough to make me leave. Again, I wish I could tell you I had the audacity to pursue my truth. I wish I could tell you I had that courage, that depth of knowledge to find my right from wrong, that strength of character, to do what was needed to win. I didn’t have those things. I continued to lose. It felt like a slow drip; every day, I’d lose just a little bit more of who I was and I’d go back and do it again the next day.

Then I hit rock bottom. In the span of what all felt like one year – the worst year of my life – I lost what I then thought was the first real love of my life, I lost my best friend to cancer, and at the end of it, when all the dust had settled I finally, and thankfully, lost my legal career.

As far as the love thing, I think when we’re young, we make more out of that stuff in our heads than it actually is; with time, I realized I gained a lot more than I lost on that front. In terms of the best friend though, that’s the most significant loss I’ve ever known. All of that strength that I couldn’t muster to become happy in life, all of that courage and compassion, all of that command over myself that I lacked in search of my truth, Adrian had all of those. In Spades. He didn’t believe the hype that keeps us scared and bullies us into the corner, that beats on us with the same stale old script: be smart, go to school. If you’re good at it, go from there to grad school, from there, to a desk you hate, to a pension you don’t have enough time to enjoy. We have no hand in writing the script. But it gets rolled up and smacks us into the corner. And we stay there, a lot of us, most of our lives, with our forearms up, taking hit after hit, never asking if we’re happy, waiting for someone else to throw in towel for us. After enough of those hits, and the right inspiration, I’m not embarrassed to say I threw in the towel for myself.

STEP 3. Make Sure You Meet Some Winners along the Way to Really Drive Home Just How Much You’re Losing at Life

Adrian helped me realize life’s too short. He didn’t give a fuck about the script (probably because he was too busy doing real things to sit down and read it.) He chose to be a student of the world.  Adrian restored an engine with artistry, learned to play his seventh musical instrument with mastery (I think the accordion was the last), he’d perform carpentry jobs with so much skill that he could work half the year, save up and spend the other half on humanitarian missions in East Africa, or months-long adventures motorcycling to the edge of the world at the Panamanian gap and back. Adrian didn’t give a fuck if he was smart enough to be a doctor or a lawyer (even though he was) because it wasn’t what his heart told him to do. He was so courageous in that way.

When you find yourself speaking at a ceremony that memorializes someone like that, your internal compass can’t help but recalibrate. You get so thirsty for meaning and truth that the script loses the allure, it loses its power over you. Eventually, I failed out of law. I didn’t leave my firm ceremoniously, with some plan about where’d I go and what I’d do. I just left. I walked down 5th Avenue with a box full of my trinkets and extra pre-tied ties that I kept for important meetings and that was it. I didn’t look back. My US cell phone was the property of the law firm that I had to return, so I remember wandering for a long time with no contact that day. I walked all the way downtown. I headed to the NYU library, looking for my best college friend who was working on his next award-winning TV script (he’s the image of a REAL winner), but I couldn’t get in without a student card. So I sat there, sweaty, in the lobby, and I just laughed into my cardboard box. I had no idea what was next.

STEP 4. Steer Into the Skid

Later that week, when the shock wore off, I started working construction and bartending jobs in New York. The charity I’d fought with, Haymakers For Hope, saved me and gave me some purpose by allowing me to act as their general counsel and New York fight manager, giving me some of the meaning I thirsted after.  I boxed a bit more, worked out way too much, and left myself open to the world, I would look up at the sky every day and try to feel which way the wind was blowing and I asked for direction – from the autumnal Manhattan wind, from the Universe, from Adrian, I don’t know. I asked for help to find some truth. I asked and I received. When I found Barry’s Bootcamp, it was my second-coming. A place where I felt I could touch people and be touched by them, somewhere where I could see my clients struggle, struggle with them, sweat with them, bleed with them, and smile with them when we all came through the other side together… I heard once “Home is a feeling.” I couldn’t tell you exactly why, but I’d found my home.

STEP 5. Justify It to Your friends, or Don’t

A lot of people say that it doesn’t make a ton of sense to go from being a lawyer in the most competitive market in the world to being a fitness trainer, back in your hometown. And they’re right. For some people, my story is one of failure.

I failed at corporate law, failed to see it through, failed to find meaning in it, failed to choose the right career path early on. And I’m thankful every day that I did.

“Open rebuke is better than love carefully concealed” is another one from Proverbs that seems appropriate. Failing out of anything isn’t easy.  Giving up a six-figure bonus for sweat and smiles is not something most of us are willing to do. And as someone who grew up poor as I did, it was all the more difficult for me.

But I will say this: if you find the thing you’re really meant to do in this world, you owe it to yourself to do it. At all costs. Do it recklessly. Do it impetuously. Do it without regard for where it’s going to take you. Life’s so short: if you get one or two great rides, you’re probably ahead of the vig.

And if you find it and you’re really meant to do it, and if you’re good at it (this one’s important, cause the free-market is a cold place if you’re gonna bet on yourself) – then the rest will fall into place. I ended up being able to return home with something I’ve helped build. Something I’m immensely proud of. I’ve been granted entry into leadership in a company that I love and I feel that I get to change the landscape of my hometown, one smile, one drop of sweat at a time.

Chris Lewarne is a member of the Inaugural Notable Board, founding trainer and Chief Instructor at Barry’s Bootcamp Toronto, as well as the man behind The Cuddly Canadian on Instagram.

Chris Lewarne