How to win a race and win at life

June 29, 2023 9 min read

How to win a race and win at life

© Maciek Tomiczeck

In a world where attention spans are shrinking and the need to consume is becoming all consuming, an event that asks for no entry fee and demands your complete attention every waking minute for the several days it takes to complete it, is a rare thing indeed.

The Highland Trail is a 550-mile self-supported mountain bike time trial through some of the most remote and rugged landscapes in the Scottish Highlands. Approximately fifty people begin riding a set route on a certain day every May with the ambition of riding, pushing and carrying their bikes 550 miles to the north west highlands and back. Only commercial services available to the public can be used to resupply from or to rest in. Riders choose how and when they eat and sleep but the clock never stops. The entry fee is a recommended donation to the John Muir Trust. There are no prizes and no support. It’s a race like no other.

The attributes commonly associated with racing are akin to those found in successful business people and many of our political leaders. Strength, power, confidence, goal-focus, charisma. As children, our definitions of success, and our road map on how to achieve it, is very straight forward. Winning is good. Losing is bad. Being rich is good. Being poor is bad. Being strong and capable is good and the opposite of that is to reveal our vulnerability and expose our failures. This is bad. Dangerous even. All human attributes have a shadow but historically we’ve colluded with each other to shine a light on some and not on others. Imagine a society that rewarded kindness and patience over and above charismatic despotism and Gross Domestic Product. Imagine a race where winning is not the point but rather a way to share momentum with those around you so that you might have an experiment with your body and mind to discover what you might be capable of. This is The Highland Trail 550.

© Maciek Tomiczeck

I’ve had countless conversations with people who insist that those of us who choose to ride something like the Highland Trail 550 do so because we are sadomasochistic, because we have attention deficit disorder or because we are insecure and have something to prove. While all of that might be true to a greater or lesser degree, I believe we all choose to challenge ourselves on rides such as The Highland Trail for a variety of complex and interwoven reasons. To assume our end goal is to experience suffering misses the point entirely.

The state I’m seeking when I set out on a mission of endurance is not pain and discomfort, it’s the opposite. Of course, I experience pain and discomfort in the course of a 550-mile non-stop mountain bike race but I do so in my day-to-day life too. Pain and discomfort are everywhere. Living a life pretending the hard things don’t exist and attempting to avoid pain and discomfort is what causes us so much suffering. Endurance for me doesn’t mean gritting my teeth and shoving my feelings away so I can keep going. It means feeling resistance to pain and discomfort and allowing it to flow through me. By being in a situation where I have no choice but to make friends with my pain and discomfort I gain perspective, strength and gratitude. It’s why, ever since I was very little, I’ve felt this insistent tug outside and towards the unknown.

I was very lucky growing up. I had enough warm and generous adults around me with adventurous sparks of their own to ensure mine was never extinguished. I had access to green space and the trust of my parents and community to explore it alone. Children need boundaries but clipping their wings entirely has serious implications for them as adults. I often wonder who I might have become had I not had the space and autonomy to play outside my house, ride my bike or walk the long way round to school.

© Maciek Tomiczeck

I’m an adult who survived the wing-clipping and yet I still allow the heaviness of routine and obligation to deaden my curiosity and sense of adventure more than is necessary. Finding balance is hard and the only way I have found to do so is by hitting stop occasionally. I appreciate it sounds counter intuitive but the all-consuming challenge that is racing self-supported through the Scottish Highlands is me hitting stop. I’ve tried for years to sit still and meditate. I can’t. I’m like the excited kid at the back of the class who wants to explore and discover rather than be told or taught. I understand those kids. We need motion to think and to find calm. It takes special energy and extra compassion to deal with us, but we’re worth it. We have some great ideas and lots of energy to implement them. Having worked with these kids for years, I agree that it’s much easier just to squash them back into their seats and dampen their disruptive spark. But easy all the time becomes boring very fast.

I have also had conversations with many people who insist that it is disrespectful to barrel head down on bikes through wild places and that it can’t be possible to appreciate your natural surroundings when moving through them at such a pace. But I don’t think it’s possible to move through difficult, remote terrain smoothly and with ease without first stopping to doff your cap in admiration and awe. Omit this humble gesture and a wild place remains intimidating. Someone who attacks a trail with anger or frustration will slip, slide, curse and stumble their way along The Highland Trail and will probably find themselves questioning their life choices and feeling utterly exhausted. I know this because I can also be that bike rider. But when I have the head space to remind myself that slow is smooth and smooth is fast the world falls back into place for me. It’s easy to become trapped in the belief that you must be going as fast as possible all the time, avoiding anything or anyone who might distract you from your self-imposed goal. I am as guilty as anyone of behaving this way in a race and in my daily life, but the folly of this becomes more apparent in these wild, special places. Here I am compelled to stop, breathe and be. After I have taken that moment, my balance on the bike is better, I’m more alert, I can manage discomfort more easily and I notice that my breath is less forced.

On The Highland Trail riders are compelled to remain awake and keep moving through sunsets, sunrises and fickle weather systems which can feel very scary and lonely. I’ve suffered countless crisis of confidence in the cold, wet darkness before the sun comes up or the rain goes off. I’ve moved through these dark, uncomfortable places and emerged utterly stripped down physically and emotionally. What follows is a period of intense calm and a humbled, energised conviction that I am both utterly insignificant and a vital part of something much bigger.

© Maciek Tomiczeck

I like who I become on these long bike rides. In focusing on one big physical challenge in the mountains, I can harness a flow of natural energy. I stop feeling stressed about everything by being consumed by the stress of one thing and I deal with negative thoughts in the moment rather than allow them to fester in my subconscious. In this set of circumstances, something as hard as racing 550 miles becomes easier than navigating my everyday life.

I find that riding long distances through remote wilderness while snatching only smatterings of sleep will, ultimately, render me defenceless and wide open to the vibrancy of the real world. This level of physical output grinds me right down until I’m as vulnerable and susceptible to joy and misery as a child. It’s then that my senses become open to the heart stopping wonder and fragility of our natural world. This wonder is right there all the time, it’s just that it’s easy to let the colours dull when you’re busy and distracted all the time.

A cold, high, remote mountain plateau is a scary and uncomfortable place to imagine yourself to be in the middle of the night but when that it is your reality, there is no room for anxious imaginings. Until you are standing there you won’t know if you’ll experience a calm, steady focus, a gripping dread or a wild euphoria but whatever happens, these are some of the best conditions I’ve ever found to fan creativity, connection and gratitude into a full-on flaming ball of fire. By allowing myself absolute heart and soul freedom while I move self-supported through wild places on something like the Highland Trail I realise that happiness is right there under my nose all of the time.

© Maciek Tomiczeck

I used to think there was a time and a place to practice self-care and empathy but that the middle of a bike race wasn’t it. Now I wonder if the circumstances that produce the highest levels of stress in us might be some of the best places to practice these ways of being. I’ve come to the conclusion that treating myself like a small child who I care about very much helps me manage the stress that would otherwise have me thrashing about in frustration. When my nephew was four he didn’t know when he was hungry. The discomfort he felt which usually manifested in shoe throwing or foot stamping, made the prospect of eating anything unappealing in the extreme. But as a caring, objective adult I would gently but firmly insist he eat something. My body needed about 8,000 calories in a twenty-four-hour period to keep moving forward on the Highland Trail but the thought of food made me feel physically ill, especially towards the end of the ride. There is a lot of trust involved in swallowing another grim flapjack when my child-like brain is screaming that she feels sick and wants to be left alone to throw her shoes around. But pausing to take care of myself has always worked and I feel instantly better and a little embarrassed by my naive, belligerent four-year-old self. I still catch myself in my everyday life yelling “Oh for f@*&k sake Lee, COME ON!” In those moments, I’m as frustrated with myself as I was with my nephew when he wouldn’t leave his Lego set and get his shoes on– but I would never have shouted at him like that. I’d have used humour, bribes, patience and compromise to get the desired outcome. So why would I think that by shouting obscenities at my own tired, hungry four-year-old self I’ll get a good outcome?

The bizarre dichotomy of placing myself on a start line in order to practice compassion, patience and gratitude is not immediately understandable. Traditional sports coaches would probably laugh out loud but what if we were given the time and space to explore other ways to win and, further to that, consider what winning or success actually looks like? Could a shift away from our growth economy mindset that supports extractivism and social inequality to a well-being economy, designed to serve people and planet, make more of us healthy and happier?

We are hard-wired to move faster in the face of adversity in order to escape it but the faster the world goes the more important to me the pause between thinking and acting becomes. Perhaps by practicing this pause I might find that not only do I become happier but I might also perform better. Maybe in letting go of what I think I know I might discover there are other ways to win.

"It's the day after completing the Highland Trail 550 and I feel like I have just now awoken from a dream. A four-day adventure of moving through the most elaborate of film sets, the most magical of dream worlds. In riding this trail that stretches the length of the Scottish Highlands, I have flown with the birds who called to me each morning and bounded with the deer who then stood watching me quizzically from hilltops. I've been changed by this. Unquestionably, mind-alteringly changed. To live like this. To move like this. To manage my body and mind like this has taught me more about myself in four days than an entire career of elite racing ever did. And the thing is, it was easy. Not the pushing of the pedals or the carrying of the fully loaded bike over col after col or the three hours of sleep a night or the managing of my food and equipment. Of course, that felt hard. What was easy was the simplicity of the doing and being. Despite the discomfort, tiredness and hunger, the miles slipped effortlessly away. Hours disappeared in the changing of the light. At no point did I feel bored or distracted ordesperateto be somewhere else in the way I often feel in my normal life. Because when the ride just becomes life and your only objective is to keep moving forwards through it, then things become very simple. Nothing hurts. Not really. The painful points come and go like the weather and in the end, like the weather, are neither good nor bad. Today I can't walk but of course I can. The midges are unbearable but of course they're not. I'm exhausted and I MUST sleep but I can stay awake if I have to. I'm very hungry but a few more moments of feeling this way won't kill me. Everything feels possible and every feeling is a privilege. Nothing feels impossible, boring or unsatisfying unless I choose it to. This was just a big bike ride but I find as a result of riding 550 miles in four days, I am quite changed."

Lee Craigie completed the Highland Trail in three days twenty-two hours, making her the fastest female to complete the route and one of only a handful of people to finish in under four days. Read Other Ways to Win for more of Lee's story.