Why losing everything could be the best thing for you


Last week, as I was ruminating over my direction in life and caught up in my feelings over recent losses – in other words, throwing myself over life’s proverbial cliff – I came across this video about Serena Williams




Scrolling through my FaceBook feed, the caption, “From Broken Nets to Grand Slam Queen” caught my eye. The timing was uncanny and as someone who believes there are #nocoincidences, I decided to let it play, rather than continue to mindlessly scroll.


While I’ve never been into tennis, I’ve always been captivated by the Williams’ sisters and their success as athletes – I mean, they practically redefined the sport. But, until I was watching this video I had no idea just how much Serena had to overcome to be at the top of her game.


As a young athlete, Serena quickly rose in ranks, dominating the sport. Then, in 2003, after undergoing knee surgery, she went from being ranked #1 to #139. Weakened by her injuries, she entered a cycle of doubt and became unsure of her next step.


No one likes to lose – especially once you’ve been at the top. Whether it’s loss in terms of job, relationships, health or status, we don’t like to lose much less talk about it.


But, the reality is loss is a part of life. Every time a marathon is ran, one runner wins and hundreds lose. When you go to vote for the next president, you’re not just deciding who wins, you’re deciding who loses. Each time you watch the Super Bowl, about 50 players who worked just as hard lose. The corporate company who just offered someone a job also turned many applicants down. The end of every spelling bee leaves hundreds of educated students in a position of loss. When judges crown a queen, the other women face defeat.


And yes, it sucks. Losing hurts. It breaks confidence. It kills dreams. Self-esteem diminishes. Qualifications are questioned and our dreams and goals are reconsidered. It happens all the time.


But you cannot have wins without losses. And that’s OK.



I’ve had my fair share of losses, second places, interviews gone wrong and denial emails received. The runner-up trophies, certificates, medals and ribbons I’ve accumulated over the years are simply a placeholder, symbolizing loss – the moments of my life I didn’t quite get “there”. Most of our life, I think, can be summed up this way: in a shelf (or a box in the garage). Sure, the “wins” can make their way onto a resume and the participation awards can make their way into the “at least I tried” category of our lives, but at the end of the day, they’re just a reminder, a memory.


As we get older, no one hands out, “at least you tried” certificates. There are no participation awards for the Real Life Shit – the times we put ourselves on a limb and ran for a leadership position we desired – the times we put our heart and soul into a race, only to lose by a fraction of a second.


There’s no placeholder for the moments our strength is tested and our passions are pushed. There’s no “at least you tried” ribbon when you’re staring at loss and your confidence in yourself is challenged – and, there doesn’t need to be.


Loss is painful, but it’s also the birthplace of growth and in order to gain anything substantial, we must first lose everything.


Want to grow your career? Be prepared to not get the second interview – or an interview at all. Be prepared to watch someone else get what you want.


Want to grow your finances? Be prepared to invest big, take risks and potentially lose it all at the whim of the stock market.


Want to grow your relationships? Be prepared to lose your ego, make sacrifices, or be rejected.



All growth requires loss and you cannot win until you learn to lose.


Sometimes it takes questioning everything you know to come to an even greater understanding of something. Sometimes we need to be stripped of all the titles and status symbols, things we hold onto that we believe define our value and worth, to realize our potential for greatness. Those incredibly humbling moments of life, if we’re willing to lean into the loss and push past “never again” and “I quit”, will teach us more about ourselves and life itself than any win ever will.



What am I learning in the process?


How is this loss serving me?



Loss can have us question our worth, our path and our purpose; but it can also help us redefine what’s truly of value.


My loss is teaching me to keep my eyes focused ahead on what I want and where I want to go, rather than looking at what someone else is doing or getting. Comparison fuels a special kind of loss, the kind that only has you feeling more lost. I’m also learning to trust what I stand for over what I outwardly achieve. It’s teaching me to not get caught up in a status or title or to define my worth solely based on any kind of metric. Instead, I’m measuring my life by my core values and focusing on ways to live these out on a daily basis: Integrity, Impact, Innovation, Vulnerability, Rest & Rejuvenation, Connection, Growth and Freedom.


As the Universe would have it, I now have permanent reminders of my values in my house, each word beautifully inscripted in a frame, replacing my collection of Post-It notes with my words on a wall. This past weekend for my birthday, my girlfriend sent me on a scavenger hunt and at each location I received one of my words – real place holders of what truly matters in my life.


Loss doesn’t have to be a place holder in our lives, collecting dust on a shelf until something better comes along to replace it. In fact, when we allow our loss to be a source of insight and awareness, we’re able to clear the shelf and make room for what really matters in life – and, we’ll understand the greatest lesson there is to know: We don’t learn to win by winning. We learn to win by learning to lose.


This week, learn to lead without a title. Learn to be a good sportsman even when you don’t make the team. Learn to serve without recognition. Learn to truly win by learning to embrace your losses.


You are enough. As you are. And where you are, is exactly where you are meant to be.