Lose and You’ll Win — How to Reflect on Failure

Cover Photo by Joseph Wayne Buchanan from Pexels

“For winners, losing inspires them. For losers, losing defeats them.” — Robert T. Kiyosaki, Rich Dad, Poor Dad

What’s your reaction when you lose?

How do you feel about losing?

I’ve lost all my life.

As a kid, as much as I tried, my older brother was always better than me at everything except for school. But even in school, I certainly wasn’t a grade A student. In my adult life, I’ve started 8 businesses, most of which are currently dead. Even within the surviving companies, most of the projects I start end up failing.

But I keep going. Losing inspires me to do better next time.

I’m not denying the fact that it sucks. But think about that:

Life is an experiment. The more you experiment, the more you discover about yourself and the world.

When starting anything, I wonder: “What’s the worst the can happen?”. And being an optimist, the answer usually is: “nothing too bad”. I figure, at the very least, I’ll have learned something.

But I guess I’ve had it easy. It was part of the way I grew up.

In “7 Ways to Prevent Your Child From Being a Sore Loser”, written by Amy Morin for VeryWell Family, there’s a point I think is particularly relevant:

Don’t Let Your Child Win

It can be tempting sometimes to throw the game on purpose so you won’t be subjected to a sore loser’s negative reaction. Although preventing a meltdown can help you in the short-term, over the long haul you won’t be doing your child any favors.

While you don’t need to be brutally competitive, avoid losing on purpose to spare your child’s feelings. Letting her win will only reinforce to her that she can’t handle losing. Each loss is an opportunity for her to practice not being a sore loser.

The way you feel about loss has been deep-rooted within you since childhood. I’m no doctor but I know a thing or two about the power of habits.

If you’re used to winning, winning is habitual, losing sucks. If you’re used to losing, losing is habitual, winning is epic.

Think about that for a bit.

I lose so frequently that I have a Win Journal to record my wins. When I win, no matter the importance, I “celebrate”, or at least, I recognize it. When you have the habit of winning, you stop realizing that you are winning, even feeling like you’re losing too frequently. That’s not good for your morale!

Do you see the mindset shift I’m trying to impart you with?

Experiment. Experiment. Experiment.

That’s a habit of champions.

Don’t believe me?

See what other champions have to say:

“All life is an experiment. The more experiments you make the better” — Ralph Waldo Emerson

“The true method of knowledge is experiment” — William Blake

“I am my own experiment. I am my own work of art” — Madonna

“The test of all knowledge is experiment. Experiment is the sole judge of scientific truth” — Richard Feynman

Without realizing it, when I started my SkillUp approach, that is, learning 3 new skills every month, practicing every day for 30 minutes each, I set myself up for success, through failure.

Phew, that’s complex!

During a podcast interview, the host made me realize how starting something new from scratch every month is a great habit because I always start from failure. I essentially started a habit of losing.

Don’t believe me?

You should have heard me play Ukulele on April 1st, it wasn’t glorious! Actually, here it is. Here’s me failing publicly:

I even tried to look happy with my performance at some point!

I did the same with Salsa Dancing, amongst other skills:

My point is:

You can’t win without losing. That’s just life. The sooner you accept that, the sooner you will thrive.

In 2017, before I started writing for real, I wrote a piece I called “2018 is the year I will fail the most”. Sure enough, I have because I did so much. It turns out 2018 is also the year I’ve accomplished the most in my life. Looking back, it’s hard to imagine that all that happened was only during the short span of 12 months.

But this piece isn’t about me. It’s about you. Ask yourself these questions:

  • What can I do to turn losing into something not so hard to swallow?

  • What is a simple habit I can start to move me out of my comfort zone?

  • How can I recognize my wins, however small?

  • What is one simple thing I failed at that I can turn into a lesson?

  • What can I do to turn that loss into a win?

  • Who can uplift me when I feel down after a loss?

  • Where and what is a safe environment for me to have failures?

  • What skill do I want to learn so bad that I’m okay to fail a few times before I’m good at it?

  • How can I break this skill down to make it less likely that I fail?

These are only a small sample of questions you can reflect on. Add your own questions to that reflection.

Always be honest. It sounds dumb, but often the person we’re the least honest with is our own self.

A journey to acceptance about losing is not an easy one since it mostly comes from years of being told that losing is bad for you. We are told that if you don’t always win, you’ll never get what you want out of life. Yet:

It is out of failure that you learn, adapt, and become better, ultimately leading to what you want out of life.

So I dare you to do the reflection above. Learn more about yourself and start your journey to rewire your brain and thrive.

You can do this!