How To Win Even When You’re Losing

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Want to hear something comforting?

Here’s it is: Everyone’s a loser.

And if you’ve been feeling like one, you’re in good company.

Been on a winning streak lately? I hate to burst your glossy (and fragile) bubble, but you will lose at something, at some point.

When you’re playing the game of life, tripping up, failing and losing face are all part of the package, there are no exceptions.

You can’t avoid the losses, but knowing and respecting this reality can set you up to be a better loser and hopefully, win more in life.

But if you’re anything like me, letting reality sink in can take quite a bit of time, so I use these steps to soften the blow and pave the way for better things to come into my life.


To win, you have to be able to overcome obstacles, and nothing will keep you stuck more than subscribing to the illusion that your problems will work themselves out if you leave them alone.

The cold, hard truth is that to fix what’s broken in your life, you have to accept that they are broken and that it will take a good amount of hard work to make things better.

If you don’t fix them — face the dysfunction, process the trauma, have the hard conversations, heal your heart — your life will stay broken, and you may never be able to grow enough to progress to the next level.

It’s healthier (and more efficient) to accept what is and deal with it before things get out of hand and way more difficult to fix.


You’ll win some, you’ll lose some — this is guaranteed and is how life works.

No one wins at everything, and no one loses every single game they play, unless they put in zero effort one hundred percent of the time.

And while it’s easy to enjoy the accolades and give yourself a pat on the back when you win, handling your losses graciously isn’t the easiest thing to do.

Losing is never fun, but the trick to losing like a champ is to lose like you’re winning.

This means accepting that things can go either way every time you step into the ring, which will help keep your suffering — and ego — in check.

And just as well.

After all, where’s the fun and magic in winning all the time?


“Winning isn’t getting ahead of others. It’s getting ahead of yourself.”

~Roger Staubach

Some people will tell you that you lose by default if you choose to opt out of playing a game (especially when everyone else is).

Let them. Better yet, ignore them.

The longer you live, the more you’ll realize that there are an infinite number of smaller games to be played in addition to the big one, and just one of you.

This means that you have a finite amount of resources, and will probably have to make some hard decisions: Which games should you play (and play hard at), and which ones should you leave alone?

If you’re like most folks, winning may look something like this:

  • Creating a family of your own
  • Buying a home
  • Carving out a successful career in (fill in the blank)
  • Retiring with enough savings
  • Finding your purpose in life
  • Traveling the world

This list can go on and on. This is where you’ll have to figure out what you want to keep, and what to cut out so that you can give your all to the games that you really want to play and win at.


“The art of knowing is knowing what to ignore.”


Before you jump into any game, you’ll need to know what the rules are and how they work.

Once you’ve sorted out what you can and cannot do, the process of narrowing down your to-dos can then be shortened considerably by figuring out what you don’t want to do.

A big part of getting to know what you don’t want is realizing that some games aren’t just energy suckers — they’re downright unnecessary.

Think of this as a crucial step in developing the laser-sharp focus you’ll need to play not just a good game, but to play it exceptionally well in the areas you want to ace at.

The more focused you are, the more likely you’ll be to win.


“You learn more from losing than winning. You learn how to keep going.”

~Morgan Wootten

Anyone who’s been at it for awhile will tell you that playing the game of life is freaking hard.

There are no shortcuts or straight lines to the top, which means that you will fall flat on your face at some point.

When you do, you’ll need to know how to regroup and get back on your feet wiser, faster and stronger.

You learn to grow more resilient in the face of adversity.

Give yourself permission to fail and learn from your mistakes.

This way, you’ll keep yourself open to moving forward despite your missteps and shortcomings instead of drowning in a self-hosted pity party that will only keep you stuck in the past.

And even if you’re not losing, taking time out just to be still can be a good thing.

Give yourself a break, and you just might be onto your next breakthrough.


Simplify Your Life: 100 Ways To Slow Down And Enjoy The Things That Really Matter by Elaine St. James I got my hands on this treasure over 15 years ago, way before simple living and minimalism became popular, and it was the first resource that introduced me to the practical, everyday steps I needed to ‘un-complicate’ my life.

Boundaries: When To Say Yes, How To Say No To Take Control Of Your Life by Henry Cloud and John Townsend Not having boundaries can end up wreaking havoc in your relationships and leave you feeling resentful, used, and disrespected. In this book, Cloud and Townsend show you how to get over the guilt of setting limits (this is particularly helpful if you’re a recovering people-pleaser like me) and equip you with the skills you need to build healthy relationships that will fulfill, not drain you dry.

Difficult Conversations: How To Discuss What Matters Most by Douglas Stone, Bruce Patton, Sheila Heen and Roger Fisher Lousy, conflict-ridden conversations strain relationships, and don’t make difficult relationships any better. Here, the authors take you into the process of managing and expressing your feelings constructively rather than constantly muddling through who’s right, who meant what and who’s to blame.

Rethinking Narcissism: The Secret To Recognizing And Coping With Narcissists by Dr. Craig Malkin I never realized narcissists existed until I became tangled up with one for several years. It was only after I discovered what a narcissist was that I understood the damage that had been done to me. Dr. Malkin, a therapist, explains the true nature of narcissism — the good and bad, how unhealthy levels of narcissism can wreak havoc on your life, how to spot red flags that you might be dealing with a narcissist, and how to not only cope, but thrive when dealing with the narcissists in your life.

The Simple Living Guide When life feels overwhelming, this guide-and-workbook-in-one will help you gain clarity with your values, well-being, career, relationships and money.

The Good Morning Guide If your mornings are typically rushed, chaotic and stressful, I made this guide to help you start your day calm, sane and strong.

Tribe Of Mentors: Short Life Advice From The Best In The World by Timothy Ferriss Nothing beats having a mentor in your life who can personally guide you from day one. But not everyone does, and if (like me), you don’t, it doesn’t mean that you can’t learn from the best. Take what you need from the likes of Ray Dalio, Ben Stiller, Bear Grylls and more in this varied but comprehensive compilation of bite-sized advice on life, work and purpose from some of the best minds in the world.


If you’re too busy surviving, chances are, you’re not thriving. You’re feeling tired, unhealthy, unmotivated and just plain worn-out from life. I created my FREE Daily Self-Care Ritual Workbook just for busy folks like you who want to take back their health, peace of mind and happiness. Get your very own copy of the workbook HERE. No spam. Just helpful, good-for-you stuff. Pinky swear.

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