Money Mindset.

Playing to Win

Playing to Win

This week I had a serious EPIPHANY and I’m telling you it’s transforming my life and blowing my mind at the same time.

And yet, it’s so simple, and something probably every guy who’s ever watched sports has known for years, and yet, here I am, literally hearing and understanding this for the first time. (Yes, I’m aware I’m sometimes a few grapes short of a Cab Sav…)

It’s this:

Playing Not to Lose VS. Playing to Win

I’ve been playing not to lose my WHOLE LIFE!




Yes, I am. I am sitting in disbelief. Shaking my head – banging my head like – DUH?! Serious Lis, where have you been the last 3.8 decades?

So to be clear, this all comes courtesy of Jen Sincero, whose book, You are a Badass, is now a must-read for anyone I meet! (Hint: Read her books!)

I have always taken the calculated safe way in life AND I mean in ALL PARTS of my life this RINGS TRUE!

Are you maybe playing not to lose, versus playing to win? BIG DIFFERENCE!

Playing not to lose with money looks like this:

  • safe job or staying with job/career/business because it’s become the safe “normal” and you know what to expect
  • 2-4 weeks paid vacation
  • saving and investing in safe ways
  • living within your means because the fear of going “ALL IN” in life is too scary
  • taking courses you really don’t want to take, but know you “SHOULD”
  • making sure your resume is chock-full of fabulous degrees, designations, extracurricular activities so you will outshine anyone in a down job market, if in fact, you need to find a job (sound like someone you know? Ahem…)
  • making sure you got Grade 10 Piano, just in case all the above don’t pan out, at least you can teach piano for $50 an hour rendering you hopefully not homeless…..

I mean don’t get me wrong.  Playing not to lose is fine. It’s definitely a way of life, and to be honest, probably most people’s way of life.

Here’s the thing: Do you really want to spend your days playing not to lose?

I will tell you that playing not to lose is my norm. However, I occasionally dip my toe into the pool of playing to win and when I do….

  • my whole heart lights up
  • which lights up my face
  • which lights up virtually every person who crosses my path
  • which means I step out into fully being me and take chances
  • which sometimes doesn’t pan out
  • which makes me frustrated and I end up drowning in Ben & Jerry’s & Beer
  • which sometimes makes me shy back into playing not to lose (something I’m good at!)

Damn! How did I spiral back here so fast?? Stuck in playing not to lose.

Beautiful, I want you to play to win in life. Whatever that looks like for you.

For me, it means doing some scary-crazy-ass-shit! Like, stepping into the person I’ve been fighting so hard not to step into because it could possibly disrupt my perfect life I’ve created for myself.

AAAAnd that’s okay. I’m terrified. I’m terrified to go BIG with my message. I’m still stuck on baby steps, okay – if I’m truthful, I’m a freakin’ good crawler, and as you know, we need to crawl before we walk…..

But what are the options?

There will come a time when you are finally done with playing not to lose, and if playing to win means to lose it all, you’ll do it.

That’s when you jump.

That’s when you ruffle feathers.

That’s when you get half of your email list to unsubscribe, or piss off people you love (not intentionally).

On that note, you are probably doing something right if you are pissing people off every day, triggering them, making them uncomfortable, and just standing in your certainty! This means you are living a life with purpose. You can’t live a life with purpose and show up without turning someone off.


The person with the most certainty wins. All the time.  (You can re-tweet that!)

And then, here is when the magic comes to play with you. The right people show up in your life, the right people listen to your message, buy your products, dream clients, dream employees, dream team starts showing up because you are being real with you and playing to win.

This is when you get to leave your mark on the world.

So, are you going ’round this earth tip-toeing? Playing not to lose?

Or are you playing to win, leaving some serious stiletto marks on the field?