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Dream Career Toolkit: What Win/Win Really Means

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I remember my surprise the first time I heard the phrase win/win. I don’t remember where I was, but I do remember the feeling of shock I had at the idea that both participants could be winners at the same time.

I was raised in a very athletic household. Lots of sports. Lots of games. You and your team either won or lost. It was a zero sum game. If there was a winner, there had to be a loser. And this is how, subconsciously, I approached life. If I wasn’t winning, I was losing. I didn’t know any better.


So, as I wrapped my head around the win/win idea, I must tell you, it was difficult. What does it mean to have everyone winning? What does that look like?

If you have these questions, read on for some practical tools to bring this concept into your daily life…

To have everyone win, first you must understand what a win would be for them. This means you have to ask them. It can be as simple as, “What would make this experience a win for you?” And you have to listen to what they have to say, and really make sure you understand it.

The second thing that’s important is to be as committed to their win as you are to your own win. This can take some soul-searching, because if you’re anything like me, it goes against all you’ve been taught about winners and losers. But, once you take on really being as committed to everyone’s win as you are to your own, a big shift will take place. Your partners and team-mates will feel your commitment, they will start to match you, and you will set the bar for everyone’s commitment.

The third concept to take on is something that for me was really life-changing… Here it is: If everyone on my team isn’t winning, I’m not winning. Conversely, if I’m not winning, they aren’t winning.

I don’t know if this is as foreign to you as it was to me, so let me explain…

First, this doesn’t mean that you or someone on your team won’t have a bad day. Of course you will. It’s life be challenged and frustrated. But, overall, the question to keep in mind is, “What’s the win for me?” and “What’s the win for each person on my team?

This is what win/win really means. That you and everyone on your team are winning out of the experience. And that you are as committed to everyone winning as you are to your own win, because you know that when one person isn’t winning, the whole team suffers. In fact, no one can really win in that situation.

Take this concept on and apply it to your daily life, your relationships and your projects, and you’ll find that you no longer have to “convince” people to work with you. The days of “talking someone into it” or persuading them are gone. If something occurs as a win or an opportunity, they’ll want to do it!

Here’s to everyone winning in every aspect of life!

Shawn Tolleson is a career coach working with screenwriters and other entertainment industry professionals. She gives you the practical tools you need to accomplish your dream career. Check out blogs, videos, classes and more at!

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