Are you playing to win…Hoping to win…or Playing not to loose?
- Douglas Watson

- Sep 13, 2025
- 3 min read
Updated: Sep 30, 2025
The answer depends on how you approach life. Do you have an abundance mentality or a scarcity mentality? Are you confident in your gifts? Are you even aware of your gifts? Are trying to go it alone or do you have a team?
In the book, Think and Grow Rich, Napoleon Hill shares thirteen common success principles he found through his research of more than 500 of the most successful people of his time. The first of the thirteen principles Hill calls the “starting point of all achievement.” The first success principle is DESIRE. He goes on to say that “wishing” will not help us achieve what we want from life. We need to have a strong enough “desire” so that nothing will stop us from achieving the goal.
So, when you’re playing to win, what does that look like? First of all, you must have clear picture of what you want, then you must have a strong enough desire to see it through to fruition.
Of course, you must have the gifts, talents and abilities to make it happen. If you don’t have them personally, you must be able to assimilate a team that does.
Next you must have a plan on how you’re going to achieve your goal…and if one plan doesn't work, you must be willing to try another one. When you're playing to win, you don’t leave anything to chance. You’re 100% all-in committed to creating and achieving your goal, no matter what.
So let me put that into context for you. In 1997, I got the idea to start a screen printing business. I was going through the check out line at the grocery store and I picked up an Entrepreneur magazine. I read an article and saw an advertisement about starting a screen printing business. The company would provide the equipment and training, including travel to Florida and teach you how to start screen printing business. So, at some point, I was all in. To make a long story, short…the next year I resigned from my job of 20 years and went full-time in the screen printing business….a year or so later I bought a promotional products franchise and went on to have a successful business.
Hoping to win starts from a place wanting to win, but you're not so sure how or if you can. People say that hope is not a strategy…that’s true….it’s not a strategy but it can be a starting point…but at some point early on, the hope must equate to a plan…some form of strategy to go from point A to point B to Point C and so on. You can’t rely on hope alone. You must create a plan that includes daily action that focuses on achieving the results that you want.
So what does that look like in real life?
In 2017, I experienced the Law of the Lid while working at a nonprofit organization. The Law of the Lid says you can’t out grow the lid of the leader above you. When we're “bumping” against the lid of the leader above us, it creates frustration. I made a decision to resign from the non profit I had been the executive director for 9 years.
I began doing leadership development training, using the borrowed ideas, beliefs and processes of others. I never really internalized myself. I was hoping to win. It wasn’t until I found my own voice, my own style that things turned around. That's when I began playing to win.
Playing not to loose is a different strategy, if you want to call it that. It’s typically based on lack or scarcity…the mindset that you lack the ability to achieve your desired goal. It’s staying in your comfort zone.
When you're playing not to loose, you don’t go “all out”. If you went all out, you might come up short, and that would look “embarrassing” and your ego couldn't take it. So rather than look embarrassing, we hold back. As Abraham Maslow states, “You will either step forward into growth or you will step back into safety.”
Here's the big question:
Are you willing to walk into the casino of life and put ALL of your chips on you?
If so, you have to push past the plateau of trying and just do it.
The only difference between the people who are successful and the people that are not is that the people who are successful take action and move forward despite their fears and failures.
The quote by Michael Jordan sums it up:
“I've missed more than 9000 shots in my career. I've lost almost 300 games. 26 times, I've been trusted to take the game winning shot and missed. I've failed over and over and over again in my life. And that is why I succeed.”
― Michael Jordan
Play To Win!
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