Cut Your Winnings

There comes a time when — no matter how much you’ve invested in something — you know it’s time to move on. 
The problem is that by the time you’ve reached that point, you’ve probably hung on way too long and your “investment” is really dragging you down. So to regain your momentum, flexibility, or sanity you let go of the investment. It’s called “cutting your losses.” And sometimes it is the absolute best thing to do.

But I believe more people are weighed down by their winnings than their losses.


Sometimes what holds you back is not a tragedy or a failure or a bad relationship. Sometimes what keeps you from your highest level of success is a moderate level of success.


It’s easy to get fooled by a few wins into thinking you’re all set because winning is often accompanied by comfort. And nothing can hold you captive more than comfort. Have you ever awakened on a Saturday morning and become instantly aware of how comfortable your bed is? AHA! So you know what I’m talking about!

Imagine, though, that you never get out of that bed, no matter how comfortable it may be. You’d miss out on the rest of life, never experiencing things that may be even more fun and exciting than 10,000 thread-count Egyptian cotton sheets.

We do the same thing with jobs, careers, relationships, and even our own personal development. We reach a point where we think, “Ok, this feels good. I like this.” And we stop right there, not realizing we may be only half-way up the mountain. We don’t realize that comfort may be holding us back from our highest potential.

I’m not talking about contentment. I believe in being happy where you are with what you have. I also believe you can be content in your life AND continue to learn, grow, and improve your knowledge, skills, and circumstances.

Here’s a good test. See if any of these statements ring true:
  • I’m comfortable in my career…but I know I could do better.
  • I’m comfortable in my friendships…but I know I could do better.
  • I’m comfortable in my marriage…but I know I could do better.
  • I’m comfortable in my relationship with my kids…but I know I could do better.
  • I’m comfortable in my knowledge…but I know I could do better.
  • I’m comfortable in my skills…but I know I could do better.
  • I’m comfortable in my income level…but I know I could do better.
  • I’m comfortable in my health…but I know I could do better.
In fact, you could use this format to test yourself in almost any area of your life. Insert anything you want in the blank:

I’m comfortable in my __________…but I know I could do better.

If the statement resonates with you after you hear it, you might need to make a change.

Here’s the tough part:

To move to a higher level, you have to cut your winnings. 

Sometimes this means letting go of your current situation, like moving on from your current job into a more fulfilling career. Other times it means stepping way out of your comfort zone, like attending an intimacy seminar with your spouse to strengthen your marriage. Heck, even reading the word “intimacy” is outside of the comfort zone of most men I know. 

When you finally cut your winnings — your current level of comfort — you will almost always gain something far greater. But only if you don’t let those comfy sheets hold you captive in your comfy bed.

So, what are the winnings that are holding you captive?





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