Successful Losers and Failing Winners

Would You Rather Be A Successful Loser or a Failing Winner?

Are Those My Only Options?

No, and here's a story that will help you look at success, failure, winning and losing in a different way.

I had set a goal with my kids back in May. For me, the goal had several purposes. I wanted the kids, upon their return to school in August, to be able to say that they had written and published a children's book on their summer vacation. In meeting that objective, I wanted to give Madeleine, 13, a chance to share her artistic talent with the world and I thought it would be a great way for Evan, who says his favorite part of school is writing, to experience the iterative process of writing something for publication.

The goal was to complete and publish the book by the first day of school. We made progress. We created a great story line, Evan has crafted a very nice draft, and Madeleine has drawn some great illustrations, but we didn't make it. 

Yesterday, I called a team meeting to give everyone a chance to assess the situation. I asked, "What was our goal? What was complete supposed to look like?"

Apparently, we didn't go a good enough job of defining that because we all provided different answers. All were pretty close, but definitely not the same. After we got aligned (again?), I knew we needed clear something else up- why this project is important to each of us?

The Assessment

"Did we fail to meet our goal?"

"Yes," Madeleine looked down at the table.

"Yes," Evan did the same. I could tell they both dreaded what they thought was coming next: a lecture on doing what you "should" do.

"I agree. Now, let me ask you this, are you satisfied with failing?"

Madeleine replied right away, "Nope."

"Good. I'm glad to hear that. Evan?"

He shrugged his shoulders. 

Curious, I asked him, "What does that mean? Are you satisfied with failing, or not?"

He looked up, "Sort of." 

I could tell he wanted to say something but wasn't sure how I'd react. 

"It's okay, Evan, I want to understand what you're trying to say. I need you to explain it for me.

"Well...sometimes...I want to lose."

"Hmmmm. What do you mean by that?"

"Sometimes, I'm going up against someone who isn't as good as me and I don't want them to feel like they always have to lose, so I lose the game."

This conversation was a great time to explain the difference between "successful losers" and "failing winners".

What Is The Success We Really Want?

You see, we have this tendency in our culture to simplify things and we often inappropriately categorize success with winning and failure with losing. The truth is, they're not the same and while I felt a sense of pride and satisfaction with Evan for wanting to give compassion to others, I knew his point needed clarification.

If you've never read any of my stuff before, it's important that you understand the real nature of success. You see, success is getting what you want. But, I'm not satisfied with that definition and neither should you be. The problem is, we can't always get what we want and my point is the results we reap actually don't make us winners or losers.

Winning and losing is about competition, a situation where two parties vie for resources, influence, power, status, or a ranking. 

My dissatisfaction with the definition of success compelled me to expand on it (notice, I did not try to change it!) so that as a very competitive person (as former U.S. Army Rangers tend to be), I could learn how to fail without believing I was also a loser. So, I determined that I wasn't going to spend my life trying to be a successful winner, what I wanted was values-driven success. Values-driven success is getting what you want and being the person you want to be. Here's the catch, you can't get what you really want if you are not first the person you want to be. The truth really is that simple!

The Difference Between Success and Winning

I recognized in Evan's answer an incomplete understanding of the difference between values-driven success and winning.

In the scenario he gave, Evan said he sometimes wants to give someone else a win. In other words, he wants to help them. 

I explained this, "In the case where you're helping someone else at a personal cost, you're not failing to get what you really want. You're actually being a successful loser, a state of being that does not give you a win but more importantly also does not prevent you from believing you can win. That's because you're intentionally doing something that will make you satisfied with yourself. In other words, you say you want to give the other player a win and then you do it. You meet your goal despite the fact that the results indicate they've won and you've lost. In the meantime, you've built trust and strengthened the connection in the relationship."

Evan nodded, I continued, "Now, that scenario is much different than this one where we have not done what it takes to meet our goal. In our case, we did not do what we said we'd do. We failed to get the results we wanted and that was because of the effort we gave, it's different than competing against others with everything we have and losing. We may not always win, but we can always be successful. We didn't lose the opportunity to celebrate meeting our goal because we had competitors who were better than us, we lost because we failed. Get it?"

He smiled and said he did.

"So Evan, I'll ask again, are you satisfied with failing?"

"No."

 "Great! So, now let's figure out what we need to do to complete our goal! I want us to be successful winners! You have drafted a great story and Madeleine has created some awesome illustrations, so far. Now, we need to finish what we started!"

I looked around the table. Madeleine smiled. Julie Smiled. Evan smiled. I smiled. Incredible! I was amazed at how focused and productive we were in that team meeting. 

How to Know When You're a Successful Loser or a Failing Winner

...And, What To Do About It

Focus on a specific situational context and use this matrix to guide you (open the .pdf so it's easier to read).

The discerning reader will take note that there is no easy path through the matrix.

This line of thinking, where finding values-driven success in the long-run is a higher priority than short-term results, isn't contrary to what we've been taught or what our culture encourages (in word, if not indeed). It's easy to understand but difficult to practice because our self-serving desire to get what we want, to win, often overpowers conviction. And, sometimes what we think we want isn't really.

I hope this article has helped you rethink the concepts of success and failure, winning and losing and how you allow them to affect your thinking and decision-making.

If you, like every client I've helped so far, have only a "general idea" of what you value at your very core, it isn't enough! Generally knowing who you want to be as you go about trying to get what you want is a sure path to becoming confounded and stuck, even if you're winning right now...even if you've always been a winner. Things change. Think about it.

Are You Sometimes a Successful Loser? A Failing Winner?

Do you know exactly what your core values are and how you define them? Do you know how to identify and define your core values? Do you think conflict, distraction, and stress in relationships come from inconsistent definition and application of values to decisions and actions?

Do you have a story that illustrates a time when you were a successful loser? A failing winner? (I do, my book is full of them and I can tell you nothing has been more satisfying than finding the courage to share them with the world so I can help people make positive changes in their personal and professional lives with confidence and conviction)

Why not share your story or your insights on this article? I'd love to read about it as well as your insightful responses to these questions in the comment section, below!

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ABOUT THE AUTHOR: Tom Eakin is the author of Finding Success and the Success Engineer at BoomLife. LEARN MORE ABOUT TOM...

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