If you want to become what Denis Waitley calls a total winner, the work begins with a single, decisive shift: change the conversation you have with yourself. Winning is not primarily a matter of talent, luck, or circumstance. It is the product of positive self-esteem — the quiet, durable conviction that you are worthy and capable — reinforced daily through positive self-talk. When you consistently tell yourself "yes, I can," you build the inner belief that fuels every worthwhile achievement. That is the answer, and everything that follows explains how to put it into practice.
The Most Important Opinion You Will Ever Hold
Long before the world weighs in on your worth, you have already rendered a verdict. Every waking moment, you are running an internal commentary — evaluating, encouraging, criticizing, or dismissing yourself. That inner dialogue shapes your actions far more than any external feedback ever will. As Denis Waitley frames it, the single most consequential relationship you have is the one with yourself:
The most important opinion I have is the one I hold of myself, and the most important conversation I can have, outside of prayer, is the one I have with myself every waking moment of my life. The most powerful words I can say to myself are, yes, I can. Success comes in cans, while failure comes in cannots. Every human being who has made a worthwhile contribution to the world has done so because of the deep-down feeling, yes, I can.
Notice the wordplay Waitley uses to make the point stick. Success "comes in cans" and failure "comes in cannots." It sounds almost too simple — but that is precisely why it matters. The language you rehearse in your own mind becomes the ceiling or the launchpad for what you attempt. People who accomplish meaningful things rarely start from certainty of outcome. They start from a settled, deep-down belief that they are capable of trying. That belief is a choice, and it is available to anyone willing to make it.
Self-Esteem: The Foundation of a Winning Life
If self-talk is the practice, self-esteem is the result — and Waitley considers it the most important quality a person can develop. Self-esteem is not arrogance or bravado. It is a felt sense of your own value that lives beneath the surface, independent of applause or achievement. It is the calm inner assurance that says you belong here and you are glad to be who you are. In this passage, Waitley describes exactly what that feeling sounds like from the inside:
This message is on the winning attitude of positive self-esteem and self-esteem is the single most important quality of a winning human being. It's that deep down inside the skin feeling of your own worth. You know, I like myself. I really do like myself. Given my parents, my physical looks, and my limitations, and my lifestyle, my background, I'm kind of glad I'm me. In fact, I'd rather be me than anyone else living at any other time in history. But I'm not conceited. In fact, conceit is God's gift to shallow people. This positive self-talk is the verbalization of inner value of a winner. And positive self-talk is the key to developing positive self-esteem. The winners in life have developed very strong beliefs of self-worth and self-confidence. They weren't necessarily born with these good feelings, but as with every other habit, they learn to like themselves through practice. Some individuals are born with much more going for them at the start.
The distinction he draws between self-esteem and conceit is worth pausing on. Conceit, in his memorable phrase, is a compensation for something missing. Genuine self-esteem needs no audience and no comparison. It simply accepts your parents, your appearance, your limitations, and your history, and concludes: I would rather be me than anyone else. That acceptance is not passive resignation — it is the stable base from which real growth becomes possible.
Why This Belief Is a Skill, Not a Birthright
One of the most liberating ideas in Waitley's message is that winners are not simply born feeling good about themselves. Yes, some people begin with advantages — supportive families, natural gifts, early encouragement. But the inner sense of worth that sustains a winning life is learned. Like any habit, it is built through repetition. If you did not receive that foundation growing up, you are not disqualified. You are simply someone who gets to build it now, deliberately, one thought at a time.
Equal Rights to Believe You Deserve the Best
Waitley is careful not to pretend the starting line is even. We are not handed identical physical or mental gifts, and it would be dishonest to claim otherwise. What we are handed, in his view, is an equal right to the excitement of believing we deserve the best we can earn and contribute. That is the great equalizer. Here he lays out both the challenge and the invitation:
Although we are not born with equal physical and mental gifts, we are born with equal rights to feel the excitement and joy of believing we deserve the very best we can work for and give to life. Self-confidence is believing in my dream when that's all I have to hang on to. I like myself, and I'd rather be me than anyone else. This is the self-talk of a winner. We learn to like ourselves through practice. Growing up, many of us were cultivated like weeds. We played inferior roles to the adults and to the TV and motion picture and sports heroes around us, and we were often reminded of our shortcomings. But you and I are on the high road to achievement and excellence from now on. We've learned the keys to inner winner self-esteem.
The image of being "cultivated like weeds" captures something many people recognize. Too often we grow up comparing ourselves to polished heroes on screens and playing fields, absorbing reminders of where we fall short rather than where we could rise. That conditioning is real, but it is not permanent. The moment you decide to take the high road toward excellence, you begin overwriting those old messages with new ones. And you do it, as Waitley insists, through practice.
Putting the Psychology of Winning to Work
Understanding these principles is one thing; living them is another. The good news is that self-talk and self-esteem respond to consistent, small actions. Here are practical ways to translate Waitley's insight into daily behavior:
- Audit your inner conversation. For one day, simply notice how you speak to yourself. Are you narrating with "cans" or "cannots"? Awareness is the first step to change.
- Rehearse "yes, I can" before you feel ready. Confidence follows action more often than it precedes it. Speak the affirming words first, then let the behavior catch up.
- Practice liking yourself on purpose. Since self-esteem is a learned habit, treat it like one. Acknowledge your effort, forgive your missteps, and choose acceptance of the person you already are.
- Refuse the comparison trap. Measuring yourself against heroes and highlight reels only feeds the old "weed" conditioning. Compete with who you were yesterday instead.
- Believe in the dream when the dream is all you have. There will be seasons when belief is your only evidence. Waitley considers that the very definition of self-confidence — and it is enough to keep moving forward.
The Winner You Are Becoming
The heart of Denis Waitley's psychology of winning is refreshingly democratic. You do not need to have started with every advantage. You do not need permission from anyone to feel worthy. What you need is the willingness to take responsibility for the words you say to yourself and to practice self-worth until it becomes second nature. That is how ordinary people build extraordinary lives — not through a single dramatic breakthrough, but through the steady accumulation of "yes, I can" moments.
Start today with the one conversation that determines all the others. Speak to yourself the way a coach speaks to an athlete they believe in. Choose to be glad you are you. And keep practicing, because the inner winner is not a person you are waiting to become — it is a person you are building, one thought at a time.