Why Winners Rarely Feel Like Winners

“I always feel like I haven’t done anything. I always feel like I need to do more. That’s how you stay hungry.” - Serena Williams

Have you ever noticed how often driven people say they feel behind? Behind on projects. Behind on goals. Behind on where they thought they would be by now.

It is easy to interpret that feeling as a flaw, as a sign that you are failing to keep up. But what if it means the opposite? That tension you feel between where you are and where you want to be is not proof of weakness. It is evidence that you are built for more. Serena Williams, one of the greatest athletes in history, openly admitted she always felt like she hadn’t done enough. That is not a lack of confidence, it is the hunger that fueled her. The same hunger that fuels leaders, builders, and top performers in every field.

The most driven people rarely feel “caught up.” They live in a constant push forward, chasing growth, chasing better. They do not sit in satisfaction for very long, and they almost never describe themselves as “winning.” Instead, they feel the pressure. They feel the urgency. They feel the gap that exists between today and tomorrow. And that gap is where growth lives.

Think back to your own moments of greatest progress. Chances are, they happened when you were uncomfortable. When you felt stretched, or when you doubted whether you could make it. That was not weakness. It was the engine of your development, and the place where transformation begins.

Here is the tricky part: Being driven can sometimes make us blind to the costs of constant urgency. Growth happens in the tension, yes, but it cannot happen without recovery. Muscles grow after rest, not during the workout. The same is true for our careers, our leadership, and our lives.

Healthy growth requires both sides of the equation:

• The pressure that pushes us forward.
• The rest that allows us to grow.

Top performers often struggle with this balance. They can accept pressure, but they resist rest. They can chase urgency, but they ignore quiet. The result is that they push so hard they eventually stall.

So here is the mindset shift: Feeling behind can be a good sign—as long as it does not become your only fuel source. Use the tension as your spark, but combine it with rhythms of rest that allow you to keep moving forward.

• When you feel the pressure of the gap, remind yourself: This is not failure. This is forward motion.
• When you feel the pull toward more, embrace it: This is not dissatisfaction. This is growth.
• And when you feel worn down, give yourself permission: This is not weakness. This is wisdom.

Serena Williams never let the feeling of “I haven’t done enough” break her. She let it fuel her. But she also knew when to step back, when to heal, and when to prepare for the next climb. Winners rarely feel like winners. They feel hungry. They feel stretched. They live in the gap. And if you are feeling that way right now, good. It means you are still reaching.

P.S. If you want to explore this deeper, particularly the idea of shifting from measuring progress against an ideal (the “Gap”) toward measuring against where you started (the “Gain”)—check out The Gap and The Gain by Dan Sullivan and Dr. Benjamin Hardy.