Would You Rather Win, or Not Lose?

Would you rather win, or not lose?

This question came to me one day. Since then, I have asked it often, especially during interviews. It is a simple question, but it consistently reveals how people think.

Most of the time, the answer is not lose.

There is no right or wrong answer. I do not draw final conclusions of someone by their answer. But it does tell me something about how they approach risk, pressure, and progress.

For me, the answer is clear.

I want to win.

Choosing not to lose often comes from a place of protection. It is about avoiding mistakes, preserving stability, and minimizing downside. In some moments, that mindset is necessary.

But this process should not be the default way to think or act.

When the goal is not to lose, we operate defensively. We react instead of plan. We measure success by what did not go wrong rather than what we intentionally achieved.

Winning is different.

Winning means defining what success looks like and then deliberately setting conditions to reach it. It is proactive. It is intentional. It is about creating margin rather than managing stress.

(Side Note: How winning is defined in a given situation plays a very large part of this. This warrants a completely new post.)

Too often, in both life and work, we are playing catch-up. We are trying to survive instead of positioning ourselves to thrive.

That is not how I want to operate.

I want to move forward with purpose. I want to set myself up for success. Whatever winning means in a given situation, I want to aim for it.

I want to win.