I had never really encountered this before.

Every project I had ever attempted was well within grasp of success. Hard work still, yes. But very little risk of having reached too far.

Every project I had taken on was something that with grit, persistence, and hard work, I could always get it over the finish line with success.

This was the first time I had encountered something that I couldn’t muscle my way through. I hadn’t really even considered that an unwinnable situation might exist. I could always get it done.

In 2022, I went through an extreme self-reflection process. This process is better known as “running for elected office.”

Have you tried it? You should try it.

As an entrepreneur whose whole business is based on myself being the product or service (In legal ways only, I assure you), I kind of thought I had the “Who am I now” question down. Running a campaign as a candidate took this to the extreme. Everything I said, did, posted or discussed was tethered quite literally to the core of who I am and the values I hold. And then the ask, “Will you pick me?”

It is a majorly tough pill to swallow to throw every authentic drop of blood, sweat and tears into something and have people very publicly say, “NAH.” Or even worse, be the target of name calling or lie spreading. I lost that race. And I had to ask myself yet again, “Who am I NOW?” and “Do I like who I am now?”

In retrospect, given the circumstances of that particular race at that particular moment, I can see now that I was never going to win that race. I had plenty of grit, persistence and hard work, but for the first time I couldn’t hard work my way to success. And that makes me think about friends and colleagues of mine that run for office knowing full well upfront that they are an unlikely winner (based on circumstances, not their skill). What an incredible feat that is… to run and give people a choice of candidates even though the odds are not on your side.

This leads back to the same question that I ask myself over and over now. “What is your definition of success?”

If we reexamine success not as winning, but having moved the needle trying, I think we would all take a lot more chances. More antes into an unwinnable game. Because who cares if you win when you can succeed at trying, showing up, or moving your part of the relay race forward.

Since learning this lesson, I am more discerning about outcomes. I am acutely aware that not winning is a possible or likely outcome. And it took until my forties to be willing to put myself in situations big enough that I don’t know if I can succeed. That seems to be the greatest win of all.

About the author:

Katie Rasoul is a keynote speaker, writer, leadership coach and Chief Awesome Officer for Team Awesome, a leadership coaching and culture advising firm. She is a TEDx speaker alumna, author of the best-selling book, Hidden Brilliance: A High-Achieving Introvert’s Guide to Self-Discovery, Leadership and Playing Big, and the children’s book, The Llama and the Balloon.

Learn more about Katie’s signature talks at www.katierasoul.com.