The Work and Rewards of Choosing Optimism

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Illustration by Jay Hilburn
Hero image
Illustration by Jay Hilburn

Living a life of optimism generates a lot of questions. Why are you so positive all the time? How do you stay so happy?

My outlook is often met with assumptions. That’s because you always see the good side. Or, I don’t want to burst your bubble. Sometimes it feels like a genuine desire to understand. Sometimes a compliment. Other times it feels like judgment.

As my kids get older and I become more advanced in my career, I find myself in more complex conversations about business and life and relationships. And, seemingly more tired as a result. Becoming more attuned to this pattern, it hit me: optimism is hard work. So I asked myself, if I’m an optimistic person, what suddenly changed?

I decided to step back and study this from the inside out. First step, inside. I wanted a raw assessment of myself.

Why am I optimistic? Was I born this way? Raised this way? Is optimism a personality trait? Am I avoiding feeling something else?

Next step, outside. I wanted to understand what others were saying and I found a juicy dialogue happening: Why optimism is a bad leadership trait. Optimists will rule the world. Realism is the sweet spot. Cynics keep us honest. Pessimism is the authentic pursuit of the truth.

What I discovered was incredibly rewarding. So now I invite you into the conversation — welcome to an optimist’s perspective.

It might not surprise you given the nature of this piece that I believe optimism is misunderstood as solely “glass half full.” The shift for me was discovering that optimism isn’t just a state of being, it’s action taken in the direction of a desired destination.

Optimism isn’t free from pain. It’s living your pain and choosing to focus only on good outcomes. I’ve experienced some of life’s most painful moments — death, divorce, cancer. All of them tested me to my very core and shattered my world as they unfolded. It was when I chose to believe there was a gift in the mess that I began to heal.

Optimism isn’t void of reality. It’s impacting change through the use of positive energy. I’m keenly aware of the world around me. Like most people, I think about the safety of my kids, and about war, human rights, a country divided, natural disasters, and financial stability. I think about the challenges of running a business, what it takes to truly transform, and the responsibilities of leadership.

When worry sneaks in, I channel my energy into solutions so can I contribute in more meaningful ways. Optimism is not blind to other perspectives. It is wearing other hats but knowing when to take them off. I am empathetic, at times to a fault. The ability to see through others’ eyes is key to fostering collaboration.

It’s a requirement to put on the pessimist hat to evaluate and poke at potential outcomes. Playing “the devil’s advocate” can be a valuable input. It’s staying there that’s limiting.

Choosing optimism is hard work. It’s a virtuous cycle of focused intent. It is choosing to see through, experience and live in the truth but channeling it into possibility. It can be fatiguing. But it’s worth it. The ripple effect of optimism is impactful. It heals our bodies and our minds and our hearts. It can be contagious. I’ve watched countless people around me take the high road in rough times. I’ve seen the most cynical become lighter. The most judgmental become open.

Pessimism is also a choice. And it’s contagious, too. It hurts your spirit, your body. It invites others in who are vulnerable to become closed. I’ve watched too many people with boundless possibility create darkness. People who blame others and stand back in judgment. People who live with a grudge. I’m sure this path is fatiguing, and it must be hard to live this way, also. I’ve just never seen the upside.

Each day brings all of us more unknowns — unexpected hard decisions, more surprises, more news, more life tests. But with every unknown, this is something I know to be true: we are in control of how we respond.

So now when I’m asked, why are you so positive? I confidently reply, because I choose to be.

Choose Optimism. Spread Possibility.

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