Hope goes Ringside: Optimists vs Pessimists

I used to call myself an eternal optimist. It was practically part of my identity, right there in my bio line. I took pride in quotes like:

“A pessimist sees the difficulty in every opportunity; an optimist sees the opportunity in every difficulty.” - Winston Churchill

“Between the optimist and the pessimist, the difference is droll: the optimist sees the doughnut, the pessimist sees the hole.” – Oscar Wilde (attrib.)

I could be found guilty of Pollyanna-ing my way through more than one social situation—painting everyone’s cloud linings silver when they were dark grey and swollen with rain. I thought I was doing the world a favour: Chin up! We can fix it!

It made me an acquired taste. If you were in the middle of something huge, you might have looked down at your locked cellphone as I cheerfully passed with my silver paint bucket—just to avoid me painting your clouds mid-downpour.

The truth is, I’m an innovative thinker. My brain is wired to solve problems, and the world rewards that orientation. I’m a solutionist at heart. I genuinely believe there’s no problem too big for humanity to solve collectively. But that doesn’t mean there won’t be suffering, loss, or failure along the way. And I wasn’t prepared to look at that bit.

My optimism, it turns out, was an avoidant strategy. I was avoiding feeling grief and pain. Obvious now, a bit embarrassing in hindsight. What I lacked were the deeper life skills for these complex, uncertain times – the capacity to be present, to sit with what is, and to let myself feel it all without rushing to fix it.

Then I stumbled across hope.

Hope, I realised, might just be optimism’s wise old aunt. She doesn’t place bets on the solution. She simply lights the candle and cups her hand against the howling winds.

Hope knows that most situations in life are, at their core, neutral. What gives them charge– what gives them meaning – is the story we choose to tell about them. That story shapes our experience. It shapes what comes next.

Hope allows me to feel pain; in fact, the pain fuels the hope. It asks me to marinate in the grief, but to squeeze every drop of wisdom and learning from it so that as I face the future, I am informed, fully formed, and ready.

It didn’t start this way, but over time hope has become less like a mood and more like a stance – an orientation. A muscle I’ve trained. Rooted in reality and pain, guided by choice.

Hope isn’t pretending everything is fine. It’s choosing to respond with the knowledge that things could be better… but they might not. Or it might take longer than my lifetime. Optimism paints the silver lining. Hope learns to dance in the rain.

And I think there’s a role for pessimists, too.

“Both optimists and pessimists contribute to society. The optimist invents the airplane, the pessimist the parachute.” – George Bernard Shaw

But I do think Aotearoa has bred a veritable army of them. Social media has supercharged the dynamic – critique has become a form of social bonding. It can feel dangerous to float a new idea for positive change, because shooting it down has become a national sport.

In New Zealand where I am from, we love to talk about ourselves as innovators– number-8 wire and all that – but the tall poppy effect means we’re often half as likely to innovate as we are to criticise. I wonder if it is the same elsewhere? 

So here’s my take: Hope is the evolution of both optimism and pessimism. It’s not asking you to bet on the future, or even to agree that it will be better. It’s asking you to be brave enough to reveal what yearning burns in your heart – and to give it room to live, even amidst all the chaos and uncertainty.

That, to me, is the honest work of our time.

Will you light a candle of your hope with me today? This Hope Dispatch is intended to help put up a barrier against the winds of change so we can protect our flames together. Slowly, but surely our lights will illuminate the way forward. 

P.S. A quick confession: last week I did a little boo-boo. I posted about a Live Mural job, but the caption dropped off mid-flight – which made it sound like I single-handedly created the whole thing. In truth, the mural sprang from the imagination of my wildly talented business partner, muralist Kelly Spencer (aka @Kell Sunshine).

The caption should have read:

“This bright and spunky 4.2-metre live mural sprang from the imagination of my wildly talented business partner, muralist Kelly Spencer (aka @Kell Sunshine). We brought it to life over 2.5 days through The League of Live Illustrators – a creative collective co-owned by five of us who love turning ideas into living art.”

Moral of the story: captions matter, especially when you work with legends.