Joan Westenberg

August 10, 2025

I'm Exhausted By My Own Cynicism.

It started as self preservation. 

After enough disappointments, enough promises broken, enough grand plans that fizzled into nothing, I developed a knee-jerk cynicism that felt like wisdom. The ability to spot the flaws before anyone else. To see why things wouldn't work before they even launched. To be the voice of reason in rooms full of dreamers.

But somewhere along the way, that voice got too loud.

Lately, I've caught myself rolling my eyes at enthusiasm. I watch someone get excited about their new idea and my first instinct is to catalog the ways it will fail. Not maliciously - I tell myself I'm being helpful, realistic, saving them from future pain. But the truth is uglier than that. I've become addicted to being right about things going wrong.

Cynicism feels sophisticated. It makes me feel like I understand how the world really works while others are stuck in naive fantasies. There's a certain pride in predicting failure, in being the one who saw it coming when everyone else was caught off guard. 

I've built an identity around being unsurprised by disappointment.

But I'm tired of it. I'm tired of the weight of always expecting the worst. I'm tired of the way cynicism closes doors before I even know what's behind them. I'm tired of how it makes me a spectator to other folks' hope instead of actively participating in my own.

What if I'm wrong about being right all the time? What if my cynicism is laziness - a way to avoid the vulnerable work of believing in something that might not work out? It's much easier to be skeptical than to be invested. Much safer to predict failure than to risk disappointment.

The optimist in me used to see possibility everywhere. Yes, that led to some spectacular failures and embarrassing miscalculations. But it also led to the best things I've ever done, the most meaningful connections I've made, the work I'm most proud of. None of that happened because I was realistic about the odds.

I'm starting to think that cynicism isn't the opposite of naivety; it's just naivety in a different direction. The naive optimist believes everything will work out. The naive cynic believes nothing will. Both avoid the harder work of engaging with reality as it actually unfolds, messy and unpredictable and occasionally miraculous.

I want to get back to building things instead of just critiquing them. I want to be surprised by success instead of satisfied by failure. I want to care about the outcome more than I care about being right. Most of all, I want to remember what it feels like to hope for something without immediately calculating the probability of disappointment.

The world has enough people explaining why things won't work. What it needs are people willing to be wrong about the possibility that they might.

I'm ready to be naive again. 

Starting now.

About Joan Westenberg

I write about tech + humans.