Maybe

Maybe

There’s an old parable I find myself coming back to time and time again, especially when things get messy.

A farmer’s horse runs away. The neighbor says, “That’s terrible.” The farmer replies, “Maybe.”

The next day, the horse returns—bringing a wild horse with it. The neighbor says, “That’s wonderful!” The farmer shrugs, “Maybe.”

The farmer’s teenage child tries to ride the new horse, gets thrown, and breaks their leg. “That’s awful,” says the neighbor. “Maybe,” says the farmer.

Then war breaks out, and the army comes to conscript every able-bodied young adult. The child is spared because of their injury. The neighbor, wide-eyed, says, “What amazing luck!” The farmer says, “Maybe.”

I’ve told that story more times than I can count. Not just because I enjoy being cryptic, but because it’s the clearest way I know to talk about resilience—especially the kind that matters when things fall apart.

Because here’s the thing: we almost never know, in the moment, what’s GOOD and what’s BAD. We can’t see the whole story yet. And, in my experience, when we try to force certainty on things—trying to label, judge, or react—it makes us more brittle, not more prepared.

Resilience isn’t about having the answers. It’s about staying upright while the ground shifts beneath us. It’s about being like a tree:

  • Strong, upright and rooted

  • Flexible enough to tolerate high winds, pests, droughts and more

  • Always growing up, rooting down, and spreading our arms out to catch rain and sun alike

  • Staying in touch with our neighbors (yes, trees do this)

When Things Fail

In technology, when a system fails, ideally we don’t panic. We investigate. We ask why it failed, what signals we missed, what stress the system wasn’t built to handle. Then we improve the design—so it can handle more next time.

But when people and organizations reaching a breaking point—when our minds fracture, our missions stall, our organizations wobble—we often experience it as personal failure. Something shameful. Something to hide or patch over.

But what if we treated stress responses—personal or organizational—the same way good technology people treat system failures? What if we learned to treat these things NOT as some kind of shameful personal failure, but as design feedback?

Breaking is not the End

A few years ago, my internal systems overloaded. It wasn't all at once. But eventually, the things that had held me together couldn't hold me together anymore. At the time, I thought it was the worst thing that had ever happened to me. But that rupture—terrifying as it was—gave me the chance to rebuild myself and my systems. Years later, this rebuilding allowed me to show up for people I loved in ways I couldn't have imagined before. The very experiences I once saw as catastrophic had actually prepared me for what was to come.

And I’ve seen the same with organizations. Not always total breakdowns. Sometimes just moments of unsustainable pressure: a ransomware attack, a funding cliff, a team conflict that turns toxic. These aren’t signs that you’ve failed. They’re signs that you’ve reached the edge of what your current systems can support.

You don’t need to start over. But you can respond with intention. You can treat stress as feedback. 

Antifragile

The old aspiration was resilience: bounce back, return to normal, shake it off.

But for mission-driven organizations today—especially those in the nonprofit sector—that’s not enough.

  • The ground beneath us is shifting fast.

  • Cyber threats are getting more aggressive.

  • Data privacy is becoming an existential need for many.

  • AI is changing the rules of how we do work and what work we can do.

  • Powerful forces are openly targeting the nonprofit sector in a manner that is unprecedented in my lifetime. 

Resilience helps you recover. 

Antifragility helps you adapt and grow.

“Some things benefit from shocks; they thrive and grow when exposed to volatility, randomness, disorder, and stressors and love adventure , risk, and uncertainty. Yet, in spite of the ubiquity of the phenomenon, there is no word for the exact opposite of fragile. Let us call it antifragile. Antifragility is beyond resilience or robustness. The resilient resists shocks and stays the same; the antifragile gets better.”

-Nassim Taleb, Antifragile: Things That Gain from Disorder

An antifragile system doesn’t just survive stress—it uses it to evolve. Think of an immune system, a burned forest, a civil rights org that emerges from crisis with sharper strategy and deeper cohesion.

I’ve seen nonprofits bounce forward—not just back—after:

  • A data breach that forced stronger digital hygiene and smarter governance

  • A policy assault that galvanized coalition-building and clarified purpose

  • A staff implosion that led to better leadership practices and trust repair

These aren’t lucky accidents. They’re outcomes of teams choosing to learn from pain—rather than be satisfied with merely enduring pain.

Practices That Build Antifragile Organizations

There’s no software platform you can buy for antifragility. But there are practices that increase your capacity to grow through stress instead of snapping under it.

Make kindness policy. 

Not just a value. A structure. Build it into feedback processes. Train your staff in how to listen, how to de-escalate, how to extend generous interpretations. Psychological safety isn’t a luxury—it’s a security metric.

Teach mental health tools.

ACT, CBT and DBT aren’t just for therapy. They’re for organizations under pressure. Help people notice cognitive distortions. Give teams a language for distress. Train people to pause -- so they are less likely to panic.

Practice holding contradictions.

"I love this work, and it wears me out."

"I trust my team, and we disagree often."

"I’ve broken down before, and I’m stronger than I’ve ever been."

Resilience isn’t choosing sides—it’s holding space for all of it.

Design for the boom.

Don’t build systems for ideal conditions. Build them for volatility. Run tabletop exercises. Cross-train staff. Clarify values and response protocols before the next rupture hits. Assume stress will come, and let that shape your planning—not your panic.

Meeting the Moment

We’re in a time of massive uncertainty. That’s not a call to despair. It’s a challenge for us to work together, get stronger together, design better systems together—so we can move through time and space together with clarity, care, kindness and strength.

Things will strain. Sometimes they’ll snap. But some of what feels unbearable today may become the foundation for tomorrow’s (r)evolution.

It is OK to fear breaking. I did. I do. Things break. But they can grow too. And grow stronger. 

Here is my only ask. The next time you fall off your horse and are laying on the ground feeling broken, please take a breath, let someone help you to your feet, and say it with me:

“Maybe.”

Bahar Eratac

Senior Vice President, Accounting Services at Family Office Resource Group

4mo

Dear Josh. Great insights. Thank you for reminding us that growth often begins at the point of breaking—and that strength can be found in connection, vulnerability, and the simple act of saying 'maybe.'

Thank you, Josh. This is so timely (in general, and for me personally). I love the humor, and the way you use language that clarifies, rather than just repeating buzzwords. Kindness, generosity, and learning to hold contradiction seem especially important right now. (For instance, I think I might agree with RFK Jr. about sugar).

Ian Jelinek

Technology & Project Management for Small Business

5mo

Real-deal stuff, my good sir… no maybe about that.

Fred S.

GSE #256, Sr Security Architect

5mo

"maybe" is interesting, its another form of "good" from Jocko Willink in my mind, but maybe less aggressive-man-ish

Tanya Dashevsky

Creative Director: Biotech & Life Sciences | Branding & Launch Strategy | Pre-commercial, Early-Phase & Post-Launch

5mo

#sage philosophy from the sensei. Thank you Joshua.

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