When “Challenging Times” became a movement

How one conference phrase turned into a 35,000-view conversation about what’s really holding nonprofits back.

IIt Started with a Phrase I Couldn’t Escape

I’ve lost count of how many times I’ve heard this phrase lately:

“These are challenging times for nonprofits.”

It opened at least three sessions at a recent conference. And it’s been in almost every conversation I’ve had since.

Every time I heard it, I found myself wondering:

When hasn’t this work been challenging?

The truth is, “challenging times” has become our sector’s comfort phrase. It makes us feel connected in our struggle — but it can also keep us stuck in it.

We talk about “the times” as if they’re something happening to us. But we can’t control the economy, the funding landscape, or political priorities. We can control how we lead through it:

✅ how we align our mission and vision,

✅ how we collaborate instead of compete,

✅ how we focus on what’s real instead of what’s right.

Maybe these aren’t “challenging” times. Maybe they’re revealing times — showing us what no longer fits, what’s no longer sustainable, and what needs to evolve.

That question — “What are these times trying to teach us?” — started something new.

From Reflection to Red Flags

That reflection turned into something I couldn’t have predicted. It led to Red Flag #1:

“Thriving, not starving, should be the new standard.” 👉 [Read it on LinkedIn]

It reached more than 35,000 people and sparked hundreds of comments from leaders who finally said out loud what they’d been carrying quietly.

They shared stories of burnout, pride in “doing more with less,” fear of funder retaliation, and deep frustration that the system keeps rewarding survival over sustainability.

And I realized — this wasn’t just about times. It was about the entire nonprofit ecosystem and the rules we’ve been told to follow without question.

What I Heard (In Your Words)

1️⃣ Exhaustion isn’t excellence.

“We wear ‘doing more with less’ like a badge of honor. But it’s not honor anymore — it’s erosion.”

2️⃣ Overhead isn’t waste — it’s the engine.

“Overhead isn’t the enemy. It’s the reason the work can even happen. We keep starving the structure we stand on.”

3️⃣ Fear has replaced feedback.

“We twist budgets to fit what funders expect. Then we’re shocked when the foundation cracks. We built it that way.”

4️⃣ The trust gap is widening.

“People aren’t rejecting generosity. They’re rejecting distance. They want to see the person, not the process.”

These reflections revealed something deeper: Most nonprofit leaders don’t start out thinking the system is broken — they believe they are.

Where This Shows Up in The Renegade Nonprofit

That belief is where we meet Maya in The Renegade Nonprofit.

She isn’t railing against a broken system. She’s quietly wondering if she should walk away. She’s exhausted, overwhelmed, and convinced she’s doing something wrong — that if she just worked harder, cared more, or organized better, things would finally fall into place.

In one early scene, after another long night leading up to the gala, Maya sits through a board meeting where everyone congratulates her for keeping overhead under 10%. The applause feels hollow.

“They couldn’t name one person on her team. Staff weren’t here to be seen. They were here to serve — quietly, efficiently, invisibly.”

She knows what it really cost — a burned-out team, a stalled project, and her own growing resentment.

Later, when a board member finally asks if the number is gross or net, Maya’s chest tightens. She’s dodged the truth before, but this time it hits differently. That’s the moment she begins to see what Elena will later help her name: This isn’t a personal failure — it’s a system failure that rewards exhaustion and calls it excellence.

It’s the same realization at the heart of Red Flag #1:

Thriving, not starving, should be the new standard.

Maya’s journey — and the coaching she resists before she’s ready to hear it — mirrors what so many leaders shared in the comments. Some lessons she uncovers on her own. Most she only faces when she can’t avoid them anymore.

Through her story, we see what it looks like to move from guilt to growth, from compliance to clarity, from surviving to leading differently.

This Week’s Renegade Practice

🧭 Practical Tip: At your next staff or board meeting, connect one behind-the-scenes investment to one visible outcome.

“Because we improved our intake process, clients now get served two days faster.” Make it visible. Once you do, people start seeing infrastructure as impact.

💭 Reflection Prompt: What story or fear keeps you from being transparent about what your work actually costs — in time, energy, or people? Naming it is the first step toward changing it.

What’s Next

Red Flag #2 drops Monday. We’ll explore what happens when “innovation” becomes another survival strategy — and how to reclaim it as a tool for thriving.

➡ If you missed the original Challenging Times reflection that started it all → link to post

➡ If you want to read Red Flag #1

➡ If you want to explore the philosophy behind it → The Renegade Nonprofit book

We don’t fix the system by shouting louder.We fix it by leading differently — together.

Until next time,

Tom