Why Good Organizations Stall Out

I’ve been thinking a lot lately about the gap between what we know we need to do and what we’re actually willing to do.

Not in theory. In practice. When the stakes are real and the consequences matter.

This year, I’ve had to make several decisions that I’ve been putting off, some of them for years. Decisions I knew were right but that felt impossible in the moment. Walking away from revenue that no longer aligned with where we’re headed. Restructuring relationships that were incongruent with our vision. Letting go of ways of working that served us well in the past but were actively blocking our future.

Each time, there was a moment where I had to choose: the comfort of what I knew, or the reality of what I needed.

It boils down to a simple truth: What got you here might just be exactly what’s holding you back.

The Pattern I Keep Seeing

Here’s what I’ve learned after 15 years working with hundreds of social impact organizations:

The biggest barrier to your next stage of growth isn’t lack of vision. It isn’t lack of funding. It isn’t even lack of capacity.

It’s attachment to what got you here.

The program that built your reputation but no longer serves your mission.

The funder who strings you along with just enough support to keep you dependent but never enough to let you scale.

The board member who helped you survive your startup phase but is now dragging your strategic thinking backward.

The team member you love, who’s been with you from the beginning, but who can no longer execute at the level your organization needs.

The “we’ve always done it this way” processes that made sense when you were scrappy but now slow you down.

The old partnerships, old structures, old identities that you’re clinging to — even though you know, deep down, they’re what’s keeping you stuck.

And the hardest part isn’t identifying what needs to change. You already know what needs to change. The hardest part is admitting you’ve been choosing comfort over growth. It’s deciding that you’re done pretending otherwise, and taking the very actions you’ve been putting off.

But sometimes it feels like you’re powerless to make that change. Or it feels like betrayal. Or it feels too risky, especially when things are already fragile.

So you don’t. And you stay stuck.

Why This Is Especially True in Social Impact

I’ve seen this pattern play out differently in the social impact space than anywhere else.

Mission-driven leaders have a unique form of stubbornness — one that’s rooted in deep values and genuine care. You’re not motivated by profit or fame or status. You’re motivated by impact. By justice. By the people and communities you serve.

And that’s beautiful. That’s why this work matters.

But it also means you’re more likely to:

• Keep underperforming programs running because shutting them down feels like abandoning people
• Accept toxic funding relationships because “any money is better than no money”
• Tolerate team dysfunction because firing someone feels like a moral failure
• Avoid hard conversations because you don’t want to be “that kind of leader”

You tell yourself you’re being loyal when you’re actually just avoiding a hard conversation. You call it resilience when it’s really just fear of change. You convince yourself that holding on is the same as showing up for your mission.

But it’s not.

What you’re actually doing is protecting your comfort at the expense of your impact.

And the sector suffers for it. Because when individual organizations can’t break through to their next stage, the entire ecosystem stays stuck.

What Actually Happens When You Let Go

I’ve watched organizations make the hard call. Let go of the beloved but underperforming program. Walk away from the funder who’s more trouble than they’re worth. Restructure the team even when it’s painful. Sunset the old brand identity that served them well but no longer represents where they’re going.

And here’s what happens:

Short-term discomfort. Long-term momentum.

There’s grief. There’s loss. There’s the nauseating feeling that you’re making a terrible mistake.

But then space opens up. New partnerships become possible. The team breathes. Strategy gets clearer. You stop spending 80% of your energy maintaining what’s no longer working and start spending it on building what comes next.

Because here’s the thing about transformation that nobody tells you:

It doesn’t happen in strategy decks or visioning retreats. It happens in the daily micro-decisions where you choose your future over your past.

Every conversation with that problem funder is a choice.
Every meeting with that underperforming team member is a choice.
Every hour you spend trying to force your new strategy into your old structures is a choice.

And those choices compound. They either move you one step closer to where you need to be, or one step further away.

The Real Cost of Inaction

When you refuse to let go of what’s no longer working, you’re not just holding your organization back. You’re holding yourself back, too.

As a leader. As a strategist. As someone who’s trying to build something meaningful in the world.

Because every time you accommodate dysfunction to preserve a relationship, you’re teaching yourself that your boundaries don’t matter.

Every time you absorb the cost of someone else’s inability to follow through, you’re reinforcing the belief that your capacity is infinite and your needs are secondary.

Every time you say yes when you really mean no, you’re chipping away at your ability to lead with clarity and conviction.

And eventually, you stop trusting yourself. You stop believing in yourself. You start to wonder if maybe the problem is you — maybe you’re just not good enough, not strategic enough, not resilient enough to make this work.

But that’s not true, unless you are unwilling the make the difficult, uncomfortable, but ultimately right choices.

And the only way to become that leader is to practice being that leader. Every single day. In every single decision.

This is the work. Not the creative work, not the strategic work — the identity work. The shedding of who you were so you can become who you need to be.

What Are You Holding On To?

If you’re reading this and feeling the weight of something you know you need to let go of, here’s what you should to ask yourself:

Is this thing I’m holding onto protecting my mission, or is it protecting my comfort?

And here’s the harder question:

What would it cost you to let go? And what will it cost you if you don’t?

Because here’s the truth: letting go always costs something. There’s loss, there’s grief, there’s uncertainty. That discomfort is real.

But staying stuck costs more.

It costs you momentum. It costs you clarity. It costs you the opportunity to build what you’re actually capable of building.

And it costs the people you’re trying to serve, because every year you give up on your vision is a year you’re not reaching your full potential.

What I’m Choosing

I’m choosing to trust that the discomfort of letting go is better than the comfort of staying stuck.

I’m choosing to believe that the organizations and leaders who are ready for this conversation will find their way to partnership. And the ones who aren’t? They’re not meant to be part of this chapter.

And that’s okay.

The real win is the integrity between your truth and your actions. It’s knowing what you stand for. It’s trusting yourself enough to make the hard call and live with the consequences.

And that’s the only way you ever actually grow.

So here’s my question for you:

What are you clinging to that’s blocking your next chapter?

Not the easy answer. The real one. The thing you know needs to change but you’ve been too afraid, too loyal, too exhausted to address.

Because I promise you: it’s not a mystery. You already know what it is.

The only question is whether you’re willing to let go.