You Know What You’re Avoiding

You can’t read the label from inside the bottle.

That’s why blind spots exist. We’re so close to our own work, so immersed in the day-to-day decisions, that stepping back far enough to see clearly feels almost impossible. There’s always another task. Another fire. Another thing that feels urgent.

But here’s what I’ve noticed after hundreds of conversations with social entrepreneurs: beneath the surface, you usually know what you’re avoiding.

And deep down, you probably know what you need to do.

You’re just really good at finding something else to focus on first. Something easier. Something more comfortable. It’s the undefined stuff that gets pushed down the list. The thing where you’re not quite sure how to get to the outcome you want.

I see this pattern constantly. A founder will be walking me through their challenges, explaining why things need to be done a certain way to fit the way the world works. They’ll describe constraints as if they’re fixed walls. Funding structures that “have to” look a certain way. Timelines that “can’t” be shortened. Partnerships that “must” follow a particular path.

And I’m listening, but I’m also seeing the situation through a different lens. The way I experience the world opens up a different realm of possibilities. So I start asking questions from that place. Not to be contrarian, but because I genuinely don’t see the same walls they’re describing.

What if the funder would actually prefer a simpler ask? What if the timeline is based on an assumption no one has tested? What if the partnership could start smaller than you think?

Something shifts when those questions land. You can almost feel the room open up. The founder pauses. They sit with the question instead of defending their original framing. And in that pause, new possibilities start to surface.

This is what I mean by a mirror. Not someone who tells you what to do, but someone who reflects back what you can’t see on your own. Someone whose questions come from a different enough vantage point that they illuminate the edges of your blind spot.

I’ve been running goal-setting calls for a social impact mastermind, and the same dynamic plays out in a more structured way. We’ll start by talking through their project, the current state, the challenges they’re facing. Then I’ll ask a simple question: where do you want to be in three months?

From there, we list out all the pieces it would take to get there. Every milestone, every dependency, every uncertain step. Then we group those pieces by month, assigning rough deadlines. And throughout the process, I push for specificity. I call out where something feels vague or undefined. I ask what “launch” actually means, or what “reach out to partners” looks like in practice.

The shift is palpable. Before the call, they were just doing stuff. Busy, yes. Working hard, absolutely. But without a clear sense of whether all that effort was leading somewhere.

After the call, there’s a map. Not a perfect one, but a real one. And something about having that map changes the way they move through their work. The anxiety of uncertainty starts to lift. The path forward feels less like guessing and more like following.

Once you see the blind spot, it loses its power. You can finally ask the right questions. Do I need more information? More skills? More help? You can make a plan. You can move.

The answers are usually already inside you. The clarity is there, waiting. Sometimes you just need someone to reflect it back.

This is why I believe so deeply in the power of conversation, of community, of showing up regularly with people who see the world a little differently than you do. Not because they have answers you lack, but because their questions can unlock what you already know.

So I’ll leave you with the same question I often ask myself: who is your mirror? Who asks you the questions that make you pause? Who sees possibilities where you see walls?

If you don’t have someone like that yet, it might be the most important thing to find.