What I Learned This Week: Why I’m Learning to Chase the Impossible

The What If Journal: Reflections from a leader in progress

Lately, as I’ve been doing more executive coaching, I’ve noticed a pattern that keeps showing up. Most of the leaders I sit with are capable, thoughtful, and disciplined. They work hard. They set goals. And more often than not, they actually achieve them.

And that’s a good thing. There’s something deeply satisfying about setting a goal and reaching it. It builds confidence. It reinforces momentum. It reminds you that your effort matters.

But the more I listen, the more I’m realizing that many leaders are quietly sandbagging themselves. Not intentionally. Not out of laziness. They’re just aiming for what they know is possible. They’re running after goals that feel safe, realistic, and attainable.

So they hit them.

And then they set another one just like it.

And over time, they stay very successful… and very small.

The Leadership Reflection

In one recent coaching conversation, I finally named what I was seeing. I challenged a leader to stop aiming for what felt reasonable and start aiming for what felt impossible. I told him something I’ve been learning myself: I’d rather achieve 80% of an impossible goal than 100% of an attainable one.

Why? Because impossible goals force you to grow.

When you chase something you already know how to accomplish, you mostly just repeat what you’ve done before. You refine it. You polish it. You get a little more efficient. But you don’t fundamentally change.

When you chase something that feels out of reach, everything has to stretch. Your thinking. Your skills. Your habits. Your courage. Your faith. You have to become someone new in order to pursue it.

That’s where real formation happens.

I once heard Jason Jaggard say it this way: when we dream impossible dreams today, we wake up years down the road and realize that what once felt impossible is now just a normal Tuesday. It’s not because the dream shrank. It’s because we grew.

And that line has stayed with me.

It makes me wonder how often I settle for goals that fit neatly inside my current capacity. How often I aim for things I know I can handle instead of things that would require me to become more than I am right now.

Safe goals feel responsible. But they rarely transform us.

Impossible goals feel risky. But they shape us into better leaders, better spouses, better parents, and better followers of Jesus.

They invite us into dependence, courage, and creativity in ways comfort never will.

The What If

What if, instead of settling for what feels achievable, you dared to run after something that feels impossible — trusting that who you become in the process matters more than whether you fully arrive?