Encouragement hurts.

Maybe you laughed when you read that. Or maybe you scratched your head and said, “Wha—?”

Because “hurt” doesn’t follow our definition of encouragement. Somehow we’ve come to believe that encouragement is to agree with someone. So we tell them they’ll be great at something when, in fact, they’re probably not cut out for the job. We feed their fantasies because that’s what we think they want.

We think we’re being encouraging.
We think we’re being a good friend.

But what we’re really doing is selling each other short.

I think that’s been the main problem in most of my friendships. I get tired of people who claim to be my friends telling me what I want to hear in the moment, only to find that their “supportive” claims are detrimental in the long run. Because they should have known that my gifts weren’t aligning with the shape of my dreams. And they should have been the ones clear-headed enough to see that he really wasn’t that into me.

en·cour·age

a : to inspire with courage, spirit, or hope : hearten
b : to attempt to persuade : urge

I always needed someone to encourage me by the standard of Mr. Merriam-Webster.

I needed the kind of friend who would try to persuade me. The one who would inspire me with the courage to find a new dream instead of letting me cling to that hope, that chance, that slight possibility that something may come of this.

I needed the kind of friend who would help me pack up and move on when my heart is still longing to linger in a place that was only meant for passing through. The kind of friend who would sit on my over-packed suitcase as she rips the zipper into place.

“Move on, Rebekah,” she would say. “It’s time to move on.”

She would be the kind of friend who would not only take me to the airport, but walk me to security and sit there and wait until she knew beyond a shadow of a doubt that I wouldn’t go charging back out those doors. Because I would keep walking if I knew she was waiting. I would keep walking and not turn around.

And I might get upset with her for a moment. I might tell her she isn’t helping when really she’s helping more than anyone else ever dared.

Because, while she didn’t tell me what I wanted to hear, she gave me what I needed. And I would always much prefer the friend who would give me what I need.

And, deep down, past the part of me that wants to stay here, I know that she’s right. The skies hold brighter things for me. There are uncharted lands that wait to be discovered. And maybe I’ll circle back to this place sometime in the future, but it wasn’t meant to hold me now. There’s no way it could hold me now.

So I’ll sit with my head pressed to the window, watching my dreams fade into clouds.

And, yes, it hurts right now, but it will be so much better in the long run.

In the long run I’ll be thankful for that painful encouragement that sets me free.