Sit Down. Be Humble.

This is gonna be one of those personal, vulnerable posts.

Humility is a weird thing. We admire people who are truly humble. But everywhere our culture tells us to be the opposite: be great, proud, and seek your best life possible.

But the truth is humility is so much harder than that. Doing humble things doesn’t make you humble, just like doing prideful things doesn’t make you proud.

It’s just something you are. Your actions come from it.

If you’re a person who believes that humility is a virtue to be sought after, you’ve probably found yourself in that beautiful catch-22. You have that thought: “Wow, I was just humble! I did it!”


Dang it.

In my own life, I’m finding that growing in humility is kind of like ogres.

I mean onions.

There’s a lot of layers.


Once I think I’ve reached my “maximum capacity” of humility, something happens to peel off a layer to expose a whole new level of pride I didn’t think I had. And it’s deeper, harder, and more stubborn to get rid of.

I think that’s the thing about having deep pride. You can’t see it unless someone shows you. And even then, you might not believe it.

To clarify, I’m not talking about healthy pride like having pride in your work or pride to be a part of something greater than yourself. I’m talking about that pride that doesn’t even need to whisper, “You have it all under control.” It doesn’t need to whisper, because you just obey it. It’s there.

If you read my newsletter, you probably read that I’m dropping this whole “what I’m building is a company” thing. After some time, failures, challenging words, and reflection, it’s the right thing to do. That’s not what I’m supposed to be doing.

Building, yes. Creating, yes. Working, yes.

But I’m not supposed to building or creating that.

To be honest, I ran out of money. Out of savings. Out of being able to pay all my bills. And panic set in a bit.

But it wasn’t the panic of “how am I going to survive?” kind of thing. I’m blessed to have lots of friends and family to help me when I’m down.

But the panic came with the peeling of the onion: seeing that I’m not the man I thought I was or projected to be.

I’ve always seen myself as smart, quick, resourceful, and able to excel at a lot. But reaching the point of “I ran out” does something to your pride.

It actually exposes the pride you already have, despite how humble you try to be.

I looked at my life and saw myself spinning my wheels.

“Why haven’t I been able to move forward? Why does it feel like I’m stuck every Summer? Why is there always some big announcement I need to make every Fall?”

Pride, my friends. Pride.

Too proud to really hustle. Too proud to do what it takes to really pursue what I’m meant to do. Too proud to think that I’d have to earn where I’m supposed to go rather than just wait for the opportunity.

“Kyle, you’re being hard on myself.”

There’s a difference between being hard on yourself and being real with yourself. It’s true I’m bad at separating the two.

But I’m really bad at receiving help, let alone asking for it. I’m really bad at doing what needs to be done, despite my hard work ethic. And I’m really bad at letting myself be ok with being imperfect, though it’s easy for me to share my issues with others.

And so I’m trying to be changed.

It’s hard, it hurts, and it’s taking longer than I’d like. But since pride comes before the fall, becoming humble has life and death implications.

So what does this look like practically?

I’m still going to be creating a lot, though I need to put some projects on hold for the immediate time being (the game, the scripts, the book). I’m focusing on setting myself up better to be able to do those things well. Which means a lot of random (and sometimes humbling) freelance work and pursuit to make my creations actually gain traction.

Already it feels like that traction is happening, which is exciting. But I’m fighting against coasting off of that little momentum. There’s work to be done.

So that’s my vague, inarticulate reflection on humility. Hopefully there’s something you can relate to there. Either way, in the morning, I’m making waffles.