Trying Again After You Thought You Were Done

This past weekend, my family and I flew into Houston, Texas to celebrate my wife’s brother’s surprise 60th birthday. It was beautiful. I got to see friends and family I haven’t seen in a long time, some faces I didn’t realize I’d missed as much as I did until they were right in front of me. Laughter, stories, memories folding into each other. One of those moments that quietly reminds you that life is bigger than whatever season you’ve been stuck in. Now, let me be clear about one thing:

I hate flying.

Hate it.

Like B.A. Baracus from The A-Team hate it. (Yes, I've reached Unc status) Flying messes with my anxiety. Every time. But over the years, I’ve learned one thing that helps, writing. When I write, I take that fear and channel it. I get hyper-focused. I put words where my worry wants to live. So somewhere between takeoff and turbulence, I started writing. And this… is what followed.

Friday, as we were leaving for the airport, someone reached out to me. They told me they had a dream about me, a dream that directly answered a question I had asked God during my quiet time less than three hours earlier. I hadn’t said the question out loud. Not to anyone. Not even my wife. There was no way they could have known. It was specific. Clear. And it came at a moment when I desperately needed confirmation.

Fast forward to Monday, back in Chicago: I set up a lunch as a simple act of appreciation for that person. Nothing more. Just a way of saying, “I received what you shared, and I want to honor it.” That was the plan. One person. But when he arrived, there was a second man there, someone I wasn’t expecting. Two men. One I knew. One I didn’t. No agenda. No explanations. Just presence. Just encouragement. Just God showing up quietly, but undeniably. And it stirred something I thought I had buried. For those of you who know me, almost four years ago I attempted to start a church. If I’m being honest, and I owe myself that honesty now, it didn’t start from the purest place. Somewhere underneath the vision was a quieter, uglier motivation: “I’ll show them.” And the Holy Spirit checked me on it. So I shut it down and quit. At the time, I was coming out of a deep place of rejection. I was desperately trying to find myself. Spiritually, I was having an identity crisis. I was trying to build something before I truly understood who I was.

For the past four years, I’ve been “finding myself.” Or at least trying to. What I didn’t realize then is how easy it is to deny who you really are when you can’t reconcile yourself with what you’ve been through. When your failures feel louder than your calling. When your wounds distort your reflection.

I kept looking for the big moment, the comeback, the confirmation, the dramatic turnaround. But what I missed was this: the life I’ve already lived, the failures and the breakthroughs, those are not interruptions to the story. They are the story. They’re the very things that shaped me.

Recently, I received encouragement that hit differently. Not hype or flattery. Just truth. And it unlocked something I hadn’t understood before: confidence doesn’t come from success the way we think it does. It comes from well, failure. From surviving it. And learning who you are when things don’t work. From discovering that you’re still standing even when validation never came. I learned the hard way that validation doesn’t come from “the many,” even though many of us were taught that it would. Words like honor, loyalty, and sacrifice, once values I held tightly, have become trigger words for me. Not because they aren’t good, but because I watched them be used without truth attached.

Still, I’m grateful for something I’ve heard the old folks say my whole life:

He may not come when you want Him to, but He’s always right on time. That saying used to feel like a cliché. Now it feels like a lifeline.

A little while back, my wife joined an over-40 double Dutch group. And I remember how frustrated she was at first. She had lost her rhythm. Her endurance wasn’t what it used to be. Her timing was off, but what she never lost was her passion, her desire. She kept showing up, jumping, and laughing at herself. Fast forward to now, three logo’d tees, 2 jogging suits, a weighted hoola hoop and a mini fan later, she’s officially part of the team. Watching her reminded me of something I forgot about myself.

As I reflected on that unexpected lunch, on those two men meeting me exactly where I was, it hit me: out of obedience, God met me in a desolate and dry place and handed me a glass of water I didn’t even realize I was desperate for. And I remembered, I never forgot how to jump rope.

I just needed someone to turn for me. No one turns and jumps at the same time. Except a fighter. And even a fighter needs someone to spar with, a coach, and an opponent. Maybe you used to jump rope.

Or sing. Or teach. Or write. Or pray. Or date. Or lead. And you convinced yourself you forgot how. But maybe you haven’t forgotten anything at all. Maybe you’ve just been trying to do it alone. We weren’t meant to self-start everything. I don't think we were designed to always be the jumper and the turner. Sometimes God sends people, not to push us, but to steady the rope long enough for us to find our rhythm again.

If you’re reading this and you’re tired, if you already quit in your heart, hear this from someone who actually gave up:

Don’t.

Or at least… don’t stay there. Trying again doesn’t mean you failed before. It means you survived long enough to get another chance. And maybe this time, you won’t do it alone.

Grace is still here. Purpose didn’t leave. And the rope is already turning. Jump when you’re ready. (Mongo one, pop up 2, all around 3, criss-criss 4, 1 leg 5....)