Do you have something you’ve been almost doing for a while now, but you can’t seem to stop preparing long enough to just do the thing already?

The email is basically written.

The application is sitting there.

You know who you need to call.

You’ve researched the thing to death, talked about it, prayed about it, made the pros-and-cons list and probably asked at least three people what they think.

So what’s stopping you?

You’ve been getting ready to get ready for who knows how long.

You’re doing everything around the thing instead of the thing itself.

I know this because I can prepare with the best of them.

There was the video I kept almost posting. The conversation I kept almost having. Things I knew I wanted to do, but somehow there was always one more thing I could reasonably do first.

Maybe I should think about it overnight.

Maybe the wording needs another pass.

Maybe tomorrow would be better.

Maybe I should pray about it a little longer.

And sometimes those are completely legitimate reasons to wait.

That’s what makes this tricky.

There are times when slowing down is wisdom. There are decisions that deserve more information, more prayer, better timing or a good night’s sleep before we charge into them.

But I also know what it feels like when I’m no longer gathering information because I need it. I’m gathering it because gathering information lets me stay one step away from finding out what happens if I actually move.

That’s different.

And I think I used to misunderstand boldness because of this.

I thought bold people felt sure. They knew what they were doing. They trusted the decision. They walked into the room, posted the thing, had the conversation or took the opportunity with this internal sense of, Yep. This is exactly what I’m supposed to be doing.

Then I watched my son make his high school soccer team.

He wanted it. He worked for it. He earned the spot.

And then he got it.

You’d think that would be the moment the fear disappeared, right?

I made the team. Clearly I belong here.

Except that’s not always what happens when we finally get the thing we wanted.

Sometimes the door opens and fear walks through right behind us.

Now the questions change.

Am I actually good enough to be here?

What if everyone else is better than me?

What if I finally got the opportunity and now I can’t live up to it?

Watching him wrestle with that made me realize something I probably should have understood about myself a long time ago.

Fear doesn’t only show up when we’re deciding whether to take the step.

Sometimes it shows up after we take it.

Which means waiting until fear disappears before we move is a pretty unreliable plan.

That changed what boldness started to mean to me.

Less I’m sure this is going to work.

More I’m willing to find out.

And for me, faith belongs right in the middle of that.

Because obedience would be pretty easy if God always gave me certainty first.

If I knew exactly how the conversation would go, whether the opportunity would work, what people would think, how long something would take and whether I’d ultimately succeed?

Sure. Sign me up.

But that hasn’t been my experience of faith.

Sometimes I get enough clarity for the next step and absolutely none for the five after it.

Which is incredibly inconvenient for someone who would really prefer the entire itinerary.

But maybe that’s part of it.

Maybe faith isn’t knowing exactly where the step leads. Maybe sometimes it’s trusting God enough to take the step that’s actually in front of me without requiring Him to show me the whole staircase first.

And I’m learning there’s another question that helps me tell the difference between preparation and hiding:

What am I still waiting to know?

Sometimes there’s a real answer.

I need more information.

I need to talk to this person.

I need time to pray about it.

Okay. Then that’s what I need.

But sometimes, if I’m really paying attention, the answer is:

I’m waiting to know it’s going to work.

Ah.

There it is.

And no amount of preparation can give me that.

Maybe you have something like that sitting in front of you right now.

You don’t need to force yourself into a giant leap just to prove you’re brave. You don’t need to call fear faithlessness or hesitation weakness.

But maybe you do get honest about what you’re still waiting for.

Do you need something you can actually know before you move?

Or are you waiting for a guarantee no amount of preparation can give you?

Maybe the next step doesn’t require you to feel bold.

Maybe it just requires you to stop asking it to promise you what happens after you take it.

Because that’s usually the part we’re trying to solve before we move, isn’t it?

We want to know the email will be received well. That the application will lead somewhere. That the conversation won’t get awkward. That the thing we’ve been preparing for will actually work.

And sometimes there’s simply no amount of preparation that can answer those questions.

At some point, the only information left is on the other side of doing it.

Maybe that’s the part worth sitting with.

What are you still trying to know before you move—and is it something you can actually know from where you’re standing?

Want to keep going with this conversation?
🎧 Listen to Episode 13: Boldness in Faith and Leadership: Taking Action with Obedience and Purpose →