Sunday, 25 May 2025

Could Have Syndrome: Walking by Faith, Not by 20/20 Hindsight

Could Have Syndrome: Walking by Faith, Not by 20/20 Hindsight

We’ve talked about “Should Have Syndrome” before. The weight of regret that comes when we look back at what we didn’t do, didn’t say, didn’t become — and somehow, all of it still lingers. But lately, something else has come up in my spirit. Another kind of reflection. Not necessarily regret… not yet anyway. It's the idea of what we could have done.

“Could Have Syndrome” is more subtle than its louder cousin, “Should Have.” It’s not fueled by guilt — not at first. It starts with possibilities. Opportunities. Doors half-open that we walked past because we didn’t trust ourselves or God enough to go through them. It's the quiet haunting of what might have been — not because we did something wrong, but because we didn’t do anything at all.

And then comes that superpower we all have — the power of 20/20 hindsight. That sneaky gift of perfect vision, after the moment has passed. Wouldn’t it be something if we had that kind of vision before we needed it? Before the decision, before the step, before the pruning?

Now, I understand the theology of pruning. We need it. Jesus taught it plainly:

“I am the true vine, and my Father is the gardener. He cuts off every branch in me that bears no fruit... while every branch that does bear fruit he prunes so that it will be even more fruitful.” (John 15:1-2)

Pruning is growth. Pruning is preparation. Pruning is God’s way of saying: "I love you enough to take from you what you would never give up on your own."

But even so — can I be honest? Sometimes, it would be nice to avoid the pain. Sometimes, I don’t want to learn through loss. I want to learn through peace, through still waters and green pastures, not just valleys and broken limbs.

I find myself in one of those moments now. Maybe you’re here too.


A New Thing (Isaiah 43:19)

Right now, there’s a possibility — one that I didn’t expect to come knocking again. It’s still too early to say anything for certain, and I don’t want to get ahead of myself. But after over two years of being single, of assuming that kind of intimacy just wasn’t in the cards for me anymore, something… or someone… has entered the story.

And it’s good. Not perfect. Not fully formed. But good.
Refreshing, even.

But do you know what else it is?

Terrifying.

I didn’t realize how comfortable I had become in solitude. In my routine. In knowing the edges of my life and staying safely inside them. I know how to function alone. I know how to pour into my work, into ministry, into helping others. But to open myself again? To risk again? That’s something else entirely.

Because if I let my guard down — if I walk into this possibility — I’m inviting the full force of “Could Have Syndrome” to whisper in my ear every step of the way. “You could have just stayed safe. You could have avoided this. You could have protected your peace.”

Or maybe… just maybe… I’m being invited into something sacred.


The Wrestling Place

You see, I’m not just a romantic. I’m a data analyst in my own mind — especially when it comes to discerning if something is of God or not. I’ll weigh it. Measure it. Cross-reference it with Scripture. I’ll find affirmations and warnings. And if I’m honest, I can find enough data to support either narrative.

Isn’t that just like the enemy too?

The enemy doesn’t always shout lies. Sometimes he just suggests a few alternative truths, and then lets us stew in our confusion.

And confusion is fertile soil for “Could Have Syndrome.”
Because the enemy knows that hesitation can destroy more than action ever will.

So where does that leave me? Where does that leave you, if you’re also standing at a threshold and wondering if the thing in front of you is holy or harmful, sacred or a setup?

Sometimes, I think the answer isn’t found in the clarity of outcomes, but in the courage of obedience. Sometimes God isn’t asking us to be certain — He’s just asking us to walk.

“Your word is a lamp to my feet and a light to my path.” (Psalm 119:105)

It doesn’t say floodlight. It doesn’t say GPS. Just a lamp — for the next step.


Three Ways to Move Through Transitions With Godly Discernment

Here are three ways that have helped me, and may help you too, when you're facing transitions and don’t know if you're dealing with a God-opportunity or a counterfeit comfort:


1. Submit the Decision Daily, Not Just Once

Most of us were taught to ask God once and wait for a green or red light. But God is relational, not transactional. He wants a walk, not just a yes/no moment.

“In all your ways acknowledge Him, and He shall direct your paths.” (Proverbs 3:6)

That word all means… all. The early days of possibility. The quiet moments of insecurity. The nights where you feel more confused than comforted.

I’ve learned that when I continually submit something to God — when I bring it back to Him day after day — something begins to shift. Not always in the situation, but in me. Either my peace grows, or my discomfort does. Either way, clarity begins to rise from the conversation.

The key is to keep submitting. Not once. Not twice. Every day.


2. Seek Confirmation Through Community, Not Just Circumstance

When you’re walking through transition — especially the kind where your heart is involved — don’t isolate. Don't try to spiritualize every sign or feeling. Invite godly voices into the conversation.

“Plans fail for lack of counsel, but with many advisers they succeed.” (Proverbs 15:22)

There’s a humility required to open up your vulnerable thoughts to someone who knows Scripture and knows you. But when you do, something beautiful happens — the burden gets lighter. The perspective gets broader. And often, you’ll receive wisdom that you couldn’t see on your own because of the emotional fog.

Your heart will deceive you. But your wise and Spirit-filled community? That’s God's gift of course correction and confirmation.


3. Trust God With The Outcome, Not Just The Process

We often say “trust the process.” But with God, it's more than that. You have to trust the person behind the process. And you have to trust the outcome — especially when you don’t know what it is.

“For we live by faith, not by sight.” (2 Corinthians 5:7)

Faith isn’t about knowing how the story ends. It’s about believing that the One writing the story is good, even when you can’t see the ending.

I don’t know how this relationship will unfold. I don’t know if it’s the one. I don’t know if it’s from God or just a good thing I’m meant to learn from. But what I do know is that God hasn’t changed. His character is consistent. His love is constant. His promises are still true.

So whether this relationship grows into something lasting or ends with another pruning, I will trust the Gardener more than I fear the shears.


Final Thoughts: Walking Forward One Day at a Time

Maybe you're here, reading this, and you're in the middle of your own “could have” moment. Maybe it’s a relationship. A career move. A ministry call. Maybe you’re wondering if that door that opened is really God or just your desire playing dress-up.

Friend, let me say this: it’s okay to not know right now. It’s okay to be unsure. What matters most is not whether you make the perfect decision, but whether you walk closely with the One who perfects your path.

Don’t let “Could Have Syndrome” keep you paralyzed.
Don’t give the enemy the power to twist possibility into fear.

Take one step. Then another. Let your lamp light the way. Let God’s voice be louder than your doubts. Let peace — not pressure — be your compass.

And if it turns out that this wasn’t the right path? God will still be there. He redeems every “could have” and turns it into a testimony of grace. He wastes nothing.

As I walk into this next season — uncertain but hopeful — I’m choosing to believe that even if I don’t have 20/20 foresight, I serve a God who sees the end from the beginning (Isaiah 46:10). And that’s enough for me to say yes to today.


Scriptures for Continued Reflection:

  • Isaiah 43:18-19 — “See, I am doing a new thing…”
  • Romans 12:2 — “Do not conform… be transformed by the renewing of your mind…”
  • Ecclesiastes 3:1 — “There is a time for everything…”
  • Psalm 37:23-24 — “The Lord makes firm the steps of the one who delights in Him…”
  • 1 John 4:18 — “Perfect love casts out fear…”

Whether this is your season of planting, pruning, or possibility — walk gently, walk wisely, and walk with Him. One day at a time.

Let that be enough.

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