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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