The Exhausting Cycle of Messing Up, Feeling Guilty, and Wondering Why You Still Haven’t Learned

Have you ever sat there staring at the ceiling thinking,
“Why do I keep making the same mistakes over and over again?”

Have you ever replayed conversations in your head like a Netflix crime documentary where somehow you are both the suspect and the detective?

Have you ever felt guilty not because you’re evil, but because you genuinely keep hurting people while trying not to?

Or maybe you’ve ever fired someone and then immediately wanted to throw up afterward because you started wondering if you were actually the problem.

Yeah. Welcome to my week.

Apparently I collect assistants the way divorced people collect “lessons.” And unfortunately, I am beginning to realize the common denominator in every situation is me. Which is honestly rude of reality to point out.

The truth is, I have a communication problem.

Not the cute quirky kind where people say, “OMG I’m such an introvert.” No. Mine is more like: “How have you survived adulthood this long without an instructional manual?”

I struggle to clearly communicate expectations. Then I get overwhelmed. Then the other person gets confused. Then stress builds. Then I panic internally while pretending everything is fine externally like a Christian woman holding a casserole dish during emotional collapse.

And eventually? Everything explodes.

The first assistant I had was my videographer for YouTube. In my mind, I thought I was paying per completed video. In his mind, he thought he was working within certain hourly limitations.

Did I clearly explain that beforehand?

Absolutely not.

Did he clearly explain his boundaries?

Also no.

So there we were. Two adults having completely different conversations while using the same English language.

By the time we finally communicated honestly, we realized we both wanted different things. So we had to part ways.

Normal people probably would’ve learned from this experience.

Not me.

No, apparently my brain said:
“Interesting. Let’s make this a pattern.”

The second assistant honestly could’ve survived if I had simply communicated one sentence:

“Hey, please stop digging for treasure in your nostril while filming me eat mozzarella sticks.”

That’s it. That was the sentence.

But instead of communicating like a mature adult, I internalized the horror.

I remember looking up while filming a food video and seeing him stick his finger in his nose and then wipe it all over his shirt right as I was about to bite into food.

At that moment, my soul left my body.

I didn’t even say anything. I just quietly posted a new job ad like the FBI entering witness protection.

To this day he probably has no idea why he got replaced.

And honestly? That’s on me.

Then came another assistant.

This one hurts because I genuinely think both of us felt misunderstood.

I communicated the schedule and consistency I needed. But from my perspective, work always felt secondary to whatever life situation came up that week.

Dog sitting.
Moving.
Trips.
Last-minute schedule changes.

And listen, life happens. I get it.

But when someone tells you a few hours before work that they suddenly can’t come in for over a week because they’re moving… your eye starts twitching like a stressed-out middle manager at Target.

The thing is, she believed she prioritized me.

I believed she prioritized herself.

So somewhere between her intentions and my expectations, communication completely broke down.

And maybe that’s what hurts the most about miscommunication. Sometimes nobody is evil. Nobody is malicious. Nobody wakes up thinking:
“You know what would be fun today? Emotional confusion.”

Sometimes two people are just living in completely different realities while smiling politely at each other.

Then came the latest assistant.

And honestly, by this point I should qualify for an honorary doctorate in Workplace Chaos.

I failed to clearly communicate how I wanted videos edited. My manager became frustrated because the final product didn’t match expectations, and I was told to let her go immediately.

Again.

Another person affected.

Another uncomfortable conversation.

Another wave of guilt sitting on my chest like an emotional sleep paralysis demon wearing business casual.

And here’s the part nobody talks about enough:

When you let someone go, you don’t just feel bad professionally. Sometimes you feel horrible personally because you know people need jobs. They have bills. Rent. Responsibilities. Families.

So now I’m sitting here wondering how many situations could’ve gone differently if I had just communicated better from the beginning.

The truth is, I beat myself up constantly.

And I know some people reading this understand that feeling deeply.

That feeling where every mistake suddenly becomes evidence that you’re failing at life.

Where your brain starts gathering old memories like a prosecutor building a court case against you.

“Oh remember THAT mistake?”
“And what about THIS one?”
“Don’t forget the embarrassing thing from 2017 at 2:14 PM.”

Thank you, brain. Very supportive.

Some days I genuinely feel like I hate myself for how slowly I grow.

Because growth sounds beautiful on Instagram.

But in real life?
Growth is humiliating.

Growth is realizing you’re the problem in situations you wanted to blame on everyone else.

Growth is recognizing patterns in yourself that are uncomfortable to face.

Growth is admitting:
“Maybe I’m not communicating clearly.”
“Maybe I avoid conflict.”
“Maybe I expect people to read my mind.”
“Maybe I shut down instead of speaking up.”

And honestly? That realization can make you feel incredibly stupid.

Especially when you keep repeating the same cycles.

That’s the exhausting part.

Not just making mistakes.

But wondering why you still haven’t changed after the hundredth lesson.

It’s like life keeps handing me the same test with slightly different hairstyles.

But I’m learning something important.

Self-hatred has never actually helped me grow.

Not once.

Hating myself hasn’t magically turned me into a better communicator.
Calling myself stupid hasn’t suddenly made me wiser.
Shaming myself hasn’t healed the patterns.

It’s only made me more anxious, more emotional, and more afraid to mess up again.

And ironically, when you’re terrified of messing up, you usually communicate even worse.

I think a lot of us secretly believe guilt is productive.

Like if we punish ourselves hard enough, maybe we’ll finally become perfect.

But perfection isn’t what changes people.
Awareness does.
Humility does.
Accountability does.
Practice does.

And unfortunately, growth is usually slower than our emotions would prefer.

I wish healing happened like Amazon Prime.

“Hello yes, I’d like overnight delivery on emotional maturity and communication skills.”

But real growth is messy.

Sometimes you learn the lesson five times before it sticks.

Sometimes you hurt people unintentionally while trying to become healthier.

Sometimes you outgrow patterns one painful situation at a time.

And sometimes the strongest thing you can do is stop pretending you already have it all together.

Because I don’t.

I’m still learning.
Still growing.
Still messing up.
Still trying.

And maybe that’s the lesson in all of this:

The goal isn’t becoming a flawless person.

The goal is becoming more honest, more self-aware, more accountable, and more willing to change.

Even slowly.

Especially slowly.

Because healing isn’t always dramatic.
Sometimes healing is simply recognizing the pattern before you repeat it again.

And maybe one day I’ll finally communicate clearly before hiring someone instead of emotionally speed-running another life lesson like a chaotic Christian Gordon Ramsay.

We can hope.

Remember you are my lovers, whether you love me or love to hate me you are still my lover!

Jesus loves you and so do I!