Dave Bailey sitting in a warmly lit recording studio, wearing green headphones with a microphone in front of him.

I Tried to Become Myself. It Was Exhausting.

How a random Wednesday morning thought led me down a rabbit hole about authenticity, self-rejection, perfectionism, and the ridiculous things we do trying to become better versions of ourselves.

I’ve spent a good portion of my life being afraid of rejection.

At least, that’s what I’ve always believed.

But this morning, somewhere between sleeping and waking, an interesting thought crossed my mind.

What if the person who’s been rejecting me all these years… is me?

Now, that’s an uncomfortable thought.

Especially when you start looking at the evidence.

My parents never disowned me. My family never excommunicated me. God never struck me down with lightning.

Not that I’m suggesting He never considered it. We’ve had some conversations. 😂

But here I am. Still breathing. Still loved. Still surrounded by family.

And yet, I’ve carried around feelings of guilt, shame, and unworthiness for as long as I can remember.

Why?

I honestly don’t know.

But I started following that thought to see where it might lead.

And boy, did it lead somewhere unexpected.

The Impossible Standards I Created for Myself

Growing up, I developed certain ideas about what it meant to be a good person.

Some came from religious teachings about righteousness, obedience, and perfection.

Some came from my parents and how I interpreted their reactions to things I did or said.

Others came from people I respected, admired, or wanted to emulate.

And of course, I added plenty of my own ideas along the way.

Over time, I assembled this imaginary version of the person I thought I was supposed to be.

Someone disciplined, confident, successful, loving, patient, responsible, and generally excellent at being human.

A pretty impressive guy, actually.

There was just one problem.

I wasn’t him.

And every time I fell short of that imaginary standard, I didn’t simply acknowledge that I’d made a mistake or failed to live up to an expectation.

I judged myself.

Sometimes I even rejected myself.

There’s an important difference between guilt and shame.

Guilt says, “I did something wrong.”

Shame says, “There’s something wrong with me.”

Somewhere along the way, I may have confused the two.

Instead of evaluating my behavior, I began evaluating my worth.

And the standards weren’t necessarily imposed on me by anyone else.

In many cases, they were standards I’d created from my interpretation of what I believed other people expected.

Think about that for a second.

I wrote the rules.

I created the test.

I graded the exam.

And somehow, I STILL FAILED!

That’s a special kind of talent. 😂

What If I’ve Been Judging Myself All Along?

Another thought came to mind.

There’s a biblical passage about being judged by the same measure we use to judge others.

I’d always interpreted that as meaning that if I judged people harshly, other people would judge me harshly in return.

But what if there’s another personal application?

What if the standards I use to judge other people are also the standards I use to judge myself?

If I criticize someone for being lazy, what happens when I have an unproductive day?

If I judge someone for being impatient, what happens when I lose my temper?

If I believe successful people must be disciplined, what happens when I can’t maintain my own routines?

Perhaps I’ve spent years measuring myself against expectations that nobody could consistently live up to.

And perhaps, because I was already judging myself, I assumed other people would judge me the same way.

Which brings me to something I’ve been thinking about for a while.

Authenticity.

I Tried to Be My Authentic Self. Somehow, I Failed.

Everywhere you look, somebody’s telling you to be authentic.

“Just be yourself.”

“Find your true self.”

“Live in alignment with who you really are.”

Sounds wonderful, doesn’t it?

Except I started wondering what that actually means.

Because here’s what I realized.

We often create identities based on thoughts, ideals, characteristics, and feelings we admire.

We decide we’re disciplined people, confident people, successful people, loving people, or spiritual people.

And then we try to align our behavior with those identities.

But what happens when we don’t?

Suppose I identify as a disciplined person, but I skip my morning workout.

Am I suddenly not disciplined?

Suppose I identify as a loving person, but somebody cuts me off in traffic and I get angry.

Am I no longer loving?

Or suppose I decide that I’m an authentic person, but then I catch myself behaving in a way that doesn’t match my idea of authenticity.

Now I’m upset with myself for not being authentic.

But wait a minute.

If I’m genuinely upset about not being authentic, isn’t that how I authentically feel?

Which means I AM being authentic!

But then I get frustrated with myself for being frustrated about not being authentic.

And suddenly…

I’ve developed impostor syndrome about BEING MYSELF!

WHO AM I IMPERSONATING?!

ME?! 😂

There are billions of people on this planet, and somehow I’ve managed to fail the interview for the one position that nobody else can fill.

Being me.

I’m the applicant.

I’m the hiring manager.

I’m the entire HR department.

And I keep sending myself rejection letters!

“Dear David,

Thank you for your interest in being David.

Unfortunately, we’ve decided to move forward with a candidate whose qualifications more closely match our expectations.”

WHO DID YOU HIRE?!

There’s another Dave?!

I’d like to meet him. Apparently, he’s got his life together.

Maybe Authenticity Isn’t What I Thought It Was

Somewhere in the middle of laughing at the absurdity of that realization, something more meaningful emerged.

What if authenticity isn’t about trying to show other people who I really am?

What if it’s about no longer needing to hide who I am from myself?

That changes things.

Because maybe authenticity isn’t about perfectly aligning with an identity I’ve constructed in my mind.

Maybe it’s about acknowledging what’s actually happening without immediately turning it into a judgment about who I am.

I’m angry?

Okay. I’m angry.

I’m insecure?

Okay. I’m feeling insecure.

I’m disappointed that I wasn’t as productive as I wanted to be?

Okay. I’m disappointed.

I’m judging myself for being disappointed?

Well, would you look at that.

Apparently, that’s happening too.

None of those experiences necessarily defines who I am.

And none of them requires me to reject myself.

I can acknowledge a feeling without acting on it.

I can recognize a mistake without making it my identity.

I can aspire to become better without deciding that who I am today is unacceptable.

And maybe, just maybe, I don’t need to start another self-improvement program every time I discover something about myself that I don’t particularly like.

Speaking of self-improvement programs…

Oh, man.

We need to talk about those.

I Set One Goal. Somehow I Got 47 Habits.

I love setting goals.

Big goals. Exciting goals. Ambitious goals.

I wake up one morning and decide I’m going to make a million dollars.

Fantastic!

I’m motivated. I’m inspired. I’m ready to conquer the world.

But then I start thinking.

What kind of person makes a million dollars?

Well, obviously, a disciplined person.

So I need to wake up early.

Exercise.

Eat healthy.

Read.

Journal.

Meditate.

Plan my day.

Track my progress.

Review my goals.

And develop all the habits that a successful person is supposed to have.

But wait!

A million-dollar entrepreneur also needs a successful business.

So now I need a marketing strategy.

A content calendar.

A sales funnel.

A follow-up system.

A newsletter.

A YouTube channel.

A Facebook page.

An Instagram account.

And apparently, I need to be on TikTok.

Because nothing says “serious entrepreneur” like a 49-year-old man learning choreography in front of his phone.

I’m trying to build generational wealth.

WHY AM I LEARNING DANCE MOVES?!

But that’s okay.

Because I’m a systems guy.

I LOVE building systems.

So I create a system for marketing.

A system for producing content.

A system for generating leads.

A system for tracking habits.

A system for managing my time.

Then I realize I need another system to manage all those systems.

And another system to track whether I’m actually using the systems that are managing the other systems.

By Wednesday, I’ve got seventeen spreadsheets, four automation platforms, six unfinished websites, and absolutely no time left to make any money.

I haven’t built a business.

I’VE BUILT A SMALL GOVERNMENT!

And somehow, I’m both the overworked employee and the manager complaining that productivity is down.

The Hamster Wheel of Self-Improvement

Here’s the frustrating part.

Every one of those habits and systems probably started as a good idea.

Each one made sense when I created it.

But I kept adding things.

One goal became another goal.

One habit required another habit.

One strategy required another system.

Eventually, the whole thing became so complicated that just maintaining it felt like a full-time job.

And when I couldn’t keep up?

I stopped.

Not necessarily because I stopped caring about the original goal.

But because I couldn’t maintain the increasingly complicated lifestyle I’d built around achieving it.

Then I’d start feeling guilty.

I’d tell myself I wasn’t disciplined enough.

I’d coast for a while.

Eventually, I’d become frustrated enough to do something about it.

And I’d set another goal!

Which, naturally, required another system.

I’m not climbing the ladder of success.

I’m running on the hamster wheel of self-improvement.

But my hamster wheel has a dashboard.

And it has KPIs!

The irony is almost too ridiculous to ignore.

I started setting goals because I wanted freedom.

Financial freedom.

Time freedom.

The freedom to enjoy life, spend time with family, create things, and pursue whatever interests me.

But somewhere along the way, I built a lifestyle with so many responsibilities that I had less freedom than when I started.

Then I blamed myself for not being disciplined enough to maintain it.

Maybe I Don’t Need to Become a Different Person

This is where the two ideas started coming together.

Perhaps my relationship with goals isn’t all that different from my relationship with identity.

I create an ideal.

I imagine the kind of person who would achieve it.

I begin organizing my life around becoming that person.

And when I can’t consistently live up to that image, I become disappointed with myself.

But what if the problem isn’t always my lack of discipline?

What if sometimes I’ve simply created a system that demands more time and energy than I’m willing to spend maintaining it?

What if I don’t need another productivity system to force myself to do more things?

What if I need a system that makes fewer things necessary?

I’ve realized that I genuinely enjoy inventing, designing, and building things.

I love figuring out how something works.

I enjoy creating a system, testing it, improving it, and seeing whether it produces results.

But operating that same system every single day?

That’s a different story.

And perhaps instead of trying to transform myself into someone who loves repetitive daily operations, I can build around the things I naturally enjoy while finding ways to simplify or delegate the rest.

That doesn’t mean avoiding responsibility or expecting results without effort.

It simply means recognizing that there may be better ways to pursue my goals than constantly trying to become an imaginary version of myself.

And that, strangely enough, brings me right back to authenticity.

I Think I’m Going to Stop Trying So Hard to Be Myself

I’m not suggesting I’ve figured all this out.

These are simply thoughts that began wandering around my mind one Wednesday morning.

I haven’t solved self-acceptance.

I haven’t eliminated my internal critic.

I haven’t suddenly become perfectly disciplined.

And I’m probably going to create another spreadsheet by Friday.

Let’s not get carried away. 😂

But I am beginning to question the idea that I need to become someone else before I can accept myself.

Maybe I can have goals without turning them into identities.

Maybe I can admire certain qualities without demanding that I demonstrate them perfectly.

Maybe I can make mistakes without judging my entire worth.

Maybe I can develop habits without interpreting every missed day as a personal failure.

And perhaps I can stop treating every thought, feeling, or expectation as a definition of who I’m supposed to be.

I can still want to grow.

I can still strive to improve.

I can still pursue ambitious goals.

But perhaps I can do those things without rejecting the person who’s doing the growing.

Because the more I think about it, the more ridiculous the whole thing seems.

I’ve spent years trying to become someone I could finally accept.

But maybe I had it backward.

Maybe I was never failing to be myself.

Maybe I was just failing to be someone I imagined.

And for the first time, I’m beginning to wonder whether that’s a failure at all.


Have you ever found yourself trying so hard to become a better version of yourself that you started rejecting the person you already are? I’d love to hear your thoughts.

This reflection began as a few handwritten notes on October 21, 2026, turned into a conversation, then a humorous video, and eventually this article. Apparently, following random thoughts down rabbit holes is becoming a hobby.

One Comment

  1. So apparently, I’ve spent years trying to become a better version of myself… while rejecting the version of myself who’s actually doing all the work. 😂

    And the funniest part? I even managed to judge myself for not being authentic enough!

    WHO AM I IMPERSONATING?! ME?! 🤣

    But seriously, I’m curious…

    **Have you ever held yourself to expectations that nobody else actually asked you to meet?**

    Or found yourself so busy trying to improve your life that you forgot to enjoy it?

    I’d love to hear your thoughts. Maybe we can compare notes from our imaginary performance reviews. 😂👇

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