How to Choose Yourself When You’ve Been Conditioned to Put Everyone Else First

Everybody tells women to choose themselves.

But we do not talk nearly enough about how difficult choosing yourself can actually be.

Because choosing yourself can mean disappointing someone you love.

It can mean giving up security.

Walking away from something familiar.

Being misunderstood.

Ending something you once thought would last forever.

Starting over without knowing exactly where you are going to land.

And sometimes choosing yourself does not initially feel empowering at all.

Sometimes it feels scary as hell.

Especially when you have spent most of your life being rewarded for doing the opposite.

Why Is It So Hard to Choose Yourself?

So many women have been conditioned to be accommodating.

Be helpful.

Be agreeable.

Say yes.

Keep the peace.

Think about how everybody else feels before making a decision.

We are praised for being the woman everybody can count on, while rarely asking ourselves:

Can I count on me?

That is why choosing yourself can create so much friction.

You might know what you want and still feel guilty for wanting it.

You might know something is not working and still worry about disappointing everyone if you change it.

You might hear your own voice clearly and immediately start questioning whether you can trust it.

That is the work so many women bring into the room with me.

We have wisdom.

We know how to handle shit.

We have spent years taking care of everybody and everything. But when you have been praised for abandoning yourself for that long, choosing yourself can feel unfamiliar.

Sometimes, it can even feel wrong.

I have experienced that friction myself.

And when I look back over my life, I can see three significant moments when choosing myself changed everything.

The First Time I Chose Myself: Taking a Chance on Me

In 2013, I took a day off from my corporate job to register my son for kindergarten.

I had just finished the paperwork and gotten back into my car when my phone rang.

It was my director.

He told me that within a few months, our site would permanently close and everyone would be laid off.

So yes, I got laid off on my day off.

And my son, the little boy I was registering for kindergarten that day, is now a freshman in college.

I remember sitting in my car with tears filling my eyes, thinking:

Oh my God. What am I going to do?

My family relied on my income.

I had built a career.

I had two college degrees.

This was not the plan.

And then I heard Spirit say in my right ear:

This is your opportunity to take a chance on yourself.

I did not know what that meant yet.

But I knew I was here for more. I had always known that.

Not long afterward, I reached out to my friends and asked them what they thought I was good at.

One friend said, “I think you should be a life coach.”

I did not even know what a life coach was.

So I Googled it.

And realized I had basically been doing it for free with my friends for years. 😂

I hired my first coach, enrolled in a six week business boot camp, and began building my business.

Choosing myself cost me predictable income.

Security.

Comfort.

Part of my identity.

I did not have entrepreneur friends around me. Even people who loved me did not necessarily understand. My grandmother wondered why someone with two college degrees would not simply go back to work.

But choosing myself required me to trust something I could feel before I could prove it.

That is often what choosing yourself looks like.

Not certainty.

Not a five year plan.

Not everybody clapping for you.

Sometimes it is simply the quiet knowing that something more honest is asking to be lived.

Choosing Myself Meant Telling the Truth About My Marriage

Years later, choosing myself looked very different.

In 2020, after 19 years of marriage, I told my now ex husband that I no longer wanted to be married.

My marriage had become emotionally and mentally unhealthy. But when you have lived inside dysfunction for a long time, dysfunction can start to feel normal.

I had recently returned from a women’s conference.

Getting outside of my normal environment and being surrounded by other women gave me enough distance to see my own life differently.

And I realized:

I do not like the life I am living.

Choosing myself did not mean everything changed overnight. It would take time before I actually left.

But something had already changed.

I told the truth.

I stopped suppressing the part of myself that knew.

I stopped going along just to go along.

Sometimes choosing yourself begins long before anybody else can see the evidence.

Sometimes it begins with finally admitting to yourself:

This does not work for me anymore.

That sentence can change your entire life.

Not because you suddenly know what comes next.

Because you stop lying about where you are.

Now Choosing Myself Looks Like New Orleans

And now, I am choosing myself again.

This time, it looks like packing up my life in Cleveland and moving to New Orleans.

I have visited New Orleans four times, and every single time, something about the city has felt like home.

But last October, I was there hosting my Grown Ass Woman Retreat.

As the plane descended into New Orleans, I felt this immense sense of joy come over me.

And I heard Spirit again:

You’re home.

I had wanted to leave Cleveland for years, but I was waiting until my children were settled into college.

Now they are.

And I get to ask:

What do I want next?

I am leaving what is familiar.

I am letting go of most of my things.

I am moving to my favorite city and beginning a new chapter without knowing exactly what every detail will look like.

And yes, that is uncomfortable.

But I know myself differently now.

I trust myself differently now.

That is what happens when you practice choosing yourself. You build evidence.

You realize you can make a decision without having every answer.

You can disappoint people and survive it.

You can be misunderstood and still be right about your own life.

You can begin again after 40.

You can start over without being broken.

Choosing Yourself Does Not Mean Nobody Else Matters

I think this is where so many women get stuck.

We hear choose yourself and translate it into:

Be selfish.

Stop caring about everybody else.

Do whatever you want regardless of who gets hurt.

That is not what I mean.

Choosing yourself means you matter, too.

Your desires matter.

Your intuition matters.

Your boundaries matter.

Your joy matters.

The way your own damn life feels to you matters.

People may have opinions about your choices.

They certainly had opinions about mine.

But I have had to learn how to stay grounded in what I know is right for me without requiring everybody else to understand it.

Because this is my life.

And ultimately, I am the one who has to live it.

When you are trying to stop putting everyone else first, begin by creating a little space between the request and your response.

You do not have to answer immediately.

You can say, “Let me think about it.”

You can say, “I need to check my schedule.”

You can say, “That does not work for me.”

You do not need a courtroom defense for having a boundary.

You do not need to make your no so comfortable that the other person never feels disappointed.

Their feelings are theirs.

Your life is yours.

And yes, guilt may show up.

Let it.

Guilt is not always proof that you have done something wrong. Sometimes it is simply the sound of old good girl conditioning losing its grip.

You can feel guilty and still choose yourself.

You can feel afraid and still tell the truth.

You can love people and still refuse to abandon yourself for their comfort.

Every Time I Chose Myself, It Cost Me Something

Choosing entrepreneurship cost me security.

Choosing to leave my marriage cost me the life and identity I had known for nearly two decades.

Choosing New Orleans requires me to release comfort and familiarity again.

But every one of those choices has also brought me closer to myself.

Because for much of my life, I did not really know Siobhan.

I married at 23. My life became wrapped around marriage, children, responsibility, religion, and all the things I believed I was supposed to be.

Parts of my truest self got suppressed along the way.

Choosing myself has been how I have come home to her.

I have learned to trust my intuition.

Hear my own voice.

Decide what freedom means for me instead of accepting the blueprint handed to me by family, religion, society, or anybody else.

And I am still choosing.

Because choosing yourself is not one big dramatic decision you make once.

It is a relationship you build with yourself.

Again.

And again.

And again.

It is keeping small promises to yourself.

It is noticing when you are about to say yes out of fear.

It is asking what you want before asking what will make everybody else happy.

It is choosing rest without earning it first.

It is allowing your needs to take up space.

It is becoming the woman who knows that her life is not an emergency room for everybody else’s problems.

You do not have to figure out your entire life today.

You do not have to know exactly where you will land.

But you can begin choosing yourself.

You can tell the truth.

You can pause before automatically saying yes.

You can let someone be disappointed.

You can stop waiting for permission.

You can trust that the life meant for you will require your participation.

Ready to Choose Yourself?

Ready to choose yourself without waiting for everybody else’s permission? Join Me for the Free Choose Yourself Masterclass.