Breaking the Good Girl Mould: Embracing Authentic Leadership

Lindsey Hilliard
Aug 1
10 min read

Updated: Aug 1

health welath and fulfilment — Breaking the good girl mould

What if the version of leadership you were taught to chase... was never meant for you?

I'm pulling back the curtain on Good Girl Conditioning — the quiet but brutal ways women are trained to shrink, perform, and lead from fear instead of truth.

For the full episode, listen on the player above

You know what I’m absolutely done with?

Watching smart, driven, wildly capable women contort themselves into watered-down, polished versions of who they really are — just to fit into leadership models that were designed by men, for men, decades ago.

We’re out here biting our tongues in boardrooms.

Softening our emails.

Saying “just a quick one!” before we speak so we don’t seem too assertive.

And for what?

So we don’t rock the boat?

So we’re seen as “team players”?

So we’re likeable?

Please...

We’ve been fed this Good Girl script our whole lives:

Be agreeable.
Be polite.
Be accommodating.
Keep the peace.
Smile, even when you’re fuming.

And if you want to lead?

Cool — just don’t be too ambitious, too opinionated, too loud, too demanding, or God forbid — too confident.

But here’s the thing: the Good Girl isn’t just harmless conditioning.

She’s exhausting.

She’s strategic self-abandonment.

And she is not a leader.

So today, we’re burning that version down.

We’re unmasking the Good Girl Leader — the part of you that’s been performing leadership instead of embodying it.

We’re talking about what this conditioning actually looks like, how it shows up in leadership, and how to start reclaiming your power without blowing up your entire life (unless that’s your vibe — in which case, I support it).

And yes, I’ve got my own story — because I’ve lived this too.

I’ve worn the mask.

I’ve played the part.

And it cost me more than I realised at the time.

So if you’re done being nice, digestible, and quietly resentful?

If you’re ready to lead like your whole self — not the version that makes everyone else comfortable?

Buckle up. This one’s going to hit.

Have you heard that quote:

“Well-behaved women seldom make history.”

Yeah… but in the police force?

Well-behaved women were the only ones who got to stay on the team.

I remember sitting in rooms full of men — all higher ranked, all louder, all absolutely certain of their authority.

They’d crack jokes about women, make sexualised comments right in front of me, and I’d laugh along.

Not because I thought it was funny.

But because that’s what you did to survive.

I learned quickly:

Don’t speak up.

Don’t disagree.

Don’t challenge anyone with more stripes on their shoulder.

You nod.

You smile.

You fit in.

Or you risk being iced out — overlooked for jobs, excluded from good assignments, whispered about behind your back as “not a team player.”

Fitting in wasn’t optional.

It was the price of being there.

And when I left the force and moved into private industry, I thought I’d left all that behind.

But the only faces changed — the rules didn’t.

My director and general manager were classic old boys.

They thought leadership was about schmoozing clients over long lunches and golf games, and they expected me to fall in line with that.

I remember eventually mustering up the courage to question their expectations — not rudely, not disruptively, just asked why we were doing something the way we were.

The shift in the room was instant.

I wasn’t “easy to work with” anymore.

I was “difficult.”

“Too opinionated.”

“No longer to be trusted.”

Which is code for: She’s not playing the game.

And I was tired of playing the game.

That was one of the moments I realised — this isn’t just about leadership.

This is about conditioning.

About all the ways women are trained to be good — even if it means betraying themselves in the process.

What Is Good Girl Conditioning?

The thing about Good Girl Conditioning is… it doesn’t just make you exhausted.

It costs you so much more than that.

It costs you your confidence.

Your self-trust.

Your ability to say, “This is who I am, and this is what I stand for.”

Because the more you shape-shift to fit in, the more disconnected you become from your actual voice.

And eventually, you start to forget what you really think, what you really want — because you’ve been so busy keeping the peace, holding it together, making everyone else comfortable.

It’s like being someone else’s puppet.

They write the script.

They pull the strings.

You smile, nod, speak when it’s safe.

And even if the strings are invisible, you feel them.

No one embodied this more clearly than Princess Diana.

Think about it.

When Diana first entered the royal family, she was the ultimate Good Girl.

She was beautiful, sweet, soft-spoken.

She smiled at the right moments.

She stood behind the right men.

She played the role the world — and the monarchy — expected her to play.

And for a while, it worked.

She was adored.

Fawned over.

Called “the People’s Princess.”

But behind the palace walls, it was a different story.

Diana was not thriving — she was surviving.

She was dealing with isolation.

Betrayal.

Unspoken rules and whispered expectations.

She was struggling with her mental health, feeling trapped in a system that cared more about appearances than people.

She was applauded for her image — but unseen in her pain.

Because in that system, her job wasn’t to be human. It was to be perfect.

To perform.

To stay silent.

To keep everyone else comfortable, even at the cost of her own soul.

And for a long time, she did.

She wore the smile. She kept the secrets. She played the part.

But at some point — the cracks started showing.

She stopped pretending everything was okay.

She started speaking honestly — about her eating disorder, her depression, her loneliness, her betrayal.

She ripped off the mask. She cut the puppet strings.

And the moment she did?

The system turned on her.

She was called emotional. Unstable. Difficult.

(Sound familiar?)

Because nothing threatens an outdated system faster than a woman telling the truth about her own life.

But here’s the thing:

Even with all the criticism.

Even with all the backlash.

Diana became more powerful — not less.

She became more loved — not less.

Because when she finally dropped the Good Girl mask, when she let herself be real, be raw, be human —

She became unforgettable.

People didn’t remember her for the perfect photo ops.

They remembered her sitting on the floor of a hospital room, holding hands with AIDS patients.

They remembered her looking into someone’s eyes and actually seeing them.

They remembered her for her heart — not her performance.

Diana wasn’t just a Princess.

She was a revolution in heels.

And she showed an entire generation of women that you can be loved — wildly, fiercely, deeply — not because you fit into someone else’s expectations or mould,

but because you finally chose to break free from it.

What It’s Costing Us

So let’s get brutally honest for a second.

Choosing to stay in Good Girl energy — even if it feels safer, even if it gets you the pat on the head, the ‘great team player’ gold star —

comes at a massive cost.

It’s not neutral.

It’s not harmless.

It’s burning you out from the inside out.

Burnout from People-Pleasing

Every time you override your own needs to make someone else more comfortable, it drains your energy just a little bit more.

And it doesn’t happen all at once.

It happens slowly.

A thousand tiny cuts of "Sure, I’ll take that on."

"No problem, I can stay late."

"It’s fine, don’t worry about me."

Until one day, you wake up, and your body feels like it’s dragging your soul around — not the other way around.

That’s not ambition.

That’s not leadership.

That’s self-betrayal wearing a productivity badge.

Resentment That Simmer Beneath “Nice”

You can slap a smile over it.

You can package it up with politeness and call it “being easygoing.”

But that resentment? It doesn’t go away.

It builds.

Every unspoken no.

Every moment you said yes to something you didn’t want.

Every time you bit your tongue when you should’ve spoken your truth.

Resentment is the emotional tax you pay for staying silent.

Good Girl conditioning teaches you that saying no is rude.

That advocating for yourself is selfish.

That having boundaries makes you “difficult.”

So instead, you say yes to everything.

You take on everyone else’s deadlines, emotions, energy — like you’re some kind of dumping ground.

Until one day, you’re so overloaded you either snap… or you disappear inside yourself completely.

Boundaries aren’t barriers to leadership.

They’re the foundation of sustainable leadership and until we start pushing these to be the norm, nothing will change.

When you’re leading from Good Girl energy, you’re not leading from your core.

You’re leading from fear.

Fear of rejection. Fear of being disliked. Fear of making people uncomfortable.

And that kind of leadership?

It doesn’t inspire trust.

It doesn’t create change.

It doesn’t feel good.

Because it’s not real.

It’s performance — and you know it in your bones.

Quick Human Design Note:

This hits different for different people too. Your Human Design type can affect how this shows up for you (which we spoke about in detail in last week’s episode) Projectors — can burn themselves out trying to keep up with everyone instead of honouring their natural rhythm of waiting for recognition and invitation. Generators — who are literally built to create and respond from joy — can override their gut knowing because they’re too busy people-pleasing and forcing themselves into things that drain them. When you’re not honouring how your energy is designed to work? You’re not just tired. You’re misaligned. And misalignment over time turns into exhaustion, resentment, and a deep disconnection from your real self.

You weren’t born to perform.

You weren’t born to obey.

You weren’t born to slowly erase yourself in the name of leadership.

You were born to lead.

And that starts by choosing truth over performance — one decision at a time.

How We Start Shedding the Good Girl Mask

So if you're sitting here thinking,

Holy shit, I've been living this,

I've been playing the part,

I've been wearing the damn mask for so long I forgot what my real voice even sounds like —

First of all: you’re not alone and you’re not broken.

You've simply been conditioned.

And conditioning can be unlearned.

You don't have to blow up your whole life overnight (unless you want to — in which case, I fully support it).

But you do have to start.

And it starts small.

Tiny cracks in the armour.

Little rebellions that say, “Actually... I choose me this time.”

Here’s how you start shedding the Good Girl mask:

🔥 1. Notice when you’re performing instead of being real.

The first step is awareness.

Pay attention to when you shrink yourself, soften your edges, or silence your truth.

Notice the moments you laugh at things you don't find funny.

Notice the times you say yes, and your gut immediately screams NO.

You can't change what you won't look at. So start by looking — without judgment, without shame.

Just noticing.

🔥 2. Feel the discomfort — and stay with it.

Breaking the Good Girl conditioning isn’t neat and tidy.

It will feel awkward. It will feel wrong. It will feel scary.

That’s not a sign you’re doing it badly — that’s a sign you’re doing it right.

Because every time you choose truth over comfort, you’re rewiring your leadership at the deepest level.

And if you’re feeling that tension right now — that “oh my god, everything needs to change” urgency — Breathe.

You don’t have to burn everything down just because you’re ready to lead differently.

Right now, the energy we’re sitting in — is about recalibration. Finding a new path. Choosing a new way. Honouring who you’ve become, without needing to destroy who you’ve been.

You’re allowed to recalibrate your leadership. You’re allowed to course-correct. You’re allowed to say: "This part of me served me once — but it’s not coming with me anymore."

Real change doesn’t have to look like chaos. Sometimes real change is just one honest decision at a time. Which leads me into….

🔥 3. Start telling the truth in small ways.

You don't have to grab a megaphone and announce your revolution on LinkedIn (unless you want to — again, I support it).

Start small: Speak up in the meeting even when it’s uncomfortable.

Tell your partner you’re not okay with something instead of brushing it off.

Set a tiny boundary that feels terrifying and wildly liberating at the same time.

Every act of truth-telling builds trust with yourself.

Every time you choose real over polite, you are breaking a chain that was never meant for you.

🔥 4. Redefine what leadership looks like for YOU.

Leadership isn’t about fitting into an old, broken system better than the next woman. Leadership is about creating a new system — one that actually honours who you are.

Maybe your leadership is bold and loud.

Maybe it’s soft and fierce and heart-centred.

Maybe it’s strategic.

Maybe it’s intuitive.

Maybe it’s a mix of all of it, depending on the damn day.

Good.

Perfect.

More of that, please.

Your leadership becomes powerful the moment it becomes yours.

Mini reflection prompt

Before we finish up today, I want you to take a minute and reflect on this:

Where in my life am I still performing for acceptance — and what’s one small act of rebellion I can take today to come back to my truth?

So here’s what I want to leave you with today:

You were never meant to lead by shrinking.
You were never meant to lead by sacrificing your truth to keep everyone else comfortable.
You were never meant to lead by being the good girl who smiles through gritted teeth and quietly burns herself to the ground to meet someone else's expectations.

Leadership — real leadership — doesn’t ask you to perform.

It asks you to show up.

Messy.

Honest.

Whole.

Human.

You don’t have to be perfect to be powerful.

You don’t have to be agreeable to be respected.

You don’t have to be digestible to be loved.

And if you needed permission to stop playing by rules that were never designed for you?

Here it is:

You’re allowed to be fully yourself and a phenomenal leader at the same damn time.

In fact? That’s the only kind of leadership the future actually needs.

So burn the script.

Drop the mask.

Cut the puppet strings.

And lead like the woman you were always meant to be — before the world told you who you had to become.

If today’s episode hit something in you — if you’re feeling the fire, if you’re ready to lead from truth instead of performance — come find me over on Instagram @freshcollective_il.

DM me and tell me what your first small rebellion is going to be.

You are meant to be wildly, unapologetically yourself.

And if you’re craving a way to lead that honours your energy, your body, your timing —

not someone else's template or timeline —

The Natural Leader Hub was literally made for you.

It’s where we do this work at a deeper level — recalibrating leadership not from pressure, but from alignment.

Real tools.

Real support.

Real leadership — your way.

You can check out the Hub at the link in the show notes — I’d love to have you inside.

Your leadership starts there.