Episode 104

full
Published on:

8th Sep 2026

The Rooms That Changed You, and Changed Me

The right room won't just change your business. It will change what you believe is possible for yourself.

In today's solo episode of She Wears the Pants, Ashley Deland shares the story of the room that forever altered the trajectory of her business and, more importantly, the woman building it. Six years ago, she boarded a flight carrying every version of imposter syndrome imaginable, convinced she wasn't qualified to sit beside the entrepreneurs she admired. What she discovered instead was something she never expected: she already belonged.

This is a deeply personal conversation about proximity, courage, and the quiet power of choosing environments that expand you. Because sometimes the greatest gift a room gives you isn't another strategy or breakthrough. It's a new standard. A new belief about what's possible. A reflection of the woman you're becoming before you're fully able to see her yourself.

If you've reached the edge of what you can build on your own, if you've been craving bigger conversations, higher standards, or simply a room where you don't have to explain your ambition, this episode is for you.

In this episode, Ashley shares how to:

• Recognize why the rooms you choose shape the future you're capable of creating

• Reframe imposter syndrome as evidence that you're expanding beyond what's familiar

• Understand why proximity changes far more than your business strategy. It changes your identity.

• Release the belief that you have to reach the next level alone

• Invest in environments that stretch your thinking, elevate your standards, and expand your vision

• Choose the rooms that call you forward instead of the ones that simply keep you comfortable

By the end of this episode, you'll understand that the most transformative rooms rarely change your life because of what is taught from the stage. They change your life because of who you become while you're in them. Sometimes the right room gives you strategy. Sometimes it gives you relationships. But every once in a while, it gives you something even greater: the certainty that you are capable of far more than you ever believed. And from that moment on, you never lead your business the same way again.

Continue the Work with Ashley

Step into your next level: Explore Private Advisory, high-touch strategic partnership, and fractional leadership support for women scaling with precision and power.

https://ashleydeland.com/inquire

Experience a full-business transformation in one weekend: Apply for Ashley’s Executive VIP Experience — an immersive, in-person strategic overhaul designed to collapse timelines and accelerate growth.

https://ashleydeland.com/inquire

Stay in proximity: For daily strategy, identity expansion, and behind-the-scenes insight, connect with Ashley on Instagram.

https://www.instagram.com/ashleydeland/

She Wears the Pants is where high-growth women come to build companies that match their calling. If this episode resonated, follow, rate, and review so more women can find these conversations.

Transcript

Welcome back to She Wears the Pants — the place where high-growth women come to build companies that match their calling.

I'm your host, Ashley Deland.

Today I want to tell you about a room that helped change the trajectory of my life and my business.

And I want to tell you about it because I think there's a version of this room waiting for you right now, and I don't want you to talk yourself out of walking into it the way I almost did.

So let me take you back about six years.

I was starting to see real success in my business. The money was coming in, things were working — but I had this nagging feeling that I had hit the edge of what I knew how to do on my own.

Ultimately - I didn't know how to leverage what I was building, I knew I needed clarity on how to reinvest and repurpose the momentum - all while taking everything to the next level.

I just knew, deep down, that I needed to get into higher caliber rooms with people who were further ahead than me.

So I made the investment to fly down to Arizona for a two-day event for entrepreneurs doing six and seven figures and beyond.

At the time it was a huge investment for me - in other words - It wasn’t a comfortable yes.

And beyond that, the closer the date got, the more terrified I became.

To the point of - the morning of I was feeling sick to my stomach and every single feeling of imposter syndrome started to show up - "who am I to be in this room," "I'm not good enough to be here” “everyone else has their shit all figured out."

But I walked in true Ashley Deland form, I knew that if I was feeling sick and wanted to throw up - that was the direction I needed to go - because on the other side of facing that fear was my potential and greatness.

And I am so glad that I listened to that feeling because those two days changed me and everything that came after.

Because the first thing that happened in that room is I realized something I now believe with my entire being.

Proximity is everything.

Just being in that room, surrounded by people operating at a level I was reaching for, did something to me that no book, online course, or amount of working harder alone ever could have.

The conversations recalibrated what I thought was possible. The mentor leading that room gave me a kind of clarity I had been chasing for months on my own and couldn't find.

And here's the part that surprised me the most. I walked in terrified that I didn't belong. And what I actually discovered in there was how much I already knew.

Being in that room - showed me my own value.

It took all of that imposter syndrome I'd been carrying and replaced it with real, grounded confidence. And I left knowing I belonged at that level and now I had the tools, knowledge and guidance to exponentially expand.

And that’s exactly what happened.

I came home on fire.

I started seriously amping up my visibility, my thought leadership, my authority here on Canadian soil and that trajectory traces directly back to saying yes to the room.

So here's what I want you to take from my story…

You cannot become the next version of yourself in the same environment that created the current one. - You just can't.

Your discipline matters. Your strategy matters. But the single most underestimated force in your growth is the room you're standing in. The conversations you're surrounded by. And the standard of the people closest to you.

Because the environments we enter shape the women we become. Full stop.

Show me the five rooms you spend the most time in, and I can tell you almost exactly where your business and your beliefs are headed.

If everyone around you is playing at the level you've already outgrown, you will quietly shrink to stay comfortable in that room. But if you put yourself in a room where the woman beside you is operating at the level you're reaching for, you rise to meet it, often without even trying.

That's just what proximity does.

And here's the thing I most want you to hear, especially if you felt that little flutter of recognition while I was telling my story.

That nausea I felt the morning of? That fear that I didn't belong? That was not a sign I was making a mistake.

It was the sign that I was finally walking toward the room that would grow me.

The fear was the confirmation.

And if there’s a room calling you right now, and the thought of it makes your stomach flip the same way mine did — that flip is a compass.

And that brings me to something I have to tell you about today, because the timing is not an accident.

Everything I just described — the proximity, the clarity, the confidence, the belonging, the women you rise alongside — that is the entire reason I built Founder Haus.

It's my private founder collective. A modern founder sisterhood built on intimacy, high standards, strategic advisory, and lifelong proximity.

Ultimately I built the room I wish I'd had in Canada — because I believe women were never meant to build extraordinary lives alone.

And our next cohort begins September 17th. Just days away.

Founder Haus is intentionally kept small. Each cohort is just six women.

And that's by design - because the intimacy and the caliber of that room is the entire point, and you can’t scale that without losing the very thing that makes it work.

So if something in my story landed in your chest today — if you recognized yourself in the woman I was six years ago, standing at the edge of her next level, scared but knowing she needed a bigger room — please do not sit on it.

Because I can tell you from experience, the women who change their lives are the ones who feel the fear and do the thing anyway.

If that's you, head to ashleydeland.com to apply or to book a private conversation with me, so we can see together whether this is the right room for your next season of growth.

A year from now, I would love nothing more than to watch you tell the story of the room that changed yours.

Until next time — keep rising into the woman your calling requires.

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About the Podcast

She Wears the Pants
She Wears the Pants is the podcast for the women building more than businesses—they’re building identities, empires, and legacies.

Hosted by globally recognized business advisor, multi-business founder, and start-up investor Ashley Deland, this show lives at the intersection of strategy, structure, and self. Each week, Ashley pulls back the curtain on what it truly takes for women to scale companies that are financially sound, spiritually aligned, energetically sustainable, and structurally unshakeable.

This is where high-growth women founders come for boardroom-level strategy, identity evolution, feminine leadership, and the inner work required to hold the success they’re building.

Because strategy means nothing if the woman behind it can’t hold it.

Continue the Work with Ashley:

Step into your next level: Explore Private Advisory, high-touch strategic partnership, and fractional leadership support for women scaling with precision and power.
https://ashleydeland.com/inquire

Experience a full-business transformation in one weekend: Apply for Ashley’s Executive VIP Experience — an immersive, in-person strategic overhaul designed to collapse timelines and accelerate growth.
https://ashleydeland.com/inquire

Stay in proximity: For daily strategy, identity expansion, and behind-the-scenes insight, connect with Ashley on Instagram.
https://www.instagram.com/ashleydeland/

She Wears the Pants is where high-growth women come to build companies that match their calling. If this episode resonated, follow, rate, and review so more women can find these conversations.

About your host

Profile picture for Ashley Deland

Ashley Deland