Summary:
In this deeply personal solo episode, I’m sharing the story of a door I almost didn’t walk through—and how saying yes to myself changed everything.

Back in 2021, after leaving my corporate career to be home with my family, I found myself in an unfamiliar space: no title, no company-sponsored development, and no clear roadmap for what came next. For the first time, I realized that if I wanted to grow, I had to stop waiting for an employer—or anyone else—to invest in me. I had to choose myself.

I take you behind the scenes of the moment I was invited into an $18,000 mastermind with no income coming in, the beliefs I had to confront about what was “possible for someone like me,” and why saying yes to the right room became one of the most transformational decisions of my life.

This episode is about permission, expansion, and the courage to invest in your own becoming.

If you’ve been standing at the edge of your next chapter, waiting for a sign—this is it.

🔑 Key Takeaways:

Stop Waiting for Permission
One of the biggest lessons I’ve learned is that no one is coming to hand you permission to grow. At some point, you have to become the person who says, it’s time.

Audience follow-up → Where in your life are you still waiting for someone else to validate your next move?

You Can No Longer Outsource Your Growth
When I left corporate, I also left behind the systems that once supported my development. It forced me to realize that my growth was now fully my responsibility.

Audience follow-up → What part of your growth have you been expecting someone else to provide for you?

Investing in Yourself Creates Compound Returns
The $18K mastermind felt terrifying at the time, but the return wasn’t just financial—it was personal, emotional, relational, and deeply transformational. The right rooms expand who you believe you can become.

Audience follow-up → What investment in yourself could create long-term growth beyond immediate results?

Challenge the “People Like Us” Story
At Canyon Ranch, I came face-to-face with the stories I had inherited about what people like me do, deserve, or have access to. Saying yes required rewriting that narrative.

Audience follow-up → What identity story are you ready to release?

Expansion Happens Through Decision
So often, transformation begins the moment we decide—not when conditions are perfect, but when we trust ourselves enough to move.

Audience follow-up → What door is in front of you right now that you’re afraid to walk through?

✨ Reflection Prompts:

• Where have I been waiting for permission instead of deciding?
• What would change if I fully chose myself?
• What room, opportunity, or investment is calling me right now?
• What belief about “people like me” am I ready to outgrow?

🧠 Who This Episode Is For:

• Women leaders navigating a major life or career transition
• High-achieving women ready for their next level of growth
• Entrepreneurs learning to invest in themselves
• Anyone standing at the threshold of a bold decision
• Listeners craving permission to want more

📩 Want to Go Deeper?

Follow Lori on LinkedIn to continue the conversation

• Book a Leadership Strategy Call with Lori: loripine.com

🎧 Subscribe to The Joy CEO Podcast

⭐️ Leave a review to help other heart-centered leaders find the show

📲 Share this episode with someone who’s navigating pressure and wants to do it with more grace

Transcript

LP_Ep_45_Final Podcast

Hey there. Welcome to the Joy CEO podcast. I'm your host Lori Pine, and this is a show for women who are accomplished. She's built something, led people, made things happen, and she has this quiet, persistent feeling that she's still not fully living the life she came here to live. If that's you, you are in exactly the right place.

And I mean that in the way that you know someone means it if you're returning. Thank you so much for coming back. You know I love you and I'm so happy you return to listen to what we have to say today. This is the show where ambitious women come to lead bigger, live fuller. And finally give themselves permission to want what they actually want.

So let's get to it. Today's episode is a solo one. It's just you and me and I wanna tell you a story, and it [00:01:00] is an absolute true story about a door I almost didn't walk through. And what happened when I finally did. Before I do, here's what I want you to be thinking about as you listen. Where in your life are you waiting for permission?

Now, I don't know about you, but if you're anything like me, I needed permission in lots of places. It has taken me a lot of time and a lot of inner work to actually be able to give myself permission. To do some of the big girl grownup things that I have wanted to do. And so where are you standing just outside of something that was made for you and yet you're talking yourself out of it, and what is that costing you?

All right, here we go. In 2021. I had just left my [00:02:00] corporate career. I'd made the decision to step back. I was going to become a stay at home mom for the next 18 months. It was really a calling, a knowing. My intuition was far greater than any sort of logic I could have put behind it. I didn't know how or if everything was going to work out, but I knew that I needed to show up and be present.

What I needed to do was really just breathe and figure out what was going to be next for me, and somewhere in the quiet of that, I had this real knowing and knowing that I needed to hire somebody to guide me, a coach, and I really knew that I could not go this next chapter alone. I had gone a lot of chapters in my life alone, kind of trying to figure it out by myself.

But [00:03:00] this one, I really had this wherewithal to know that I needed somebody to help me. So I hired a coach and she took me through some really beautiful work around dreams and purpose and legacy stuff that I had never given myself time or permission, or the space to actually think about. And when you do that kind of deep excavation work and you start to really think about what it is that you are here to do and what's your unique ability and why the universe created you in the way that you've been created, then you really start to focus on yourself as opposed to being somebody's.

Mom or being an executive or being the CEO of your house, the one who makes everything run. And [00:04:00] what happened is I actually had to unlearn many things in that season. For most of my corporate career, I had this expectation that. And let me just say this with some naivete that my company did, the investing in me, my company sent me to trainings.

My company had hired resources for me. I, I had a lot of privilege when it came to that, and they would see my potential and they would pour into me and what I could bring to the company, and that the organization was always the one to develop me and. Oftentimes it wasn't me developing me. That was pretty naive of me looking back.

It was almost kind of an outsourcing where I was handing the responsibility for my own, becoming over to someone else's budget and someone [00:05:00] else's priorities. I didn't really stop and consider what was my responsibility and what were my priorities. So when I left the corporate world altogether, that illusion.

Disappeared altogether. There was no company, there was no development budget. There was no performance review where somebody else decided that, Hey, I needed these three trainings and I would just go into, you know, the corporate university site and check, check, check. But instead it was left to me. I was the one who needed the clarity, the confidence, and the rooms.

That I saw other women, other entrepreneurs, other business owners standing in, and so I needed to get myself into those rooms with those women so I could hear what it was that they were doing and [00:06:00] what it was that they were thinking in order to grow myself. Nobody was going to do that for me. So about six months into working with my coach, she invited me to join her mastermind group.

Now, this was her, what she called her elite women, and it was a 12 month program for $18,000. Now let that soak in for a second. I had no income. I left my job. I had just walked away from a salary and by any rational measure, this was fiscally irresponsible. This would've been like an absolute no, can't even consider it, but I actually sat down with my husband and I looked at it with him.

We discussed it. I turned it over. And I really didn't think [00:07:00] it could be for me. And then I asked myself this one question, what was my alternative? To stay home alone in my head, trying to figure it out all by myself to be isolated from the very women who were building what I wanted to build. Who were a few steps ahead of me, maybe many steps ahead of me who could see what I could not yet see who had made mistakes that maybe I wouldn't have to make because they would share with me where some of the gaps were and how to not step into those gaps.

I joined, I took the leap of faith and I joined, and while there was one little critic on my right shoulder who was saying, no, no, no, you can't do this. This is ridiculous. There was also another, maybe a little angel on my other shoulder that was saying. You absolutely must do this. [00:08:00] If you wanna grow, if you wanna have the impact you wanna have, if you wanna get to the places that you wanna get to, you have to invest in yourself.

And here's what I want you to know, people notice. People notice my growth. People noticed that it wasn't just my personality. It wasn't just some gift I was born with. What started to happen to me after being in that Mastermind was the result of being incredibly intentional about where I put my money, my time, and my energy.

Those three things, money, time, and energy. While some of my friends were in New York City buying really fancy handbags, and God knows I love a fancy handbag. At that time and that season of my life, I was buying [00:09:00] rooms. I was buying access to women who inspired me, and I aspired to be like. And I was buying a coach.

She had built something that I was very curious about and I wanted to know more about it, and I was buying this experience that was going to expand me in, in ways that I really couldn't even articulate. I just had this knowing and this feeling that I would be better off as a result of spending 12 months in this container with these women.

There is real power in investing in yourself. It's like compounded interest. It grows and it grows at an exponential rate that might not logically make math sense. Every room you enter makes you more and more ready for the next room that you're going to enter, and you're going to grow and expand and possibilities become bigger and less [00:10:00] scary.

Every investment in your own growth returns something that goes on your balance sheet permanently, because nobody can take away those learnings and that becoming from you, they're yours to keep. Here's what nobody talks about again. How could I ever build a $20,000 mastermind group if I had never actually been in one?

If I hadn't experienced it, been behind the scenes, walked through it, seen what happens, how could I ever build one for my clients, for the people who would entrust me with their monies? And so it was really important that I do the thing that I actually aspired to do. It would be like. It would be like trying to build a [00:11:00] restaurant when you've never actually eaten in a restaurant.

So I needed to experience it. I needed to know the quality, the care, the transformation, the things that made me feel seen and held so that I knew what to build towards. Honestly, so I also knew what I would do differently. What would be my signature thumbprint? What would be my version of generosity? What would be my way of holding space and love and joy for the women who would come to me?

You don't get that from just a book. You don't get that from taking an online course. You don't get that from somebody telling you about it. You get it from experiencing it, and that's the only way you can get it. So with this program that I signed up for. Came something that I didn't necessarily anticipate.

It was a trip, and she [00:12:00] included it into her program two nights and three days at Canyon Ranch in Tucson. She was very wise and very insightful because she knew that ambitious leaders. Like me, rarely invested in ourselves yet we were stressed, we were overloaded, we were on the verge of burnout. And if you've ever been to Canyon Ranch.

You know what it's like, but if you've never been, let me paint a little picture for you. It's bougie. It's luxurious. It's so beautiful. There's something sacred about the land. It's, it has energy vortexes on it. It's in the desert. It holds you and you can feel it from the moment you arrive on the property.

It's indulgent in the best sense of every word. Once you arrive, everything [00:13:00] is included. They say, yes, Mrs. Pine, how can I help you? Happy to help you, Mrs. Pine, like everything is there and they are catering to you at all times. It is the kind of place, however, that growing up, I wouldn't have even known to want.

Because growing up in a small one, traffic light town, places like this weren't even known to me. And there's this voice that still lives in my head, and maybe you have your own version of it. There's this voice that says People like us don't do that. People like us don't go to places like that. People like us don't spend money like that.

People like us don't need that much. That voice has a [00:14:00] name. It's conditioning, it's upbringing. It's every unspoken message that you absorbed about who you were worth and what you were allowed to want, and because the trip was included, well. Because somebody had built the container and I just had to show up inside of that container.

I went and I gave myself permission to go. Here's what I want you to understand about that moment. I didn't walk through that door because I had finally conquered all of my worthiness wounds. I didn't go because I had done enough inner work to feel like I deserved it. I went because the container made it easier for me to say yes than to say no.

I went because I loved the women. We [00:15:00] had now been meeting weekly on Zoom calls. We had gotten to know each other inside the virtual aspect of the mastermind group, and I really wanted to meet them in person and there was permission that was baked in. Someone else had done the hard work of making it available to me, and all I had to do was not refuse it.

I can't tell you how much the experience expanded me. There's no other word for it. It expanded. It expanded me. Something in me got bigger, something that had been held tight. Started to breathe. I laughed. I cried. I hugged these women. I stayed in that Mastermind for two more years, and I went back to Canyon Ranch two more times.

And then in [00:16:00] 2024, I hosted my own retreat at Canyon Ranch in Lennox, Massachusetts. So the woman, me, who almost didn't go, became the woman holding the door open for others to experience something so spectacular and so expansive that really, it's hard to explain unless you actually. Do it for yourself. And this October, I'm going to do it again.

I'm going to take a group back to Tucson, back to Canyon Ranch, back to the place that started it all for me. This time, again, with a small group of women. And the reason that I'm sharing this story with you now is because I just returned from five days there, where one of the women from that original group hosted her own retreat last week.

I was an attendee supporting her, and it was [00:17:00] such a privilege to watch her thrive. Shine, rise into her own beautiful radiance with her business and what she was doing, and to witness that and experience that and be a part of that was such an honor. So here's what I really want to land with you today, because I know who's listening to this.

It's early April. It might not feel like spring where you are. I know where I am. It's cold and gray. The ground might still be frozen, the wind might still be bitter, but you know, something is trying to come through, like those daffodils are starting to pop through the ground. My landscaper delivered the mulch today, and just the idea that the mulch is on the ground seems to feel like spring is coming.

You can feel it. You can feel that it's on its way, [00:18:00] and we're in this fire horse year. All that power, all that momentum that we are just generating and moving forward with, and you might just still be a little bit on the outside of it, waiting, waiting to feel ready, waiting to make it make sense, waiting for someone to tell you it's okay.

I'm telling you, it's okay. The investment, you keep talking yourself out of the program, the retreat, the coach, the room full of women who see what you can't see about yourself yet, that is not an expense. That is the highest returning investment you could possibly make into your own portfolio because every version of you that has ever grown.

Every chapter that has ever expanded you has been on the other side of a door that you weren't entirely [00:19:00] sure you were allowed to walk through. You are allowed, you have permission. The fire horse does not wait for perfect conditions. Neither should you. So if there is something right there that you are spotting, you've got your eye on it, you too might have a devil on one side saying, no, this is so ridiculous.

And you might have another little voice on the other shoulder saying, it's time to rise. Make the investment. You're going to expand and be better. Be careful which voice you listen to. It could change everything for you. So that's our episode today. I am cheering you on. I believe in you. I believe in the investment and the possibility and all that is on its way to you.

Next week we're gonna sit down with an A DHD coach, and she is amazing. It will be a [00:20:00] lovely conversation. We went places in our talk that I really didn't expect us to go. I think it's gonna open up something for you Until then. Give yourself permission for something this week, something small, something real.

Notice where you say, people like me don't do that. Even if you don't say it out loud, notice if that voice is in your head somewhere, and then get curious about who told you that and question if it is still true today. Alright. I'm Lori Pie and the joy CEO, and I'm so glad to be doing it with you. I'll be back here next week and I can't wait to have you with me so long.

Everyone. Thanks for listening to the Joy CEO. I hope today's conversation left you feeling seen, stretched, and a little more grounded in your own joy. If something resonated, be sure to hit subscribe. Leave a five star review and share this episode [00:21:00] with someone walking a similar path. And if you're ready to take this work deeper.

Connect with me on LinkedIn or Instagram at Lori Pine or head over to my website, lori pine.com to learn more about coaching retreats and how we can work together. Because joy isn't just personal, it's powerful, and when you lead with joy, you don't just rise, you bring others with you. Until next time, keep leading with heart and don't forget to claim your joy.