Connected AF
Connected AF — Modern Conversations for Expansive Lives
What does it mean to create a truly rich life? One defined not simply by what we have, but by the meaning we create, the relationships we nurture, and the experiences we share. This is the question we are obsessed with exploring.
Hosted by Rebekah Hogan, Connected AF brings together honest, thought-provoking conversations that challenge how we think about success, fulfillment, connection, growth, and what’s possible for our lives.
Because we can build big things, create meaningful impact, and want more for our lives without sacrificing ourselves in the process.
The question is: what does that actually look like?
Connected AF
Redefining a Rich Life
What happens when you get the things you thought you wanted… and realize they still don’t feel like enough?
In this conversation, I share what it was like to check the success boxes and still feel disconnected from the life I had built. We talk about the patterns we carry with us, the difference between responsibility and blame, and the possibility that sometimes the problem is not that what we have is not enough — it is that we never stopped to ask if it was actually what we wanted.
We explore:
- Success that looks good but does not feel good
- Wanting more without making your current life wrong
- Why meaningful human connection matters more than ever
- The hidden loneliness behind leadership and entrepreneurship
- The breaking point of having “everything” and feeling it is not enough
- Taking responsibility for the role we play without taking on blame
- Recognizing when success is built on someone else’s expectations
- Redefining success through values, self-trust, and honest reflection
- Why change can cost you comfort and even relationships
- Using triggers as a signal for growth and expansion
- Integrating hustle with joy and presence
- Expanding the definition of wealth beyond things into experiences and connection
If you have ever reached a milestone and thought, “Is this it?” — this conversation is for you.
Connected AF® — Modern conversations for expansive lives.
If this lights you up or gives you something to think about, follow the podcast, share it with someone you want to continue the conversation with, and leave a review. It helps more people find Connected AF.
So - I invite you to lean in and join the conversation because we are going to have some great f*cking conversations.
Follow Connected AF and connect with me here:
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What would your version of a rich life actually look like? Let's keep the conversation going. Join me over on Facebook in the Cafe Society
When Success Feels Lonely
SPEAKER_00Welcome to Connected AF, where we have modern conversations for expansive lives. These are the conversations that challenge the way we think about success, ambition, fulfillment, relationships, personal growth, and how to actually build a big life without losing yourself in the process. Because I think a lot of us are realizing we don't want to sacrifice ourselves for success anymore. But the bigger question is what does that actually look like, right? I'm Rebecca Hogan. Let's dive in. I hear a lot of people talking about leadership, about the entrepreneurial journey, and about how incredibly lonely it can feel. And I'm gonna go a step further and say that maybe there's something even more lonely. And it's that moment when you realize that you have checked all of the boxes, you've done everything that society has told you will make you happy. You've got the house, you've got the car, you've got the family, you've got the closet full of designer clothes, you've got everything on the outside. But on the inside, you still don't feel like it's enough. And that moment is the loneliest moment that I have ever felt. Because it's realizing that you don't feel like there's anybody that you can talk to. Because how can you tell someone, I have everything, I have everything that you want, and it's not enough. I found myself in that moment about seven years ago, after an emotional evening, and I was sitting there with my back up against the wall, literally. My back was up against the front door. I was sitting on the cold concrete stamped floor of this 1927 Spanish-style house we were living in in Beverly Hills. So I watched my husband walk up the stairs, leaving me there to sort through all of the emotions that had erupted out of me. I used to say we were one margarita away from splitting up because I got really good at ignoring how I felt about
The Night Everything Cracked Open
SPEAKER_00stuffing down my emotions, about drowning them. I got really good at drowning how I felt. So I didn't have to deal with it. And the first margarita, you know, it would take the edge off. By the second one, I would start to feel kind of human again. And by the third one, the filter was gone and it was like, you know, and a volcano had erupted, and all of the emotions would come out, and everything that I had been suppressing would come out, and that night was one of them. And as I sat there, I thought about just like burning it all down, just running away. And I remembered something that my dad had said to me. He said, At some point, you have to take responsibility for the role that you played in the situation. He said, I'm not saying that it's your fault. I'm not saying that you asked for it or that you caused the situation, but what role are you really playing it? Because the truth is that wherever you go, there you are. So you can run away, you can burn it down, you can do all of those things. But at the end of the day, you're just going to keep creating the same situations over and over again until you do the work on yourself. And this was the moment where I realized I had to change my life, I had to do something. And this is the lonely journey. And this is why I want to have these conversations here, because when we start realizing that our definition of success, everything that we've spent our life striving for, and we achieved it, or we came pretty fucking close and it wasn't enough. When we realize that I'm going to invite you to consider this is where I got whenever I realized that is that it was never that the stuff wasn't enough. It was that they just weren't my dreams. And when you realize that, that you have literally spent the majority of your life trying to fulfill somebody else's dream, somebody else's expectation of success, somebody else's reality. When you realize that, this is a moment where you can either get upset, resentful, you can start feeling bad about your situation, or you can say, What role did I play in that? And what role do I want to play in the future that I'm living? And this is where all of the freedom comes in, and this is why I want to start having these conversations. Connected AF is a platform for us to have
It Was Never Your Dream
SPEAKER_00like deep conversations, conversations about stuff that we haven't felt like we could talk about before. Conversations about how we're feeling inside and where we don't know how to share these with anyone else. Because let me tell you, when you start reevaluating your life and you look at like that the success isn't yours, and you start saying, What does success look like to me? And you start asking yourself, what is important to me? And you start realizing that, you know, maybe the beliefs that you've carried with you for your entire life, what got you here, isn't really as important as you thought it was, that maybe there's something deeper inside of you that you have truly been seeking that has been fueling all of this achievement and success. You just didn't know how to name it. And when you start naming that and you start understanding how you really feel inside and what is important to you, and you start listening to yourself, this starts shifting your beliefs. It starts shifting how you show up for other people. And I'm gonna be honest, people don't always like whenever you change the role that you play in their life. And this is where it is truly the loneliest journey. If you don't have a community, if you don't have other people that you can have these conversations with.
Building A Place To Talk
SPEAKER_00I want to create more expansion in my life. I want to create more possibilities. I want to be able to enjoy like all of the technology in the world, all of the beauties and the luxuries and those things. And I am doing that unapologetically. And this podcast, this space, is so much more than a podcast. Connected AF is a platform for conversations. Right now, we're here on this podcast. My vision, my dream in the future is to be able to have live podcasts, to be able to have live calls. As a matter of fact, we are going to have live calls to bring people together to have these conversations. I want messages, conversations down in the chats. I want people to know that you are not alone in this. Because whenever I was 41 years old and I realized that I had no clue who I wanted to be when I grew up. And I only knew that what I had built so far was based on everybody else's dreams. And it was time for me to find what my dreams were. And that's whenever I realized like we need a place, an adult playground, a place where we can explore what lights us up, what conversations do we really want to have? If we could create anything, what would we create if it wasn't for money, if it wasn't for achievement, if it wasn't for external validation? What would you create? And to have a space to not only have those conversations, but to be able to try that stuff on. You know, I had spent so much time working on businesses that I didn't take time to take care of myself. What does self-care look like? What does self-love look like? We hear these words all the time, but what does it really look like? What does it feel like? How do I do that? I didn't even know where to start with this conversation. And I know right now I'm gonna touch on something that might be a controversial topic, and I'm gonna do that plenty of times in this podcast. So get used to it. I can promise you I'm gonna trigger you. And um, that is fabulous because triggers are just the outside edge of our current beliefs and the ability for us to grow. So if I trigger you, um, I'm gonna invite you to lean in a little bit more because that is literally the edge of your expansion.
Why AI Cannot Replace Humans
SPEAKER_00And so, anyway, AI, Chat GPT or Claude or any other AI um chat, these are not human connections. And I'm going to invite everyone to recognize that we need to connect with each other and humanity. We need to normalize that connection. We have lost so much connection with ourselves, with other people, um, with our beliefs and something greater than ourselves. Especially, I know I can speak from experience. Whenever I was so busy proving that I deserved the life that I had built, when I was so busy earning everybody else's approval, seeking that validation. I didn't take care of myself. I didn't connect with myself for sure. I didn't connect with other people because where was the time? And I didn't connect with something greater than myself because the goal was the thing that was the greatest external thing that I needed to achieve, because I was so out of touch with myself that connecting with something else just didn't even make sense. So the idea and concept behind the Evelyn and Connected AF are both third spaces where you can connect with yourself, connect with other people, but connect with your vision, your reality of what there is out there that's greater than you. When we can connect to
Hustle And Soft Life Together
SPEAKER_00that and recognize that we are that, it is within us, then we can give ourselves permission to connect with ourselves. And only when we learn how to connect with ourselves can we really get good at connecting with other people. So this is a journey inwards so that we can go outward. But this is not about self-help. This is not just about personal development, this is not about achievement. It's about finding how all of those things can exist together. Because I feel like there is so much information out there where it's, you know, there's hustle culture and you know, optimizing your day and your energy and all of the biohacks. And then there's the anti-hustle culture, right? Slow down and allow and receive, as if those are two separate things that can't exist together. And success and fulfillment, success and joy, you know, you've got to work so hard that you don't actually get the chance to enjoy this stuff. These things are not mutually exclusive. And that is the point of these conversations is that these are not things that you can have one or the other. These are things that can come together and we can dance between both sides of that, and we can see the full spectrum, and we can truly find joy in the life that we're building. The joy is not something that you achieve at the end, the whole purpose, and so this is my thing. We hear all the time it's all about the journey. It is only the journey because life is progress. If you are not progressing, you are dying. Life is progress, so it is only the journey. And this is why so many of us get to one place and then we don't even take the time to celebrate it. We just move past because we need to keep progressing. The reason why we don't take the time to celebrate it and
A Bigger Definition Of Wealth
SPEAKER_00why it feels unfulfilling is because we're not connecting with the joy, the energy of the thing that we're trying to achieve. We're not living it as we're achieving it. And this is the space where we get to come together and define what that truly looks like. What is wealth to you? I now have such an expansive definition of wealth. It is not just about my bank account or how many square feet my house is, or how many houses I have, or how many cars, or what model my car is, or what brand my shoes are, or my purse, or it's it's not about the achievements. It's not about the things. I love them and I enjoy them, and it's so much bigger than that. It's about the experiences, it's about the emotions, it's about the connections, the conversations and being. So I invite you to lean in, join the conversation. If this lights you up, please review this podcast and bookmark it, follow along because we are going to have some great fucking conversations.