Full Story: Why Olivia Carr Left Her 8-Figure Business Empire

[00:00:00] 14,000 women in midlife being pushed out of the workplace labeled as too difficult. We do not yet live in a world where it is psychologically safe to turn up to work and share the truth of what is really happening in your world and know for sure you will be supported through that. Olivia Carr spent over a decade building Shhh Silk from her spare room into a global luxury brand. And at 44, she walked away from it and started rebuilding from zero income.

[00:00:27] Olivia Carr, What she's built since is called the midlife truth. Olivia Carr, I just was becoming less tolerable of performing in a non-human way. There were certain expectations to just shrink the part of me that is going through this huge physiological change as a woman. This is not sustainable. Olivia Carr, When did the idea that there was something off start to creep into your conscious thoughts? Olivia Carr, I owned the business for the first nine years and I really wanted to take the brand global and I'd seek some external funding a couple of times.

[00:00:57] Olivia Carr, I was the moment where things shifted and it was no longer just my business. However, I think it needed to happen. Olivia Carr, For the woman listening, what is a first small step? Olivia Carr, Definitely start to build. Hilary DeCesare, Hilary DeCesare, Welcome to Relaunch to a Rich Life. So good to see you.

[00:01:21] Hilary DeCesare, So nice to be here. I just got quite emotional and I got chills listening to that back. So thank you for that really beautiful, like the depth in that intro felt. I felt it. I felt it. Thank you. Olivia, from the very moment I met you, I had a strong connection. You have done so much and there's always the bumps in the road.

[00:01:45] And some of us have had not just bumps, but deep potholes where we're like, oh my God, is the car going to get stuck and is the tire going to like literally like come pulling off?

[00:01:57] And you know the question by now. I want to have you describe the most significant relaunch moment. And you've described this one, really, you put it out there on Instagram. And I need you to kind of walk us through what it was and the whys behind it.

[00:02:24] Gosh, like you say, there's been so many of those relaunch moments in my life. And my answer to that previously to this year would have been, you know, finding out I was pregnant at 19 with my now 25 year old daughter. I mean, that was a huge sliding door moment for me. It changed the trajectory of my path as a woman.

[00:02:44] However, having gone through that experience, I would say that this year, choosing to walk away from my own global brand, you know, we'd built it up to eight figures. And like you say, on the outside, it looked like everyone's measure of success. And there was just this knowing, this deep inner knowing in me that something is not right. This just doesn't feel like it doesn't fit anymore.

[00:03:10] Like whether I've outgrown it or it's outgrown me or we're just not compatible. Like, and I just couldn't reconcile with it. And it was, to be honest, it was like dulling my sparkle. I was waking up in the morning, not recognizing who I was anymore. I was feeling as though I couldn't speak my truth. And I was like, this is not worth it. And I have actually seen so much of your work and I admire what you do.

[00:03:39] And to paraphrase you, you often talk about a rich life, not being, you know, about money. And yes, money is important, but it's so much deeper than that. And so for me, I would say that this year, that was actually though the scariest, hardest part was choosing. And it was a choice, choosing to walk away from my financial security. You know, I still have my son at home who's 20. I have a mortgage, you know, all the responsibilities that a lot of us have.

[00:04:08] And in a lot of ways, people may have looked at that and went, one, that's crazy. Is she having a midlife meltdown? Maybe. Maybe. Or is she having a rebirth? Hopefully. But it made no sense on paper. Like, you know, I haven't talked yet much about this openly, but one of the things as a woman, I'm a huge advocate of is making sure you always have what I call like an emergency fund. I don't know what you call it in the States. We have the same. Same. Yeah.

[00:04:35] It's something as a woman that I'm passionate about teaching my children. And I'd been building my own little, I guess, I guess for these moments, for these moments that you don't know when they're going to come, that you need a little safety net. It was my, it was my parachute. So I had, I did have that behind me. So when I say I'm building now from zero income, yes, I haven't earned an income since the 4th of June. We're now in September. But I did have my emergency fund.

[00:05:03] So I'd given myself a, you know, about a half a year runway that I knew I could at least trust myself and take the plunge. Now we're coming close to the end of that runway. So I've just started rebuilding and launching officially sort of in the last week. But I probably would have done it without it. To be honest, I probably would have done it without it because for me, there wasn't really an option to keep going when I felt like my life didn't feel like mine anymore.

[00:05:28] And that's a really bizarre place to land, especially when, as you say, on the outside, I was living my old dream and I was definitely living many other people's current dream. So it's a very bizarre place to be. Yeah. Let me ask you, how long did you have silk? How long were you part of that? Yeah, 11 years. 11 years.

[00:05:55] So this is really interesting because I had a company for almost seven years. And the ending, my ending of this company came with a board member doing a Ponzi scheme and he ended up in federal prison. It was terrible, terrible. And I had built this up. It was my baby. I had a couple incredible co-founders. We had great teams. We were really, you know, it was a security company to keep kids safe online.

[00:06:23] I mean, all the elements of just meaningful work. And you had this company and you created your, you know, early to market with the silk pillowcases. And it took off, as you said, eight figures.

[00:06:40] When did the idea that there was something off, when did that start to really creep into your conscious thoughts? Yeah. Yeah. So I guess what I can share is I owned the business myself for the first nine years. And I was, I guess, in a lot of ways. I was ambitious and I had a lot of kind of growth a couple of years ago.

[00:07:10] And I really wanted to take the brand global. And I knew I couldn't do it without funding. So I made a decision. And again, I'm owning this part of my journey. It's all happening for me. But I made a decision to go out and seek some external funding a couple of years ago. And probably that was the moment where things shifted. And I think that would be the same for any brand. The moment you get an external, whether it's advisors, investors, a new co-founder, like it shifts the energy.

[00:07:39] It shifted the energetics of the business. And quite truthfully, it was no longer just my business. So I can look back now in retrospect and say, okay, probably the energy shifted a lot when I made that decision. However, like I say that and I sit here like thinking deeply into it.

[00:08:03] I think it needed to happen because this last two years for me as a woman, as a business leader, as an entrepreneur, as a mother, as a fierce female in the world, I have learned so much about myself. I have learned what my values are. I have learned how deeply I value my abilities to speak truth, to be brave.

[00:08:30] All the things that I don't think would have ever been tested if I had just continued through the world as a sole entrepreneur. I didn't have anybody kind of bringing these parts out of me that have always been there that were maybe lying dormant. Like I think I am the bravest power. Like my power was activated during that time. So for me, that's probably what shifted. Like if I think back, I remember feeling this like I'm in perimenopause.

[00:08:58] I remember feeling this internal, we call it rage. For me, I called it the mother of dragons. This dragon energy came alive in me and I had never tapped into that. I now realize that is my precious feminine power. I don't think I... Okay, but hold on. Yeah. Before we get to this dragon power that you have, I got to go back. Because something... Go for it. There are listeners right now that...

[00:09:25] And I know I beat myself up when I thought after the fact, how did I not see the signs? I should never have let this person come in and start to help with investment and then board seeing that, all this stuff. I really was like, wow. There were some errors of judgment that I had to kind of go through a series of forgiveness

[00:09:54] to myself and an understanding and a realization that the failure that I was perceiving, and you mentioned about like bringing capital in. And I had 63 people invest in this company. I mean, 63, you talk about losing like control of your baby. I'm like, whoo! I had a lot of people with a lot of different thoughts coming in. But I want to ask you, how did you...

[00:10:23] If this is really only a couple of years, the best part of this interview right now is you are literally in it. You are in the shift from old identity to your new identity. It is happening before us, everyone. This is so exciting. But I want you to go back and you've had this like power shift within you from that feeling

[00:10:51] of rage and oh my gosh, what's happening and losing control, losing the ability of what you'd built to that eight figures. How did you... How did you... How did you get through this? How did you like help yourself not go crazy and also feel like you're strong enough to move through it? Yeah. I mean, there was some pretty dark days.

[00:11:20] So the... When I finally sort of had a conversation with my team and I employed my family, so that was a really hard part. I had my mom who's in her 70s. She ran our customer service division. She's been with me since the beginning. I had my son. Anyway, so I wasn't just letting the team go. I was really reshifting the lives of my family, which was a huge burden on me. Everybody is doing so well now and it ended up being the best thing ever. But I had some really, really tough times around April this year.

[00:11:51] It's, you know, it's funny because the thing that cracked me open the most was something so seemingly insignificant. It was the day I was sitting in my office. You know, we've had all the energy of the team. I had crystals everywhere. There was just so much love in my physical space. It's where I spent majority of my life for the last decade. And I just watched everything get minimalized down to a couple of boxes.

[00:12:17] No one can prepare you for watching a life. And I imagine people go through this maybe when they separate marriages or they lose a loved one and things are really minimalized down to quite literally two boxes. And I just remember sitting on the floor. Everything was gone. And I was, I was in the fetal position.

[00:12:41] I was probably having like some sort of release, trauma, breakdown. I'm not sure. Grief. Actually, it was, it was grief. And experiencing grief from a business is also a really hard thing to explain to people because it's, it's not a physical human. It's not a pet. It's a business and it's, it's a material thing.

[00:13:08] But for me, it was like you say, it was a lot of my identity. I'd grown up in this business. My kids had grown up in this business. And I went into a really deep period, probably for about two months of grief. And I lost my grandfather. That's actually not that long. It's going to be interesting. And I'm going to do this. I'm literally going to put on my calendar to call you. Well, you and I talk now, so I won't have to like, but I'm going to put it on my calendar in January just to say you made this comment.

[00:13:37] Because I remember I thought, you know, I'm like the queen of bounce back and relaunch. And I'm just going to, you know, no problem. And I mean, it was a lot. And there, there was trauma associated with it. And I, you know, I, it was, it was an interesting process. And what you're doing, you're doing it before I did it. It took me almost a year and a half to really kind of launch into my next venture.

[00:14:08] I, I really, I leaned in my children, which is wonderful. You know, fortunately I had them and I was able to like put my energy and to build back and to lift up my tank and to do all that. But I'm curious because, wow, as you said it with your, your child's in it, your family's in it, you built it around a lot of different people.

[00:14:34] There is the weight of the world when you are responsible. And for those that don't have your family in it, we get it. There's the weight of the people who work for you and decisions that you're making around your business. And, you know, what you're going through, Olivia, it, it, it could be what somebody else is just in a very, in a different way. Right. And you said it's like a divorce. It's like a death.

[00:15:03] For me, it was absolutely equal or worse than my divorce. That's how bad it felt to me. That's when I think about it. And it, it, it was a lot. It was a lot. But, but I am who I am. I am the business leader.

[00:15:21] I am, I am able to talk and coach people at the highest level because of all the things that I had to go through in all of these relaunches. That's literally why I'm probably the CEO of relaunch, right? Because, hey, you don't become the CEO of relaunch unless you've had a lot of these.

[00:15:44] So when you think about you and you, you were talking that you were already starting to get that burnout feeling, right? But you were actually more like breaking. What was happening to you? Was it at this time after you had kind of begun the sale of part of your company or did it happen before? No, it definitely happened before.

[00:16:15] And I think midlife for me, my own lived experience of midlife has really been over the years, over the past sort of three to four years, I've noticed my tolerance really shift. I love that about me. But it's meant that, again, things I would have said yes to so many times in the past.

[00:16:38] Yes, I will continue to put myself on international flights, on a ridiculous travel schedule to build this thing for what really? I just was becoming less and less tolerable of almost performing in a non-human way. Like I felt like there were certain expectations, whether they were self-imposed or whether that's just my projection of how it felt.

[00:17:02] I really felt like there was this expectation to just put that down, shrink the part of me that is going through this huge physiological change as a woman. Just dial it down. Just put it in a box. It's just inconvenient right now for where we're headed. And so I already felt this isn't, this is not sustainable. This is absolutely not sustainable.

[00:17:26] And kudos, there are many women who continue building at the height of the heights, pinnacles. They get through this season and they keep going and I take my hat off to them. But for me, it just didn't feel like that was, that wasn't the race I wanted to be in anymore. And it might be deeper than that. Like we did some amazing things. Our brand, our DNA, our tagline was called doing good is in our DNA. So there was meaning.

[00:17:55] The things we were doing community were really meaningful, but I wasn't feeling the impact. It wasn't getting up in the middle of the night to fly to another country. That wasn't feeling like, it just wasn't feeling like this is it for me.

[00:18:12] Like, and when you stop valuing, you know, the financial success of something and you start looking at, well, measure of success to me means how I feel first and foremost. Like my health. When those intangible things start to become my North Star.

[00:18:36] There's a problem because the minute you bring, you know, partners in investors, even hotel partners, there's this expectation of me as, as at the helm of my business. That I will continue to grow this thing because we have global partners involved. And I just wasn't prepared to, to continue going at the way I was. So brave that you literally like, no, I'm not doing it.

[00:19:04] And this midlife journey for you has now turned into the midlife truth. So the bridge from where you were and the things that you weren't allowing yourself to see, to feel, to do with your health, with who you are, with the inner truth of who you are has now kind of percolated to the top here.

[00:19:34] And now you're really heavily leaning into the midlife truth and having these conversations. What about the conversations is really, we always do things that, you know, kind of help us get through what we are trying, you know, what we need to figure out and all this. What are you figuring out?

[00:19:57] What are you noticing by all these conversations, these witness conversations of hearing people that are, that's really like, hey, I needed to hear this and I'm starting to piece it all together. All, all us women want to know what is the missing puzzle piece here? Oh, it's so much deeper than that. So I think I set out probably thinking I would find, you know, similar answers to what you're expecting me to say.

[00:20:27] And I can certainly draw upon a lot of the wisdom that I've listened to. But I think honestly, over the last kind of six plus months of every week, listening to multiple women in these really deep, raw, vulnerable, or very brave conversations is just how much women need and crave to just be seen in this season of life. Not to be fixed.

[00:20:57] You know, a witness conversation is quite unique. You get to speak for an hour and no one is interrupting. No one's trying to hijack what you're sharing. No one's trying to make your experience their experience. There's so much power. And that's what I've seen a woman who gets this one hour. And it's more often the first time in a woman's life where she has been given space for an entire hour to just be seen and witnessed in her,

[00:21:25] what I call like in her fullness, whatever is alive in that moment. Nothing is scripted. She doesn't have to. There's no question to answer. Just I always open every conversation with just tell me where you are in life right now. What's alive? To me, the responses, it's been more the felt experience of seeing these women, like even a question like that.

[00:21:50] Like we walk through this world and especially in the workplace, there isn't space for this. And so really for me, I mean, we all know so much, especially in America, there's some amazing women doing really powerful things for midlife, like incredible things. And I know you've been involved in a lot of that.

[00:22:12] But for me, I really care deeply about taking that into corporates and saying, you know what, let me come in and facilitate space for women to just open the conversation about how they're really feeling. Psychological safety. Workplaces need to hear it. They have the policy. It is not lived experience. Like, that's my body of work now.

[00:22:38] Allowing these women to show up exactly as they are at work, not having to pretend and like I did, shove it down, quieten my voice, don't say the thing, don't be difficult. No. Blind for me seeing them going through this is hard. You know what you're doing? We like to call it, you know, relaunching into relevance.

[00:23:02] Because for so many women, they feel like they get to midlife and beyond. And it's like, how do we remain relevant? And that's what you're giving them a platform.

[00:23:16] And when you talk about, you know, what's alive, how many times have we heard people introduce themselves and they say, you know, hi, I'm Hillary and I'm the CEO of the relaunch. And it's like, blah, blah, blah, blah, blah, blah, blah. And maybe, you know, there are a few that are like, oh my God, I'm like, you know. But a majority, you're just saying the words.

[00:23:45] And, you know, I do things called connection calls. And I go right to what is the thing that you're fired up on that you're working on right now. Not all the other crap. I don't want to hear about all the other, the blah, blah, blah, blah, blah. It's like, what about what you're doing today? Light you up.

[00:24:08] And what I'm hearing from your conversations is that these conversations are just like, you're like fueling your soul. You're lit up. You're fired up on these conversations. And so where do you think you're going to, you get them into corporate, but what ultimately, Olivia, are you hoping to do with this?

[00:24:33] What would be that like future version of you that is speaking on a platform to an audience? And what are you delivering at that point? I feel like this might seem like a little like unicorn pie in the sky.

[00:24:54] But I think for me, what true success looks like is for, I say women because I work with women, but truly I have a son and it's equal for me. It's for humans to feel brave and safe enough to speak their truth, you know, their own truth. So that's not projecting on, hey, I think you're whatever. No, my truth is this. I'm really struggling.

[00:25:22] Or, hey, you know, when you asked me to do that thing at work, I'm not sure I really understood. Like, can you just guide me? Like, the truth is that I'm questioning myself because I keep forgetting words in meetings because I'm going through perimenopause and I'm feeling judged. And like, and I just want to be, I just want to be acknowledged in that. Like, I want a world where it is safe to go to work and be your true self and actually be able to speak truth.

[00:25:50] That seems really like, oh, but we should just be able to do that. I can guarantee you in all of the witness conversations I've had, 14,000 women every year in Australia in midlife being pushed out of the workplace, labelled as too difficult. We have stats and research on this. We do not, over here, we do not yet live in a world where it is psychologically safe to turn up to work and share the truth of what is alive, of what is really happening in your world.

[00:26:20] And know for sure that your job will be safe and you will be supported through that. And for me, yeah. Hold on, hold on. Because I'm just, I'm going back to, and again, I, my, my foundation came out of Silicon Valley, right? High tech. A lot of men.

[00:26:40] And I'm just, and I'm like, okay, you're coming in with this utopian version of like, you know, all of these great things and really being able to talk the truth. How do you get men on board? Hmm. For me, that's like, that's a really interesting one because it's probably less a gender issue and it's definitely a systemic issue.

[00:27:08] But I spent months banging my head against a brick wall being like, the system is broken. The system, you know what? The system in my belief is not broken. It's exactly how it was designed. So to say it's broken means that it can be easily fixed. So I'm less about let's fix the system, which, you know, in my lifetime, that's a dead end for me, I believe.

[00:27:32] And it's more around how can we create a new environment inside a system that everyone, men will also agree, is broken. You know, I've spoken to enough men in corporates who are going through just the same amount of pressure as you or I. So it's a system, not necessarily a gender.

[00:27:52] But to answer your point, I think reassuring men that as women, we know that when we say something needs to change for women, we're actually not saying that men are the problem. We absolutely need men to champion the same things that we're asking for, which is really equality at the end of the day. It's it's look, it is a huge task, which is why for me, I'm trying to create a ripple. I'm trying to be brave.

[00:28:21] I'm not trying to be fed to the lions alone. Being there, done that does not work. Yeah. So let's let's go to because some of these conversations are very large. Let's go to something practical for the woman listening who recognizes that, you know, the quiet you described, the sense that her life doesn't fit anymore. The idea that I can't say I call it the I'm done moment.

[00:28:50] I'm done. I can't keep doing this. What is a first small step? Not the whole reinvention, but just the first step that somebody could take. I think for me, it's what we spoke about at the beginning. Definitely start to build some sort of exit fund, emergency fund, a pivot fund, make it fun. If you don't have the means to necessarily do that with your income right now, I'm big on like flip things.

[00:29:20] Like what have you got in the house you can flip? Because truly every five dollars you can put aside, it really starts to add up. So let's not try and say where are we going to find $50,000 in one go. Absolutely. That won't make you feel good. But look around and start in your own home. Start with your own skill set. Can you put something on Etsy? Can you? I don't know that you guys are having this moment with a lady, Jessie Jean in America, who's all online talking about flipping furniture. Like, can you go to garage sales?

[00:29:48] Can you like there is a level of work that needs to happen initially to get you to that place where you can pause. If you want to be able to do it in a way that, because what we don't want in Australia, the largest cohort of homelessness right now is midlife women. A lot of these women are people leaving either domestic violence marriages or being pushed out of the workplace without an emergency fund.

[00:30:14] I'm not advocating for putting yourself in higher risk or danger. But just try and get yourself enough security. You know, maybe do get a second job. So many like opportunities now online. And I mean, gosh, I look at my mom who was in her 70s and, you know, thinking she was never going to get employed again. She went for two interviews and landed both the jobs and one of them just on a phone interview.

[00:30:41] So hey, my bonus, my bonus mom right now, 85 years old, goes into work every single day. So never, never stop believing there is something you can do. So if someone wanted to be a part of the witness conversation with you or just start really being honest about their own version of this, where should they go? So the easiest is my website, which is just my name. So oliviacarr.com.au.

[00:31:10] There's a page on there where you can pre-select and book your own time to have a conversation with me. And LinkedIn is where I do all of my writing around midlife. And I share some, I share a lot more than what we can share today about things that we just sort of touched on that just get women thinking. And they start conversations in their own workplaces. And that is often where you find your people.

[00:31:37] I think my other quick thing that I would mention is aside from building an emergency fund, make sure you have some really powerful women around you. And I think that's where your community, communities like yours are so important in this season of life. Like do not go this alone. Absolutely do not go this alone. Olivia, thank you.

[00:32:00] Thank you so much for being willing to actually just talk about the version of you that you like were willing to walk away. And I think the fact that you're doing it in public, you're doing it, you know, on Instagram, you're doing it. People need to hear this. And for those listening, I want you to sit with this.

[00:32:22] So much of what we're taught about success stops accounting for us right around the age Olivia is describing, right? The woman who keeps growing aren't the ones who push the quiet down. They're the ones who get honest about it. We do it and we do it out loud with someone, you know, who won't flinch like an Olivia, like, you know.

[00:32:47] And the room becomes so important, the women that you're surrounding. So for those listening this week, if this and there's a version of that quiet in your own life, find a person that you trust. Say the truth. Say the things out loud that you're like, oh my God. You know, we hold things back. And then what happens? We blow, right? And find Olivia on Instagram.

[00:33:15] We'll have all of the links in the show notes. The Midlife Truth. And you can talk to her more about the witness conversations, where the project is headed next. And don't forget to subscribe to Relaunch to a Rich Life so that you don't miss episodes like this. And if this one landed for you, send it to a woman that you know needs to hear it. And we will be back again next week.

[00:33:45] Take care. All right. Your next level is waiting. Thanks for tuning in. This is amazing what we're doing right now. ReLaunch to a Rich Life If today's episode sparks something in you, don't keep it to yourself. Please share it. I'll tell you more later about how that actually helps you have more success yourself.

[00:34:12] Subscribe so you don't miss one episode. Let's create unstoppable momentum together. So until next time, keep relaunching, keep rising. And remember, it's go time.