233: On Sensitive CEOs and Building a Soulful Business with Rose Cox
8 Dec 2025 · 34 min
Podcast episode (Oct 17, 2023) of The Freetime Cafe featuring Jenny Blake interviewing Rose Cox about leading businesses as highly sensitive people. Topics include defining the Sensitive CEO, boundary-setting, managing small teams, pausing projects (Rose pausing her Sensitive CEO podcast after ~1 year/50 episodes), intuition in business, and practical accommodations (client days, device boundaries, sabbaticals).
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This is your time. How can we earn twice as much in half the time with joy and ease while serving the highest good? That is our guiding question here at the Freetime Cafe, your home for heart based business. I'm your host, Jenny Blake. Join me for conversations with authors, friends and fellow business owners as we explore ways to free your mind, time and team to do your best work. Now onto today's show.
Welcome back Free Timers. I am so delighted to be here today with Rose Cox. She's the founder of the HSP Business School and host of the Sensitive CEO Podcast we met I have to give big thanks to Dave Asprey, who had me on his show when FreeTime was just launching after we met in an elevator at a dinner event at the TED Conference of all random things. And Rose and I have been in touch in all kinds of different ways ever since I've been a guest on her show. She's a BFF alumni and she is just the most wonderful, joyful person. Her unique blend of soul science, systems and strategy combines 20 years of her experience in the fields of online business, hypnotherapy, coaching and psychology to help her clients build a successful and sustainable business aligned with their energy and their soul. You can see why we're fast friends. She works with highly sensitive people, empaths and introverts who have amazing gifts to share with the world but struggle with both the business strategies and the mindset to fully step into their own. Rose, welcome to the show.
Oh, thank you Jenny. It's such an honor to be on Free Time. I've been an avid podcast listener to your wonderful show for a while now and I think I Told you last year you were my most listened show in 2022.
I am so honored and I never even saw those Spotify stats. So just knowing that that was true for you and there was a little card you got, I mean that's the honor of a lifetime. And we decided to do this conversation as a kind of crossover coffee talk, catch up because you shared some big news with me before we hit record about your business and your projects. But before we get there, I just wanted to ask you if you could share with free time listeners. How do you define a sensitive CEO?
I guess my definition of a sensitive CEO is to run our business in a way that aligns with our sensitivity. And when I say sensitivity, I'm not using a term that defines us as being weak in any way. I think it's just honoring the HSP trait that I know many of us have and doing business in our way and making it work for us, having the right boundaries in place and really honoring our sensitivity in an aligned way.
You mentioned boundaries. What do you think that sensitive CEOs with struggle the most? And of course, as I'm asking you that, I'm thinking, oh, let me count the ways.
One of the biggest things is people pleasing and setting healthy boundaries. Because as people pleasers, obviously we like to make everybody happy, but in the long run we're not making ourselves happy and obviously other people. So by setting the healthy boundaries, we're really protecting our own emotional well being and also understanding the limits to balance the sensitivity with self care so that we don't become drained in our businesses.
On the subject of being a sensitive CEO, I feel like one of the things that people don't talk very much about are the challenges of managing people, even if it's contractors, where as a sensitive person I feel more overwhelmed by managing people or navigating their emotions or their motivation or any of it. And it's not just people pleasing in terms of clients, it's a real sense of it requiring an unnatural amount of energy for me to work with a large team. And that's probably why you and I connect. Because I'm all about delightfully tiny teams out of necessity in a way, because I often feel too sensitive around the people aspects of the business. Have you seen that with any of your clients?
Yes, definitely. When we're working with other people, we want to do the best by them, obviously. But personally for me, I have a very small team. I only have a podcast editor. Currently it's my only team member and I'm always really mindful of, oh, I hope that it's not too much for him to edit on this show, and I hope that I've made sense or if I've had to cut something out. And I feel really guilty. I don't think I make a good manager at all. And I remember an episode on Free Time that you did, I think. Can't remember who your guest was now, but it was wonderful, wonderful giving permission about managing a team or even having that small team and really honoring them as well.
I can relate to what you said of feeling bad sometimes with, let's say, certain assignments, or I get really sensitive to the communication, like, ooh, there's a punctuation mark shift. Are they mad at me? Did I do something wrong? Am I being overbearing? Am I a bad client? If they're having me on as a client, even if they're part of my team, it's like, oh, it's just this tiring narrative around it. So before we hit record, you were sharing some news with me that you've decided to pause your podcast. And I maybe wouldn't have made the connection if you hadn't said, you know, in keeping with being a sensitive CEO, I'm going to pause this project for now. And I'm always fascinated by people who give themselves permission to stop doing something or to pause, even if you don't know when you're going to resume. And so I'd love if you could take us behind that decision and where you're at with it.
It's something I've been thinking about for a while, and I only very recently decided, actually only last week. I've just been feeling really tired this year. There's been a lot going on, and I know I've been running my podcast now for. It will be a year, actually, this coming week. It will be a year. And I've done around 50 episodes, so pretty much one episode a week. And I've been pretty vigilant about keeping that schedule, and I just feel I'm ready to have a bit of a break from it. As I said, I've got a podcast editor, so I'm not doing that side of it, but there's always the other bits to do and then the energy of getting on a call, even I find it draining sometimes.
So I decided I'm going to pause it for a bit. I don't know for how long. Could be a year, it could be longer, it might only be a couple of months. Because something I do love about the podcast, which I know we talked about when I interviewed you on the Sensitive CEO show a while back was it's such a wonderful way to meet people and it's so nice to connect on podcasts and get to know our guests. So I know that I'm going to miss that side of it. But I'm excited about pausing, having the break and I'm also pausing a little bit from other work. I think the decision. It seems funny saying this, but I'm going to be 60 next year, which sounds kind of weird because I don't feel 60 at all. Well, I'm still 58, but it's the end of next year, but I just feel it's time to slow down a little bit. I've always been very driven. I've always worked pretty hard and I feel like chilling out a bit and going down to the beach a little bit more often than I do and doing more yoga. And I'm actually just starting a yoga teacher training next month, which I'm very excited about. So there's a few personal projects coming up that I'm going to spend more time on.
Well, happy early birthday, even if we're a year and plus out. It's funny, I have a lot of friends who are turning a big decade this year and maybe some next year, but multiple friends of mine, I'm turning 40, maybe even by the time this goes live in October. Another friend just turned 40. A handful are turning 50, a few are turning 60. And it's so interesting, just the checking in that we do with ourself at these decade markers, because on the one hand it's somewhat arbitrary, a number or a birthday, you know, but on the other, it's like a really interesting time to take stock of the previous cycle, the previous 10 years, and then look ahead to the next. Was it hard for you to make this decision about the podcast and slowing down with some other work? Did you have any anguish or uncertainty about it, or have you been pretty clear for a while?
Definitely a lot of anguish and uncertainty. Yeah. I've been questioning, am I doing the right thing? Should I be pausing it now? It's just getting momentum now. I'm getting a lot more downloads, obviously, because it's been over a year or just coming up a year, and part of me feels guilty like, should I be doing this? Should I be stepping back now when I have put so much into it? So yeah, it has been a hard decision, but I've been doing a lot of journaling on it, a lot of reflection on my walks, and it just Feels right. It feels really right to be doing this right now and having this pause.
And have you designed yet what you're going to be doing, like, once things pause? I had an interesting conversation, maybe you heard it with DJ Dodona, about sabbaticals and how sometimes those of us who are maybe recovering overachievers, we think we need to actually get a lot done during the sabbatical or, oh, I'm going to ramp these projects down, but I'm going to write a book. And that it's actually hard to let ourselves just go into a liminal state and do less. So I'm just curious how you're approaching this. Do you have any goals for this next phase or are you going to let it. See where it takes you?
It's interesting you mentioned that episode because that really helped me. I remember listening to that on one of my many walks a while back, and I remember thinking, oh, you always have the most perfect guests when I need it. And I do remember that episode. And so much of it was, yeah, yeah, I relate to that so much. I don't have any plans. It's funny, I have even the last few weeks. My husband's actually in Europe at the moment. So while he's traveling, I'm thinking, well, I can step back a bit too. But I haven't. I haven't managed to have a break at all myself and spend less time away from the computer. So I guess one of my goals is to spend less time at my computer and out of my office or even if I took the laptop to the beach, just to have a change, just to go somewhere different and have a break.
That's a great goal. Just less time on the computer. I second that. I know sometimes I only work on my computer. I don't watch content, I don't procrastinate on any procrastination sites. It's just for work. And when it's closed, it is closed. Like, I can't stand to look at it because I do have an office in the apartment that we're in now in New York City. But also the computer is an office. Like, the computer represents work. It's one of the ways I've always created a little bit of psychological separation. And I actually get quite antsy if people text me about work on my phone because I'm like, no, no, no, that's not the work device. You know, I know for a lot of people it is, but feels so good to close the laptop sometimes.
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I'm curious. After a year of podcasting, what are the big themes you noticed? So you did an episode a week. You connected with all these people. What stood out to you or what messages would you want to kind of excavate from all of that? For fellow sensitive CEOs, the main messages.
From my guests would be doing business in a way that serves you as well as your clients, but setting those boundaries. I know we've talked about boundaries, but that seems to be such a big theme with a lot of people. And the other one would be working with fellow sensitives. I think a lot of the people I've interviewed, their niche market seems to be working with other HSPs and introverts and empaths and working together because we understand each other is such a nice way to run your business rather than working with people who don't necessarily have the same values or feel the same. Think the same, think it helps. And I know that a lot of my guests have businesses around the HSP trade.
When did you launch the HSP and sensitive CEO brands? I would imagine that's been a journey for you too, as I know it has been for me of putting that out front like I call it heart based business, but my private community used to be for side hustlers and solopreneurs and creatives. It was like for everybody, you know. And then at some point I got clear it's for heart based business owners. And so much shifted when I did exactly what you're saying. But I never thought about it through this lens of putting out the beacon to work with fellow sensitives or fellow heart based people. But it is such a game changer. It's like going into warm water after a cold lunch or something.
I love that analogy. That feels so good. I totally Agree. I know I used to work with anybody when I did my hypnosis and coaching and even when I had my web development business. And sometimes it would great. I think sometimes working with people that didn't have the same, I guess the same nervous system in some respects it sounds funny, but there was something when I launched the HSP business school and when I put it out on my website that I was only working with highly sensitives and introverts, it felt so good, as you say, and getting into warm water, it felt so right. And even at the time I realized that most of my clients were actually HSPs and I was able to share the trait with them because they didn't know about it. But once they did, it really helped them to understand themselves more and get more of an understanding on why they feel or think a certain way.
That's so interesting that you are already attracting that and it makes sense this piece around boundaries and doing business in a way that serves you. I keep coming back to it because I think one of the things that gets in the way and I know it certainly did for me a little more in the past, but I'm sure it still shows up in certain ways, is that a lot of times my first impulse is to say what's wrong with me? So if I'm overly sensitive or I've been told my whole life you're too sensitive, you're too sensitive. And so sometimes I don't always know which boundaries to set and then I'll see or hear of a fellow business owner having some really strict boundary, which is now what I've tried to do even in writing free time and sharing what I eventually got to in terms of how strict I am with my schedule. But sometimes I need to hear what someone else is doing to go what I can do that that's possible. For example, coaches who used to have a no money back if you cancel within 24 hours like that always felt so bad to me. And I always felt like even if someone has a crisis an hour before our call, I'm not going to take their money. And maybe we're not meant to have our call on that day. I always saw it as a bonus hour for me. It was usually never a problem. And of course if someone was going to abuse a policy like that, that would not be good. You would talk to them about it. But it's just interesting to me the self talk around this before we even get to oh yes, you have permission to do business in a way that serves you. There has to be a piece of recognizing it's okay to have these needs or to have these extra needs or extra sensitivities around some of these things.
That's so interesting you mentioned that about those strict policies about no money back. And I'm totally with you. I always put the clients first. And if there was something that came up, you know, an hour before, then, yeah, I would give them another call. I wouldn't take their money and it wouldn't feel right. But then I guess if they're pushing boundaries, then, yeah, that might be a different story. I love the idea. When I started out with the hypnosis, I always used to sort of open up my calendar. I worked Saturdays, I worked every day of the week. I didn't work Sundays, but I loved the idea of just having client days. And I didn't know that you could do that. So I totally changed. I think a year into it, I took Saturdays out and I took Mondays out. I think probably six months after that. And then I took Fridays out. And now I only work with clients one day a week. I just have that block. But it was seeing what other people do and it was thinking, yeah, you can do that. You can just have one day for clients or two days for clients and you don't have to have your calendar open all the time. And that was a bit of an eye opener for me and it helped me to set clearer boundaries.
What other creative things have you seen clients or friends set up in their business to accommodate their sensitive nature?
So the client days and then also days for podcast interviews and then having a total day off. So having a Monday off either for self care or for working on your business. And I generally do Fridays is generally my admin day. And just working on the business or doing more yoga or coming to the beach more, it really depends. I know a coach that I worked with a while back. She would have a week off every month, which I tried to implement. I got as far as blocking the calendar out. So I would not take calls or clients or interviews, but I would still be at my computer. I still found that hard to have that week off. And I also know people that have a month off every quarter, which I really like the idea of too. So moving towards things like that is definitely something I'm going to be moving into as well.
What about the piece of being a business owner and a sensitive CEO because it's built in right there to the title, just around the day to day uncertainty of running a business. And now I'm not saying all sensitive CEOs are the same. I mean, some introverts or sensitives might be super creative and kind of thrive, creating something from nothing and being internal and so solving problems. Like, there's a lot to like here. But I'm wondering from the mindset piece overall of just the challenges and pressures inherent to running a business, what themes that you see that are unique to sensitives in general? Knowing that we can't just say for everybody.
Creativity, definitely. I think by nature we're very creative and.
We have that, I guess, that depth of processing, that's one of the traits that Elaine Aaron talks about, the lady who coined the term hsp. And I think having this depth of processing makes us really want to dive into topics, whether we've created these topics or topics that we're really interested in. And of course, curiosity is a huge one. And love of learning. I know so many HSPs that I talk to and spend time with. We absolutely love to learn and love devouring everything we can about a certain topic and reading, listening to podcasts, doing online courses, and I think it's a beautiful sight for us.
Aren't podcasts the best? Because it's like you get to hang out with a friend, but there's no talking involved. You're just quiet in nature, walking.
Sometimes I'm listening to a podcast, and especially yours, and I just burst out laughing because I just think, yeah, I love that so much. And it all resonates. And as you say, it does feel like you're talking to a friend. And so many guests that you have on, I feel like I know them. I feel like I know you so well. But even your guests, I feel like that I know them because they all resonate so much.
I love that. Yeah. And it's like our brain probably doesn't know the difference in a way. I mean, of course we know that in person, connection is wonderful. And if you're someone that gets overstimulated, your mind just doesn't know the difference. Like, we could be on a walk with two friends and you're mostly in that quiet observer mode and. Or be sitting at coffee with these two people. So I can totally understand and relate to that. Like, I love listening to podcasts. I think that's why I love creating them so much because they, oh, they're just so wonderful and relaxing. And I don't have to tell anyone who's listening because you're here listening.
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You recently did an episode speaking of your podcast on intuition and I feel like this is a big gift that everybody has, but there is something about being empathic, highly sensitive, even introverted that I just think intuition is a superpower that comes out especially strongly for these types. I would love to hear your take on this and how you've developed your intuition over the years.
I love intuition. I used to think it was something magic that it wasn't available to all of us.
Me too, by the way. I used to think only special people had that.
Yeah, so I thought it was a superpower. But then even before the hsp, before I understood more about the HSP trade, I realized it is available to anybody who really has an interest in it and wants to hone it. But I guess ways that I've really learned to develop it further is Meditation has been a big thing for me and I have been meditating for many years. But recently I've been following a guided meditation. I used to do TM Transcendental Meditation, but I've been following guided meditations to speak with my higher self. And it's such a wonderful way to connect with your intuition and really understand what it is, what it is deep down that you want. And it can even help to answer questions, you know, if you're sort of having decisions. I even talk to my higher self about the podcast, should I pause it or not? And getting those clues, getting those nudges from Some people call it universe, some people call it higher self. There's so many ways. I think journaling is a wonderful way as well. I do a lot of journaling and even being in nature, just walking, being around.
Trees and just the ocean, just being in nature and absorbing everything around you and looking up at the sky. Sounds a little bit fluffy when I talk about it, but there's just something about having that nature, being surrounded by it. And I'm very blessed. Where I live, there's A lot of water and a lot of forests around us and national parks. I do spend a lot of time outside when I'm not in my office.
Yes, exactly. We'll be spending more time out there.
You've heard me probably say it on the podcast. One of my gripes with the business arena is that they say, like, intuition is not a strategy and it's all about the data and the numbers. And of course, my response is intuition is data. It's just data of a different kind. What's your take on the role of intuition in running a business?
I think intuition helps us with making decisions, like important decisions. And I think it's a huge part of running a business. You get a sense with your intuition. You get a sense with not just about people, but about if you're looking to develop a product or something in your business, you can get a real sense with something that really lights you up. Or if it's just something that might look good on paper, that's the data. It's much more important to follow your instinct and something that makes you feel good rather than something on paper that might say, yeah, that could be such a lucrative product. But in the long run, if it's not something that is going to make you feel good or make others feel good, then it kind of defeats the purpose.
I haven't read this great tip. I can't remember if it was in Tribe of Mentors or Tools of Titans, one of Tim Ferriss big books. I love them both. And there's this guy who asks his team when he has his week full of meetings or if someone's requesting a meeting, they include that person's photo. And so especially when somebody was requesting a meeting or he didn't know them, he would look at their photo and almost get a vibe check to see it intuitively if he wanted to meet with that person or not. I thought that was really interesting.
Oh, I love that. Yeah, that's very interesting. I love both of those books as well.
Okay. You know, because you listen to the show that the last question I always ask is if you could give fellow business owners permission to do something differently or drop something altogether, what would it be?
It's so funny. I was listening to the two episodes recently. It was two parts, wasn't it? So 20. So there were 40 permission slips. Is that right?
Yes. The Big Bonanza episode. Yeah, for episode 200 and 202.
Oh, I love them. Love them. And I was thinking, how am I going to come up with a different permission slip? They've all been done.
But one that I would really love to share is to remove email and other social apps from your phone. And it might sound a bit scary to some people, but I know you were talking before, Jenny, about using your phone, just not for business. My belief is to not have email on your phone, to not have any social apps on your phone and just check an email on the computer. And if that sounds a bit scary for some people, then you could always start off just removing apps on the weekends and give yourself permission to totally step away from your business on the weekends. And then you can build that up slowly, take it off at night. And it's easy to put apps on and off your phone if you feel you need it during the day. So that's my permission slip.
That's a good one. I know it's hard to cope with something new now that we've had over 200. You know what else you just reminded me now, at least on the iPhone, there's a setting that if you're in different modes, like focus mode, sleep mode, you can take the number off of the apps of how many notifications. So whether it's email, social, any app that has a little number that shows you how many unread things you have, which are so annoying, so you can just take them off either forever or during different modes on the phone. And I really appreciate that. Like, I have a mode that I set up called vacation mode, and it's like all the numbers go away. It's a beautiful picture of this lake at Central park with trees and the fall foliage, and it's like just a calming backdrop photo, different lock screen and no numbers on the apps. And even that is calming.
That sounds beautiful. And I love that I don't have notifications. I have no notifications at all on my phone, so I never get those numbers.
And I'm just so happy it's that serendipity popcorn at work. Because who could know that? I met Dave, serendipitously that you've been a part of his world for a long time, but living across the planet from where the two of us met, which was across the country from where I live, you know, and it's just so fun to see these kernels pop and this connection that you and I have made and to see it continuing and really becoming something is. It's so rewarding. And I love the work that you're doing, and I can't wait to see what this pause brings for you and this sabbatical and slowing things down. Pausing the podcast. I know that whatever emerges will be incredible and I just can't wait to follow along.
Thank you so much, Jenny and I just really appreciate this connection that we've got. It's just so lovely to connect with you. I feel very blessed.
Me too. Well, thank you so much, Rose. Enjoy your time off the pod and listeners, thank you so much for being here. Have a beautiful rest of your day everybody.
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