Hey BOSS Ladies

 How Collaboration Protects Your Energy and Grow Your Business with Holli Howard

• Candice Dorsey

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Hey Boss Ladies,

Welcome back! In this episode, I sit down with the incredible Holli Howard, founder of Positive Living Coaching, a BOSS lady who has pivoted not once, not twice, but three times to create a purpose-driven business supporting women healing from childhood trauma.

We get real about how trauma impacts self-worth, the importance of volunteering before making a major career move, and how collaboration can protect your energy and scale your business faster. Holly breaks down what it means to shift from corporate structure to CEO mindset, how to work in your zone of genius, and why hiring help isn’t just smart, it’s essential.

We also talk about our own collaboration journey (yes, the journals, the courses, the design magic ✨) and how partnerships like ours help bring bold visions to life. This one is a full-on masterclass in doing business with heart, alignment, and power.

Grab your notebook, you're gonna want to jot some of this down.

💡What You’ll Walk Away With:

  • Holli’s journey through 3 powerful career pivots
  • How volunteering can open unexpected doors (and job offers!)
  • Making the leap from side hustle to full-time CEO
  • Structuring your business to serve YOU
  • The importance of energy-protecting collaborations
  • Why you should only operate in your zone of genius
  • How trauma-informed support creates massive ripple effects

🔗Connect with Holli Howard:

💼 Ready to grow your network, amplify your voice, and actually plan collaborations that move the needle?

Join us at the next Hey BOSS Ladies: Connection + Collaboration Hour
✨ Register here → heybossladies.com/event

Let’s build relationships that build your business.
Now’s the time. Let’s BOSS UP. 🔥

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Follow Me on Instagram: @csdorsey_hello
Listen on Apple Podcast | iHeart Radio

Hey boss lady. Welcome to the Hey Boss Lady podcast. We're real conversation, powerful connection and intentional growth collide. I'm your host, Candace boss, founder, community builder, and your biggest hype lady around here. We don't do surface level. We talk strategy, systems, success, and the real stuff that happens in between. Whether you're tuning in on your morning walk during that client work, sprint. For a late night hustle session. I'm glad you're here. Let's get into today's episode and boss up together.

Candice Dorsey:

Hey, boss ladies. Welcome back to another episode of the Hey Boss Ladies podcast. I have the boss lady herself, Holly Howard, who is the founder of Positive Living Coaching. Hey Holly, how are you doing today?

Holli Howard:

It's so nice to be here. Thank you for having me.

Candice Dorsey:

Yay. I'm so excited. So tell everyone who you are and what you do.

Holli Howard:

So my name is Holly Howard and I'm the founder and coach at Positive Living Coaching. I basically focus on women who've experienced childhood trauma. Yes. And we're gonna definitely dive into that. So tell us, how did you get to ball status and what was that journey like for you? So I call this my third and final career. I I. off as a hairdresser for my first, 20 Of my career. And then I did end up going into child welfare. I hadn't gone to college for one semester. Long story. But anyway, I ended up going to college in my thirties and I, I loved hairdressing. It was a great career. And then I decided it wasn't my full passion. decided I wanted to go and get an education and go into child welfare. So in 2012, I started my child welfare career, and that was, that's truly where my passion is. I have a heart for that. I there's a lot of things that I could have done after graduating from college and I had the benefit being able to work in child welfare. I did a little bit of volunteer work to make sure it was the jump that I wanted to make. And then I did, and I had a year career in child welfare. During the time that I was in child welfare is when I started Positive Living Coaching. And I did have a couple different things that I focused on, but ended up really making this a full-time thing this year. It's just been. It's been really nice to be able to focus on my own. My child welfare was my second career, and now I call this my third and final career.

Candice Dorsey:

I love it. Yes. I'm gonna say, wait for just a moment'cause you did. Mention about volunteering before you actually started. So I want to point that out because sometimes we get into, we jump into something and then we jump into it. We doing it, we're like, this is not what I want to do it, but I like the fact that you actually volunteer first

Holli Howard:

yeah.

Candice Dorsey:

just to get your feet wet into doing it. And then you say, okay. Now I'm gonna go ahead and make the chef of doing it. And I think that's very important because when I started any position that I wanted to do, I dabbled my toes into it to see if I wanted to do it. And then when the position came up, then I'm like, okay, I'm going to apply for it. So I think that's very important because oftentimes we just jump into something and we find oh, this sucks. I'm going somewhere. You get what I'm saying? Yeah.

Holli Howard:

And I had a career that I loved. I was supervising the spa. I worked at a beautiful resort hotel that's right on the Gulf of Mexico. And it was just such a beautiful, wonderful job with great people. And now all of a sudden I'm going to go and do something totally different. I'm like, oh, what if I regret it? So luckily they, they have a guardian ad litem volunteer program. So I went and I did that for eight months. And the other benefit of doing that. Not only did it just say to me, yes, this is absolutely something that I wanna do, but when I went to go interview for that position, people knew me already. So that helped with getting a job in that field too, because they already knew the quality of work I did. They already knew my heart was in it. And so it just became a easy position to get.

Candice Dorsey:

Oh, that's pretty. See and it helps so much especially when people know you, that is that helps a whole lot, especially the hiring manager.

Holli Howard:

Yeah

Candice Dorsey:

so tell us, what's one pivot that surprised you the most and taught you something game changing about yourself?

Holli Howard:

So that was actually just making my most recent move. I, there was some things that, that happened. Again, I love that career. My heart is in that career. We had such a amazing team for so long, and some changes happened last year that I just didn't resonate with anymore and I decided, I just need to go and focus on something else. And I did start looking for other jobs and I said, wait a second. I have this business that I'm doing on the side that I didn't give. I did a lot of, a little bit the years from 2018 to this year. Again, a lot of, a little bit, and I ended up saying, wait a second, I have my own business. I give what I give to these past two careers to my business, that will be. All I need to do. So that was the biggest pivot, having that aha moment and, taking that chance of leaving and just putting it all into me. I think that's something too that, that so often we do, if you have a plan to work out, oh, I'm gonna walk on the treadmill today. if you don't have that set appointment, maybe you do it, maybe you don't. But if I was gonna meet you for a walk at 12 o'clock today. I'm gonna be there'cause I'm committed to that other person. So I'm like, I just need to make sure I put my own self in that role, put that business as this is something I'm gonna focus on and this is what I'm gonna give my all just like I did to those other two agencies I worked for.

Candice Dorsey:

I love that because

Holli Howard:

Yeah.

Candice Dorsey:

we do that shift, that focus for our business, we are so used to like. Their ways and their structure, and we get accustomed to that. Like we get accustomed to the things that we need to do for someone else. But then when we shift over to us, it's I don't know. It's kinda oh, but if we think about, okay, this is how they would structure and I was able to get dah, let me shift that over to my business and set it up not the same way, That structure and have those things in place. Have those things on my calendar, have those appointments because. Like having that mindset that, this is for me and I need to get this done. Is my business. I can run it how I want to, but I can still have some structure and format in place.

Holli Howard:

Yeah.

Candice Dorsey:

I like when you brought up that analogy I'm supposed to go, I need to go walk. I'm supposed to go walk, but if I have that appointment set to walk with someone, then I know I'm gonna be there. And that's the mindset we definitely need to have. When it comes to our business, and it's hard for me, so that's why I brought that up.

Holli Howard:

Yeah, and putting protocols in place,

Candice Dorsey:

Yeah.

Holli Howard:

putting appointments in our calendar, really structuring. I am writing a book and Fridays are my days that I write that, that I focus on the book. I try to, other times in the week too, but Fridays are my day where that's just gonna be my whole focus. Nothing else.

Candice Dorsey:

I love that. Yeah, I definitely need to put some of that on my calendar. I'm putting everything else on my calendar, but except for what I need to do in my business as this, as a CEO. Yeah.

Holli Howard:

absolutely.

Candice Dorsey:

All right, so let's dive into how collaboration protects your energy and grow your business. Can you talk more on that?

Holli Howard:

absolutely. And that actually, you bring up what has pivoted for me, another pivot that I had that was just. I am so grateful for this and I'm gonna be directing this right at you, Candace, because we have just for the audience, we have a wonderful lady, Dr. Abigail Joseph, that we go and do some events with. She has rubber deck sessions where we get to collaborate together and bring ideas that we have and be able to untangle those ideas. And one of the things that I brought to that session was design work. I often joke with her, and now you've seen it a lot, that I just don't have a creative bone in my body. And that sounds weird being a hairdresser, but I was even my hairdressing, I was more with methodical I dresser not a creative hairdresser. so when I was talking about. Some things that were just holding up on, getting some courses that I had written, I had done. I, that was my passion. I loved doing it, but now I need to put it on my website. I need to have that design with it. I just was stuck because it's not my way. I not good with Canva. Abigail said hey, we have somebody right in here that can help you with that. And that's when you and I started working together. That first step was really just getting the website up because I had revamped it from what I had been doing. I had a little bit of a change of focus in, not only did I get the thumbnails for the website, but then I'm like, oh my gosh, these are so pretty. And I wanted to expand it and make journals from them. So I have. This beautiful inner voice reset method journal that this design is 100% Candace. This open. If you look at the pages she created, you created this design that just, I have one for every course, and I have one for my coaching program, so this is the one for my coaching program. So again, just by signing up they get this sent to them. And again, I just, you design this so beautifully, Candace, I love just all the little intricacies that just make it so pretty. That, so back to my point, the collaboration design is not my forte. I would've never been able to create something like that on my own. to me, that's. That's okay. I did learn in a one of the courses I've taken throughout the years. Somebody had noted, write a on a piece of paper, take a piece of paper, cut it in half, have a side a, side B, you're gonna write down every single thing that you have to do. Now as a business owner, an entrepreneur. There's a lot of stuff on our plates. So on this piece of paper divided into section A, write down everything about your business that you love, that you thrive in. That is your jam. And then on side B, write down everything in your business that you have to do but is not your, your forte. And the goal is do the left hand side higher for the right hand side. I know as we're starting out. Businesses, it's not necessarily easy to just, you don't have all the money in the world to just go out and hire people, but one, there, there is a budget for some of it. There's other collaborations that you could do, do a trade exchange of some sort. Some of the stuff you might have to at the beginning just. Do it. Okay, these are the things I don't like, but I'm gonna do it. But that design work for me is just, it's really hard for me. I just don't have that creative eye. Now, once I have something to go off of, I can play around with it. But again, these on my website is, it's just beautiful. I love going to my courses section because they're all there and it's just so pretty. And then to, when I. Decided I wanted to do a journal with it. I don't know what to do for the journal. And so I collaborated with you, hired you, and now I have these beautiful journals. So not only does that talk about collaboration, but it also just talks about how important collaboration is to really help. We're not good at every single hat that we're wearing. So to partner and collaborate is just so important.

Candice Dorsey:

I love that. Oh, thank you.

Holli Howard:

Thank you.

Candice Dorsey:

I love that so much because yeah. That is that's very important. And see, being creative is my jam.

Holli Howard:

Yeah.

Candice Dorsey:

love to be creative. And so funny we mention this, I took the Working Genius test and I found out that I'm more of the. Getting the ideas going, like getting and being happy about that and just doing the creative process. And what's really I'm struggling with is like the ex the finished part. Because when I'm in something, I get another idea, boop, right on top of that, and it just stacks on top of each other. And I'm like, can you gotta stop doing that? You can't. You can't do that. You need to finish it. So I have to have Chad, GTP give me like something like, we need to finish what I'm doing and I need you to help me with some sort of checklist to focus or something like that. But being creative and doing especially the things that I do for you, Holly, is it really helps. Like it's more relaxing for me because I'm not it's not a stressor, it is not like somebody telling me, you need to, we gotta get these numbers and these deadlines. I get to be me creating for someone else. And then they actually appreciate it. And I think that for me is like. All the joy and more than I can like ever imagine, because when you're working for someone else, you're working for their business and you try to come up with creative ideas. But if it's not their vision, they're like, okay, no, we're gonna do this. And it's

Holli Howard:

yeah.

Candice Dorsey:

We don't need to do that. We, it is. No, it's not. It's not pretty. It is.

Holli Howard:

Yeah.

Candice Dorsey:

so yeah. I thank you so much because working for you is so relaxing and I just get to just be creative and I love it so much. So thank you for picking me.

Holli Howard:

Win-win. That's collaboration at its core. Just being able to up, help people receive the help, collaborate on it. And really I did have one of my supervisors actually at the spa that I was working at before I. Jump ship to, to go to child welfare. She always said things like, many hands make light work and just all these beautiful sayings. And one of the sayings is, she says, I hire people that have, other strengths that I don't have because that makes the team super strong. And even as a solopreneur. We're not doing everything on our own. That collaboration piece is so important because we do get to bring others expertise in and just make things better.

Candice Dorsey:

Yeah, that's true. And I really wish a lot of, especially in corporate and these jobs, I really wish that they see that more in their employees because when you're working for someone. It is like everybody is doing the same thing. So like for me, when I was a supervisor, everybody was funding. Everybody had numbers. Everybody need to hit it, and everybody need to do it the same way.

Holli Howard:

Yeah.

Candice Dorsey:

And I've been thinking like each person does things differently.

Holli Howard:

Yeah.

Candice Dorsey:

Like everybody's not gonna hit them numbers. What is it that this person does that we can just have them hone in on that skill to make everything, flow, but they didn't get it. It's all about numbers. I was like, no, it's all about people.

Holli Howard:

It's all about people. It's all about people. And when you can help them to shine, you're just gonna have such a better environment. In my child welfare world, quite a few years back, they created something called a case manager support specialist. they, the my, the one that was on my team, which I just love her so much, she always said, I do the paperwork so you can do the social work. And I love that. And then in one of our team meetings, they did a quiz. I'm not gonna remember a personality assessment of some sort. I'm not gonna remember which one it was, but it was very interesting that the, I remember, I think I was a blue and orange or whatever, but the admins were like predominantly in a different area than I was in. And it was interesting just to see how those, all the people who were doing the social work piece were more similar, and then the people doing that admin piece had their strengths too. that was just so amazing to see because we do, that concept just made things go. It was one of the things that was really helpful in that world.

Candice Dorsey:

That's good. Yeah. Yeah. I totally get it. So I was like, when I grow my business, I'm gonna make sure I have this person doing this. And, I don't like people doing stuff that they don't wanna do,

Holli Howard:

yeah.

Candice Dorsey:

yeah.

Holli Howard:

they shine, then it's, yeah. Not

Candice Dorsey:

Yeah, it's the truth. Yeah. Alright, this has been great. So as you know here at Hay Boss Leagues, we're all about connection and collaboration. What type of collaborations are you looking for right now?

Holli Howard:

Yeah. So right now again, because I've really connected to so many people, like my business piece is good. Where I really wanna collaborate is with other people that work in, that are trauma informed, that work with women that have had childhood trauma. My way of doing things is I'm very self-focused. My focus is on self-worth. I had self-worth shattered when I was a young child, and I know what I had to do to get through everything. I know that some people really, the body holds the score and some people are really holding onto that trauma internally. I'm not a therapist, so I will, if there's. Somebody comes and does an interview, they, I have an application process. So if they start, need to collaborate with therapists for, if it's okay, they need something more. Some people really need that sound healing or somatic. And where that's not as much my strength. I wanna collaborate with others to make sure I have people I can refer to. and also just having, different podcasts and having these conversations because these conversations are so powerful if somebody hears what they're doing, that people will feel, not so alone. So really, if people,'cause you have hey, boss ladies, if there's other people that have. That are coaches that are trauma informed, that just have a little nuance with all of this. I'd love to, to meet and talk with them. I also have a little story that I like to share with the story is not my own. The story itself is have you heard of the Starfish story?

Candice Dorsey:

Oh.

Holli Howard:

the, it's. It's a story analogy. I'm not sure exactly, but the story goes, and I'm very bad at verbatim, so forgive me for that. But the story basically goes there. There was a storm and thousands upon thousands of starfish washed up on the beach, and after the storm passed, all of these starfish are still on the beach and a little boy comes up and picks up a starfish and throws it back in the water to save the starfish. Picks up another one, throws it back into the water, and then some person comes up, sees what he is doing, and he's like, why are you even bothering? You're never gonna make a difference. There's thousands of these starfish on the beach, the little boy picked up another one, threw it in the water and said, I made a difference to that one. And I love that story. And I feel like when we work with people and we have what we have, we really get to work with people and help people in that moment of their need. collaborating with other business owners and other people that also do what, similar to what I do, I say we're gonna get together and we're gonna clear that beach. So that's my little thing that I add onto it because together we can clear that beach we can help people together. We can do so much more.

Candice Dorsey:

Oh, I love it. That is so cute. I love it. I love the story.

Holli Howard:

Yeah.

Candice Dorsey:

that is so true. If you could just help a help one person. That's a difference. You did something in someone's life, you took the time out to help them and put them back into the water. I love that. Oh, that's so cute, Holly. I'm gonna have to steal that story.

Holli Howard:

Absolutely. collaborate, share, a village and there's a lot of stuff going on

Candice Dorsey:

Yeah,

Holli Howard:

that it's

Candice Dorsey:

it is. It definitely is.

Holli Howard:

together and it's not about anything, oh, I can't share that, or I can't work with somebody. It helps so much when we do.

Candice Dorsey:

It does. It definitely does. So how can people connect with you?

Holli Howard:

so my website is positive living coaching.com and that's where, it has my coaching program. Again, my coaching program. I do wanna make sure. That I'm the right fit for the person and that I'm the right fit for them and I can help them. And then they resonate with my messaging and everything. So there is a section on there where they can book a call with me, and then I have my courses as well. The the notebooks are actually, I give away the notebooks for free when they purchase the course or the program. That's all on there. I do have Facebook and Instagram that I'm on Positive Living Coaching. Is that, and if they wanted to reach out to me personally, my email is holly@positivelivingcoaching.com. And just to throw it out there, I'm sure this is gonna be in the show notes somewhere, but my spelling is HOLL i@positivelivingcoaching.com.

Candice Dorsey:

Perfect, and we'll definitely link those up in the show notes. Thank you Holly, so much for coming on the podcast.

Holli Howard:

Thank you for having me. I so appreciate it and everything that you do.

Candice Dorsey:

Thank you.

And that's a wrap for today's episode of Hey Boss Ladies, if you love what you heard, don't forget to follow the show, leave a review or share with a business bestie. And if you're ready for deeper conversation and powerful connection, join us inside the hey boss ladies collaboration experience happening every month. The link is in the show notes below. Until next time, stay bold, stay brilliant, and keep showing up like the boss you are.