Boss Your Business - The Podcast

Yvonne Heimann [00:00:01]:
Did you ever think scaling your business could be easy and not involve in 24/7 hustling? Today, we’re discussing the common problems entrepreneurs face when trying to scale without burning out. There’s the challenge of maintaining work-life balance, followed by effectively leveraging one’s skill while managing time. Lastly, the constant demand of being a parent and a business owner. Offering a solution to these issues, I'm joined by Cailen today, a scale-up accelerator and business coach. From early entrepreneurial ventures to building a thriving coaching business, Cailen has seen it all. She brings invaluable insights on creating a high-ticket group coaching model that requires minimal time yet yields significant returns. We’ll dive deep into her approach on cutting work hours, setting boundaries, and focusing on high-impact activities. Expect to walk away with strategies to earn more while working less, and feel inspired to make bold, lasting changes in your business life.

Yvonne Heimann [00:01:12]:
I am so excited to have you on Cailen. I think we were one of the ones where we missed past just a couple of times to get you on the episode, and we finally made it happen, guys. We finally made it happen. So I am so happy you get to join me today. Welcome to Boss Your Business. And my audience already knows which question is coming first because it's the most fun one to start a conversation with. Cailen, you are doing a scale up accelerator. You are helping people scale their business.

Yvonne Heimann [00:01:50]:
Making this really simple, though, people, we are not talking about hustling their ass off. So we'll dive deeper into this. Did a little Cailen know this is what you're gonna do? That you're gonna help people scale their business and teach them and do? Or did you have the whole I'm gonna be a teacher kind of child's dream?

Cailen Ascher [00:02:13]:
No. Young Cailen did not know exactly what I was gonna be doing now, but she definitely had an entrepreneurial spirit. I remember one year, I think I was five or six years old, I colored seashells at the beach and set up a stand. And I think my mom actually paid some kids down the beach to, like, come and buy the seashells to support my tiny little business stuff that nobody wanted. But, yes, all through. All through high school, through college, I was always finding my own way, creating jobs and businesses and things that would make me money on my own terms. And so when I graduated from college and I went to a traditional liberal arts school, I majored in completely useless things like art history and French. I guess I just wanted to be a traveler or something.

Cailen Ascher [00:03:01]:
I don't know. But I entered into the world, like, not being totally clear on what I wanted to be doing. But I did have a sense that I wanted to make a difference. I wanted to help people. I felt particularly called to work with women. And I took a number of forms over the last. Oh, God, almost 20 years. Started out in interior design, and I had my own interior design company.

Cailen Ascher [00:03:27]:
And I guess I thought designing beautiful homes would help people live beautiful lives and, you Know, fulfill me along the way. I landed in yoga for a while and was teaching yoga. And that's kind of what got me into the business realm, is I started marketing myself as a yoga teacher. I made a website. I started landing some cool gigs and cool classes, and other teachers were asking me, how are you doing that? They thought the only way to be a yoga teacher was to be in a studio and teach classes and get paid $10 an hour. And here I was, like, building a brand. And so that's how I started with coaching. I started working with other yoga teachers, helping them build a brand and kind of become a little business unto themselves.

Cailen Ascher [00:04:10]:
And after I had kids, I lifted the yoga piece out and just continued on the business coaching journey.

Yvonne Heimann [00:04:17]:
But I guess I'm like listening, listening to your story. First off, heads off to mom for generating traffic, right? Because pretty much what she just did is marketing. Because the moment somebody stands there, chances are somebody else is gonna come and stand next to whoever is looking at your stuff, right? And then also looking, just looking at, at your progression, I'm pretty sure you are pulling from all the things you have done. You are pulling from all your education, from your arts and all the things to now do what you are doing and help your clients how you are helping them. And that's one of the reasons why I love this question, because it's just so much fun seeing. Now, looking back, I'm like, we never have an idea looking forward, but looking back how suddenly all of those and pieces work with each other.

Cailen Ascher [00:05:18]:
That's so true. Yeah. Following that thread is really interesting. And I love being a student. Like, since graduating college, the traditional education path, I've invested, oh, God, probably over $200,000 in coaching and programs and masterminds and retreats and to accumulate this knowledge. So, I mean, at this point, I guess that's the equivalent of a master's degree or a doctorate or something, right? Like we, these, you and I, right, these coaches who have been on this journey for decades accumulate this knowledge and then also just through, through experience, through making mistakes and learning from them and then wanting to be able to share how to do it better with other people.

Yvonne Heimann [00:06:02]:
I love that. So I would love to dive a little bit deeper into the change that happened now, dropping the yoga and really stepping into this coaching, because you talk about making 100k per year with one zoom call a week. Now I being in this niche and getting content served every single day in this exact area, I am personally excited that us women are finally stepping up to the game and telling the hustle bro culture to go f off. Because honestly, who wants to work 24/7 so I love your approach of really focusing on, okay, let's make this easier. So how did you make this easier?

Cailen Ascher [00:07:01]:
Yeah, that's a really juicy question and I'm going to do my best to create a linear response to it.

Yvonne Heimann [00:07:15]:
We're trying to not make it too crazy for you guys.

Cailen Ascher [00:07:18]:
Yeah. So what really was a profound shift in my business journey was becoming a mom. My daughters are nine and seven, and when I found out that I was pregnant, I realized I didn't want to hustle anymore. That was for my earlier twenties, right? I was, like, working all the hours, doing all the things, like, hustling for it, and I was like, I don't want to have to continue with this energy and also be mothering a baby, growing into a kid that's going to need me. And so I really, honestly considered for a while of just, like, pausing, like, taking a break from everything, shutting the business down, being a stay at home mom. And there's nothing wrong with that, but I knew ultimately, I wouldn't feel fulfilled. At some point, I would regret that decision. And so I, you know, sat.

Cailen Ascher [00:08:17]:
I do a lot of meditation and journaling, and I sat with it, and I said, like, what would really feel good? And the answer that arrived was a three day work week. I was like, oh, I don't have to subscribe to this, like, 40, 60, 80 hours a week thing. I can determine what my schedule looks like, what this business looks like. And that was really a turning point. I mean, prior to that, I was making, I don't know, 20, $30,000 a year. I was in my early twenties. I was picking up a lot of side gigs. Like, I was making it work.

Cailen Ascher [00:08:50]:
I was hustling. When I shifted to my three day work week, I got so focused on how I was spending my time, how I was showing up, what I was putting effort into, what I was saying no to. I had my first six figure year, and I was like, ah, there is something here. There is something to this. There is something about creating an intentional container for your work. And it aligned so all of my priorities and then also gave me these beautiful four day weekends with my little baby girl. And so that was really a turning point back then. I mean, this was almost ten years ago.

Cailen Ascher [00:09:28]:
My daughter's turning ten next month. Back then, I was doing one on one coaching, and then after a few years of that, that started to burn me out. And I got pregnant with our second daughter, and I was like, oh, my gosh. Being on back to back client calls all day while, you know, eight months pregnant and trying to figure out how to take a maternity leave from all these clients isn't doing it anymore. I'm like, how can I upgrade again? What does this next iteration look like? And that's when I switched to a group program, a high ticket group program, all of my beautiful vip clients on one call a week. And it was so honoring of my schedule, my needs, my lifestyle, and it was honoring of them too, because what I realized in my own behavior is I was exclusively investing in group programs, masterminds, places where I was going to be in community with other women. And yet I wasn't offering that to my own clients. And so that was a huge aha for me.

Yvonne Heimann [00:10:21]:
Yep. Hmm. So what I'm hearing is you actually set boundaries. What a concept.

Cailen Ascher [00:10:30]:
I know.

Yvonne Heimann [00:10:31]:
And why, why I'm wording it like this because I often see the perception of boundaries are something bad where in the sense of not making yourself as available, yes, boundaries are good. Telling people, no, you don't get to treat me this way. Whole nother story. We totally agree on this, ladies, but we often struggle. And a lot of my clients also struggle with the idea of setting boundaries in your business. Now, the opposite that I have seen to making this decision of, hey, my boundaries is three days and you focusing on what do I need to do to make these three days happen. Now you are suddenly focused on what is making money, what is converting, how. How can I show up best in the smallest amount of time.

Yvonne Heimann [00:11:25]:
Now, what I see on the opposite, if we are not setting those boundaries is this. Ego numbers. That's what I call them. Ego numbers. Where it's like, cool, I care about my traffic on Instagram. Maybe not even the following, maybe really just the engagement. But have you ever actually looked at the conversion rate? Where are you putting your time? Where are you putting your effort? And when I believe when you get to this point where you are past the initial stage of learning, where I do believe test all the things I don't subscribe in this first initial, getting to the 50k, getting to the 100k to one offer, one niche, one program. But that's a whole nother story.

Yvonne Heimann [00:12:14]:
I believe in that you should test everything. You should do everything. But when coming to this, okay, now we are upgrading. We want to get to those five hundred k, to this million dollar business. We need to focus, we need to set the boundaries. And your boundary was like, I just want to work three days a week. That's it. Now suddenly it's like you have your north star, you know exactly where you want to be.

Yvonne Heimann [00:12:40]:
And so suddenly all of the noise where everybody is telling you what you should do fell off. Is that what happened? Am I hearing you right?

Cailen Ascher [00:12:49]:
Yeah, that's exactly what happened. It was just, it was. First of all, it felt so empowered to choose what I wanted and to stand for what I wanted. And I did have the thoughts of, like, well, I'm working with one on one clients. What if they can't meet on a Tuesday? What if they're hoping for a Friday night or a Saturday morning? And you know what? I didn't ever have one client give me a hard time about my school hours on those three days. They made it work if they wanted to work with me. And it was so affirming of everything I was choosing, every step along the way, as I really anchored into what I wanted, I was getting positive feedback, which just made me realize, ah, this is the way to do it. Trust your intuition, trust your gut, and then also make bold moves.

Cailen Ascher [00:13:32]:
Take action. You need both. You can't just, you know, feel good all the time and everything's going to flow to you. You have to move your feet as well. But it was that beautiful pairing that really got me in my early days. Like, a lot of my clients wanted to work with me because I worked three days a week. They're like, how do I do this for myself? And now my clients want to work with me because I have one zoom call a week with all my clients, and I make half a million dollars a year. It's when you show up in integrity, that's what really attracts the amazing clients into your business.

Yvonne Heimann [00:14:02]:
And I think it's also a vetting program, because when people commit to something, they will show up, period. If they don't commit to it, they will use the time as an excuse to not show up. You already started talking about it. And I love how you let into this. Even with "just working three days a week", life happens. And let's be honest, we women, often enough actually just have three weeks in a month where we fully function or kind of mostly should be kind of functioning. How do you show up bossing your business? How do you get through times? How do you stay on this level and continuously grow with your business?

Cailen Ascher [00:14:58]:
Well, I guess the answer is it's always learning, it's always up leveling. And there's always moments that feel like you're in a pit and other moments where you feel like you're on the top of the mountain. I definitely am better at regulating myself, and that's been a journey of way back, starting with yoga, of understanding nervous system regulation and a steady place, because there are so many fluctuating things when you are an entrepreneur and things change week to week, income changes, you know, there's a lot being thrown at you, but for me, the most important thing is to anchor back into my core mission. And my core mission is, yeah, I'm a business coach. I teach people how to make, you know, six figures with one zoom call a week. That's all flashy marketing. But for me, deep down, it's really about helping women shine their light and doing that in a way that provides them with time, freedom, and financial freedom, and that they get to do fulfilling work that they love, and they're filling their cup. Like, that's my mission.

Cailen Ascher [00:16:02]:
And whenever I'm feeling a little wonky, I realize I'm focusing too much on the surface level stuff, the nitty gritty business data, and I need to, like, drop back into that deep mission within me, and then I feel that sense of, like, let's go. Then that comes back.

Yvonne Heimann [00:16:22]:
I love that. And you already touched a little bit on the mindset of things. What are some things you do to boss your mindset, especially when things might not be going as you expected or hoped them to go?

Cailen Ascher [00:16:40]:
Yeah. The things that really help me get back into a more regulated place and, like, feel that. That optimism and that vision again. I mean, for me personally, I usually try to sit in meditation every morning, whether it be for two minutes or 20 minutes, just some quiet reflection time, ideally before I've interacted with anybody, before I talk to my husband or talk to my girls or feed the dog or anything like that. Little bit of time for me to get in touch with that voice within is really, really key, honestly. I mean, talking, my husband's such a supporter of me and my business, and I know I would not be here where I am without his belief in me. And so there's moments when I'm. My self belief is dimmed a little, and I just go to him, I'm like, oh, my God, I'm gonna dump all of this on you.

Cailen Ascher [00:17:31]:
And then he reflects back my highest potential. And that is, you know, feels so, so good when you have those people in your life who can hold that mirror for your highest potential and bring you back to who you want to be, who your best self is. And I also just. I I'm a personal development addict. Like, I love reading all the books. Like, my nightstand is just piled with books, and I bounce between them. And as much as I love business strategy and we're talking about, like, having a three day work week and setting up a schedule and making money, I love that softer side of things. I'm like, okay, I want to get to know my soul.

Cailen Ascher [00:18:13]:
And I have an astrologer who helps me plan my business according to my chart. And I love diving into my human design and all of those modalities to help me understand me on a deeper level, helps me show up in my business in a more authentic way and be more honoring with how I'm running my business and how I'm setting up my schedule and how I'm leading my team and all of those aspects.

Yvonne Heimann [00:18:39]:
And I think a lot of that work and that growth is feeling home in ourselves, if that makes any sense, where it's like, developing our own pride, our self love, and having it in here rather than having it all out there. But when we get into a struggle day, having somebody like, I'm blessed enough to have a partner, too, where I can fall back on that external validation just maybe for a day, when I'm like, what the hell am I actually doing? And can fall back on somebody and just take that energy and take that love and take that external validation just for a day to fuel that back up again. I'm like, okay, cool, I'm back. Awesome. Now let's. Let's get back to it and really having that. That relationship, that support system, and for everybody listening or watching, it doesn't have to be a romantic partner. It can be your best friend, it can be your mastermind, it can be your support group, whatever it is.

Yvonne Heimann [00:19:51]:
Having at least one person in there where I do the same thing. I'm Literally, just like, dude, I am. Do you. Do you have eight minutes? Right when we have one of those meltdowns, I just need to unload. And I'm literally at a point where I then also say, it's like, I need to unload to you. I need to let this go. I just need to get it out of me. And then please tell me why I'm awesome.

Yvonne Heimann [00:20:17]:
Because I just need external validation for the next five minutes for me to get back into where I need to be. So I always love seeing when that support system actually is also in your home. Yeah. Because often enough, looking at it, the rest of my family, they have no clue what I'm doing. The rest of my family has. My mother halfway understands what I'm doing. My grandpa has no idea. So as much as they want to support, it's.

Yvonne Heimann [00:20:47]:
It's. It just not really is the same thing. So I always love seeing when my guests do have that support system, especially when it's home. Now, how is business nowadays? We talked about how you got here. We talked about some of the mindset shifts, and the business shifts are happening? How is business now? How does it feel to be here?

Cailen Ascher [00:21:17]:
It feels pretty amazing, honestly. It feels. Yeah. It's one of those things where if you had told me back when I was, like, just stepping into my three day work week as a coach or back when my daughter was. My first daughter was born and said, hey, this is what it's going to look like. This is where you're going. I think I would be in a little bit of disbelief. Like, it has afforded me so many beautiful opportunities to, you know, support my family.

Cailen Ascher [00:21:40]:
I have aging parents that, you know, were able to help support and take care of, and we purchased vacation homes, and we get to enjoy them, and I get to take time off and actually go on vacation and be unplugged and spend so much time with my girls. I mean, they're both in school now, but when they were little, that I would have full days with them and get to, like, play and just be a part of their childhood, I feel so fortunate. And when I see my other mom friends who are in dropping their babies off at daycare early in the morning and not getting them until the evening, and then they just have an hour and bath time, and then it's bed again, and, you know, everyone has to choose their own path, and you'd have to do what's right for you and your family. But I just feel so fortunate that. And again, this goes back to the support of my partner, that he was on board way back in my twenties when I'm like, hey, like, I'm not. I'm not getting a job. I'm not doing a traditional thing, like, I'm making a job. I'm being the boss.

Cailen Ascher [00:22:39]:
I'm doing these things, and he's been there and, you know, cheering me on and supporting me, and it's enabled me to get to a place where now the business feels like an entity separate from myself. It doesn't feel this thing that's like, I have to, like, care for and take care and push up the hill to make it work. It's like a machine that's running on its own, and that feels really good. When you get to that place.

Yvonne Heimann [00:23:02]:
What would you tell somebody that's at the beginning of this journey?

Cailen Ascher [00:23:09]:
I would say it takes time, and that's not what we want to hear, and that's not what is. Don't we all right. And that's not what we hear on social media. But you have to commit for the long haul, because if you're in a. "Well, if I don't make money in 30 days or 60 days or 90 days, I'm out". That is never the energy that builds into lasting success. It has to be.

Cailen Ascher [00:23:43]:
I'm all in, no matter what. I actually had a moment. I think I was. I don't know, I was driving back from a doctor's appointment for my daughter or something and I was having just one of those low moments where I'm like, oh, my gosh, I don't know if I can do this. I'm juggling motherhood and this business, and business isn't doing what I want. And then I was like, you know what, though? I'm not going to stop. Like, I'm not going to stop. So if I'm not stopping and I keep learning and growing, there's no other option than success on the other end of it.

Cailen Ascher [00:24:13]:
And I think when you get to that place of full commitment, there's no other option but success. And it might take a year, it might take three years, you know, it might be longer than you want. But when you look back, I know it's a path of no regrets. Doing it that way of like, going in all in on myself.

Yvonne Heimann [00:24:35]:
And you have a training for the audience that helps them make exactly that happen. Do me a favor, tell the audience what it's about and where they can find it.

Cailen Ascher [00:24:47]:
Yeah, absolutely. It's this amazing little 20 minutes training. It talks all about my approach to high ticket group coaching. Coaching. It's called how to make 100k a year with one zoom call a week. And it gives you a high level of how this business model can work for you, for your business. And if it's something that's really appealing to you, it also gives info about how to connect with me and my team.

Yvonne Heimann [00:25:05]:
Love it. And as always, you know, the links are going to be in the description. We're making it really easy for you. Cailen, thanks so much for joining me today. I'm so happy we were finally able to make it happen. And anybody watching and listening, make sure you hit that subscribe and follow button because I have a whole bunch of another amazing women coming your way. Thanks so much.

Cailen Ascher [00:25:30]:
Thank you. Bye.