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Entrepreneurship

Episode 195: Making $100k+ a Year, Working Part Time with Cailen Ascher

January 16, 2024

Chasing Simple Marketing

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Cailen discusses leveraging group coaching to serve more people in less time leading to making $100+k a Year.

Making $100k+ a Year, working part time, with Cailen Ascher

We all started our businesses so that we could make more and work less, right? That’s essentially what every business origin story boils down to. And I’m right there with you. I recognized that as a 3rd year teacher, I wasn’t ever going to make much more than I was already making. And I had too many missed chances to spend time with my husband due to conflicting schedules. So I started out on my own path.

And early on into my entrepreneurial journey, I came across today’s guest, Cailen Ascher. She was sharing all about the fact that she worked full time, but only in 3 days a week and I was FLOORED. Although I’d started my business for time freedom, I hadn’t known that time freedom like that was even possible.

Cailen Ascher is an award-winning Business Coach with a 3-day workweek, a mom of two little girls and the creator of Scale-Up Accelerator™ — a program that helps coaches create and launch a highly profitable Premium Group Program that can bring in $100K+ per year with ONE Zoom call a week. Cailen has been featured in Business Insider, Huffington Post and Inspired Coach Magazine and has been interviewed on top podcasts like Entrepreneurs on Fire and She Means Business Podcast among many others. She is also host of The Soulful Business Show™ which airs weekly. Her programs have helped 1000s of coaches & service providers transform their lives and businesses with her proven strategies for working less, making more and living better. Cailen lives in Bucks County, Pennsylvania with her husband, two young daughters and a spunky dog named Olive.

Today, you’ll hear Cailen and I discuss what the shift to working so much less looks like, and how she did it. Spoiler: she leverages group coaching to serve more people in less time, and she’s going to also share some tips on how to do that yourself if that’s a business model that seems like a good fit for you.


Links and Resources Mentioned in This Episode:

  • When it comes to creating your monthly content calendar and sitting down to create your content (because you’re batching it, right? 😉), the first step is not writing in the monthly calendar. It’s not even writing your categories and important dates on the calendar. If that’s where you’re starting with your content planning, well, all you’re creating is a plan. But what you need is a strategy. What’s the difference? A strategy is like the inner structure of a building, while the plan is the decor. A strategy is what helps you achieve your goals, and your plan is how you achieve them. Your strategy is where you’re leading your audience, and your plan is what you’re talking about and when. Without having a strategy first, putting together a plan will simply mean pulling ideas out of thin air. So, how do you start with a strategy? By starting with your goals, and working backwards to ensure you’re moving your audience toward them. What are your yearly goals, quarterly goals, monthly goals, and weekly goals? And how can you translate them into content your audience wants to ingest? You’ve got to consider those questions before you even begin deciding what it is that you’ll post about. And if you want a simple way to create both your strategy and your plan? Grab your Chasing Simple Content Planner. The planner is my number one bestseller – And for good reason too, because this massive 130+ page planner was designed with strategy in mind. It’s not merely a place to write down what you’re going to post, and when. Yes, that’s part of it. But first, you’ll walk through intentional pages full of strategic questions to get your brain moving in the right direction before you even start writing down your topic ideas. In addition to the traditional calendar pages, you’ll find: Yearly planning pages Monthly prep work Monthly reflection questions Repurposing worksheets and so much more! If taking your content to the next level is a goal of yours, the Chasing Simple Content Planner was created for you. Grab yours for just $27 at amandawarfield.com/planner/
  • Get Cailen’s free training which reveals How Coaches Are Earning Over $100,000 Per Year With Just ONE Zoom Call A Week. Grab that over at http://www.CailenAscher.com/free
  • This week’s action step: Ask yourself “What do I want to be known for?”
  • This week’s book recommendation: The Complete Works of Florence Shovel Shinn
  • Find me on Instagram and tell me you completed this week’s action step: @mrsamandawarfield

Cailen discusses leveraging group coaching to serve more people in less time leading to making $100+k a Year.

Cailen Ascher is an award-winning Business Coach with a 3-day workweek, a mom of two little girls and the creator of Scale-Up Accelerator™ — a program that helps coaches create and launch a highly profitable Premium Group Program that can bring in $100K+ per year with ONE Zoom call a week. Cailen has been featured in Business Insider, Huffington Post and Inspired Coach Magazine and has been interviewed on top podcasts like Entrepreneurs on Fire and She Means Business Podcast among many others. She is also host of The Soulful Business Show™ which airs weekly. Her programs have helped 1000s of coaches & service providers transform their lives and businesses with her proven strategies for working less, making more and living better. Cailen lives in Bucks County, Pennsylvania with her husband, two young daughters and a spunky dog named Olive. Get her free training which reveals How Coaches Are Earning Over $100,000 Per Year With Just ONE Zoom Call A Week. Grab that over at http://www.CailenAscher.com/free .

Social Links:

http://www.CailenAscher.com

https://www.instagram.com/cailen.ascher/?hl=en


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Rather Read? – Here’s the Transcript!

*Just a heads up – the provided transcript is likely to not be 100% accurate

Amanda Warfield: We all started our businesses so that we could make more and work less, right? That’s essentially what every business origin story boils down to. And I’m right there with you. I recognized that as a third year teacher, I wasn’t ever going to make much more than I was already making. And I had too many missed chances to spend time with my husband due to conflicting schedules.

Amanda Warfield: So, I started out on my own path. And early on into my entrepreneurial journey, I came across today’s guest, Kaylin Asher. She was sharing all about the fact that she worked full time, but only in three days a week, and I was floored. Although I’d started my business for time freedom, I hadn’t known that Time freedom like that was even possible.

Amanda Warfield: Kaylin Asher is an award winning business coach with a three day work week, a mom of two little girls and the creator of scale up accelerator, a program that helps coaches create and launch a highly profitable premium group program that can bring in six figures each year with one zoom call a week.

Amanda Warfield: Katelyn has been featured in Business Insider, Huffington Post, and Inspired Coach Magazine, and has been interviewed on top podcasts like Entrepreneurs on Fire and She Means Business Podcasts, among many others. She is also the host of the Soulful Business Show, which airs weekly. Her programs have helped thousands of coaches and service providers transform their lives and businesses with her proven strategies for working less, making more, and living better.

Amanda Warfield: Katelyn lives in Bucks County, Pennsylvania with her husband, two young daughters, and a spunky dog named Olive. Today you’ll hear Katelyn and I discuss what the shift to working so much less looks like and how she did it. Spoiler, she leverages group coaching to serve more people in less time and she’s going to share some tips on how to do that yourself if that’s a business model that seems like a good fit for you.

Amanda Warfield: You’re listening to episode 195 of the Chasing Simple Podcast, and I’m your host, Amanda Warfield. This episode was brought to you by the Chasing Simple Content Planner, and you can grab your own at amandawarfield. com slash planner.

Amanda Warfield: How do I find time to create content without overwhelming myself? Where should I even be showing up in my marketing? How do I come up with fresh content ideas? Where should I be focusing my marketing efforts? What is lead generation anyways, and how do I do it? Are launches still a thing? And most importantly, how do I put it all together to market my business strategically?

Amanda Warfield: Can I really grow my business without spending all of my time marketing? These are some of the questions that float around in your head when you think of marketing. Welcome friend, this is Chasing Simple, where practical marketing strategy meets simplicity. I’m your host, Amanda Warfield, simplicity focused content marketing and launch strategist, speaker, educator, and author of Chasing Simple Marketing.

Amanda Warfield: I traded in my classroom lesson plans for helping creative entrepreneurs sustainably fit marketing into their business without it taking over their business. so that they have time to grow their business, take time off, and live the life they dreamed about when they first decided to go out on their own.

Amanda Warfield: When I’m working, you can find me working with one on one clients, such as The Contract Shop and Rebecca Rice Photography on their marketing strategy and copywriting, or helping my students simplify their marketing and launches. And when I’m not, you can find me spending time outside with my husband, Russell, Reading in our hammock, watching Gamecock Sports, traveling, or forcing our cats to snuggle me.

Amanda Warfield: If you feel overwhelmed by marketing, you aren’t alone. Many entrepreneurs find marketing frustrating, overwhelming, and simply an obligation. They know they need it, but they don’t enjoy how easily it can suck up their time when what they really want to be doing is the thing that they started their business to do.

Amanda Warfield: Which is why I’m here. To help make marketing simple and less time consuming. So that you can spend less time on your marketing, and more time growing your business and doing what you love. Each week, I’ll bring you transparent conversations, actionable steps, and judgment free community to encourage and equip you.

Amanda Warfield: So grab yourself a cup of coffee or whatever your drink of choice is, and meet me here each week for love, support, practical tips, and advice on uncomplicating your marketing and business. Let’s do this entrepreneurship thing together, shall we? When it comes to creating your monthly content calendar and sitting down to create your content, because you’re batching it, right?

Amanda Warfield: The first step is not writing in the monthly calendar. It’s not even writing your categories and important dates on the calendar. If that’s where you’re starting with your content planning, well, all you’re creating is a plan, but what you need is a strategy. What’s the difference? A strategy is like the inner structure of a building, while the plan is the decor.

Amanda Warfield: A strategy is what helps you achieve your goals, and your plan is how you achieve them. Your strategy is where you’re leading your audience, and your plan is what you’re talking about and when. Without having a strategy first, putting together a plan will simply mean pulling ideas out of thin air. So, how do you start with a strategy?

Amanda Warfield: By starting with your goals, and working backwards to ensure that you’re moving your audience toward them. What are your yearly goals? Quarterly goals, monthly goals, and weekly goals. How can you translate them into content your audience wants to ingest? You’ve got to consider those questions before you even begin deciding what it is that you’ll post about.

Amanda Warfield: And if you want a simple way to create both your strategy and your plan, grab your Chasing Simple content planner. The planner is my number one bestseller, and for good reason too, because this massive, more than 130 page planner was designed with strategy in mind. It’s not merely a place to write down what you’re going to post and when.

Amanda Warfield: Yes, that’s part of it, but first, you’ll walk through intentional pages full of strategic questions to get your brain moving in the right direction before you even start writing down your topic ideas. In addition to the traditional calendar pages, you’ll find yearly planning pages, monthly prep work, monthly reflection questions, repurposing worksheets, and so much more.

Amanda Warfield: If taking your content to the next level is a goal of yours, the Chase and Simple Content Planner was created for you. Grab yours for just 27 at amandawarfield. com slash planner. Hi, Galen. I am so, so, so excited to have you on. I feel like I’ve been saying this with everyone, but I’m just really excited about this batch of interviews.

Amanda Warfield: You are someone that I have been following since. 2018, 2019, way back in the beginning of my business. So it’s, it’s a real nice like full circle moment for me to have you on as a guest for chasing simple. So can you just real quick tell everyone who you are and what it 

Cailen Ascher: is that you do? Yeah, absolutely.

Cailen Ascher: Thanks so much for having me on Amanda. So I’m Kaylin Asher. I’m a business coach. I specialize in helping coaches and aspiring coaches create high ticket group programs so that they have a more spacious schedule and are able to have a scalable offer instead of kind of getting. Trapped in creating another job for themselves with back to back one on one calls.

Cailen Ascher: And, you know, I kind of went down that path for a while and I realized it was not a good fit for me, my energy, my, you know, my lifestyle. I’ve got two young kids and my husband and all of that. So I really love helping women create programs that You know, really help other people, but also support them in the process so they can serve from that place of overflow and not feeling depleted by, by doing our good work in the world.

Cailen Ascher: So you’re pretty 

Amanda Warfield: well known for having a three day work week and then also teaching others how to have a three day work week. Can you kind of. Back us up and tell us how that all began and how that came about for you. 

Cailen Ascher: Yeah, absolutely. It’s such a good question and one that I talk about a lot on podcasts because I feel like that schedule is like the magical unicorn of schedule, the three day work week.

Cailen Ascher: So what happened for me was I, I started my coaching business when it was just me and my husband. We didn’t have any kids, you know, as we were kind of chatting beforehand, I definitely have workaholic tendencies. I love my business. I love the work that I do, so I can just fill all my hours all the time with it.

Cailen Ascher: But that wasn’t actually translating into clients and money. I was spending lots and lots of hours. But what I’m realizing now is not on high revenue generating activities. And then I found out I was pregnant with our first daughter. And so it was this weird moment where I was like, what I’m doing isn’t sustainable at all.

Cailen Ascher: We have this new little baby arriving who I want to have time with. And I want to be a really present and hands on mom, but I don’t want to let my business go. And it really felt like this. insolvable problem for a while. I took some months off right after she was born, which was wonderful. And I, this idea landed for me one day, I was like, what if I had a three day work week?

Cailen Ascher: Instead of working five days, I’d have three days of work and four day weekends. It like, it just felt like the balance was really there. And then, The clincher was, well, can I make money doing this? Can I, can I actually make my business, you know, you know, at the time, I think I was making like 20, 30, 000 a year.

Cailen Ascher: It was not, you know, where it is today at all. And I was like, I don’t know if I could even sustain that if I’m only working three days. And what happened in that 1st year of stepping into my 3 day work week was that I made that and then some and within a year or so, I was at the 6 figure level and I realized now it came because that transition came because I, I put my values 1st, my time, my energy, my family.

Cailen Ascher: And allowed my business to support that instead of thinking, I had to put all of my time and my energy into my business in order to be successful. And so, I mean, that translated into a lot of a lot of other actions and mindset shifts and all of that. But the basis of it was, is that I was really defining what success looked like for me and and owning that and and not feeling like I had to go above and beyond that in order to create the business that I wanted.

Cailen Ascher: So, it started because I stepped into motherhood and, you know, since then. It’s really impacted a lot of the work I’ve done over the years with my clients because I’ve, you know, I realized a lot of people step into their coaching businesses because they want, they want freedom, they want flexibility. And then they kind of just default to their habits and patterns that they learned from society or from their nine to five job.

Cailen Ascher: And it’s not really the business they want once they get it going. And how can we repackage that, redesign that into something that really feels good and makes them a lot of money in the process. The 

Amanda Warfield: idea that, you know, you’re working all the time and yet you’re not actually generating that revenue that you wanted in the, the time you’re spending, isn’t connected to revenue generating activities.

Amanda Warfield: It’s such a gut punch because it can feel like, no, I need to do all of these things. Everything I’m doing is important, but then you hear about all of these people like yourself who do scale back and they spend way less time working and then their business grows and it’s always kind of mind blowing.

Amanda Warfield: And I feel like we could spend. Honestly, multiple episodes, just talking about why that is and, and the mindset shifts that occur when you do take that step back and are forced to work well are forcing yourself to work less. But I think my biggest question is how do you overcome those mental blocks?

Amanda Warfield: Because so often in theory, and again, we were talking about this before we hit record, but. Yeah. I’m spending this year really focusing on working less. My husband’s working a shift schedule. And so his schedule is always changing and I’m matching my schedule to match his so that we can spend more time together, which is incredible.

Amanda Warfield: But it means that I’m working significantly less than I ever have. And those mindset mental blocks are they’re hard. And it’s just, I want to work. I love working. I love what I do. It’s fun to problem solve and to, to do all the things and to run a business. But I know those workaholic tendencies aren’t actually helpful and in the long run are probably harming my business more than they’re helping it, but it’s the, the mental blocks that make it so difficult.

Amanda Warfield: So how did you overcome all of those when you decided to take those steps back? Yeah, 

Cailen Ascher: I think, and you know, I still have mental blocks coming up, right? I’m not at this place where I’m like, I have no blocks in front of me. We all, we all deal with them. And so I think the first step, and it seems like you’re there for sure with what you just shared, is self awareness of being aware.

Cailen Ascher: That these thoughts aren’t serving you, that these habits aren’t serving you, that the things you’re doing aren’t for your highest evolution and that just that the awareness breathes some space between you and that thought, or you and that action. And you’re not, you’re not the thought. You know, you’re not a workaholic.

Cailen Ascher: You’re someone who has workaholic tendencies at this moment in time, or someone who used to have workaholic tendencies. Like, we want to do that. Like, always put it in the past. So I think that awareness is really key. And then something that I’ve been asking myself that is really useful is. When I come up to something and like there’s a thought or a decision, I ask myself, like, am I approaching this decision from a place of lack and fear or from a place of clarity and expansion?

Cailen Ascher: And you can use whatever words feel good for you, from fear or from faith, like, but where is this action coming from? Where is this decision coming from? And that gives me such instant clarity. Because this happened the other day, there was. You know, people, you know, we, I have a woman who’s taking all the sales calls for us.

Cailen Ascher: And there were people, a lot of people booking calls with her. And there were some that I was like, should I cancel these calls? Like, they don’t seem like a great fit, but I don’t want to hurt anybody’s feelings. And my husband was just like, where is this thought coming from? Is this coming from like your highest successful self, or is it coming from a place of lack?

Cailen Ascher: And I was like, Oh, you’re right. It’s coming from that place of, you know, back in the day when, like, you don’t want to cancel calls because that means you’re saying no to clients where now we’re, we’re at a point where we’re scaling and like, we have to kind of make those tougher decisions. And it was, it’s so helpful.

Cailen Ascher: To have something that can kind of just call you out on your own behavior. And so I would recommend if that resonates, like, having a question or having something that kind of pulls you back from that quandary of, like, should I do this? Or should I do that? Or, you know, you’re engaging in a habit that you don’t want to be engaging in and just be like, where is this coming from?

Cailen Ascher: Is this coming from my highest self? Or is this coming from, like, My old self, my residual self, the self that, you know, got me to where I am, but isn’t necessarily the person who’s going to take me where I want to go. That’s 

Amanda Warfield: so good. It’s such a, such a important question to ask ourselves that I know I struggle.

Amanda Warfield: I struggle with that slowing down and becoming self aware. I’m really good at being self aware in, you know, retrospect. Like, oh, that, that was this, but it’s really hard to notice in the So it’s a very important question to be thinking on. I’m curious what roadblocks either mental or physical you butted up against when you first decided, okay, I’m going to work three days a week.

Cailen Ascher: Yeah. I mean, the first roadblock was just like, oh my gosh, will this even work? Like, will I make enough money? Will there be enough time in those three days to get all the work done? And I proved to myself pretty quickly that when I put. Structure around my work hours. I was much more efficient and effective and how I was using my time.

Cailen Ascher: I kind of equate this to, you know, when we started out, my husband and I were living in like this, like, 600 square foot cottage. It was adorable. You know, we just have stuff for that space. And then, you know, we found out we were pregnant. We moved to our house now, which is like a 5 bedroom house. And there’s so much more space.

Cailen Ascher: And I was like, Oh, my gosh, it’s going to take us forever to like, get all the furniture and the things we need and it’s like, all of a sudden, now this house is packed. It’s like, it just happens so quickly. And so I think whatever container you’re giving yourself, and especially if you don’t have a container for just like, I will work whenever to max capacity.

Cailen Ascher: The time is going to fill. You’re going to find ways to fill the time and a lot of it is going to be like redoing stuff, rehashing stuff, like pulling apart things that don’t really need to be pulled. You know, like, we just get into bad habits where if you know, oh, I only have like 3 hours today to work.

Cailen Ascher: You’re going to make highest and best use of that time. And so it really pulls into focus. What are the most important activities and what is, like I said, like, revenue generating business growth, you know, planting the seeds for clients and money. Like, those are the activities we want to spend our time on.

Cailen Ascher: Not like. Playing in Canva or tweaking our website or, you know, all those things that might seem fun and enjoyable and they can be, but really, if you have three hours, those shouldn’t be the activities you’re doing. It should be doing the stuff that’s going to grow the business, make money, patron clients.

Amanda Warfield: It’s funny because I’ve seen this happen myself this week in particular. So as we’re recording this, it’s obviously batch week for everyone’s listening. You know, I do batch week every single month and every single month I batch the whole next month. Or every single month I set aside a week where I batch the whole next month’s worth of content in that one week, get it scheduled so that I’m not sitting there and marketing every single day during the month.

Amanda Warfield: And I have more flexibility with my time because my marketing is working for me. But this week in particular, and once or maybe twice a year, depending on how many guests episodes I end up doing, I also do a guest interview batch week where I batch all of the guest interviews for the entire year. I’m doing those together this month, which has been a fun experiment.

Amanda Warfield: And I realized that I’m completing my typical batch week work in just an hour or two every morning. And I have finished that work faster than I ever have yesterday morning. I messaged my friend and I was like, I’m already, I’m already pretty much done with my, all of my April content right now. And normally this takes me a full work week to do that much content.

Amanda Warfield: And it’s really amazing the way that it really just expands to whatever space you give it. And I posted on my Instagram stories about that. And I had so many DMS of people being like, I do the same thing when I give myself more time for whatever it is, but in particular batch week. It takes all of that time.

Amanda Warfield: And so it’s been very interesting to see that for myself, and it will certainly be a challenge. I give myself moving forward to see if I can even further simplify and shorten what my match week looks like. But you’ve mentioned the revenue generating activities a few times now. Can you kind of walk us through what those look like for you?

Amanda Warfield: And How you determined what you were going to spend your three days a week on and what you weren’t, because I, that’s definitely going to be the biggest thing for everyone is how do I cut back on what I’m doing? I feel like everything is vital. So how do you know? 

Cailen Ascher: Yeah, I mean, for, for all of us, and depending on the role that you have in your business, I mean, right now I do have teams.

Cailen Ascher: So that has shifted what I spend my time on. But if you’re pretty solo in the business doing all of the things, obviously, there’s going to be some administrative stuff you need to do each day. Like, you need to check your inbox. You need to make sure that, you know, if there’s little things that need responding to timely stuff, absolutely.

Cailen Ascher: Like, it’s not about ignoring those things, because those are important. And if someone needs to hear back from you, it’s important they hear back. But generally, when we’re talking about revenue generating activities, These would be marketing activities. These would be, um, outreach activities, you know, reaching out to people who might be, um, that you’ve been in correspondence with, or if you do any kind of advertising, like checking your Facebook ads, updating those, those types of things, or, um, one of my favorite, which is happening right now is, is visibility, you know, getting out there in front of other people’s audiences, speaking on podcasts, online summits, um, Conferences in person, if you can, now that the world’s open back up, um, you know, those types of things like leveraging your time in a higher capacity, and then also some of the, the revenue generating activities can look kind of mundane, but depending on you need to be consistent with stuff, right?

Cailen Ascher: Like sending emails. I send emails every week to my list at least once a week. And if they didn’t hear from me every week, Okay. The right people wouldn’t show up as buyers for my programs and so it might not look like this, like, like, super, like, sexy, exciting thing that you’re doing, but some of that background nurturing on through your email through your social media content.

Cailen Ascher: If you have a podcast, like, you don’t have to do all the things, but pick. Like, 1 or 2 places where you’re going to show up consistently and let that be enough, but be consistent because if people are never hearing from you on email, or if they check your social media, it hasn’t been updated in 4 months, or if you had a podcast for a hot minute, and now there’s no new episodes, and there’s no reason why people aren’t going to check it.

Cailen Ascher: There’s not that social proof that you are, like, out there doing the work and that’s what builds know, like, and trust over time. You know, people have signed up for your email list, getting those regular emails. And so that’s always been really important for me. I still, you know, I don’t have a copywriter.

Cailen Ascher: I write all of my emails. I do my own podcasting, like. This most of the social media content, I create myself because I really want people hearing from me so that if they’re interested in working with me, they have a sense of what I sound like, and what I act like, and all of those things. And it’s not just me behind the scenes, like, playing in my business.

Cailen Ascher: And so, and another key piece of it for a lot of us is business development. And so that can look like. New projects that you’re working on new things you’re rolling out or also like learning be working with a coach or working inside a program to develop new skills or to, you know, step into that next level of your business, whatever that looks like.

Cailen Ascher: But. I would say a lot of times when we’re coaching, especially when we’re 1 to 1 coaching, it’s like 70, 80, 5, 80 percent of our time is spent serving our current clients. And then that little remainder of like, 15, 20%. Is what we use to try to make, get more clients and make more money. And really, we want to almost have the inverse of that, like 70, 80 percent of the time we’re planting seeds for clients.

Cailen Ascher: We’re planting seeds for money. We’re planting seeds for growth and then in that little bit of time, that remainder of time is where we’re serving our current clients and not in a way we’re like. You know, once they pay us, I don’t care anymore, but just we need to start thinking of switching how we’re spending our energy.

Cailen Ascher: If we want a business that’s sustainable and growth oriented. And that’s why I love the group model, because you can make highest and best use of that 15, 20 percent remainder, however much, you know, like that little bit of time you can coach in such a powerful, impactful way when you have a group model.

Cailen Ascher: Rather than trying to like cram all your one on one clients or limit the number of one on one clients you have, you can still make a really big impact with that less time. So that’s been a big upgrade that I’ve made that’s opened up my three day work week even more was making that transition from one to one to group coaching.

Cailen Ascher: I love that you 

Amanda Warfield: talked so much about spending a large chunk of your time on your marketing and your visibility because So often, that’s one of the first things we’re told to outsource and don’t get me wrong. I am a content strategist. I do that. I am the person that people outsource to is so often it’s made to seem as if it’s just something you can brush under the rug and you so you can focus all your time on your clients and on the back end of your business.

Amanda Warfield: And it’s all important. But if people don’t know you exist, they won’t work with you. And so I love that that was your perspective shift of, I need to spend more time marketing and less time serving clients on a one to one basis. And so you moved into group coaching and I know that you have just been wildly successful with that.

Amanda Warfield: I’m curious what you’ve done to make that switch so effectively, because I already know that there are people listening, going, I can’t even get enough one to one clients to feel like I could make a group coaching program. So how do you make that shift effectively? 

Cailen Ascher: I think a lot of us are introduced to good group coaching as a downsell cheaper option to one on one.

Cailen Ascher: So we’re told, okay, first you create your one on one offer and then you create your group offer, which is cheaper. And then you make that into a course. And then you have a tripwire, you know, like we have that whole Ascension model. But what I love doing is. Making the program, the group program, the signature high ticket offer of the business.

Cailen Ascher: And it’s not to say you never coach one on one again, but it’s just lifted to such a VIP premium level that you really get to cherry pick your very best clients. If you even want to do it at all. So if you’re charging currently 3, 500 for one on one, you know, like three months of one on one coaching that group program.

Cailen Ascher: Should be 3500 like we want to come in and replace it or even create a program. That’s maybe a little pricier. Like, can we make it even better and higher value somehow? And so we’re not taking a step back where it’s like, oh, now I need to get 3 clients in my group just to replace that 1, 1 on 1 client.

Cailen Ascher: We want to make sure it’s an even switch out. And another thing is that because of that, I mean, the programs we help our clients create are, you know, on the least expensive side, like 3000, all the way up to 10 So these aren’t programs that we then need to go get 50 clients for. You can get five, eight, 10 people.

Cailen Ascher: And that can be like, You know, you’re almost making six figures from one enrollment, depending on your price point. And so what we really focus on is like intimate high ticket group coaching that you don’t need to have these massive enrollments for, but you can still have that massive, like that massive launch number, you know, like a 50, 75 K launch.

Cailen Ascher: By making sure you’re putting this program together in a way that’s really high value, because ultimately people don’t really care if you’re getting most of the time coached 1 on 1 or in a group, or they don’t that’s not what’s important to them. What’s important to them is a solution that’s going to work.

Cailen Ascher: And if you have a proven process that can help them that we can. Package up into a repeatable model for group coaching with maybe some, you know, specialization like we give our clients a couple one on one calls to make sure they’re feeling really that high touch aspect. But if you’re able to do that and get them the results, they don’t, they benefit more almost from the group because they’re with a little cohort of individuals who are doing the work alongside of them and they have accountability partners and they have this like mastermind energy on this path of change, rather than it just being you and them every week on a call and you’re like their only reference point.

Cailen Ascher: There’s no other, no other perspectives. And so what I found is a lot of my My clients like the group model a lot better than one on one once they’re introduced to it. And I know from my own experience, I exclusively invest in group coaching at this point. Like I want to work with, yes, a very educated mentor, but I like the idea of being surrounded by people doing the work together.

Cailen Ascher: It brings me confidence and faith that we’re like all on the rise together. 

Amanda Warfield: Absolutely. I’m, I’m the same way at this point. I will almost never invest in one on one coaching just because. The relationships that you build within these other people that you’re being coached with. It is truly priceless, really.

Amanda Warfield: I mean, some of my greatest business friends come from a mastermind that I invested in years ago. And gosh, I have a client from that. I’ve got an incredible business friend and it’s it’s not that you go into those hoping for those things, but well, maybe the friends, but when it comes out of it, it’s always like, oh, this is all because I.

Amanda Warfield: Invested in something and invested in a program. And I invested in my situation for this first one I invested because I really loved the educator that was teaching it. And I wanted to learn from her and then I got out of it and I was like, Oh, that was great, but even better is the relationships that I’m building.

Amanda Warfield: And so that’s always something I consider when investing now in group coaching programs is what am I going to get out of it from the educator? What am I also going to get out of it from the people that are going to be doing it with me? 

Cailen Ascher: Yeah, it’s so true because. Being an entrepreneur can be such an isolating journey.

Cailen Ascher: You know, you’re I’m in my office alone, you know, on a computer screen and it’s It can feel really solo. And so, if you are in a group program, you’re instantly tapped into a network of people who share similar values, have similar vision, are ambitious, are successful, um, it just immediately surrounds you with, with peers and a support group.

Cailen Ascher: And I mean, I feel very fortunate on the home front that I’m super supported, but I know that everyone feels that way. And so I think. You know, getting into a community, a small intimate space like that can be so, so beneficial 

Amanda Warfield: for someone who is thinking, okay, maybe this is something I want to move more towards.

Amanda Warfield: What are some tips for getting started in creating a successful group coaching offer right off the bat? And what are some common mistakes that you see? 

Cailen Ascher: Yeah. So I think what’s really important is that you pick a specialty for your program and kind of Opposite of that is when you go to general, that’s a mistake where it’s like, this program could help all people on the planet or all women are all mothers.

Cailen Ascher: And it’s like, okay, maybe that feels like you’re getting narrow by saying mothers, but how can we make it more specialty? Like, are these working mothers? Are these stay at home mothers? Are these mothers of women? Yeah. Babies and toddlers, or these mothers of school age children, or these mothers whose children have left the nest, and they’re looking to reclaim a sense of identity.

Cailen Ascher: There’s so much nuance in there, and we really want you to be a specialist when we partner with you to create a group program, because that is what is going to make it a no brainer investment for your right clients. If it’s really kind of general and wishy washy of like, oh yeah, we’re going to up level together, and it’s going to be amazing.

Cailen Ascher: It’s just like these big, like, open ended blanket statements. That doesn’t really get people excited. You want to be kind of polarizing and share, like, the, the specific methodology that you have for this specific person and the transformation they most desire because that’s That’s what people are going to pay for.

Cailen Ascher: You know, that’s when they’re like on the call, like, how can I give you money now? Because I’m so excited to work with you inside this special container you’ve created just for me, because it feels, it feels like the one on one aspect where, you know, we can kind of customize for our clients. You know, we have to we can’t do that with a group program.

Cailen Ascher: So instead we have to pick a specialty so that the right people feel that level of customization, even though we’ve created a program that can help multiple people at a time. And so I think that’s, that’s a really powerful shift. In general, in our business, because I think when we start in one on one coaching, we have the opportunity and sometimes it’s important to explore.

Cailen Ascher: It’s like, when I first started coaching, it was like, some people needed more mindset stuff and people needed more marketing stuff and some people needed more sales stuff or a mix or, and they wanted to be coached differently. Some people wanted, you know, lots of plans. Other people wanted to talk just in big general ideas.

Cailen Ascher: But when you make a group program, you get to decide, like, what do I stand for? What’s my mission? What’s my message? How do I want to show up as a leader? How do I want to curate this group and this energy and this environment? And it really takes you to that next level in your business because you, you really are forced to not let your clients take the lead, but you take the lead and you decide what it’s all about.

Cailen Ascher: And that’s really exciting and powerful. And Instantly, like makes your marketing better, makes your sales better. Like it improves everything across the board because you’ve gotten focused and specific. You know, it’s funny. My next 

Amanda Warfield: question was going to be, how do you market this? How do you actually get people into your coaching program?

Amanda Warfield: But you just, I feel like you hit the nail on the head. It’s all about being specific because if you’re shouting into the void about, Oh, I help. Writers get their book published. Well, it’s kind of niche, but it doesn’t tell me what my pain point is yet. If you go and you say, I help entrepreneurial writers get their book published, that’s a whole different story.

Amanda Warfield: And I mean, that’s, I found my book editor specifically because she markets very specifically to entrepreneurs turned writers, entrepreneurs turned authors is what she calls them. And I was like, Oh, that is, that’s me. You know, how to. And it books that are just like what I’m doing. And so that very specific getting really niched down is how you market the people.

Cailen Ascher: It’s so true. And it feels good. I mean, it feels good to have that level of clarity and specialization because the coaching industry is crowded and, and I don’t think that’s a bad thing. I think there’s also a higher demand for coaching than ever before, but it’s a lot different to be a social media strategist versus an.

Cailen Ascher: Instagram reels strategist, right? Like, if you’re going to create a program, if you’re like, oh, I can help you with all things, social media. Okay, yes, maybe some people would be interested if they want, like, really broad social media strategy, but if you can give them, like. A deep dive into a specific area, rather than just kind of a blanket version over lots of areas.

Cailen Ascher: That’s so much more valuable to people and they really associate you with that thing and see you as an expert. And that’s a lot more valuable for so many reasons, you know, just, you know, people really are going to gravitate towards you and you’re going to be referable, you know, it’s like, okay, if someone wants Transcribed Social media.

Cailen Ascher: It’s like, oh, yeah, maybe your name will come up. But if someone’s talking specifically about, oh, my gosh, like, I know I should be doing Instagram reels. And I know there’s like, best practices and I feel like they’re changing all the time. I don’t know what to do. They’re like, oh, you should absolutely talk to so and so, because that’s what she does.

Cailen Ascher: Her program’s all about that. And it does. It makes you so much more referable. And I’ve noticed that in my own journey as I started focusing more and more on high ticket group coaching. It becomes so much more referrable because not all business coaches focus on that. There’s lots of different approaches to building a successful business, but if people align with my approach, then I’m the person that whose name they’re sharing.

Cailen Ascher: So 

Amanda Warfield: we know we need to be niched out. We need to know what our niche is and who we’re helping and how we’re helping them. Is there anything else that we need to have in place before creating a group coaching 

Cailen Ascher: program? Yeah. You need to know that. The journey that you’re taking them on, like, where are they starting from?

Cailen Ascher: And where do they want to go? And that’s going to help you. We call that your framework, but that’s going to help you build out your curriculum because. If you aren’t quite sure where they want to end up, it’s going to be really hard to create a cohesive curriculum to get them there. So you have to figure out what is the shiny destination that they’re.

Cailen Ascher: Aiming for that. They really desire that they want to have at the end of it. And then you can reverse engineer the steps, the milestones along the way, and also the obstacles that they might meet along the way as well. Because then you can anticipate those obstacles and create content in your program to help them.

Cailen Ascher: Remove them or eliminate them all together. 

Amanda Warfield: So important that transformation is key. And that’s when I’m working with clients, that’s the one thing that we always end up having to go all the way back to, because you can’t have a content strategy without knowing exactly what it is that you’re giving your people.

Amanda Warfield: So super important. If you could give everyone just one action step to take after listening to this episode, what would it be? 

Cailen Ascher: I would say this is what landed for me. So I’ll share it. Um, ask yourself what you want to be known for. And don’t worry if what you start, I would get a pen and paper, get your journal or whatever and ask right at the top.

Cailen Ascher: What do I want to be known for? And don’t worry if what comes pouring out of you doesn’t immediately seem related to your business. Don’t force it to seem related to your business. Just let it flow, but I guarantee there’s going to be some golden nuggets that come out. Flow onto that paper. If you’re not self censoring that are going to inform your business in some way, shape or another, right?

Cailen Ascher: Like who you want to be working with or how you want to be working with them or shifts you need to make to your schedule or where you want to be visible or how you want to be visible. There’s going to be something that flows out of you that gives you additional clarity. So I would, I would ask that and and see what arrives and then go from there.

Cailen Ascher: And then if you 

Amanda Warfield: could give everyone 1 book recommendation, 

Cailen Ascher: what would it be? Oh gosh, I have so many books. I have piles of books on my nightstand. Gosh, there’s two that are coming up. The one I’ll recommend is one that I’ve tried to read several times over the years and it just wasn’t landing for me. So if you pick this book up and you’re like, this is not for me, put it down for three years and then go back.

Cailen Ascher: But it was, um, it was actually the complete works of Florence Goldschinn. Her most Famous book is called the game of life and how to play it. And she was an author back in the thirties, um, thirties, forties, and she. Totally was tapped into something beyond herself, definitely like channeling information about how to align with your desires and create them.

Cailen Ascher: And I just found it so interesting that after all these years of trying to read this book, just in like the last six months, I finally. Picked it up again and everything was clicking. So I’ll offer that in case it’s going to click for somewhere, someone else, because it’s been around for a long time.

Cailen Ascher: There’s a lot of wisdom in there. Okay, perfect. 

Amanda Warfield: We will link to that in the show notes. Now, if anyone’s listening and they’re like, I need to learn more about group coaching and how I could potentially implement this in my own business, where can they find 

Cailen Ascher: you? Yeah. Over at kaitlynasher. com, my main website, um, got lots of information about how to make group coaching work for your business.

Cailen Ascher: Got an awesome freebie. It’s called how to make over 100, 000 a year with one zoom call a week. Um, it’s a quick like 20 minute training. It takes you deeper into my, um, my model for group coaching and how it can work for your business. If it’s something that’s of interest to you. Awesome. 

Amanda Warfield: And we will link to all of that in the show notes friends.

Amanda Warfield: Caitlin, thank you so much for being here today. I really 

Cailen Ascher: appreciate it. My pleasure, Amanda. Good to see you. Good to see you.

Amanda Warfield: Thank you so much for joining me here today, friend. You can find this episode show notes, as well as all the resources you need to simplify your marketing over at amandawarfield. com. If you liked what you heard here today, Be sure to subscribe to the podcast so that you never miss an episode, and if you could take a moment to leave a rating and review, it would truly mean the world to me.

Amanda Warfield: Ratings and reviews are the number one way that you can support a podcast and ensure that it sticks around for many more episodes to come. I’ll see you next time. Now go out and uncomplicate your marketing and business.


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