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Ep 3: How To Run a Successful Business Working Just 3 Days a Week with Cailen Ascher

Business Coach Cailen Ascher shares how to create the life you want...three-day workweek and all.


Elizabeth: Hi, everybody. Welcome back to Ascend and Transcend. I'm Elizabeth Pearson, and today I'm very excited to welcome Cailen Ascher. She is a business coach and overall badass and has a wonderful way to help us work less and make more with her three-day workweek program, which you can get online and on her website. She's got lots of really good freebies, so be sure to check it out, but I wanted to welcome Cailen to the show. Thank you so much for being here.

Cailen: Thanks for having me, Elizabeth. I'm so excited to be here today.

Elizabeth: We'll just start out. We were kind of chatting a little bit before we started recording about your journey and how you went from having different businesses. She said she was never a traditional nine to fiver, which I love. I feel like that was probably something your soul nudged you away from early on, like most. I would just like to hear a little bit about your background. I know that you're a mom of two children as well. I think it's really important, for not only women who are working in a professional field, but also as moms, to try to find time to be as efficient as possible while still making time to listen to our souls and let that be our guidance. So why don't you tell us a little bit about your background and your journey?

Cailen: Happy to, yes. As you mentioned, I've never had a traditional career. I'm very much unemployable at this point in my life.

I embrace that, but you're right. Ever since I was young, honestly — a kid, a teenager — I was always thinking about what I wanted to create and what I wanted to offer that felt like an authentic extension of me. I had this like feeling in the pit of my stomach, like this yearning, to do something meaningful and purposeful. I didn't know what that was, but I knew it wasn't gonna be found in a cubicle, in an office. I luckily had very supportive parents and amazing partner who all were on board for me to just be on this journey of exploration. That's really what my twenties were about. I started a number of different businesses, all of which I loved at that moment. They served my purpose and I got from it what I needed, but it was really around the time when I became a mom for the first time that I started to feel tired.

I had been pushing with a certain kind of energy to figure this out for so long. I was exhausted and I was pregnant and this baby was arriving. I had this moment where I was like, should I just stop? Is my purpose rather just be a present mom for this new little being that's arriving? What came to me — after sitting with that for a few months, I took some months off after she was born — was that there'd be some point when that didn't feel like the right choice anymore. That there'd be some regret involved or something that wouldn't make me feel like the most fullest expressed version of myself.

I didn't know what it would look like, but I had this concept of having an abbreviated workweek, just working three days. Prior to that, I had been teaching yoga, and I actually was working with some yoga teachers and yoga businesses to help them build more of an online presence. I had always been intrigued in the online world. I had a blog for a really long time; I started blogging back in like '07 or '08. I didn't realize I was coaching them, but I was coaching them.

After my daughter arrives, I take some time off to reflect. I discovered the coaching world for the first time, and it cracked me open like, "Oh my gosh, there's these powerful, feminine women showing up holding space for others to them transform their lives." It felt like this amazing pay it forward. It's something I've been trying to do for myself for so long. What if I could create a container that supported other women in that process? It was like this complete 180 of the way I had been looking at my business and my life.

I learned from the coaches that inspired me and created that first high ticket offer while working just three days a week. That first year when I found coaching and stepped into my three-day workweek and had my brand new baby — that year I really began to hit my stride. I made more money that year than probably the previous three years combined in my business. Then, the year after that, that was my first six-figure year, and I also found out I was pregnant with my second daughter at the time.

I shared that piece of it, because becoming a mom is what really unlocked this new path for me, these new priorities, and allowed me to more powerfully step into my purpose. Then when my second daughter was coming, I realized, "I have to think about ways to outsource, to automate pieces of this business." The business still grew that year, and I took four months off after my second daughter was born.

It's been a lesson for me after all those years of hustling and working so hard that these little beings are arriving in my life, I'm taking more time off, working less than ever before in the business, it found itself. It was really amazing to be on that journey.

Elizabeth: Children are this wonderful gift of perspective. What is the hustle costing you? I probably, like you, felt the same way. It was costing — I did have a like corporate sales job — but it was costing me way more than they were paying me, because ultimately, they could never pay me enough to feel like the sacrifices that were being made for them were equivalent to the sacrifices I was making to myself, first and foremost, but also to my girls.

This idea of a three-day workweek: a lot of people say — I've written articles on this as well — four-day workweek. A lot of people think it's a pie in the sky thing and that you really do have to grind and hustle and really exert a lot of effort to produce results. I don't believe in that, but I would like to hear you explain why you don't believe in that either.

Cailen: I don't believe in it because I tried the other way.

I tried it for about seven years of really like pushing, hustling, burning myself out, not to mention all the mindset stuff that's going on that accompanies that kind of energy: just beating myself up in my own brain. Actually, the most powerful thing for me was just witnessing my pregnancies. The fact that all of a sudden I was pregnant — and they were surprised both times. We were married and kind of trying, but the babies: they arrived when they wanted to. That felt pretty effortless on my part, which was amazing. I know that's not everyone's experience. Then the pregnancy: I mean, their body just knows what to do and you just allow it to happen. It was really interesting.

I was like, "Oh my goodness. If creating a human is easier for me than running a business, I'm doing something wrong." There's something unbalanced here. That was a really powerful lesson. It's not about not doing work. It's not about being lazy. It's about waiting for the inspired action to arrive for you, to trust that even it goes a little against the grain or a lot against the grain of what people are telling you to do, that it's right for you and the people that you are meant to serve and you are meant to reach.

That's honestly a lesson I'm still learning because culture has powerful storylines that tell us that there's a certain way to create success and a certain way to do things. But the more that I release my rigid expectations, my rigid agenda, and play more in my business — what can I do today? How can I show up? Sure, I have structures that keep me supported and allow me to serve in a bigger, more powerful way. The structure helps to a degree. But when you are rushing through life, just trying to get to some end destination, that energy never produces the feelings of ease and abundance, fulfillment, joy, peace, all of that stuff that you want to get, because they don't match up.

Elizabeth: You hit on something that I couldn't agree with more: it's this conditioning, whether it's the societal conditioning, whether it's the environmental conditioning that we have. I think when people hear three-day workweek, or that you even want that, to your point, it's: "Well, you're just being lazy." Or if you're making enough, or you're making multiple six figures three days, then why don't you just bump it up to six days and make double. It's this thirst and this conditioning to consume and always want and need more. But when you really trim it down and you do embrace this art of allowing things to flow into your life without the effort that everybody thinks needs to be exerted to get something, then you realize that it is probably enough. Then once you realize it's enough, it expands again.

It's the beauty of it. This hustle culture is so toxic. It's especially toxic to women and mothers. I loved Lean In. I personally feel like Cheryl Sandberg is a hero, but it's not for everybody. It is very different, but I think it's more about making those decisions and then sticking to it. If it's a three-day week or whatever, do not feel like you have to validate it to people why you're only working three days a week. Because they probably think you could work more and make more money and who the fuck wouldn't wanna do that? That is what I feel like is the really incredible thing about your story and mine as well. I love it.

My husband will be on conference calls and I'm like, "You know what? I think I'm just gonna like catch up on my TV today." He just looks at me, and I'm like, "Or I'm just gonna read, or I'm gonna meditate, or I'm gonna go for like a jog at the beach." I just don't care. I'll actively post it on Instagram too. "Here's me not working today 'cause I just don't want to." I think that that's okay. I think that actually feeds into the manifestation of the bigger things. Would you agree?

Cailen: Completely. I think we need space for stuff to come through. If we're constantly in doing mode, there's no room for creative thoughts to land, new ideas to come through. I can remember when certain big ideas came through in my business. It was never while I was at my computer typing away. It was while I was on a jog or while I was on vacation or in the shower. It's never when you're doing and doing more.

Elizabeth: How do you keep the discipline then? What is the fine line between being disciplined and then having, I assume, an incredibly efficient and effective three days versus kind of peppering it out to maybe five or six half days? Take us a little bit through the ideology behind this, and then if you can share any sort of tactics with us that would be greatly appreciated too.

Cailen: First and foremost, I think you need to figure out what works for you. Everyone's energy's different. At the time when I set up my three-day workweek and — and honestly, it's going to be in transition, my girls are getting to school age, so it might shift with the school schedule — but I had this brand new baby and I wanted to have four day weekends with my husband and the little baby. My mom and my sister were available to watch her in our house on certain days. I collaborated with them to make it a win-win situation that we could have in-home childcare from family members. It was what made sense for me at that season of my life. It's worked for a good long while: my girls are still young, they're four and six. I still like that because my little one's not in school on Mondays. During the summer, we take a lot of Fridays off or half days. Right now Fridays, while they're in school, my husband and I often spend at least the afternoon together, if not most of the day. We go out to lunch and do stuff that we wanna do together.

That, I think, is really important too. This is not about everyone having a three-day workweek, although that would be really freaking cool.

Elizabeth: I think there'd be a lot of happy people walking around if we could get a three, even four-day week. But this slug, this five-day slug, to have two precious days to yourself, which most people spend at least one of those mornings hungover. It's crazy. It just doesn't feel like a life well-lived.

Cailen: It's an antiquated system, right? It was developed back during the industrial revolution because men were believed to have eight good labor hours in the day.

Elizabeth: Really?

Cailen: That's why it started. We're so far beyond that, right? One of the beautiful things that came out of this pandemic was that we got a glimpse of: "Oh, we don't have to go and sit in an office for an arbitrary 40 hours, plus or minus, a week, just because we've always done that? There's other ways of doing this?"

I have a friend who was saying that because of the pandemic, she was able to drop her girls off at school and pick them up for the first time ever. Now that she's transitioning back to work, she's not gonna be able to do that anymore. This was like a little glimpse of: "Oh, my life could be something different than it is now."

Elizabeth: Well, that's why nobody's going back to their job. That's why so many of these people are standing up and saying, "You know what, I'm not going back to the office five days a week." That's why it's so hard to fill these jobs. The pandemic came and everybody did these mass layoffs, which just obliterates company culture and trust with an organization. Then now all of a sudden everybody's vaccinated and it's like, "Well, come on back." "No, I don't think so."

I think it's great. I hope there is this revolution, especially with mothers who say, "You know what? I got just as much done doing that pickup and drop off, and I'm gonna come in and my hours are gonna be flex" or "I'm gonna have a couple days a week home from flex."

Cailen, tell me this. You said that you started outsourcing some things, and I feel like this is applicable to female business owners, but also the women who have more corporate America jobs. What are some of the things that you were able to outsource that you felt made the biggest impact, which freed up this time?

Cailen: What I did to even figure out what those things were, cause sometimes we can be so lost in the weeds, was I took notes during my days. A couple days in a row, I set a timer on my phone every hour. I stopped, jotted down what I did, and then after those few days, I looked back and I was like, "What do I actually enjoy doing on this list? What do I clearly not enjoy? What am I not good at?" It was really easy, by just looking at the data on the paper, to see where am I wasting my time, essentially.

For me, I realized there was a lot of piddling around in the inbox and scheduling stuff. I still write my own content, but scheduling it on all the social media platforms and via email and just doing that administrative work, essentially. I realized if I can free up even just a couple hours a week by paying another woman, who hopefully really likes doing this thing (being that behind the scenes, moving pieces person), I can support her and her business, and I get a couple hours back. I can get another client that more than pays for her — like 5x, 10x pays for her time.

It gave me permission to do that. Honestly, when it comes to the first first things I outsourced (those were the business things), but the first thing I did was hire a house cleaner. This is not a good use of my time. I'm not good at cleaning. I don't really like it. I mean, maybe that sounds a little like princess or whatever.

Elizabeth: It's all what your means can afford.

Cailen: Exactly.

Elizabeth: I think there's a difference between saying "I can't afford it" and being cheap with yourself. I mean, I'm sitting here drinking a $5 Starbucks. That's not going away. That is something that I will spend on myself every day and feel really good about it. I don't care. But same as you, I have a wonderful support system here as well. Deanna is my rock and she does the stuff, to your point, which I don't feel is a good use of my time.

You can outsource, even professionally too, I'll add. A lot of my clients come and they say the same thing. There's just not enough hours in the day. Some of them are in very specific roles. Or they have very specific businesses, and they're like, "I'm on a call with a client, and then afterward, I have to send a recap or a proposal" and they're drowning in the admin. If you can find somebody who can help out, who's got that background (if they have a background in PR or something like that), and they can translate what you're saying. Then they can be taking notes on the call, and they can be drafting the proposal for maybe your final review before it goes out. Same thing with client proposals or client agreements or things like that. Just have them sit in on the call, take the notes for you, and then you can take a look at it before the final product goes out. It's a huge time saver.

Cailen: Yes. It's not about once they handle it, you're not allowed to look at it or touch it, but just remove all the time you're spending with it. You can have that final look over, give it your seal of approval, and that's enough. You don't have to be all.

Elizabeth: Do you have a virtual assistant then?

Cailen: Yeah, I have an OBM.

Elizabeth: How did you find her?

Cailen: Oh goodness. She's been with me for five and a half years. She's been with me a long time. She was a referral. I was at asking around in a Facebook group, an online community I was a part of at the time, and just saying, "Who's an amazing person to handle these certain things?" When she started her role was much different than it is now. We've really grown together. As trust was developed, I handed more and more over to her. She really runs the back end of the business.

Elizabeth: I think that that's something that people struggle with too. It's like, "Well, where do I find these people?" That's gonna take time to find the help and then train them. But it's a means to an end. To your point, I think even if you are trying to build a social media following or whatever, even with this podcast, I reached out to other women that I really respect and said, "Hey, who do you use as a producer?" Then they refer me to this woman who happens to be a minority and a single mother, and she's such a hard worker. She does such a great job. So it's like, "Okay, great."

Even on Instagram or, to your point, Facebook, you can reach out to other people who seem to be doing it well and then ask them who they use. Maybe you use their person too, or that person has a referral. To your point, I don't think you have to go in blind and start having to feel like you have to weed through a whole bunch of candidates.

Cailen: No, that would be completely overwhelming. I think the best people I've connected with have all been referrals. That feels good. That's how I've gotten some of my best clients: they've been referred to me. It feels just like a very natural place to connect with those right individuals.


What is your plan for scale? I know that it's going to change as your girls grow and go back to school and things like that. With everybody, life has different demands at different times. Do you foresee yourself being able to sustain the three day that you have right now? Even if the additional two days, like if the girls are at school, that they just become think days for you or meditation days or just self-care days?

Cailen: I think there might be a little bit of transitioning partially just because I like my work so much that some days, I just feel inspired. I love having a day where I get to do my fun projects. Nothing that is needed right now, but these big things: like, there's an app I wanna develop. I just want to spend a couple hours researching it, because that is something I wanna do and not feeling like I'm not being productive.

One of the things I'm doing to help to scale the business itself is the last six months have been dedicated to building an automated webinar funnel for our signature group coaching program. That's gonna really enable the business to just grow you whatever capacity, no matter how many hours I am or I'm not working in a given week.

Elizabeth: How is that going? Because building a funnel, I mean, we hear this, right? Like any entrepreneur, especially a coach, I feel like it's so incestuous. Everybody's like, "Buy my coaching" and this and that. I've invested in some stuff like that. It just feels "ugh" to do the webinar and the funnel and all of that. I know that they work and then you have to support it with ads. But how is that process going for you? Is that something that you're doing on your own or were you able to outsource and get support in the creation?

Cailen: That's not something I'm doing on my own. This is a beast of a project if I'm being perfectly honest. It's a big project. My right-hand gal, my OBM who I mentioned earlier, Raven, she is really building it. I get to create the content — I write the emails, I recorded the webinar — but then she built the thing. Because I'm not good at that, not my zone of genius. I am working with a coach who has, I think it's an eight or nine-figure business at this point, that's built on the back of these funnels. I know I'm learning from the best, but it has been a long-term project. You have to be in it for the long haul.

Elizabeth: I know I keep teeter-tottering on that too. LI love my one-on-one clients, but — I'm sure you feel this too Caly — there's only so many hours in a day. It is an energy demand on you, but super fulfilling. So it's like, "Do I keep that and then get this immense joy and fulfillment, or is it time to really kind of wake up automate the bulk of this?"

I think that can be a really hard transition for people too. With any business that you have, hiring people and then kind of entrusting them with a piece of you and your baby, which is your brand, and feeling safe enough to do that, and like they'll be a good representation of that. Was that hard for you?

Cailen: It was, yeah. I think that it took me a long while, and like I said, she's been with me over five years now. But it did, it took a long, long while to really develop a level of trust where I could know that if I just give her the bare minimum, it's gonna be handled probably even better than I could do. In the beginning, there's a lot of like, "Did you do that? Let me check it. How'd it go?" It's been a while. And it's learning how to work with someone. She's got different rhythms and patterns and things that she needs.

We've had other people in and out. We have a VA and a Facebook ads manager and other transient people who have commented on the business. But I know, right now, one of my top priorities as the CEO or the leader of the business is to make sure she's happy in her role because now the business needs her. That's been an interesting shift from it going from everything's mine and here's a little bit for you. Now, she's got so much on her plate that I'm like, "How can I keep you happy? Because I wanna make sure that you're happy here and that we have a great relationship." Just checking in and making sure that she's feeling fulfilled by her work too.

Elizabeth: I think that's a big piece of it, too, when I've been at a crossroads about, "Do I outsource that piece or not?" I've always defaulted into, "But what if they don't do it as good?" And my husband always says, "But what if they can do it better?" I think sometimes that's hard, especially for an entrepreneur to hear, that anybody could potentially do something better than even you could. But clearly, there are people out here who are experts in these different things. To your point, so many more people are really craving that work-from-home flexibility and the on-demand work that now is the perfect time to outsource, let things go. Whether it's just domestic tasks, whether it's getting your spouse or your partner, if you have one, more involved in supporting those things so that you have more free time.

Because another thing I hear from women is, "Well if I worked less, I would just do more household chores. More would come up. I would just go to Target twice a week instead of once, or I would do this or that." To your point, you have to have a plan of what am I then gonna do with this time that is back for me. Is it going to be focused on deep inner, spiritual exploration or self-care? Is it gonna be on new business strategies, how to scale, different things like that? It's very important to have some sort of structure around that. Otherwise, it could very well end up being binge days on your couches, especially if your kids are at school versus being productive.

Cailen: Yes. Completely. I know for me, and I don't think I really understood how to honor it until probably becoming a mom, but that I need a lot of quiet time and space and "me" time. I had that by default before, and I didn't realize that I really, really needed that. I still catch myself like, "Oh, I picked up my phone again. I'm gonna put that in the other room. I'm gonna take a book. I'm gonna go sit on the porch. I'm gonna go lay in the sunshine. I'm gonna go for a walk. I'm gonna can finally get back to yoga, now, I'm gonna go to my yoga." I've been doing my own practice, but I get into a class once in a while. Feels really good.

Elizabeth: It sounds like the main takeaway is that it's really good to deeply evaluate your schedule, what you're spending time on, where you're focusing your energy, and then creating that space to listen to your spirit and your soul and that energy, that nonphysical being of you, that is trying to guide you. If we can just shut up long enough to hear it a little bit and then maybe get it amplified a little bit, that will provide you with these answers. But when we're in the hustle, when we're in the grind, when we in really the distraction, which is what all of that is, then we aren't gonna be guided.

A lot of times that will come out as feeling like you're driving a car with a parking brake on. You can still go — it'll grind and it will go — but you're gonna have to exert a lot of energy to do it versus just slowly letting it down and then seeing how much further you can go, how much faster.

Thank you so much for this time, Cailen. Everybody go to Cailen's website, it's gonna be linked below, but it's, and you can learn all about her three-day workweek. You can take her course to help you to help create that framework and that structure. Also, check out her website for lots of really great free content. Thank you so much. She's got a great freebie there as well.

Calien, what is one thing that you wanna leave these wonderful women who have tuned in today with?

Cailen: I think something that's really important to remember is that the journey, the path that you're on, has to align with the destination of where you wanna go. If you want to go to a place of ease and abundance and living your best life, you can't get there by hustling and grinding and pushing yourself to the brink and feeling so alone in the process. You have to open yourself up, like you said, to that greater energy around us, to allow ourselves to feel supported, to feel that sense of ease on the journey to get to where we want to go, because it's not gonna match up otherwise. That's something that I always remind myself of, and hopefully, that's helpful to whoever's listening now.

Elizabeth: 100%, if you're grinding and hustling, you're just gonna perpetuate that. The end is going to be a grind and a hustle. If you allow and you go with the flow, I mean, I don't know who said that first, but I swear to God, everything just boils down to that. Then you'll probably effortlessly get there, and it might not even be the destination that you have in mind. It's probably something a lot better.

Thank you so much for your time today. Everybody tune in next week. We'll have another fantastic guest. Thanks a lot again to Cailen Ascher, our guest this week.

Cailen: Thanks, Elizabeth.




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