Cailen is a Clarity Coach for women entrepreneurs who want to live their fullest potential professionally and personally. Her teachings have helped 1000s of women define their purpose and deliver it in a meaningful, impactful and profitable way. For weekly lessons to find and live your fullest potential visit CailenAscher.com.
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Worst Entrepreneur Moment
- The Baby effect is real, Fire Nation… Tune in to hear why you shouldn’t wait for it to happen to YOU!
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Cailen Ascher: Yes, I am.
Male Speaker: Cailen is a clarity coach for women entrepreneurs who want to live to their fullest potential professionally and personally. Her teaching has helped thousands of women define their purpose and deliver it in a meaningful, impactful, and profitable way. For weekly lessons to find and live your fullest potential, visit cailenascher.com. Cailen, take a minute. Fill in some gaps from that intro and give us just a little glimpse of your personal life.
Cailen Ascher: Sure, of course. So I think the first thing I’d like to share is I’m a personal development junkie, and I think that’s basically what led me into coaching, is my whole life I’ve always been seeking out my thing. I love reading self-improvement books and studying mindset and doing yoga and learning about wellness and nutrition and meditating. And I realize that instead of just consuming all that information, I could really turn it around and help people change their lives using all those tools. And so as I’m evolving into the best version of myself, I seek to help others to do the same.
Male Speaker: Loving all of this. And Cailen, you have quite the journey you’re going to be sharing with Fire Nation today. We have a lot of ups; we have a lot of downs. We have some pretty cool breakthroughs to discuss. But first and foremost, we are entrepreneurs, Cailen, and I want to live in the present for a minute here. And that present is how are you generating revenue today? How have you created a viable business around your brand?
Cailen Ascher: Right now my main source of revenue is through one-on-one coaching, working with these amazing women entrepreneurs and helping them really up-level their mindset so that they can up level their business and fulfill the purpose that they were put here on this earth to do.
Male Speaker: And you can see, Fire Nation, how Cailen just has that dialed in. I mean, she knows who she’s serving. And even more importantly for a lot of people, you know, she knows who she’s not serving. She’s not trying to serve the world right now. She has her target market. She has her avatar, and she’s figured that out. Now, what I do want to do, Cailen, is take a dive into your journey. And again, talk about some good times or maybe talking about some bad times coming up; but specifically what you consider your worst time, that worst entrepreneurial moment that you’ve experienced to date. So Cailen, you know, don’t hesitate here. Don’t try to cover this up. Like let’s just really get down into that worst moment and let’s hear that story.
Cailen Ascher: Sure, of course. So I think the worst entrepreneurial moment for me was probably -- it happened when I was coming back from maternity leave. I had taken a really nice maternity leave. It was like three and a half, four months long, and during that time with my daughter I really did a lot of reflection on my purpose and on my business, and I just realized, hey, that it just didn’t seem like the two were jiving. I should mention my business at the time was not the business that I have now. And I felt that I have really begun to lose that spark and that enthusiasm, and I had this moment, this sinking feeling of like, uh-oh, not again. And I think a lot of us who are entrepreneurs can relate to this because a lot of us are serial entrepreneurs and we kind of -- we keep seeking, we keep searching for that thing that is the thing we’re supposed to be doing. And so after returning to my work, after this time off with my daughter, I really -- I just didn’t have the energy for my business. I felt like working on it was almost -- if it wasn’t what I truly, truly wanted to be doing, that I didn’t want to devote any hours to it being away from this little tiny person that I loved so very much. And even though it was a good business and a good fit, it wasn’t a great business and a perfect fit. And it didn’t really light me up any longer. And that was really kind of terrifying. I mean, throughout my 20s, like I was saying, I’m this serial entrepreneur; so I knew this feeling that was so familiar and it was time to move on and to grow, but I really didn’t expect that feeling to hit me again. I was nearing 30, I just had my daughter; I really thought I had it figured out.
Male Speaker: Right.
Cailen Ascher: And like I didn’t want to tell my husband, I didn’t want to tell my friends. I was so ashamed that this feeling was hitting me, and it was a major low. And I really just felt like a failure, like I had let myself down and everyone else who had been rooting for me and supported me to get to this point in my business. But I knew that I couldn’t keep ignoring it. I knew that if I was going to continue on this entrepreneurial path, something had to change. And so with my husband’s encouragement, I enrolled in a program, which for me [inaudible]. And after working through about a quarter of it -- and the whole time I was applying it to my business at the time, thinking that just something needed tweaking with this business that I had. And then I realized after about a quarter of the way through it that I needed to restart the program, I needed to work on it from scratch as if I had no business idea and be open to any idea that would find me. And when I opened myself up to that possibility of something new and exciting and better coming down the pipeline, a new vision hit me. It was almost like a bolt of lightning. And in this rambling email that I sent to my husband after one of these modules that I went through and the work I was doing, I wrote down the words “find clarity in your life and business.” And I thought, yes, that is what I need. And that is what I want others to have, too. And it was kind of -- you know, you teach what you need to learn yourself, and it was this moment of realization that this path, this journey that I had been on and this quest for finding my purpose, is a quest that so many people are on. And if I can play a small part in that and helping them align with their purpose and really live their fullest potential, that that is what I needed to be doing. And I shifted my business and I repositioned myself as a coach; before that I was doing a lot of online programs. I really was keeping my community at an arm’s length, which was because they weren’t the right community. And everything shifted when I invited my clients in and started working more intimately with people, and I haven’t looked back since.
Male Speaker: And you’re the 1200 episode that I’ve done, Cailen, with great entrepreneurs who have just rocked and rolled and they’re doing great things. There’s been a lot of themes that have come up, a lot of different things. And one of those themes for sure as something that I just saw coming up over and over again that I actually ended up coining the baby effect, because it just seemed so often so many drastic life changes were happening when, you know, either a mother or a father would be looking at this child, this helpless -- this little baby that they loved so much. And they’re saying, man, like this is really making me reflect on life. And for a lot of people, it just took their business to the next level because, you know, what was holding them back was they were scared to make those outbound phone calls, to knock on those doors, to make things happen. And it’s a lot more scary not to provide for your baby than it is to make an outbound phone call, so they were breaking through some pretty big barriers.
Cailen Ascher: Yes.
Male Speaker: But other people like you, you know, had experiences like I want to be doing what I’m proud of, what I love doing that’s going to allow me to spend more time potentially with my child or at least be happier around them because I’m going to be doing something that I love. So this baby effect, Fire Nation, is real, and it doesn’t always just have to be a baby. It can be, you know, a job firing, economic downturn; there’s just a lot of huge scenarios that happen that just force people into this big life shift. And one thing that I like to say is, you know, use Cailen’s shift, use somebody else’s shift as your major reason for a life change. You don’t have to wait for your own baby or a firing or economic downturn. You can just say, hey, I can see that it’s worked for other people; I’m just going to use that mentality and I’m going to do this shift now. So you don’t need to wait for that crazy time; you can learn from people like Cailen and like others who have been there, who have done that. And that’s my big takeaway, Cailen. In just like maybe one sentence or two, like what do you want to make sure Fire Nation gets from your worst moment?
Cailen Ascher: I think that we have to realize that when we have that worst moment, it’s often the start of something really great and something really amazing and a necessary change. Growth is scary. Change is scary. And so when you have that low point, it’s really just that starting energy, that fire, if you will, of something really profound that needs to come through.
Male Speaker: Cailen, you’ve had a lot of ah-ha moments in your life, and you just shared one when you were going through a new course and you said I’ve got to start this thing from scratch, I need to come at this from the beginner’s mind, like I need to get out of my own head here, the curse of knowledge that I have about what I think I’m good at or what I should be doing. Let’s start from scratch. And that was a really powerful ah-ha moment that you’ve had. And you’ve had a ton of those throughout your journey, and do you maybe want to share a little more detail about that one specifically or maybe you have another epiphany light-bulb moment that you’ve had. You know my audience. Like, you know Fire Nation. Take us to a moment that you had this epiphany, and tell us that story.
Cailen Ascher: Sure. It kind of piggybacks off of the story I just shared of my worst moment. And I think one of my biggest ah-has, and I kind of alluded to it at the end there, was when I realized that I wanted to be coaching people. I realized that I needed to basically look at the way I was formatting and structuring my business and kind of tear it apart. I had it -- I was saying I was kind of keeping my clients at a distance. I had all these programs and courses, and I really wanted to automate everything, but that’s because I wasn’t in love with my ideal client. And once I realized who I really needed to be working with, I realized that I needed and I wanted to be working one-on-one with them and not to keep them at an arm’s length and be offering just exclusively these online courses and group programs because I didn’t have the desire to coach before because I was operating from -- I wasn’t operating from my area of genius, essentially. And when I stepped into that zone, when I really owned what I wanted to be doing and I redefined my ideal client, I wanted to coach. I wanted to get to know her. And this is the first time I had ever felt like that, and I realized that this, this is what it’s supposed to be feeling like when you’re building a purposeful business. That’s really an authentic expression of your greatest gift, that you want to be interacting with the people that you’re serving on a really intimate way. That doesn’t necessarily mean coaching; that’s what it meant for me. But I really wanted to serve them to the best of my ability, and coaching was the way to do that.
Male Speaker: Fire Nation, you can hear the passion, the excitement in Cailen’s voice when she’s talking about this. I mean, don’t you want that for yourself if you don’t already have it? I mean, don’t you want to give yourself the opportunity to find that thing that is just meant to be for you, that passion, that fire that’s burning within? I mean, Cailen, I loved how you put it in the last story about how you were keeping your audience at arm’s length, and that should be a huge hint. I mean, Fire Nation, are you doing that? Are you keeping your audience at arm’s length? Because if you are, it may be time to check yourself because you should want to be embracing your audience, hugging them, holding them. I mean, when I was just on the podcast with Paradise Cruise, you know, a little while ago, I mean, I was just like these are amazing people, I love the people who chose to come on this cruise, these are my people because this is my audience. And you should feel the same about yours as well. So, great ah-ha moment, great share, Cailen. It’s great to see you kind of come into your own there. And just like you did for the worst moment, what are you going to make sure Fire Nation gets from your ah-ha moment story?
Cailen Ascher: If you’re not totally in love with your clients and your customers, you really have to look at what you’re doing and why you’re doing it and maybe -- and it’s not that you have to make a huge shift like I did, but maybe just infuse a little more passion, a little more purpose, a little bit more you into your business. I mean, I don’t -- just to be clear, I don’t love my community the way I love my daughter or my husband, you know, it’s not this like all-encompassing, all-consuming love, but there is a very real part of my heart that is totally dedicated to those people that I’m serving. And I really do love them, and I can authentically write that and say that to them. And if you’re not coming at it from that place, it just takes a little bit of inner work, and I’m sure you’ll find that missing element that makes that love bubble up inside of you and makes you want to serve them to your utmost capacity.
Male Speaker: I love that point that you shared that it doesn’t have to be a massive major shift. I mean, Fire Nation, don’t look at it like it has to be this life-changing moment. It’s not like you’re going to become a character in Eat, Pray, Love. Like, you’re not taking off for India. Like, it can be a small shift. It can be a little tweak in your business because picture it this way: If you’re in San Diego and you take off from New York City and you do a 1 percent, just a 1 percent shift, by the time you land, you’re going to be in like, you know, Canada somewhere because that 1 percent over time adds up to something huge. So you can make a small shift that makes a big difference in your business over time. It doesn’t have to be right away or just massive or obvious at the beginning. Now, Cailen, what is your biggest weakness as an entrepreneur?
Cailen Ascher: I would say that I can tend to get a little anxious and impatient when things don’t happen fast enough. You know, you put in a little time, a little work, and you want to see the big results right away, and that’s been the hardest thing for me, the biggest lesson, is to just kind of fit with things and trust the timing of your life.
Male Speaker: That’s why I love the book The Slight Edge by Jeff Olsen because he just shows so eloquently how in that book just the small things done right every single day doesn’t feel like a lot at the beginning, but it adds up to massive success in the long run. Now, Cailen, on the flip side, what’s your biggest strength?
Cailen Ascher: I would say my biggest strength as an entrepreneur would be big-picture thinking. I can very clearly see where I’m headed and the big vision, and that’s something I work a lot with my clients on actually, is getting that big picture really fleshed out for them so that they have that pull towards their dream rather than feeling like they have to push themselves. And that’s probably why I get so anxious and impatient, is because I see where I’m headed so clearly.
Male Speaker: Now, you have a lot of cool things going on, but what’s the one thing that has you most fired up today?
Cailen Ascher: Oh, the clients that I work with. I have the privilege of coaching the most amazing entrepreneurial, passionate, talented women, and it’s so personally rewarding to see them take action and see the results that they’re getting in their businesses. I just worked with one client who landed ten new clients after our first session, and another one booked an ongoing client, and it’s really just miraculous to see what these women do. And it makes me so, so very proud of them when they really start stepping up and living the life of their dreams right now. It’s really amazing.
Male Speaker: Now, speaking of miraculous, Fire Nation, we have miraculousness waiting for you in the lightning round. But before we get there, we’re going to take a quick minute to thank our sponsors. Cailen, are you prepared for the lightning round?
Cailen Ascher: I am.
Male Speaker: What was hold you back from becoming an entrepreneur?
Cailen Ascher: Honestly, I have to say I was raised in a household of entrepreneurs, so I always knew this would be my path. I was very fortunate in that way. But once I entered on my true entrepreneurial journey, I would say the biggest thing that needed a change was my mindset. I really needed to embrace the money mindset, the success mindset, and the belief that I deserved everything that was coming to me and was destined for it, that it wasn’t until I really stepped into that place of belief and self-confidence that things really took off for me.
Male Speaker: What’s the best advice you’ve ever received?
Cailen Ascher: Two things pop into my mind: The saying that perception is reality and also that whether you think you can or you think you can’t, you’re right. I think Henry Ford said one or both of those, but the voices that I hear those quotes in are my parents’ voices. Those are the things I heard growing up.
Male Speaker: What’s a personal habit that contributes to your success?
Cailen Ascher: Morning meditation. I sit for 15 to 20 minutes in a dark, quiet house every morning, it’s nice, before my husband and my daughter wake up, and I give myself that time to reconnect with my true purpose and my true desires, and it makes me a better person all around, and a better business person definitely.
Male Speaker: Share an internet resource like [inaudible] with Fire Nation.
Cailen Ascher: Oh, the one I’ve been sharing recently is Calendly. I use it for booking all my coaching sessions, and it’s really easy to use and it’s a very attractive platform and it’s nice because it integrates with all the calendars that you use, whether on Google or what have you. It’s very user-friendly. I like it a lot.
Male Speaker: Now, if you could just recommend one book for our listeners, what would it be and why?
Cailen Ascher: Oh, there are so many good books. I would say one I read recently. It was The Big Leap by Gay Hendricks, and it’s really -- it was really a game-changer for me. He explains in it that we all have this threshold, which he calls an upper limit, for feeling good. And when we hit -- when we expand out and hit that limit we set for ourselves for feeling good, we tend to self-sabotage. And at first I wasn’t totally sure of this concept; but as I read more and more, I realized that this was a pattern that was showing up for me again and again in my life and in the lives of my friends, my family, and my clients. And so I’d recommend that people check it out. It’s very enlightening.
Male Speaker: It was, and I’m a big fan of Gay. I actually interviewed him a few months ago. So Fire Nation, check out that interview. He definitely rocked the mic. And I know you love audio, Fire Nation, so I teamed up with Audible. If you haven’t already, you can get an amazing audio book for at Yourfirebook.com. Now, Cailen, this is the last question of the lightning round, but it’s a doozy. Imagine you woke up tomorrow morning in a brand new world identical to earth but unknown. But you still have all the experience and knowledge you currently have, your food and shelter is taken care of, but all you have is a laptop and $500. What would you do in the next seven days?
Cailen Ascher: I think what I would do is I would seek out connections. I think more than anything else in my life, the connections I’ve made with the people in my life have shaped me and really made my life what it is today, made my business what it is today. And I think without the support of friends and family and future colleagues in this new, unknown world, I would really set out to find my people, you know, friends, pseudo family, creatives, entrepreneurs, big thinkers, and people who would share my vision of creating purposeful lives and businesses. That’s what I really get jazzed up with, is when I connect with people who think big and have a real vision for themselves. And I think I would set out to find them anywhere and everywhere, both in person, online, and make sure I had everything in place, you know, website, social media, email, et cetera, to make sure I could make the most of those connections. And probably ultimately I would end up doing work, doing the work like I’m doing now as a clarity coach. But I think the first step, as within all businesses, is building community. And so I would definitely start there.
Male Speaker: Cailen, let’s end today on Fire with a parting piece of guidance. The best way that we can connect with you, then we’ll say goodbye.
Cailen Ascher: Sounds good. So I would say to the listeners that know that everything you imagined for your life and for yourself is possible. You have those visions that you have for yourself and those dreams that you have for yourself for a reason. They’re yours. They were given to you for a reason, and they’re yours for the creating. So live with that belief every day, and the things that you seek will start seeking you. And you can find me and more information about everything I’ve got going on over at cailenascher.com; it’s C-A-I-L-E-N-A-S-C-H-E-R.com.
Male Speaker: Fire Nation, you’re the average of the five people you spend the most time with, and you’ve been hanging out with CA and JLB today, so keep up the heat. And head over to eofire.com; just type Cailen in the search bar. Her page will pop up with everything that we’ve been talking about today, her website, recommended resources, books, all that jazz, and of course go directly to her website, cailenascher.com, and we’ll have that link up on the page as well. Cailen, thank you for sharing your journey with Fire Nation today. For that, we salute you and we’ll catch you on the flip side.
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