From Watercolors to Life Design: Evolving Your Business with Ashley Jablow

RACHEL COOK: Hey there, CEOs. Welcome back to another episode of Promote Yourself to CEO. Today I'm so thrilled that my friend and client, Ashley Jablow, is joining us. Not only because she's an awesome person, but I've had the opportunity to get to know Ashley over the last four and a half, maybe even five years coming up on, when she first found me and came to me to work through her business. There is nothing more gratifying for me as someone supporting small businesses than to see someone who had something I knew was so incredible and magical and special, finally embrace that and do the thing I told them was so amazing. It's going to take time and they have to go through their own process and journey.
But it has been so amazing to see everything in your journey over the last several years come around full circle. That's what I wanted to bring you on today to talk about everything that has happened in your business and this journey you have been on.
To get started, why don't you just let us know a little bit about how you came to entrepreneurship? Because your background—you never really thought this was the direction. Tell us a little bit, Ashley, about the start of your business.
ASHLEY JABLOW: It's so true, Rachel. I never expected to run my own business, let alone love it as much as I do. I grew up in a family of entrepreneurs. My mom has had a retail business for 45 years now, and before that it was my grandmother's antique store. So I come from a long line of women entrepreneurs and yet almost nothing about being an entrepreneur sounded exciting to me when I was young and early on in my career.
I've worked across a whole bunch of industries and sectors—from the nonprofit sector to open innovation crowdsourcing, corporate consulting, government consulting. But it wasn't until I got laid off a number of years ago and really had that rug pulled out from under me that I even started considering: could I freelance? Would people pay me money to actually do work for them? So my journey into entrepreneurship has been sort of slow going. Now that I've created this career and this role for myself, I'm not sure that I'm really employable. I think I'm committed now.
RACHEL COOK: Absolutely. I remember when we first met, you shared how you started the Wayfinders Collective after being laid off, and that being laid off was such an actual gift for you. I think you're not alone. I think there's a lot of belief out there that you start a business because you've always dreamed of entrepreneurship or you have this big passion you want to turn into your business. I just don't find that to be true for so many folks.
I find for a lot of women entrepreneurs especially, there's usually some catalyst—maybe they're laid off, maybe there was a restructuring, maybe you know, they've had a personal change in their life and they just have to figure out a new way forward. So it's kind of like you accidentally became an entrepreneur, maybe without really having that big initial vision for it. But now you have been working for yourself since 2017, 2018? That's a long time, especially considering most small businesses throw in the towel under two or three years.
When you launched with Wayfinders Collective, tell us a little bit about what it started as, and then jump forward in the timeline. What is happening now?
ASHLEY JABLOW: Well, it's funny because although I never expected to be an entrepreneur or my own boss, I have always gotten excited about founder stories. I remember even very early on listening to "How I Built This" and thinking, "Ooh, that sounds so exciting." It didn't mean I wanted to do it, but I thought it was exciting.
When I first realized—it took a couple of years of freelancing. I sort of joke that my body started a business and then it took a couple years for my brain to switch on and say, "Oh, I've started a business. What am I doing with all of this?" That was probably about the time that we first met.
Originally, my intention for Wayfinders Collective was to be very much as it sounds—a community of people finding their way through work and life, doing it together in one of the most, perhaps universal human experiences, which is asking and answering the question: who do I want to be when I grow up?
What's funny is that business, although I had the idea of it all those years ago, it really only has started to show up in maybe the last six to 12 months where I've picked my head up and realized, "Oh, Wayfinders Collective is actually what I wanted it to be all those years ago." So it's taken a while to actually edit and refine and grow.
And now I really can say that this business—whether I'm coaching one-on-one with a client in career or life transition, or facilitating a life design or innovation workshop, sharing my journals, speaking on stages—it's really exactly what I hoped it would be. It's just taken a handful of years to get there.
RACHEL COOK: And that, I think, is the journey of entrepreneurship. Sometimes we have this preconceived notion of what it's going to look like, of what it's going to feel like. So we just keep putting one foot in front of the other and then at some point it's like, "Oh yeah, I actually did that. I actually built the thing I set out to build."
What's so funny about it is I think a lot of people have this belief that it's just going to be a lot cleaner of a journey than it is. And you and I both know it is not a clean and clear cut journey. There's so many ups and downs in it.
One of the things that when we first connected and started working together that you shared with me that made me really know you weren't just another coach was when you shared a bunch of watercolors that you had started doing during the pandemic. Can you tell us a little bit about that 100 Days Project and what that has turned into?
ASHLEY JABLOW: Well, I have to say, you know, that expression "careful what you wish for"—it has taken a while to get to this point and also like, wow, I could have never expected where I'd be at this moment.
So back in 2020, right before the pandemic, I was making most of my revenue in my business through in-person facilitation—traveling to client sites and teaching or training. And as you can imagine, in one fell swoop in March of 2020, my entire business basically got wiped out. As we all had our worlds turned upside down, nothing really made sense anymore except for me to pick up my watercolor brushes.
It's funny because I never would have thought of myself as an artist. It's still an identity that I'm practicing, like putting on. At the same time, I just knew I wanted to make something and I had found out about a project on Instagram called the 100 Day Project where people commit to making 100 pieces of art of any kind for a hundred days in a row.
I thought, "What else am I doing?" So I decided to give it a try. I started this project, "100 Days of Designing My Life," which is a series of three by five watercolor postcards that showcase different innovation and life design frameworks, visuals, quotes—just kind of images that I'd even been playing around with in my head and in my coaching practice.
So I started to make them. I think I got through day 66 before life just kind of got in the way. In the end, it took me about two years to finish all 100 watercolors. And then of course, as you know, the big question after that was: what am I going to do with this stuff?
RACHEL COOK: Well, and this is the question I had when we first met. I remember you coming to my office and we were talking about how you were going to get clients into the program you were creating. You were creating a group coaching program. I had gone through all of your online content, all of your Instagram, and I was like, "Okay, what are you doing with all these watercolors?" And you were like, "I don't know."
I was just thinking to myself: these are a hundred pieces of content that are so unique and different because there's a million coaches out there, right? There's a million coaches promising to help you figure out your life. There's not a lot of people who are able to make these kind of very high level concepts feel a little bit more concrete so you understand them because there's a visual element to it. That's something you're really gifted at.
ASHLEY JABLOW: Yeah.
RACHEL COOK: Between your facilitation background and all of these other skill sets that you draw from—I mean, this woman does not go anywhere without a flip chart, post-it notes, some markers. She loves herself a two by two. She's going to visually explain these concepts in a way that really makes them land. I thought that was so powerful because, one, that's a skill I don't have. I knew I was good at a lot of things, but that kind of stuff, I don't know how to do that. But I also know in this whole world of coaching, it's so easy to blend in.
At the time, you were kind of resisting doing something a little different because, well, no one else was using these kind of artistic renderings of concepts as a way to grow and connect their audience. So I just remember sitting there with you being like, "This is a hundred pieces of content. This is something you can use. This is an asset." And you were a little resistant at first.
ASHLEY JABLOW: I wasn't just resistant. I remember bursting into tears, Rach. I remember. Being part of the CEO Collective, going to the retreats, the online calls, and even the in-person masterminds—you know, they were so instrumental. Your community and your mentorship, the mentorship of other coaches in the program, it was just so instrumental in helping me first see that I had something uniquely valuable and to really practice believing it and almost metabolizing that. And then also just really supporting me as I went through multiple years of sitting with the question of like, "What might this become?"
So I really have so much gratitude to you and to the community because, yeah, I'll never forget being in your office and you saying, "Ashley, you realize you have—if you post two watercolors a week, you have a year's worth of social media content." I just completely lost it. Total tears. I knew you were right and I was freaked out and it was all the things.
RACHEL COOK: Right. Well, it brings up so much of our insecurities and not-enoughness, and especially because as humans we want to belong and we want to fit in. But as business owners, if you fit in too much, then no one sees you, no one notices you. So you really have to be willing to embrace the risk and put yourself out there, put your stuff out there. Especially challenging when it's—you know, you don't have other examples of other people doing it that way.
ASHLEY JABLOW: Yeah.
RACHEL COOK: I knew we could get you over that, but it did take a while for it to happen. Fast forward several years, you finished the whole series of a hundred.
ASHLEY JABLOW: Yes, yes.
RACHEL COOK: And then what happened that inspired you to turn those into what became four journals? Tell me about that whole process and when that came together.
ASHLEY JABLOW: There is often, whether you own your own business or you're moving through any kind of life change or setting goals, such a desire to get clarity immediately—like yesterday. I think for me, one of the biggest lessons I've taken away from creating these journals is that if you could personify clarity as a being, you have to wait for clarity to come to you. There are certain things you can do that invite clarity to move more speedily, but clarity will arrive if you create the conditions for it to come.
I spent multiple years. If I finished the watercolors in 2022, it wasn't until 2024 that I definitively said, "Okay, I know what I'm doing. I'm going to create a set of four guided reflection journals, each one based on the four steps of life design." It took me a long time. I thought about planners, card decks, calendars, mugs—like the whole thing.
Then I was sitting in a wine bar, of all places, in New York City with my mom and one of our friends. Just in conversation we start talking and it comes out like, "Wait a minute. We could create these four journals." When I say we, I mean I really was like, "I need everyone here." We could create these four journals and I literally walked out of that wine bar. I know the date because it was the day after my birthday, February 24th, 2024. I said, "I'm writing these journals."
RACHEL COOK: The day after my birthday, Rachel.
ASHLEY JABLOW: I know, which I love.
RACHEL COOK: Day.
ASHLEY JABLOW: As soon as I said that on your birthday, Rachel, I walked out of that wine bar and I said, "I'm making these into journals."
RACHEL COOK: Yeah.
ASHLEY JABLOW: Yeah. And that's when the adventure really began.
RACHEL COOK: Well, and it was so great because there's a million things you can do. This is where there's so many ideas and so many ways we can take intellectual property, because that's really what it comes down to. These are your ideas, your concepts—yours are just visual, right? But there's a million ways you can deploy those. It's so hard to figure out exactly what the right format is going to be, exactly how you want to deliver it, how you want people to use it.
So what led you to the journals versus like a card deck or anything else? What happened there that made you think, "Okay, journals is the best option"?
ASHLEY JABLOW: I think it really had to do, probably, with being back in your office and you saying, "Ashley, there's content here." Looking back over it, I had been writing Instagram and LinkedIn posts about each of these watercolors, so I already had some content.
RACHEL COOK: Yeah.
ASHLEY JABLOW: So I figured I'm going to start with what I have. I have since experimented with greeting cards and prints and t-shirts and all sorts of things, but the real foundation was: what do I already have that I could work with?
RACHEL COOK: Yes, exactly. And I have to say, when you landed on journals, it made so much sense, especially because you have this background in facilitation. I knew you wanted people not just to have it as like an inspirational little watercolor, but really something they could use and process what they're thinking and start to put those ideas into action.
So when you decided to do a journal, tell us a little bit about what that looked like—the process of actually developing it, putting it together, all of those pieces of the puzzle.
ASHLEY JABLOW: It's really interesting because I really wanted the journals to work, right? I really wanted this to be a success. But I think I also felt like my 100 day project needed to be wrapped up. It needed some kind of final finish to it. I don't know if that's everything that made it possible for me to kind of hold this project a bit more lightly, but having created programs, having invested a lot of money and time and attention into making something look perfect and then launching it and realizing it was totally a flop—I've done that before.
RACHEL COOK: We all have.
ASHLEY JABLOW: No matter how many times you and others have said, "Ashley, you don't need to do it that way." But I think I knew that this project was personally important to me, and I also knew that I needed to break it down into bite-sized pieces so that I could actually finish it.
I had this sense, having been in business long enough and knowing myself well enough, that if I said I was going to do this and I just stayed behind my computer and worked on it quietly, it would never actually get done. So truly in just one bold stroke—like I'm going to sit down with my morning coffee and LinkedIn—I decided to shortly after deciding on the journals to share that I was going to make them. Before I had even written a single word in a Google Doc, I told people, "This is what I'm doing," and I tagged everybody I could think of.
And boy, that was an amazing forcing function. Once I let people know I was doing this, people started getting excited. They started asking about pre-orders. So I actually ended up taking pre-orders before I'd even written a word. That was definitely like, "Oh shoot, I've got to do this now. People are paying me money for this."
It was interesting because originally I thought, "I'm going to get pre-orders and then I'm going to write all four." But again, I realized knowing myself and knowing my process, I needed more mile markers. So what ended up happening was I told people about volume one. I took pre-orders for volume one, and then I wrote volume one. Then I did the same thing over and over again for volumes two, three, and four.
It was actually a very sort of rinse and repeat process over the course of a summer. I wrote all four journals in seven months. What started out as an idea in a wine bar in February became four books in my hands by October.
RACHEL COOK: It was so amazing to see how quickly it came together. But I think this is the power of building in public. What you just described—this is something that in the startup world, they're talking about building in public all the time. This is something the rest of the entrepreneurial world can really embrace, especially women in entrepreneurship.
I think we tend to get hung up on things having to be perfect. I have to do everything exactly this way. I have to come out of the gate making it look a certain way or have it executed a certain way. You were willing to be like, "Okay guys, here's what I want to do." You tagged everyone you knew, so one, you had that validation very quickly. People were like, "Oh, this is it." They all knew you. They all knew your work. They knew your abilities as a coach and a facilitator. They had seen so many of these watercolors, so people were excited out of the gate.
I remember when you put that pre-order page up and then you had this one picture of your first batch of 50 pre-orders once you actually had them in your hands. I was just so excited for you because it's very rare that you launch something and actually have 50 people who are saying, "Yes, I'm buying from you" right away.
ASHLEY JABLOW: Yeah.
RACHEL COOK: That was amazing.
ASHLEY JABLOW: It was thrilling. It was thrilling. And I think, also, just such an interesting validation because to your point about—I'm a coach, there are a lot of coaches. How do we differentiate ourselves? I think there's also the question of: what signals is the market sending me? I love coaching and I love selling coaching. But consistently what people reach out to me about and respond to is my art. So it was really interesting to lean into that and say, "What would it look like if I experimented with this?" And you're right, it created so much traction and so much momentum and for me, so much confidence that not only can I do this, but I am doing this.
RACHEL COOK: Yeah.
ASHLEY JABLOW: There's nothing better than making something and putting it out into the world and seeing people respond so positively to it. It was just so gratifying.
RACHEL COOK: How did it feel to put it out into the world and see all that feedback instantly?
ASHLEY JABLOW: I mean, it was scary. It makes me smile like, honestly, I look back on last—because it was last summer, it was just a year ago that I finished the journals. I think I was like a woman possessed. Once the clouds parted and I decided I was doing this, I did it.
And it was only later, like looking back months later, looking at that post on LinkedIn where I tagged 200 people and I was like, "How did I get the guts to do that?" Or like hiring a designer to lay out the books and then putting them up online to print—"How did I ever figure out what an ISBN number is, right?" But I just took it one step at a time and I was, yes, absolutely scared, but also very purposeful and knew that this needed to come out into the world.
RACHEL COOK: It's so true that there's a co-creation process here. I think this is another thing I want more women entrepreneurs to embrace. Because so many of us have this ingrained perfectionism, we really hesitate to build in public. We really hesitate to go through these initial steps to get validation and to see how people feel and co-create with our communities.
Tell me about once you launched the first one and started getting feedback. How did that inform finishing the series?
ASHLEY JABLOW: It was like the motor went on overdrive. When I started hearing from people, I remember even before I'd written the second volume, I had people who'd bought the first one saying, "Do you have a digital copy of the second one I can use? I don't even need to wait for print. Do you just have it?"
And I was like, "I'm sitting at my desk on a Saturday afternoon writing it as we speak, right?"
RACHEL COOK: Yeah.
ASHLEY JABLOW: Truly it has changed the way I think about launching. It's changed the way I think about sharing my work. It really has solidified for me that people want to support us and they get so excited seeing other people be brave and going after their goals and their dreams. So, as scary as it seems, the payoff is so worth it because you not only receive all of that support from your community, but you show other people that it's possible.
RACHEL COOK: What has happened as you've shown other people what's possible? Have you heard any interesting stories or tidbits from folks who have leveraged using your journals into creating the life that they really want?
ASHLEY JABLOW: Oh, it's just been so incredible to get feedback about people using it both for deepening their sense of self and their understanding of who they are, all the way to making really new and concrete life changes. I've heard about people using the questions with their partner over the dinner table or with their teen who's graduating from high school.
Because each journal includes some narrative along with the piece of art, as well as multiple reflection questions. So I like to say I'm not giving out gold stars. There's not one right way to use it. But to know that people are opening it up, seeing what gets sparked, and using that as a way to further their own inquiry about themselves and where they're going in their lives—it's just so wonderful to see it out in the world and impacting people's lives. I wish I had done this years ago.
RACHEL COOK: Well, and as you said, you just had the one year anniversary of all the journals being out into the world, and you threw a really lovely event to celebrate it, which I was so excited to attend. It was awesome because there were so many other members of the CEO Collective there, which I kind of knew some would be there—those who live in the Richmond area. But then some who weren't from in town and had driven in for the event. I saw your mom, got to see your husband. You have really put an amazing community around you.
What has the impact of having this type of support system been for your business over the last few years?
ASHLEY JABLOW: I mean, I wish I could quantify it, but it's really unquantifiable. Especially at this party a couple weeks ago, I felt, first of all, to throw yourself a party if you haven't thrown yourself a party—that's not related to your birthday, that's not because you're pregnant or you're retiring or whatever—but a party truly to celebrate your success. That was probably the scariest part about this whole thing, and it was so incredibly worth it. In large part because I just felt so supported by so many people.
That support is what enables me to also be brave. So the party wasn't just to celebrate the first birthday of the journals, but it was also to announce a new project that I have recently launched into the world as well. To be able to be in that room and essentially make an in-person ask very much like I did on LinkedIn last year, but to be able to say to those people, "This is something new that I'm building out in the open yet again, and I really not only need your support, but I want it because I believe that what this is going to become is still kind of unwritten. I really invite everyone's contribution to help shape what it becomes."
RACHEL COOK: It was so amazing and just wonderful to be there and to celebrate you, to celebrate this huge milestone, what's coming next. It just feels like this is the very beginning. Yes, you've been in business for almost 10 years now, but it almost feels like this is launching you on a new path and a new direction with a lot of excitement and a lot of energy behind it that is different. It's very different from when you and I first connected and it was like, "COVID shut down my business. I started a business because I was laid off." Now it's like, "I'm birthing this body of work. It's very intentional and very purposeful and very aligned with who you are and how you show up in the world."
So I'm just so excited and so proud of how much has come together for you with all of these incredible journals. By the way, where can people come take a peek and get one if they want to access one of these journals?
ASHLEY JABLOW: Absolutely, yeah. So my latest creative project is called Life Design School, which is really a creative studio for anyone navigating transition or designing their next career or business or even life chapter. So all of my journals are available on lifedesignschool.co/shop, and I'm sure we can put the link somewhere, Rach, but absolutely.
I would love it if people wanted to check out the journals. It's a great place to get started and get a taste of how my brain thinks about things.
RACHEL COOK: Well, and I'll put my own testimonial in there because when you launched them, of course I was on the pre-order list and my husband and I both did them. My husband journals all the time. He's a big pen-to-paper guy. I tend to be a verbal processor more than a writer, so I would talk with him about the questions. But he would spend every morning going through it.
He has now done all four journals and is so obsessed. He wrote you the loveliest note letting you know how much he absolutely loved these journals. But they inspired him to start trying some things that he hadn't tried or thought of trying before. I think it's pretty common for people who are really creative to get caught up in "what's the simplest, easiest way for me to try this on and see if this works?" They really sparked something for him to try out a lot of new things that he'd been curious about. So I highly recommend these journals for anyone. I think they're wonderful.
ASHLEY JABLOW: Oh, that makes me so happy. I just got the nicest email from your husband and it still makes me smile thinking about the impact that the journals have had—even if it's been a little bit of a nudge. It makes me so happy to hear.
RACHEL COOK: I love that. Well, as a longtime member of the CEO Collective, I mean, you've been with us really for the last few years. You've attended over a dozen CEO retreats, if not more. If you scroll through any of my photographs on my site where we've taken pictures at CEO retreats, Ashley is easy to find with the curly hair. But how has the CEO Collective shown up in this whole journey for you? What role has it played for you in supporting you on this?
ASHLEY JABLOW: Well, I've already spoken to the community, which is just lovely. These are some of the biggest heart-centered entrepreneurs I've ever gotten to know. So it's not just relationships business owner to business owner, but really friends. To your point, I had friends in the room at this party and they are friendships that we've made through the CEO Collective.
I think there's also the credibility and legitimacy that I have received being part of the CEO Collective. I remember the first time—and it took me even a little while being part of the collective—getting comfortable with the idea of being a CEO.
RACHEL COOK: Mm-hmm.
ASHLEY JABLOW: Even just trying that on like, "Am I really? Does that count?" I think being part of your world, Rach, and learning the operating system, learning the planning approach—you know, every quarter—it has just really helped solidify that I'm not making this up. There's real substance here. I'm not playing pretend.
I think for a lot of, certainly for myself, but a lot of other women business owners I know, there is this imposter syndrome. There's this sense that someone's going to find me out, that I'm not actually doing this for real. Being part of the CEO Collective really helped me have a structure to support me and feel like, "No, I really am doing this." I put that in practice and that helped my business. Over time, I can see how that's really grown my confidence.
RACHEL COOK: That is so incredible to hear. It's funny—you always think what you're offering is a little different than what you personally think it is. These are the types of things I hear from my clients: what they get is the confidence, what they get is the sense of community and having people who have their back. What I think I'm bringing is systems and structure, and that's part of it. But it's so much more than that, and it's just amazing.
It literally is the best feeling when I get to be out in the world and see my clients coming together on their own, connecting together, building those friendships. Because we live in a day and time where there's so much going on. It could feel so isolating to be doing the type of work that we do. But when we have that community, when we have that circle behind us, we're so incredibly powerful and we really can create our own economies. We don't have to be at the whim of whatever's going on out there in the world. We have more control and more power than we think we do, but it really hinges on us coming together and bringing that collective together.
So I'm thrilled that you've been a part of it for so long. I'm thrilled that we're friends. Thrilled that I got you to move to Richmond so we could spend time together. That's another story for another day. But I love that you are in the collective and in my world now. So thank you so much for jumping on today and sharing your story.
Are there any final thoughts that you want to share with any entrepreneur or CEO who is on that precipice—they know they have something bubbling up, but maybe they're a little nervous or scared or not 100% sure if they're ready to jump into putting their work out there? What would you share as your biggest lesson from this journey?
ASHLEY JABLOW: The first thing that comes to mind is: do it messy. It's hard, it's uncomfortable, but really the only person who expects perfection from you is you. And if you can let that go, what I've found is not only does that create momentum for you because you're actually moving forward, but you really do inspire other people and people genuinely want to cheer you on.
So even if it's a mistake, even if you realize, "You know what, I started down this path and now I need to make a course correction"—people will support you. You won't know that you need to make a course correction unless you get started. So do it messy.
RACHEL COOK: I love that. So that is a perfect way to end this conversation. Thank you so much for joining me, and thank you everyone who listened along to this conversation. Make sure that if you have any ahas or insights, head over to Instagram. I will link all of our Instagrams so you can let us know any thoughts, insights, or feedback.
You can check out Ashley on Instagram and on LinkedIn, where I know she shares from these watercolors we've been talking about and other amazing content around designing your life very intentionally. And of course, check out everything she's doing over at Life Design School, which is such an exciting new chapter. I love how you said "a creative studio for designing your life." I think that's going to be such an incredible new chapter for you.
ASHLEY JABLOW: Thank you, Rach. This is such a joy. Anytime I get to spend time with you, I'm a happy camper, so I really appreciate you.
RACHEL COOK: I love this.