65. Finding Your Why as a CFO with Ashley Harlan - Part 2
8 Dec 2025 · 31 min
Ashley Harlan discusses her shift from corporate employee to entrepreneur, including a difficult low quarter caused by indecision about people. A client-scoring exercise helped her narrow her focus to serving therapists and solo practice owners, aligning her business with her personal values. She emphasizes returning to your 'why' for motivation and finding a mentor to model.
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Hey there, My name is Michael King and this is the CFO Report. You are listening to part two of my interview with Ashley Harlan. If you haven't listened to or watched part one yet, I want you to hit pause right now. And we've included a link in the description below to part one. But we're basically continuing our conversation where we're talking with Ashley, unpacking the process that she went through to really identify what she wanted to do as a fractional cfo, who she wanted to do it for, and maybe more importantly of all, why she wants to do those things for that particular audience. So let's go ahead and dive back into my conversation with Ashley Harlan. So thinking back, kind of shifting gears now, thinking back over the last three or four years of your journey, what would you say has been the biggest mistake that you've made along the way? If you could tell 2019 Ashley CEO Ashley something, one thing that would move the needle for your firm more than anything else, what do you think that would be?
Wow, that is a great question. Because I feel like I made a lot of mistakes. I think I would tell myself that it's not going to be as easy as you see it. I think I had these like rose colored glasses on when I first branched out into entrepreneurship. Not that I didn't think I was going to have some hardships, right. But I definitely felt like it was going to be a lot more linear, like a straight up type of deal with success. And it hasn't been been that it's not necessarily all about business or the getting clients or the finances or all of that. It's been more so not recognizing that my identity had to shift from working for someone to being the person that people work for. That identity shift has been tough, right? It's been really hard. And if I could go back to 2019 Ashley, I would tell her to be okay with the identity shift because the mistakes have come when I've tried to operate, operate in an identity that I didn't have anymore.
What is that identity shift? How would you describe it?
You know, when you work in corporate, you become like an expert in what you do and you only have to do that one thing. When you run a business. You have to be a generalist. You have to kind of know a little bit about everything to keep the lights on and no one is telling you what to do. It's challenging to be self disciplined. You is challenging to make all the decisions before I would say I was much more of a perfectionist. I was Much more of a processor and a thinker. And as an entrepreneur, you have to be much more decisive, and you have to be okay with failing, and you have to be okay with succeeding, and you have to be okay with those, like, things happening in the same day within an hour's time, you know, so that identity shift from I was great and I was killing it in my corporate life, you know, I had climbed the ranks, I was making great money, and in entrepreneurship, I'm a baby, you know, I'm starting from the bottom again, and I'm having to figure this thing out. And there's no roadmap, there's no boss to knock on the door or a colleague to turn to beside me and ask the question. And so that identity shift of this is on me. There's no one to blame, there's no manager to call and complain to. You are all of those things. My mistakes have been more around operating in that old mindset.
When it comes to self discipline, do you have any tips that you would offer people? There's no one around you necessarily to hold you accountable, especially when you're just starting more of that solopreneur kind of role. Any tips or tricks, best practices that you can offer up around finding self discipline?
I think I've probably mentioned this a couple of times as we've been talking, but for me, I try to always go back to my why. And I have to remind myself of that. Probably the last quarter is my coach. You know, I was struggling. You know, I was really struggling with how I wanted to run the business, how I want to grow the business. Felt very stuck. And the thing that got me back into the game, I would say, and get off the sidelines was to go back to why I started the business in the first place, is to be able to be a change in my community, to be able to help business owners to build businesses that they love, that can increase their lifestyle. I am of the belief that, especially for underrepresented communities, that entrepreneurship is the best way for us to close the racial gap. And so when I start to tap back into the justice that I want to be able to have the impact that I want to be able to have the lives that I'm changing. When I tap back into my why, it is intertwined with my self discipline. Because now it's like, okay, it's bigger than you, so you just got to go do the things that you got to do, because if you don't, you're going to just stay where you are. So. So it's the motivator, but then also the reminder that it's not just about me. It's about the other people that will be impacted or not impacted by my lack of taking action. Right. We can think about our current clients, but for me, it's like, okay, the therapist who needs me, they will never find me if I don't market myself. The family that wants to be able to take their first vacation won't have the money if I don't go out and help the client to be able to set the money aside to go on the vacation. Right. So it's just kind of peeling back and making it less about me and more about the purpose and the why.
The call to service? I think when we realize that inside that this is so much more than just about us and trying to do our thing, I think for the people that unlock that call to service, it really elevates you to an entirely different game. It's almost unfair, right? Because it gives you that motivation and the discipline and that obligation to push on.
Obligation. That's a good way to describe it. You feel obligated, then you start feeling bad because you feel these people that are connected to you, you know? And so if you don't do what you're supposed to do, then. Then they won't get the help that they need.
What about around making decisions? And when you talked about your identity shift, you said, I've got to start making decisions. That can be a paralyzing thing as a CEO, as an entrepreneur, because there's so many options. Like you said, you don't have the boss that you can knock on his door, or the coworker, hey, how did you do this? A lot of times it feels like we're on that lonely island. How do you push through? Just kind of ripping off the band aid when it comes to making big.
Decisions, in some ways, I feel like I have a skill. I don't know if it's just natural. I've just always been an action taker. I kind of have some privilege in that area that, like, all right, you just gotta take action. I get antsy if I'm procrastinating, so that's probably one thing. But also support. Sometimes you just need people to tell you just gotta make the decision. So, you know, maybe that's a slack message to you. And you're like, ashley, why are you coming to me with this? You know what to do.
You know, just do it. Other colleagues, you know, other folks in our mastermind. I'm a part of some Other organizations. And sometimes it's just having people to listen to your thoughts. I'm very much someone who has talked my thoughts out, and I can talk my thought out. And I'm like, oh, okay. That's the decision. Right. I think it's knowing yourself and knowing that there's really not necessarily any bad decisions. You make the decision in an entrepreneurship, it's gonna go one of two ways. It's gonna go great, and then you just keep going, or it's gonna not go so great, and you just know not to do that again. I think it's just making the choice to make the decision and live with the consequences. With knowing that you can always change and pivot and do something different if it doesn't work out.
Yeah. I think one of the most freeing things for me is recognizing the downside. I asked myself, what's the downside of this? What's the worst thing that could happen? And I think the reality is, most of the time, the downside that we have from. From our decisions is pretty limited. It's very few decisions that we make over the course of days or weeks or months or even years are potentially catastrophic if we choose wrong. And so just make that decision, it's going to either be great, or it's not. If it's not, we'll pivot and figure something else out. And all of a sudden it's like, all right, I quit stressing over this and just choose the red pill or the blue pill and move on with life. Last thing I want to ask you about on this topic. You said as part of this new identity, you have to be okay with failing so hard.
How do you think through that?
I think failure is just inevitable. We're all going to fail. And I think when you're an entrepreneur, you fail so much. Like, things just don't work right. You have a great marketing plan, it flops. You hire the person, they're terrible. You know, you so excited to get the new client, and you guys just don't mesh well together. So it's kind of like the repetition of the failing fast. And you build up like this buoyancy muscle. Like, you get knocked down, you get back up, you get knocked down, you get back up. And so I think it's just embracing that more so than trying to run away from it has been my saving grace with failure. It teaches you so much more than the successes because you know what to do differently, you know how to do things differently. You know, this work, this didn't work. It is just Leaving crumbs behind. What you need to do to be successful in the future.
There's a great TED talk years ago by this guy, retired General Stanley McChrystal, and he talked about as leaders, there's this important distinction that we have to make and that's the distinction between failing and being a failure, right?
Yeah.
We can't take on this identity that we're a failure just because we failed once or twice or multiple times. I love that metaphor you gave of like the buoyancy muscle. Right. We fail and, you know, we pop back up again. When we take on that identity as a failure, that's when we don't pop up again. So as long as you're willing to pop back up again, as long as you keep that buoyancy muscle, then you're not a failure. Right. We're just, we're making mistakes. And I love, I love thinking about baseball with feeling. You know, a great hitter hits.300, which means they're only hitting the ball 30% of the time, you know, and they're making millions and millions of dollars a year to fail. 70% or most, that's good. 30% is good. And I would say, gosh, 30% is probably good for a entrepreneur too. All the little things that you do. And so you've got to just start being comfortable with the fact that most of the things that you're, you're going to do aren't going to work out. But going back to that decision making thing is like also recognize that the downside is not as bad as you think when you do fail. When it comes to generating CFO reports for my clients, my firm has two non negotiables. The process has to be accurate and it has to be efficient. That's why my firm only trusts Giacon. At its core, G Accon is a data connector between accounting platforms like QuickBooks and Xero and Google Sheets. But Giacon is so much more than just a data connector. Right out of the box. You're going to get hundreds of templates for all the reports that CFOs and accountants need to run for their everyday workflows. Everything from balance sheets to P and LS to AR aging reports. Or you can use G Accon like my firm does to create our custom CFO reports every single month. My favorite part about Giacon is the that you can set it up to automatically create all of these reports. That means every month I'm getting fresh reports with fresh data ready to deliver to my clients. And because GFON is Automated. That has completely eliminated the need for my team to download data from QuickBooks, upload it into Google sheets, manually apply formulas, all of those things that take up a lot of time and are prone to errors. In fact, gcon has completely replaced all the other tools, services and workflows that we are using to generate CFO reports. GCON is literally our one stop shop for making all of our CFO reports automatically every single month. If you're ready to start saving time and reducing errors, then you need to check out GFCON right now. Be sure to use the link in the description below to save 30%. That means you can get started with GFCON for as little as $28 a month. Join my firm and over 10,000 other firms and try GFCON today. Another thing I wanted to touch on is you just, you said a couple minutes ago that you really struggled last quarter.
I did, yes.
What was going on last quarter that you really struggled with and what does that journey look like for you? Because I think a lot of times. And let me like, let me just give some context around why this is so important. I started my firm seven years ago and I, I constantly hear people talking about how hard entrepreneurship is. The struggle's hard and you're going to feel depressed and you're going to be like this and it's going to be so rough. But I don't see a lot of people talking about like, what does that struggle? What are the struggles that you see? What does it feel like, what does it look like? And how do you kind of pull yourself through it? I know you've lived that cycle. I think it's important for people to hear what does struggle really look like day to day? What does it feel like? And then how do you pull yourself through it to the other side?
Yeah. So I think it goes back to decisions at the top of the year. I had hired a new assistant and some things that transpired at the end of 2022. And instead of me just ending the relationship, that person who wants to make things work and, and I wanted to, you know, give a second chance. Although my instincts are saying this is not a good fit. Right. I didn't do that. So I was left at the top of the year with us parting ways right when clients are coming back for meetings. And that was stressful. And trying to hire another assistant during that time, having a client that wasn't a good fit for us anymore, not being decisive in that situation for fear of losing the income and not just cutting it off because, you know, they weren't showing up to meetings, they weren't responding to emails, and then, you know, when they needed something, they wanted it like that. And you know, it was very much a season of you can't continue to run the business like this going forward. So losing that client, losing that assistant, recognizing that I needed to up level my leadership and be more decisive in certain areas when it comes to people, you know, sometimes we can be decisive in processes or systems or finances, but with people, for me, with people, it's a little more of murky water. Right. And so being down on myself about that, kind of beating myself up for not being is decisive and is assertive with ending both of those relationships had me second guessing my ability to lead the business. And I think when that questioning, can I lead the way I need to lead? Had me not marketing because I'm like, well, if I bring on more clients, can the team handle the amount of clients? Can I lead the team to be able to support the clients? So I was just kind of going through this whole spiral about my ability to run the business, knowing that I want to go after a different type of client for us to, to work with and questioning my skill set. Did I have the skill set to be able to support those people and coming to the decision that no, you don't have the skill set, you can help clients who are making X amount of dollars in revenue. So I just kind of made the choice to stay, stay small and stay in my comfort zone. But I am not someone who operates well in my comfort zone. Like, I need to be pushed, I need to feel excited, I need to feel like I'm striving and need something to work towards.
You're in your comfort zone. You're staying small. I need to go bigger. What was the aha moment for you? Or was there a moment where you're like, wait a minute, I'm feeling this way and now I'm recognizing I've got this problem.
I'm going to say this very bluntly.
Mike got into my ass about it. That was the aha moment. Because I was literally like, no energy, just. We were on our call. I was just there. It was, you know, I normally have questions and I'm ready for our call. And I was just very nonchalant and just didn't care. And you just straight up told me that I needed to go bigger, I needed to challenge myself, I needed to get out of my comfort zone, that I was bored.
That's what I was looking for.
I was bored. With my really helped me to like kind of see something that I didn't see in myself at the time. You know, you were encouraging but hard truths. Right? You are capable of being able to do more. And I needed to push myself and get out of, you know, the, the current niche that I was in because it wasn't allowing me to flex the technical skills that I do have and it wasn't pushing me to continue to up level my skill set. That conversation with you was kind of that turning point for me to get my stuff together.
That that's what I was looking for is when you said you were bored. And I think that's that to me is somebody that works with all kinds of people in this industry. The number one sign that somebody's playing small is they get bored. Right. It's not challenging. They don't feel stretched anymore. Like that to me is the biggest signal, hands down, that it's time to level up your skill sets, your client base, the challenges that you're solving, the impact that you're bringing to the world. My message is really honing in on this is like people are listening. If you're bored with the work, it's probably because it's time for you to level up. It's time for you to go bigger. One of the things that I saw that had such a remarkable impact on you during that quarter where you were, you were really struggling was when you realized that you wanted to work with a very specific, different kind of client. What was that journey? Like, who were you working with before? And then how did you go like kind of realize, oh, this is, this is who I want to serve? And why did that excite you so much?
Yeah, so I was primarily working with coaches and consultants. I built my business working with them. I have some other kind of service providers sprinkled in there, but primarily about 60% of my clients were in that coaching consulting world. And we started reading in the mastermind, 100 million.
Million dollar offers. Yeah, he had some kind of exercise in there. It was late at night. It was probably I was reading this and doing this exercise like 1am in the morning. And what I did was I listed out all of my clients and I did a scale of 0 to 5. And I took some of the things that you said, you know, like, am I being challenged? Do they have a complex type of business that really requires having someone like me on their team? Do I enjoy working with them? Does the team enjoy working with them? Do they have an innovative industry that I see that they're going to be able to experience growth over the next few years because it's really important for us to work with growth oriented businesses. So kind of had this like list of things and to take my bias out in some ways, I just gave them a score from 0 to 5 and I just ranked it to see who was at the top. And the two that rose to the top were my therapist. So one is a solo practice and one has a group therapy practice. And they met all the criteria of what I wanted to be able to work with. And the last piece of that for me was back to my why. And my core values is impact. I would not be sitting in this seat today having a conversation with you if it wasn't for my therapist. You know, being in therapy for eight years, doing it before it became really popular. You know, definitely a lot more conversations around mental health today. But when I first started going, it was very much taboo in the black community, in church community, you know, Christian church community. And so it was a struggle in some ways to not feel like I was crazy going. But I understand the impact of their work. I understand the identity shift, right? My therapist was able to help me go through that identity shift from 9 to fiverr to entrepreneur, to help me through a lot of highs and lows in the business and in my personal life. And so like, who better for me to help, you know, who better for me to be able to encourage them because they are humans helping humans and they tend to think in some ways that they don't deserve to make good money, they don't deserve to have large thriving practices. Right. They don't deserve to be able to pay themselves well as they grow their group practice. And so it just felt like alignment, divine alignment for me to be the financial, you know, encourager and motivator and thinking partner for therapists to help them to grow practices that, you know, help them to help humans like they want to do it and stick to that mission, but also be able to make money and live well for themselves too.
So it's a the better part of three or four years for you to go through working with different kinds of clients to finally identify, hey, this is my ICA group therapists practice owners into. And to get really energized by that. Do you think you could have shortcut that process or did it, did you just have to kind of go out and get your feet wet and try some different things?
That's a good question. I think I had to just go out there and try a few different things because now that we have made the choice to do this, even from a team perspective, from my back office side of things, I'm starting to see, okay, we can have standardized processes, you know, from a bookkeeping standpoint, because we do the bookkeeping for the majority of our clients, from my reporting standpoint. So, you know, shifting from the CFO report to this is your profitable practice plan report. Right. You know, I can be a lot more tailored and customized. I can understand what their needs are, so I can go deeper, which I think serves my personality well, because going wide and being in multiple industries had me feeling a little off. You know, I didn't feel like I could really hone in on my expertise in something because I'm popping from this thing to this industry to that industry. So from a practice management side, for my firm, for my own sanity, you know, being able to go deep into an industry is exciting to me. I'm at the very top of doing this, you know, so I'm still figuring it out. But it's been enjoyable so far.
It's. It's been encouraging to watch from, you know, three or four months ago. So, like, when we had that call, you were, like, barely there.
Yeah.
Like, it's just. It's a totally different person. And I think that one of the key things was just figuring out, like, oh, this is who I'm called to serve, and this is why. And it really does. Like I said earlier, it's like more of that obligation now, the calling. It makes life so much easier. Last thing. I'd like to unpack real quick. I have no idea where this is going to go.
Okay.
I didn't tell you I was going to ask you this, but one of the things that I've observed over the last month or so with you is you have found your voice in a really cool way. Right. I see so much more confidence. I see so much more passion and power coming from you. What is that about? What's been the catalyst for that?
Can you.
Is there something that happened or can you put your finger on what's. You're just operating on a different level, Ashley, than you were. Oh, yeah. It's a night and day difference. What. Do you have any idea what's going on with that? Because it's. I mean, power is the word. Like, I just see you showing up with such power and confidence right now.
Yeah. I think I don't really have a succinct answer to it. Using my voice has been something that at one point in time, I was very comfortable with. Doing. And then, you know, life happens and you have some failures and you start to second guess yourself. And I think I just retreated for a good portion of time, you know, because I didn't want to say the wrong thing or I didn't know how I was going to come, come across or trying to be politically correct, you know, like all of these things that are kind of going through your, your mind. And I think just over time, especially once I realized who I needed to be serving and that this is the divine alignment that I feel like I have is giving me that confidence to just show up more as myself, you know, just to whoever is for me will be for me. And whoever is not for me, they'll just continue to scroll or they won't have to work with me. But, you know, it's just more tapping into this is who I am. I don't have to try to pretend to be anyone else, you know, and the more I am myself, the more I'll attract the right people for me anyway. I have to, you know, I post and I, and I say things and.
I don't log in because I don't know how people are going to react or, you know, I may run something by you and say, I don't know how this is going to go, but trying to build a muscle, you know, continue to build the muscle of using my voice and to think about the impact that I want to have. And if I don't use my voice, no one's going to know about me.
If I don't use my voice, nobody's going to know about me. I love that. If you had to give one nugget of advice to those that are coming after you, those that want to find their voice, they want to find their why, they want to find their calling, what would you give them?
I would say to find their rabbit.
To find their rabbit?
Yeah. Have you heard that term before?
I don't know.
So a rabbit or some people may call it like your North Star or whatever, like find someone who is doing the thing that you want to be able to do, but they're maybe they're three, four or five steps ahead of you. But the key is they have to be doing it how you want to do it, right? So it's not that they're just doing the thing and they're successful. So for me, I needed to find a rabbit or, or my North Star, someone who had similar values of someone who was building a successful business, but also really cared about family and community and, you know, giving back and enjoying life for themselves. Right. So it wasn't just about making a lot of money, but also, you know, having a great lifestyle. They needed to be a servant leader. They needed to have, you know, a coaching mentality, you know, So I. I searched high and low for that person, and I kind of stumbled upon them from a YouTube video. And then I went down this whole rabbit hole. Here we are today. And so I think, what. What's the saying? Like, you can't be what you can't see. And although you don't look like me, we come from totally different backgrounds. Right. The way you've grown your business and how your values and what the things that are important to you align with mine. And so you are three, four, five steps ahead of me. But even if I was never in the mastermind, I still would be able to gain a lot from just watching you on YouTube or on LinkedIn or whatever to say, okay, this is how I want to build my practice. This is how I want to build my business. So I think it's just important to find someone that you can follow. They can mentor you from near or far. But I think it's important to be able to have exposure to what's possible. And having a rabbit or that North Star person gives you that exposure.
I've never told you this before, but I know the video you're talking about where you've kind of found me.
Yeah.
And two or three days before you commented on that video, I told my team that we need to pack up the YouTube channel and not do it anymore.
Really?
Yeah. Like, Gretchen, my. For those of you that don't know Gretchen's bias, is it. I told her, I was like, the YouTube channel is not working. It's not having the impact that. That I had hoped for. It's not getting the. The views and the. All the, you know, vanity metrics. And then you reached out and you're like, I saw this video. And in the video, I talk about how I turned down a client that didn't align with our values.
Yeah.
I remember the conversation you and I had. Like, it was yesterday. And you're like. That really spoke to me. Like, I needed to hear that. The whole reason that I've continued with the YouTube channel was because of the feedback that you gave. And, you know, we've. Yeah. So I appreciate you letting me know that that's. That you found that value in the channel is the only reason it's still here. Because you knew, because you.
I still watch. I watch other video.
So I appreciate you. But, Ashley, thanks so much for carving out the time to be here today. Gosh, I've known you now for a year. I get to meet you in person. I know, 30 days in Dallas. So I'm so excited. But, yeah, thanks for being here and sharing your story and go do a great job on that call you've got coming up here later today.
Thank you.
All right. Thanks. All right, my friends, that's it for this week's episode of the CFO Report. I hope you found this episode helpful. If you did, it would mean the world to me if you would hit that, like, button, the subscribe button, and if you would leave us a review. It really does help to get the word out. In the meantime, I can't wait to see you right back here next week, my friends. See you there.