Her Next Chapters

94. From Teacher to Solopreneur: Becky McCleery’s Tips for Starting a Business While Raising a Family

• Christina Kohl

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I usually talk about careers in the context of landing a great job—but in this episode, we’re expanding the conversation to include building your own business.

My guest this week, Becky McCleery, went from teaching fourth-grade to running a thriving business as a solopreneur strategist and community builder. Her journey from passionate educator to unfulfilled working mom to successful entrepreneur is packed with lessons for anyone considering a career pivot, whether that’s finding a new role or creating one for yourself.

Becky and I talk about:

  • How she transitioned from teaching to entrepreneurship while raising a family
  • Why starting small beats waiting for perfection
  • The 90-day rule every new business owner should follow before making big changes
  • Common mistakes new entrepreneurs make—and how to avoid them
  • The role of community in sustaining motivation and momentum
  • Why an idea that already exists is a sign of market demand, not a reason to quit

This conversation blends inspiration with practical steps so you can explore self-employment with confidence—whether you’re leaving a traditional role, making a midlife career pivot, or building something entirely new.

You can connect with Becky on LinkedIn or at www.beckylytermccleery.com

You can learn more about Becky's free Soloprenuer Sisterhood or her paid Aligned Momentum Mastermind community for new and established business owners. 






Christina Kohl:

Hi and welcome to Her Next Chapter's podcast. I'm your host, Christina Kohl. I'm a mom of three and soon to be an empty nester. I'm also a certified HR pro who restarted my career after being a stay-at-home mom for over a decade. I created this podcast to connect with moms who have an empty nest on the horizon and are wanting to redefine their identity outside of motherhood, which might include a job search. On this show, we'll have raw conversations about our ever-changing roles as moms. We'll hear from women who restarted their careers and share tips for a job search after a career break. So if that's you, you're in the right place. Friend, let's get started. Well, welcome to this week's episode of Her Next Chapters.

Christina Kohl:

I am excited to have a special guest with us today. Becky McCleery is joining us and she is a solopreneur strategist for heart-centered women with service-based businesses. Her work with clients allows them to make a greater impact as they build purposeful, profitable and sustainable businesses that work for them. And Becky also loves bringing women together to support one another and is the founder of the Solopreneur Sisterhood, a free community designed to help solopreneurs come together and amplify their impact through connection and collaboration, and I met Becky earlier this year through the sisterhood and gotten to know her, and I'm really excited to have her come and talk about what it's like to become an entrepreneur if that's the career path for you and she's going to share kind of her career history and the pivots that she's made and talk about what it takes to step into business for yourself, All right, Well, Becky, we're so excited to have you join us today.

Becky McCleery:

Thank you so much, Christina. I'm so excited and honored to be here.

Christina Kohl:

Oh, thanks. Well, like I said in the introduction, you are an entrepreneur and you help other entrepreneurs. If you could back up a little bit and share with the audience your story, your career journey, and bring us up to how things evolved, to where you are today.

Becky McCleery:

Yes. So it's kind of a long journey because it started probably about 18 years ago, but I will speed it up for our purposes today. So I'm one where I never dreamed about having my own business from the time I was pretty young. I wanted to be a teacher and so that dream never left. I went to college, I got the degree I was fortunate. I found a job within a couple weeks of graduation and then that fall I started teaching fourth grade and I loved the kids that I worked with, didn't always love the system that I was in, but I felt like, okay, I did it, I'm living my dream. And then, if we fast forward three years after that, by that point I had gotten married and we were having our first child.

Becky McCleery:

And when she was born I will say I was naive. Before I became a mother I thought I kind of had the perfect combination I would be able to have the job I wanted to do, make the difference I wanted to make and have time with my family evenings, weekends, summer break, winter break, all of that. And it didn't take very long after she was born to realize this is not going to work for me, because teaching, I think with a lot of careers too. You put a lot into it, it takes a lot of your energy, and I was coming home and I was just not being the mom that I wanted to be. So very early on I started thinking, okay, what else can I do? Because this was it, this was all I had ever imagined and I had never considered anything else. And so I think it was about the time that she was a year old, I discovered life coaching and I liked the idea of coaching because I felt like it could allow me to continue to make a difference and help people and have the flexibility to be home with my daughter and be the mom I wanted to be. So I did the training while I was still a teacher and it really wasn't until our third child was born. So I had my son about the time that I finished graduating from the life coach certification and then the following year had our youngest another girl and it was at that point we realized the cost of daycare was going to pretty much be my salary as a teacher, because we had the three kids so close together, they were so young and it was really just not worth it. So that's what pushed me to finally take that leap into having my own business, and I will say that I made probably every mistake you can make, because I learned about being a coach, but I learned nothing about building a business. So I really thought you put up a pretty website, people will magically find you, you have clients, and none of that happened.

Becky McCleery:

So I spent a number of years kind of trial and error and then found myself into found my way into being a kind of an accidental virtual assistant. I had been making connections online. A woman I had connected with online asked if I would help her in her business, and I, through trying to make my own business work, I had learned all kinds of technology and different systems that would work, and so it kind of was a natural fit, and so that was back in 2016 when I started with her and it really grew from there. I was a virtual assistant for a few years for multiple businesses. I learned a lot along the way.

Becky McCleery:

I reached a point where I was ready to do more than just complete tasks. I wanted to support business owners, and so I moved into online business management and that worked for a few years. And then, with my longest client, I became her director of operations and realized, okay, I can't continue to support all of these other clients the way that I had been, but I really wanted to help more women succeed in business, and so it's taken me a little while to figure out. Okay, what does that look like? Because it's not in the same work I was doing, but last year I started just some free networking calls where women could come together for an hour and connect, and through that I had women who were reaching out saying, hey, can we do this more? At the time, we were just meeting once a month, and so I felt like there's a need for more community here. I did some market research and I decided to give it a go, and so that led to the creation of the Solopreneur Sisterhood. And, yeah, that's where we are today.

Christina Kohl:

Thank you for sharing all of that. So you've been on the backside of a lot of businesses throughout the years and you've probably seen a lot of stop and starts, failures, pivots turns, and I'm just wondering for the woman listening who is ready to do something new and different and wants to branch out on their own what's the advice you have for someone who's just getting started? Go there first and then start talking about what are some of the common mistakes that you see people make that you can help them overcome.

Becky McCleery:

That's a great question. So if I think back on my own journey and then also how I've worked with other business owners, my recommendation is to just give yourself some time to brainstorm. Don't worry about editing your ideas or judging whether you think it's possible or not. Just allow yourself to start throwing ideas out there as far as what you might want to do and once you have a number of ideas out there, start sorting through them and think about kind of the practical aspect. So, for example, when my kids were really little, it was suggested to me that I do in-home daycare and I thought about that and I thought, well, I could do that. That's not really the life I want to be living. I want to have the flexibility to go do things with my kids and not have a whole crew of other kids at our home to be living or no. Actually I could do this, but this isn't really the right path for me. That will help you to narrow it down a bit and then at that point, once you have something you want to move forward with, you want to start sharing that with more people. So put together a small offer. You know, if you are a graphic designer, maybe there's a small package you could create, helping someone to create some templates that they could use for social media. If you're a copywriter, maybe you could offer to write a sales page for someone or a few emails for someone. Start testing it out and seeing one how you like the actual work. And two, is this something that people are really interested in and something that you think you can stick with?

Becky McCleery:

What I think held me back at the start was I felt I had to figure out what I was going to do for the rest of my life. If I was replacing teaching, I felt that I had to pick one career path for the rest of my life. And what I've learned is to ask myself can I stick with this for at least one year? Two years, I think, is a little bit better, but if I, can I stick with this for at least one year? And if so, then for me at least, that's a sign to give it a try.

Christina Kohl:

Yeah, that makes sense, and I've seen a lot of my fellow entrepreneurs pivoting lately. I'm noticing this. I was talking about executive coaching and now I'm talking about nutrition, and it's great to be able to see that example that you're not married to one thing forever and ever, so being flexible. And the other thing that I've noticed is that, because I fall into this trap of like I think, and I think, and I think, and I think, and I plan, and I plan, and I plan it's not until putting something into action that you really get the momentum and the feedback to be able to and it's okay to be messy action, but knowing that until you actually take those steps, you're not going to make any progress or or any learnings or any growth. It's just ideas and so that's. It's scary, but that's what annual.

Christina Kohl:

For those that have been with me since the beginning or if not, go back and listen my very, very first episode of this podcast. I rerecorded it six times before I published it and then I heard it, and I came home and rerecorded it six times before I published it, and then I heard it and I came home and rerecorded it again, and basically what I'm saying in that message is. I've decided to not have to do this perfectly. I'm going to show up imperfectly, and I hope that's okay with all of you. And now I'm on episodes. I don't know, I'm in the nineties 90 episodes or so.

Christina Kohl:

So they're not perfect, but they're out there and I'm learning and growing as I do it, and so that would be my advice, piggybacked on top of yours. You're not making a decision forever and ever and ever. It's going to evolve and change as you learn more about it. So I think that's great advice. Well, what would be? So let's say that someone listening has their idea. You mentioned graphic design. I'm going to brush up on my graphic design skills. I'm going to put a small offer out there. What are some other components, some foundational things? And again, to keep someone from cycling in their mind of planning, planning, planning, thinking, thinking, thinking, what are some foundational steps that someone can take to launch their business?

Becky McCleery:

Yes. So I'm not going to get into some of the practical things like the legal entity, financial stuff, all of that right now. I really recommend that when you're first starting out, you don't worry about getting everything set up for a business unless you're 100% certain that you want to do that. Just because I've known some people that go through the trouble of creating an LLC only to decide, oh no, this isn't for me within the first month, and then they've wasted that time and that money. So at the start, if you're just doing a few projects for people, I wouldn't worry about that. So what I would do is be really clear on what you are offering. If you need to, you can do some research.

Becky McCleery:

We live in this great time where you can go and find other people who are doing similar work to what you're doing. Kind of see what they're putting into a package. It's going to be your own work, it's going to be unique, but if you're thinking I have no idea how to put together a package, you can start looking for ideas out there. Then you really want to be sharing this with everyone. So it could be a case where you have people in your own network that might either need what you're offering, or know people who need what you're offering, and so I would have a simple email or a simple message that you're sending to them and saying hey, I'm giving this a try, here's what I'm offering. I would limit it, say I'm looking to work with three people or I'm looking to work with two people, just to give it a try.

Becky McCleery:

Here's what I'm offering. You can do this for free if you want to. If you're feeling really uncertain about what you're doing, doing it for free is going to be an easy way to get a yes. However, if you're able to charge a little bit for it, I've found that you normally get people who are a little more invested, and, ideally, you're going to get better feedback from them on your work as well, which is important. So, reaching out to everyone, you can think of sharing it with other people, and then you'll want to.

Becky McCleery:

There are all kinds of communities online where you can be connecting with new people. So if your network you're thinking no one in my network needs this One, just remember that they know people who might need it and then start looking for those online communities where you can be connecting with other people and sharing your offer there as well, and I think my biggest recommendation is this is probably going to take more time than you think it is I think we have this idea that I'm going to share this and I'm instantly going to have clients, and that isn't often how it works. So if you put something out there and you don't get results the first day, my best recommendation is to keep showing up, keep reaching out, and if you keep showing up and letting people know here's what I have to offer you will connect with people who need it.

Christina Kohl:

Yeah, I think that's great advice. Just start with people, you know, and I like the idea of charging at least a little bit, because then it's going to be more. Both parties are going to take it more seriously. Yeah, that's great advice. Challenges that aspiring entrepreneurs might get blindsided by, like they're just things they haven't thought about, or where have you seen people get derailed and how can they overcome those things? Kind of a big question.

Becky McCleery:

Yes, I was like well, there are so many, I'll go into a few, so one you kind of addressed. I see a lot of business owners and I say this with love, because I definitely have done this too take so long thinking and planning and trying to figure things out before they put anything out there. Or people who are saying, oh well, I have to have my website ready to go before I can put anything out there. And my recommendation is what you said Just take some messy action. It does not have to be perfect. You are figuring this out as you go.

Becky McCleery:

I'm the same way where it does not matter how long I have planned. Once you actually start doing something, you see things that you didn't see before because you're in the middle of it, and I find that it starts to come together more quickly, more easily, when you're taking action. Otherwise, you can stay stuck in that planning mode for months or years. So that's one is to take some messy action. The other thing that comes to mind for me is that I've seen we tend to not give things long enough to play out. So I see a lot of business owners get so excited about a new offer a new idea.

Becky McCleery:

They send out one email or they put out one post. No one buys, and then they start to slip into that self-doubt. And so my recommendation is, if you're committed to giving something a try, commit to at least 90 days. So if you're looking to connect with new clients, if you're looking to build with new clients, if you're looking to build your network, whatever strategy you're going to give a try, let it play out for 90 days and then evaluate before you jump to something new. And then I think the third thing I'll bring up is having your own business is going to challenge you in ways that you probably did not anticipate, and so it's really important to have that support network.

Becky McCleery:

You might be fortunate enough to have people in your personal life who are cheering you on. For me, that was my husband. You also might have people in your personal life who have no idea what you're doing, and they might wish you the best, or they might think this is nuts and not be supportive. I will say that I had a lot of people in my personal life who were saying what are you doing? This is crazy. You have a stable job. Why would you change to anything? So if you don't have those people in your life, find a community. There are lots of communities online. You might have a local community of business owners, people who can understand your journey and cheer you on.

Christina Kohl:

Yeah, I think that's so true because if most people are not solopreneurs, most people have a job, and that's definitely true in my social circle and people are excited for me and cheering me on, but still a little of confusion, like why did you leave your career behind and what do you do exactly?

Christina Kohl:

And and I will say like so, so I'm part of the solar solopreneur sisterhood. Um joined that group with you in January and that's been really helpful to talk to other people that they might be a communications coach or a virtual assistant or a podcast coach or all different types of solopreneurs, but we all are all business owners and it's really been a supportive community to be able to say like, okay, this is what I'm struggling with and have someone that understands it, and to be able to for me to even open up to share about some of the challenges of being a solopreneur, and so that's been a real gift, that community that you've created. And with that, let's talk about that community. How, if someone is interested in whether they're 10 steps in or they're at step one, what is it? Tell us more about the solopreneur sisterhood. Yes.

Becky McCleery:

Okay. So this kind of came about. As me taking that messy action, I will say I had thought for years about what do I want to do outside of the director of operations role? What? How can I be helping more business owners? And I did exactly what I told people not to do. I spent way too much time trying to figure it out in my head rather than just going out and testing things.

Becky McCleery:

So somehow last summer something shifted in me. I decided I was really going to focus on building my network, because I still had a lot of people who knew me for operations work. I was getting referrals for that, which is appreciated, but I didn't want to continue doing that for more businesses. So I realized, okay, I need to kind of rebuild my network, get to know people and take it from there. So I was doing all kinds of coffee chats, which is really just like a 20, 30 minute call where you're meeting someone, you're learning about their business, they're learning about your business, you're seeing how you can support each other, and I loved connecting with women. But I also realized, oh, I am working later and later in the day because I still have work to do and I'm spending hours on these coffee chats. So I was just thinking, okay, there has to be a better way. One, I need this to take less time and still connect with people. And two, a lot of the women I was meeting I would then follow up with an email saying, hey, you need to meet this other woman that I was talking to and I was introducing them to each other. And so I thought, you know what, what if we did a networking call? I do not like being the center of attention, so the idea of hosting was kind of terrifying. And then I thought you know what, what if I brought someone else in to be the guest co-host and we could kind of spotlight her? And so that's what we did. I had someone who I had had one of those coffee chats with. I reached out to her, presented the idea, said hey, would you be willing to be my first guest co-host? She said sure, and then we both invited people we knew to come together for this. And really it's just one hour. We have small breakout rooms, we have conversation starter questions that the guest co-host creates that in some way ties to her business or her interests, and it's just a really nice way to come together and connect with people, get to know some new people. We also have it's a spreadsheet, but we call it the connection dashboard so that everyone who comes can enter their information. So that way, if you met someone that you really wanted to get to know more than you could in that short session, you can follow up after the call and connect with them. And so that's where we started.

Becky McCleery:

And then, really early on, that was June of 2024. I had people reaching out who said, hey, I love that. Can we do this more than once a month? And I was like I don't really want to do this on a regular basis. I could commit to once a month, but I decided to do some market research to say, okay, what support do women need? What could we do beyond this? And what was amazing to me is I heard from I did a survey for this.

Becky McCleery:

I didn't actually do calls for this market research.

Becky McCleery:

I heard from about 100 women and some of them were new in their business.

Becky McCleery:

Some of them had been in business for years and had a lot of common challenges.

Becky McCleery:

They'd had everything on their plate.

Becky McCleery:

They didn't know what to focus on.

Becky McCleery:

They loved the clients they were working with, but they didn't have a steady stream of clients coming in, they felt like they were always kind of hustling, trying to make things work, and even though they loved what they were doing, there was still kind of that question in their mind like, can I actually do this?

Becky McCleery:

Is this going to get easier? Is it going to come together? And so with that, I decided to do a beta test of a mastermind program and I also decided you know what I think I want a free community as well, and a link for you that you can share, christina, and it's really for any woman who has her own business or is starting her own business and is doing it because they want to make a difference and make an income. I describe our members as heart-centered, meaning they really care about helping people, and I think that shows up in the community too, because so members have like the free community. They can be building connections there. We also have the monthly networking calls and we have a number of free workshops that different members of the community are volunteering to host and kind of share their expertise.

Becky McCleery:

So, I think that's a benefit too, and that some members are choosing to share their expertise with others and to support each other. So I think it's a really beautiful place for women to come and build those connections and receive that support.

Christina Kohl:

Yeah, one example today I don't know if you saw I put a post. I think it was yesterday I put in a post about Dubsado, which is a software platform to help manage your business and workflows and all of that. And I'm on their email list and they said hey, coming up next month, they give like a I don't know 10 day window. You get 35% off and if you have an affiliate link you'll get that discount too. So I'm like surely someone in the solopreneur sisterhood is an affiliate of Dubsado? So I went and posted that in there along with the other information, so other people can see it too.

Christina Kohl:

And at least two people responded like yes, I have an affiliate link and they'll save 20%. So combined I'll save 55%. Also, now everybody else in the community can see that as well, them as well. And if they weren't on Dubsado's marketing list, they wouldn't necessarily know that there's this opportunity to get 55% off their first year. So it's just a great. You know, that's just one little teeny example of the networking component in it and the support. So you mentioned the paid community. How does that differ?

Becky McCleery:

to the paid community. How does that differ? Yes, so Aligned Momentum is the name of the paid mastermind community and we are reopening the doors in August of 2025. And really, that one is intended to give deeper support. So the free community we have the online platform, we have workshops you can attend as you wish and the networking session once a month, and that's pretty much it. And then Aligned Momentum is where you can come together on a regular basis with a small group of women who are there for in-depth support and also to give greater support, and so we have a couple of different options for mastermind call times, but basically that's where you get to come once a week.

Becky McCleery:

Share one thing in your business that you would like support with and receive support from the other members, and it could be a case where you know you have a challenge you're facing and other people can help you brainstorm a solution for that. Or it could be you have something you want to create and you're not quite sure about your next steps and others in the group can support you with that. And then we also have the online community. For that, we have office hours where I offer more support with strategy or systems, and we'll have the quarterly planning retreats, which is a time every quarter where we come together it's virtual for now and we plan out where do you want to go in your business in the next 90 days, what are your most important priorities and goals.

Becky McCleery:

And I really love that because it's just a time for us to come back and get out of the busyness of day to day and get really intentional with our business. And so we are changing the format. It had previously been launching once a quarter and I realized, you know, I don't want women to feel like, oh, I just missed out, so it is going to be open for Evergreen. So if you're listening to this when the episode first comes out, we'll be open for enrollment, and if you don't hear this episode for a few months down the road, we'll also be here for you.

Christina Kohl:

Okay, good to know. Well, thank you for sharing that, and we'll make sure to put the links in the show notes for both the, because you can be in both groups. You can be in the free group, which is obviously larger, as well as the mastermind Aligned Momentum group. So we'll put both of those links in the show notes. And you said that's opening up in late August, so this episode will air before then so people can get in as soon as stores open if that's something they want to pursue, so that's great. Oh, and I had a quick question that came up because I do have some listeners that are out of the US Do you have people that are from around the world, or is this mostly people that are US based?

Becky McCleery:

That's a great question. Yes, I will say that I am thrilled that our community, the free community, has more, but even the mastermind community has some. We have members from around the world who join us. So if you're looking for the mastermind, we do have set call times and those are listed on the sales page, the information page for it. So you might want to check that with your time zone to see how that works out for you. As the group grows, we'll add more time options, so feel free. If you really want to join and this does not work for your schedule, you can always reach out and let me know and we'll consider that for a future time.

Christina Kohl:

But yes, I love that we have women from around the world coming together to connect and support one another. Yeah, yeah, that's great. I know, when I work with my clients that are in England, it's a seven hour difference, so it's my morning and their dinnertime that we need, so it works out and that's the beauty of the tools that we have in this day and age that we're able to get. I mean, you and I are in different time zones and we're on this call together, so it works, okay. So any final words of wisdom for people that are making career pivots or thinking of branching out, particularly your expertise of being a solopreneur, and it could be something that you've already shared, but just like your final chance to tell the listener something encouraging, motivating, as they are starting on this potential journey, this path, this potential journey, this path.

Becky McCleery:

Yes. So my recommendation is to trust yourself. So, if I think back on my journey, I was really conflicted about whether or not to leave teaching and really pursue this or not, and deep down, I just knew you know what for the life I want to be creating. This is not the path for me, and I need to be willing to give this a try, and I will say, it hasn't always been easy, but I've never regretted that choice. And so, whatever if you're looking at getting another career or you're looking at starting your own business, my recommendation is to just trust yourself. Other people are out there, uh, creating their own business. You can absolutely do it too, if that's what you want to do, and I think sometimes we just hold ourselves back because of that, that lack of self-trust yeah, that's.

Christina Kohl:

I think that's great wisdom and insight, and I'm gonna add to it something that came to my mind, because sometimes I'll see, like, oh, I have an idea, but oh, it's already being done. And instead of that being like, well, it's already done and there's no room for more, it's like no, that's proof that, yes, that there's a market for it and that it's a business model that works. And you, as an individual you know, whether it's you or me or someone who's listening we bring different, unique things with us as we approach the work. So it might be a similar topic, but no one is us, no one has our uniqueness, and so I want to encourage people.

Christina Kohl:

I'll just add if there's something that you want to do that's already being done, great, because that's proof that that's social proof, that there's a need for it and that it's um, there's a, there's a market for what it is that's on your heart that you want to do and you'll bring, you'll bring your uniqueness to it. All right, well, becky, thank you so much for taking the time today and to um share your story and to pour into my audience. I really appreciate it and we'll definitely have those links so that, if people are interested in learning more they can at a minimum. Can they join the free society, the solopreneur sisterhood, now, or is that our doors closed until August for that?

Becky McCleery:

That is open at all times. As we're recording this, we're moving to a new platform, but by the time this episode comes out, okay, it will be available.

Christina Kohl:

Okay, so people can join that like right away, just to kind of explore it and then um and learn more about the, the paid mastermind group, at the same time. Yeah, okay, perfect, all right. Well, becky, perfect, all right. Well, becky, thank you so much. I really appreciate you being here. I really appreciate you being here today.

Becky McCleery:

Thank you so much. It was lovely joining you today.

Christina Kohl:

All right. Well, everyone, that is it for this week's episode, so we'll catch you next time. Thank you so much for listening today. I hope this episode hit home for you and, if you haven't already, be sure to connect with me on LinkedIn and say hello, so I can personally thank you for listening. Until next time, remember your story is uniquely your own, and your next chapters are ready to begin.