Dive into a transformative journey from solopreneur to CEO! In this exciting special miniseries, Tonya Kubo and operations expert Gwen Bortner guide you in making the transition to becoming the leader your business needs. Discover how to break free from the day-to-day grind, delegate tasks effectively, and grow your company with confidence. Whether you’re a seasoned entrepreneur or just starting out, this episode is packed with practical strategies and mindset shifts to help you step into the CEO role and lead your business to new heights. Tune in now and start your journey to becoming the CEO your business needs.
—
Watch the episode here
Listen to the podcast here
From Solo To CEO: Pivotal Shifts To Become The Leader Your Business Needs (Part 1)
This episode I am so excited about. It is our very first special miniseries. We’re doing a four-part series. I think it’s going to be four parts. Gwen might make me cut it short because Gwen is the queen of efficiency. We are talking about making the transition from being a solo entrepreneur or solopreneur to becoming the CEO your business needs.
If you feel like you are stuck in the day-to-day grind, you’re wearing every hat in your business, and trust me, we have all been there, but you want to learn to step into the CEO role, as my friend Mary Williams says, to put your CEO pants on and grow your company with confidence, this is going to be the episode for you. This is the one to save and come back to time and time again.
I am joined by my absolute favorite operations expert, Gwen Bortner. In this series, we plan to break down the critical elements of becoming a CEO. We know that we all start somewhere. Outside of the work I do with Gwen, I am a solopreneur. I don’t even have a VA. Gwen has a delightfully tiny team that I get to be a part of. There’s that process that you have to go through. It starts with changing how you think. There’s a bit of a mindset shift that sets the stage for everything else.
Gwen, what I’d like you to do is kick us off because you have 40 years of experience, and quite honestly, I do not. I want you to give us an example of somebody you know. It could be a client or an associate whom you have witnessed successfully make that leap from solopreneur to CEO. I’m curious if you could identify what you observed as the turning point for them.
Turning Points
I think it’s important to clarify that even if you are a solopreneur, you can still be a CEO at the same time, even if you never want anybody else on your team. Our friend Mary says it’s partly a mindset of how you’re approaching the business. Often, we think of those as two separate things, if I’m one, I can’t be the other and vice versa. No, you can. You probably can’t be both at exactly the same time, but you can definitely be both without changing the structure of your business, hiring a thousand people, or any of those things.
One of my clients, who has been a long-term client, quite honestly, I’ve watched really make a major transition. When she started with me, she was a true solopreneur. There was no one else working with her in any capacity. I think she might’ve had an intern or two, but they were truly interns. They were not even like VAs.
This is what they’re doing. It was someone to come and follow in her footsteps. When we started working together, it wasn’t long before we were helping her think about what had to be in place, because, in her case, she did want to grow. She did not want to stay the size that she was. Not that that was the right answer; it was the right answer for her, but it was getting her to shift her mind about what that meant and what she needed to do to make that happen.
She, like so many solopreneurs I know, immediately thought it was about bringing in a lot more of what I’m going to call low-level people: interns, early-stage VAs, the task people who are just going to do tasks. The problem was, like with most solopreneurs. The problem was that there wasn’t much outside of her brain that she could hand to somebody. That makes hiring those people not nearly as effective because we can’t, and I know we’re going to get into delegation later, but you’ve got to have it outside of your brain.
One of the things I suggested to her early on was that she actually needed to hire someone who could do some of the same level of work that she does. This is a woman who is extremely specialized in a highly technical niche and has lots of years of experience behind her. She’s like, “I can’t possibly find anybody.” It was like, “Yeah, but you need to start thinking about it.” It was one of the first times I saw it.
It comes up from time to time, and we know what it is, but there was this wall that came up in her face that was like, “I am very uncomfortable. This seems very wrong. I’m not happy with this comment.” Luckily, she and I had a fairly good relationship even before we started working together. It didn’t throw me off too much, but I was a little nervous. It was like, “I don’t know,” because I had made her extremely uncomfortable. This was someone who did not get uncomfortable easily.
It sounds to me like you were stretching her.
I was totally stretching her. It took her only about 24 hours before she got to where she needed to be. I’m receiving an email like twenty, it’s like, “I thought of three people.” It was that pulling out of where she was in the doing. It never occurred to her that someone else could be doing alongside her instead of for her.
What I like about that is, I know, and I’m speaking for myself because I’ve gone from solopreneur to building out an agency to shrinking back for a bit. The reality of wearing all the hats in your business holds you back. When you go into a room and you talk about how, like, “I’m so busy, I’m doing this, I’m doing that,” all anybody ever wants to talk to you about is handing off those tasks. “Get a VA to do it.” If one more person tells me that I can have a VA work for me twenty hours a week for a whopping $100 a month, I might actually scream. I get it, because you’re in the room, and you’re focused on the things that bother you, and you can’t get out of it. All you see are the tasks.
What you did for this business owner was help them appreciate that while the tasks may have been overwhelming, what was using up their time, and offloading those was actually going to be more work since everything was in their head. All that institutional knowledge was in their head. In order to be able to step out of the business far enough to see the bigger picture, they needed somebody who could work without knowing everything in their head. They’d have their own head of stuff to bring to the table.
That was similar enough that there was only going to be shorthand communication instead of very detailed communication.
Mindset Shift
No, I like that. What I’d like to address next, because I think this is a really good launching pad, is why it is so important to shift the mindset from doing everything yourself to stepping into the CEO role? I understand you just gave a great example of the actual practicality of doing it, but in that 24-hour period in the story you told us, some leaps and bounds had to be made inside her brain. Talk to me about that.
Her brain works really fast. For most people, that would have been a week-to-a-month process. I wouldn’t have felt bad about that at all. That would be completely normal. The fact that it took her, and typically it’s like a 24-to-48-hour turnaround time, is like, “Okay, I’m there.” She’s a bit of a unicorn for that. That’s one of the things, and I get it. The thing that was going on was her getting comfortable with it. “They’re hiring me, and someone else is doing the work,” which I think is a big deal for all of us, raising my hand here.
When we have been the primary deliverer, or is that even a word, deliverer of services? We’ve also been marketing ourselves. What if I’m not the one delivering it, does it still count? Particularly if I’m not advertising myself as an agency where you’re hiring other people to help in the process. I don’t advertise myself as an agency because I’m not an agency, but that doesn’t mean you sometimes don’t consult with my clients. That was also a step that was not automatic. Of course, you’re going to. That was not just a given. That’s a shift when you’re moving from that solopreneur world into that CEO world. Even though I still deliver most of the services, I don’t know, 85%, 95%, a big chunk of it.
From that standpoint, I probably still really am a solopreneur, even though we do have a tiny team. But the CEO part is being able to say, “When am I actually not necessarily the best person to be delivering the services?” When we’re in that solopreneur mindset, we are always the best person to be delivering the services, but the CEO mindset says, “Am I, or is there possibly somebody else, or something else, or a tool?” You can fill in lots of blanks there. But is me doing this really, really the best thing not only for the business but for the customer as well?
Solopreneur Vs. CEO
It feels like it could be a hard pill for some people to swallow, and working with them personally may not be in the best interests of the business or the client. I am wondering, though, if that’s a big difference between being a solopreneur and a CEO. What do you think? I know there are other differences. What would you say are the top two next differences between them?
One of them is being able to actually step back, find time, and think strategically about the whole business, not just either the part that you’re really good at, or the part that you love, or the part that makes you happy, but the whole business, which inevitably has some elements that are not your favorite part. That’s just the nature of these things. I don’t know anybody that says, “I love every little aspect of my business.” I don’t think that exists. There probably is that, but I doubt it. Being able to look at all of that strategically, as a whole and with some objectivity, of course, we can’t truly be objective about things because we’re in the middle of it. That’s a thing. That would probably be, to me, the next thing. All of these are parallel.
It’s not a one, two, three order. It really is like it’s this, and that, and that.
The other is being able to start seeing how to create. I always loathe using the word balance because people always think of this. To me, balance is not that. It’s this, doing this, doing this, doing this, doing this. Being able to create balance over time means sometimes we’re putting more effort here, but then we’re putting less effort there. Later, we’re putting more effort here. When I say balance, I mean being able to think about balance holistically for the entire business. Especially if you’re a solopreneur, for you too. Something I hear at Genius Network is they talk about the million-dollar racehorse. When you’re a solopreneur, you are the million-dollar racehorse. You are the one that’s actually creating the money.
When you're a solopreneur, you are the million-dollar racehorse. You are the one that's actually creating the money. Share on XIf you had a million-dollar racehorse, would you run it every day until it was worn out, every single solitary day, so that you killed it, or you made it lame. You would train it, and you would run it, and you would put it in races, but you would also give it time off, and you would make sure it ate well. You would make sure that it was sleeping properly and doing all of the other things, too. We forget that, especially as a solopreneur, we forget that we are, using this example, a million-dollar racehorse. That’s part of the balance. You can’t not ever have the horse run because then it’s also not a million-dollar racehorse, but you can’t have it run constantly, either.
Limited Growth
That’s good. As I said, I always use the goose that lays the golden eggs. I say, “If you cook the goose, you have no eggs,” and sometimes we’re guilty of cooking our own goose. We’ve got the differences, which I think are three. I know I can’t think of any others that I have seen across the board. I see those three. I’m wondering, is it possible? I was going to ask this a different way, but is it possible to grow without shifting your thinking from solopreneur to CEO, or does everybody eventually have to come to terms with this?
I think the answer is if you don’t, you’re going to hit a limit. I can’t tell you what each limit is because I can imagine a limit where someone has a million-dollar business as a solopreneur and is not thinking like a CEO. I don’t know what that is right off the top of my head, but I can totally imagine that. Whereas for most people, they’re probably barely going to hit six figures before hitting their limit. I don’t think it’s a number kind of thing, but I do think it’s a combination of energy and health and a number. There’s a whole lot of things there. I think at some point, the growth will stop if you aren’t thinking like a CEO.
When I think of adopting the CEO mindset, I think of creating a process or system or a routine around consistently planning for the long-term. I’m not just thinking about, “How do I get through the month? How do I pay the bills?” Some businesses are great with cashflow, but, “What business do I want to have in a year? What business do I want to have in five years?” Using and relying more on data to drive decisions than intuition. I love my gut instinct. I’m not going to lie, Gwen.
I love it. I find that my business has fewer peaks and valleys when I let data drive my decision-making versus just going on gut instinct. I also thought that it was the systems. It’s going back to the example you made when all the information lives inside your head. If, for any reason, you have to take time off, good reasons or bad reasons, the business can’t move forward because nobody can read your mind. Would you add anything else?
No, I think, and I do think that’s why there is limited growth until you start thinking like a CEO. Not that it’s too limited, because there are a lot of people who don’t really take a CEO mindset and have a business that makes them happy. It’s not like that is the right answer. If you’re feeling stuck, if you’re feeling like you want to be able to do more, like you should be doing more, it could be not having that CEO mindset, that you’ve got too caught in the delivery and the action, in the doing, and not being able to step far enough away to do the strategic thinking. Quite honestly, we talk about strategic thinking like it’s all you have to do. It’s super easy to think strategically.
It is not. If you haven’t had lots of opportunities to be exposed to it and experience it and go through that process, that’s a really hard thing. I think that another reason people get caught is because they’re told that they’re supposed to think strategically, and they’re like, “Okay, I guess that’s what I’m doing.” Like, how would you know?
It’s how would you know? I talk about this all the time with you. So often, people don’t understand the difference between strategy and tactics anyhow. When you tell them to think strategically, many times they actually think you’re telling them to just map out more day-to-day.
More things to do.
Thinking Vs. Doing
More hands-on stuff. You’re like, “Not what I meant. Words I said, but not what those words meant.” What do you think prevents most women? I say women because that’s our listenership, but what prevents most women from stepping into that CEO role? What’s inside their head, inside their heart, do you think? I don’t know.
This is a big generalization because that’s what generalizations are. This doesn’t mean absolutely.
By definition, they are big in general.
Big in general, which means it doesn’t necessarily apply to everybody. We have obviously been, and still are, in a patriarchal system. Part of that system is that women have been more valued for doing than for thinking. Being strategic is more about thinking and less about doing. We get in our minds that it must not have been valuable if we’re spending time doing strategic things and I can’t show you something for it. It was probably a waste of time.
I’m going to ask you to say more about that, but let me explain why first. Whenever I hear other people talk about, like, “What’s preventing me? What’s my head trash around stepping more strategically, spending more time on my business than in the business?” what I hear said around the rooms is I hear people say, “Well, that’s imposter syndrome.” I like, “You don’t mean to be, but you’re being a bit of a control freak. You’re just scared of losing control of your business.” Some people will say, “You just have a healthy, like an unhealthy attachment to things.” What you’re saying isn’t actually any of those. You’re not describing imposter syndrome.
You’re not describing control-based fears. You’re definitely not describing like pink puffy heart love towards super certain tasks. What you’re talking about is deeper, and yet resonates on a much deeper level than the idea of imposter syndrome does to me. Say more about this idea of not getting value for thinking versus doing and why, if that’s true, then why is that so important?
Historically, the men have done all the thinking, and they make the plans, and then the women implement them. I’m going to go back a couple hundred years when farming was a big deal because often, it was the way that you actually survived.
You and I have farming-ish backgrounds.
We have farming backgrounds, but I’m really talking about several hundred years ago. What you would typically see were large families because what they were actually creating were hired hands.
I was going to say workforce.
They were creating a workforce. It’s really part of the process. The planning was left to Dad, and Mom was about the implementation of the doing of raising them and getting them capable enough to start taking direction from Dad to do the next set of things. Once they were old enough, they could carry a heavy load or wouldn’t chop off a finger or all of those things. There is this setup that I do what I, as a woman, do what I’m told. Even though I’m telling myself, it’s more important for me to do what I’m telling myself to do than it is to think about what needs to be done. Gosh, that sounds convoluted when I say it, but I really think it’s true.
No, it does. I’m going to ask you, just to prepare you, some practical steps on how to do what you’re describing.
I think the big thing first is you’ve got to be okay with not producing something for a chunk of time on a semi-regular basis. I don’t mean like every day, because I still do a lot of activity during the day. I do not always do strategic thinking. I’m doing lots of strategic thinking but on behalf of others. I’m not doing a lot of strategic thinking. I’m not CEO-ing in my own business all the time. Saying, how often do I need to be? When should I be doing this? Based on a lot of different factors, you can figure out different time frames. At least once a quarter, you should be taking a chunk of time. When I say a chunk of time, I mean like half a day.
That’s helpful.
To say, and it may be more, but a half a day to say, “What do I want? What’s going on? What are these bigger-picture things? How, what have I got? What’s the data I’ve gathered thus far? What can I look at, do some analysis, and make some decisions that I can do as a predictive activity that will have a relatively high likelihood of being true?” All of these things are a bit crystal ball-y. We don’t always have the answer, but the more data, the more times you do it, the more accurate it becomes. At least quarterly, but depending on what’s going on with your business, its speed, if it’s growing, and if there are lots of changes, it may need to be done once a week.
When you're a solopreneur, you are the million-dollar racehorse. You are the one that's actually creating the money. Share on XIt may need to be more often. One of the things that we do that I find really useful is we do an accountability process that’s weekly. We’re doing a little of this every week. We have monthly staff meetings, which allow us to do a little more of it once a month. We have quarterly planning meetings for our staff, which allow us to go deeper once a quarter.
It’s not like there’s a one-and-done answer for us. Our particular process may not be appropriate for everyone. I’m not saying that it is, but we’re taking a little bit of time to get out of the details, think higher regularly, and look at the bigger picture of things. Setting aside that time and getting comfortable with not producing anything.
Better Business And Life
Here’s the hard question, Gwen. I love that. Thank you for walking through a process, because even if the weekly, monthly, or quarterly cadence doesn’t work for somebody, I think our listeners can find a place, like find at least one aspect of that that could work for them. That sounds hard. I know you’re smiling because it is hard. I feel like you need to tell me, I want to say you need to sell me on this, but that’s not really your personality. I want you to tell me how my life will be better for doing it. That’s what I want. How is my life going to be better? Am I business going to be better? If I do this hard thing, by your example, I may not actually feel like it is real work, and other people around me may not see it as such.
Most people won’t see it as such. Just be okay with that. Know that.
Just suck it up.
Just let that go because if they are not in a similar role, they will not understand its value. Just leave it at that. The thing that you will start being able to do, and this is another one of those things that takes practice. The first time is not going to have this, like, “My entire business changed because I took four hours to do this.” That is not the way this works. It’s incremental, and we start getting better and better and better. You’ll find some tools that you could use. There are all sorts of things that you may want to do, depending on who you are and what your personality is.
You may want to meditate before you start so that you clear your mind. Some folks want to do yoga. Some folks will walk while they do a lot of this. It’s not like there’s a perfect answer for how you are going to do this. The key thing is you will start having thoughts that your brain hasn’t had space for before because it was worried about, “I’ve got to get this thing done and this thing done and this thing done.” I’m going to use my perfect example of it that happened when I was doing my quarterly planning retreat. I was thinking, “It’s time for me to find someone that’s really more of an executive-level assistant, a much higher assistant.” I’ve been hiring VAs, and they weren’t quite delivering what I needed to deliver.
I realized it’s like, I need to take some of my own advice. Finding that person’s going to be really hard. I was thinking about this, and this was not my first rodeo. I’ve been doing this quite a bit. All of a sudden, what popped into my head was, “I should ask Tonya.” It was truly during one of those times. You and I had been meeting regularly and talking regularly at that point for a couple of years. It wasn’t like I didn’t know who you were, that we just met, that I had no idea what your skillset was, that I didn’t know much about you, all of the things that would seem obvious, like why had I not thought of Tonya?
None of those things were true. It was that I hadn’t had space enough in my brain for my brain to actually say, “I’ve been trying to point out to you, you should think about talking to Tonya about it.” As soon as it came into my brain, it was like, “That is the best idea ever.” I didn’t know if she would be interested, but I also knew the second I mentioned it to my husband, he had the exact same reaction.
It was like, “That’s the best idea ever.” He also knows you, and he could have come up with the idea. It’s not his job to be strategic about my business, but it’s the exact same thing. You’ve got to give your brain space to have these ideas that when you have them, you’re like, how did I not think of that before? It’s because it’s been busy doing other stuff.
What I love about that example, aside from the fact that it was about me, is that I like being the answer to a longstanding problem. We had the conversation, and in six months of working together, you had enough space. I had enough of a handle on the business to be like, actually, you don’t need an executive assistant. You need a thought partner in your business. You need the other side of the coin. We were able to develop from there, but we never could have gotten there if you hadn’t made a point to give yourself that important thinking time. I don’t know who it is. I’m sure somebody listening will tell me who made this quote, or I’ll Google it afterward, but it’s the time to think the unthunk thought.
That is exactly it.
I think that is so important. This is really, really good because I think too often we get told what to do, and where nobody ever takes the time to tell us how our life will be better on the other side. When it gets hard, it’s just easier not to push through, to be quite honest. It’s easier if you don’t have somebody constantly pointing out to what the other side can look like. I’m going to end us here because this is a series. This is just part one, folks, just part one. In this episode, we’ve explored the differences between being a solopreneur and stepping into the CEO role. As Gwen was very careful and very adamant about pointing out, it is okay.
If you always want to be a solopreneur, however, you are still going to need to put your CEO pants on every now and then. Quarterly, monthly, weekly, depending on your business and what you’re doing. We’ve discussed the importance of making that mindset shift because it is the longest distance you’ll ever have to cross is the space between your ears.
Making that mindset shift for your business growth, we talked a little bit about what holds you back, but honestly, what Gwen mentioned is just the fact that it’s hard to feel like thinking is as valuable as doing, right? That piece holding you back prevents you from embracing the hard thought work that is required to become really a true CEO. How can making that shift actually bring you more freedom? This is what all of us want in our business.
That’s how we get a thriving business, even when we’re not doing everything by ourselves. If any of these topics resonate with you and you want some tailored advice, we would love to connect with you. You can visit us online at TheBusinessYouReallyWant.com. Make sure that you join us for our next episode in the solo to CEO series because that’s when we are going to discover the essential leadership skills that you need to manage a team, even if the only person on that team is you.
Mentioned in the Episode
- This is Part 1 of 4 in the Solo to CEO series. Listen to all episodes in the series:
- Find all resources mentioned in the episode at The Business You Really Want
About Your Hosts
Gwen Bortner has spent four decades advising executives and entrepreneurs in 45+ industries. She helps women succeed in business without sacrificing happiness by identifying their true desires and aligning their business functions. She spots overlooked bottlenecks and crafts efficient plans toward sustainable success that center your values and priorities. Known for her unique approach to problem-solving and accountability through the G.E.A.R.S. framework, Gwen empowers clients to achieve their definition of success without sacrificing what matters most.
Tonya Kubo is a marketing strategist and community builder who helps entrepreneurs build thriving online communities. As co-host of The Business You Really Want and Chief Marketing and Operations Officer (CMOO) at Everyday Effectiveness, she keeps conversations on track and ensures complex business concepts are accessible to everyone. A master facilitator with 18+ years of experience in online community building, Tonya takes a people-first approach to marketing and centers the human experience in all she does.