When Doing Everything Becomes Your Biggest Business Problem

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The Business You Really Want | Business Problem

The hardest part about growing your business isn’t hiring people or finding customers. It’s letting go of being the person who does everything. In this anniversary episode, Gwen Bortner and Tonya Kubo revisit their second-most-downloaded episode: From Solo to CEO Part 1 – Pivotal Shifts To Become The Leader Your Business Needs.

Here’s the uncomfortable truth: being good at your craft doesn’t make you good at leading a business. Entrepreneurs excel at firefighting (and sometimes starting fires), but CEOs need to step back and let others hold the extinguisher. That transition requires both leadership skills and management skills — a combination that’s harder than anyone talks about.

Gwen breaks down why this shift feels like fractioning your identity, why you can’t just think your way into being a CEO (you have to act like one), and why true delegation is so much more complex than writing a checklist. Tonya explores the boundaries you’ll need to set — with clients who want you personally, with team members who work differently than you do, and with yourself around protecting thinking time.

They dig into the identity crisis that comes when you’re no longer the best at the thing you built your business on, why “I could have done this faster myself” will always be true (and why it doesn’t matter), and how to own which problems are actually yours versus your team’s. The reality: Growing from solo to CEO isn’t about getting bigger. It’s about getting comfortable with not being the one who knows all the details anymore.

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When Doing Everything Becomes Your Biggest Business Problem

Revisiting The Podcast’s Second Most Downloaded Episode

One year ago, we launched The Business You Really Want, and you have made it clear which conversations matter most. Gwen, we are talking about our number two most downloaded episode. A year ago, we introduced the concept of the mindset shift that unlocks business growth without burning out our CEO. That starts with changing your thinking from being a Solopreneur to a CEO. Transitioning from doing everything yourself to thinking like a CEO. I think it’s very important to point out that this was our most downloaded episode up until about eight weeks ago. Just so we’re clear.

It was number one, but we bumped it.

We did. We bumped it, which is still surprising, but we’ll talk about that next week when we talk about our number one most downloaded episode. Gwen, we have heard so much about this episode. This is probably one that has given us the most emails, the most responses, because it forced people to think differently about how they view themselves as a business owner, as their business changes, what it really means to be a leader, and what it actually requires of you to build a true business. What do you think of all of those things that have made it so profound to readers?

I think it’s the place everybody struggles is, unless you’re starting with the plan of getting some major funding and really wanting to start as that major CEO, which I don’t think most of our readers are in that camp. I’m not saying they cannot be, but I think that that’s not the majority of who we attract to this podcast. Unless you’re doing that, you start out as a solo.

You start out as the person doing all of the things, wearing all the hats, all of those pieces. That transition to being a CEO isn’t just a tactical move of you’ve got to have the business big enough and all the things that go along with that. It is also a mental move. People talk about it, but I think, is often the case here in the business, you really won’t talk about it differently, which I think gets people interested in it about how do we go from being that solo brain entrepreneur to that CEO brain entrepreneur.

Also acknowledging that not everybody can do that. If you pay attention to a lot of the what I’ll call the big boys out in the world, they often are no longer CEOing their business because they can entrepreneur it, but they cannot CEO it. It’s two different things. There’s a big mind shift there. I don’t think we talk about that enough because it’s a big shift, and it’s not for everybody.

Difference Between An Entrepreneur And A CEO

Do us a favor and give us the definition. Explain, when you say they can entrepreneur it but they cannot CEO it, what does that mean to you?

For me, the difference of entrepreneuring is one of my favorite quotes that we talk about all the time from Dan Sullivan is that entrepreneurs are really good firefighters, which means sometimes they’re also really good arsonists. Entrepreneurs really are good firefighters. They get in and they can figure out how to do something, and they’ve got all these ideas and are doing all of the things. At some point that doing all of the things is not helping the business.

An entrepreneur tends to do things in big ways, but they become less effective at some point. This is when they usually bring in a CEO. Share on X

It’s actually becoming detrimental to the business because at some point, and it varies on the business, and there are all sorts of things, that what the business needs to be is just fundamentally boring. It needs to be doing things in a very boring, consistent way. If it’s being done in a boring, consistent way, there shouldn’t be a whole lot of fires. There probably are some, but they should be little tiny spot fires, not big giant blazes.

We need the entrepreneur not going in and saying, “This is boring. I’m going to somehow make it exciting for me.” The CEO is about saying, “How do we keep things consistent in doing what they need to do?” Even if they’re growing, even if they’re doing some of the other things, but they aren’t doing it in this just dramatic way. An entrepreneur tends to be doing it in big, dramatic ways.

Not that that’s wrong, but at some point, it becomes less effective than they want it to be, which is usually when they bring in a CEO, they become president of the board or some other role, and often go build another business, which is great. Good for them. It’s also why you hear a lot of entrepreneurs talk about getting bought out. “I sold my business.”

That’s because it’s no longer the business that they want to be doing as a true CEO. When we talk about solo to CEO, we’re really talking about a phase in between those two. To me, a true CEO is usually running a multi-million, many-personed business. When I say many person, I’m usually talking in the hundreds of people business. Below that, it is a CEO role, but is often done in an entrepreneurial way. That’s really what we’re talking about, going from solo to that.

We’ve given the example of the traditional example of what most people see when they see from entrepreneur to CEO. Now, which I think is important background, because I think sometimes when you’re a business owner and you go to, I’m going to say a retreat, a mastermind, whatever program, and they say, “You need to think like a CEO.” I know I’ve sat in those seats, too. The examples everybody gives you are like Steve Jobs, Mark Zuckerberg, whatever.

You’re like, “I don’t want a company with thousands of employees. I didn’t create some amazing tech thing. I don’t see myself there.” It is hard to see the difference. For you, meaning, thinking very specifically about our readers, what do you think the reader today needs to know most about the shift from thinking like a solopreneur to thinking like a CEO under this definition? Go ahead and just summarize the definition as well.

To me, this definition of CEO really is about the leader of a company as opposed to the doer of a company. A leader of a company can still be doing. There is leadership by example. There are servant leadership examples that people talk about. There are lots and lots of ways to lead. I’m not saying it’s any one of these particular ways, and it can be a combination of all of them, but it’s the difference of leading as opposed to doing.

To me, an entrepreneurial CEO is both a leader and a manager. I had a great friend, we did programs together where people would say, “I don’t want to be managed, I want to be led.” Our argument always was, we’re arguing about the wrong thing. That these are not two opposing things, and one is right and one is wrong. They’re both things that need to happen. Sometimes things need to be managed, and sometimes things need to be led.

If you have only a leader with no management, there are certain things that fall through the cracks. If you have managers who aren’t leaders, there are also other problems that go with that. To me, this entrepreneurial CEO is actually doing some of both, which is tricky. I think that’s the thing no one talks about is that’s a really hard combination of skills.

What do you think makes it hard?

They are very different kinds of skills because leading is about big picture thinking and about inspiring and wanting people to follow you. Entrepreneurs, I think, can get to that space generally more easily because they tend to be big picture thinkers, they tend to be inspirational, they tend to do all of those things. In this transition phase, you also need to be a manager.

   

The Business You Really Want | Business Problem

   

A manager is more about the how and the details and some of those other aspects, which, on the whole, giant generalization here, entrepreneurs generally suck at. Love them, know them, have them. I get it. That’s part of the skill, I think that gets really hard in that entrepreneurial CEO world is that there’s the leader piece, but there’s also this management piece that needs to be done.

I think a lot of entrepreneurs become entrepreneurs because they don’t want to be managers. This is where it becomes tricky because either you’ve got to do it or you’ve got to find someone who can do it, who’s good at doing it. People who are good at doing it, you aren’t going to find them at $10 an hour in the Philippines. That becomes the next problem. How do we fund that position? It’s a very chicken-and-egg issue.

I think it’s interesting how you break it between leading and managing. I think that’s accurate. I feel like a lot of solopreneurs, though, aren’t even there yet, especially if you’re a solopreneur operating as a service provider. It’s all so integrated into who you are and everything you do that I think it’s hard to even think like, “My job is to be the visionary and I need to bring on people to implement.” You don’t even know how to instruct the implementation because for you, it’s so integrated into the visionary, the leadership. It’s all jumbled together.

The whole parsing it out is part of the challenge of moving from solo to CEO. I think that’s one of the huge issues.

Dealing With And Addressing Identity Crisis

I wonder if as you’re parsing it out, does it feel a little bit like you’re fractioning your identity?

Yeah, absolutely. You and I’ve talked about it before in the way that you’ve approached your role before and how we’ve changed it now. When it’s all in your brain, it’s so easy to communicate to yourself.

It’s very efficient when it’s just me.

Aren’t we all? As soon as I’ve got to share it with you, it adds a level of complexity. When I have to share it with you and somebody else, that adds even more complexity. That’s where the problem falls into the issue.

Something that I’ve seen that I think would be valuable to people reading to talk about is, because I hadn’t thought about the fractured identity piece of it, but I have witnessed the identity crisis. When you’re working with somebody, and they still feel like they have to jump in and fix everything. They get frustrated that they have to jump in and fix everything. “Why am I paying people if I’m always going to have to go fix everything?”

You have to point out to them, this starts and ends with you. You have to stop jumping in. You have to work through your team. You have to let that person you hired solve the problems because that’s how they’re going to learn, because that’s how you learn. I find that a lot of times, some anxiety comes from it. The business owner almost doesn’t know what to do with themselves.

A lot of entrepreneurs become entrepreneurs because they do not want to be managers. Share on X

Back to the same Dan Sullivan quote, there’s a huge piece of, “If I’m not fighting fires, what use am I?” If I see there’s a fire, then obviously I should go get the fire extinguisher.” It’s like, “No, someone else can get the fire extinguisher. It doesn’t have to be you.” You may need to tell someone, “Go get the fire extinguisher.” You don’t necessarily have to go get it and use it. You may say, “You need to go get it now. We don’t have to use it.” “Let me show you how to use it.”

That feels so inefficient, but it’s only inefficient the first time. It’s not inefficient every time after that. What this is back to, and I’m sure you’ll put the link in the show notes, is delegation. True delegation is hard, and it’s very uncomfortable. That’s part of going from solo to CEO is actually getting comfortable with and good at delegating, which really is more of a manager skill as opposed to a leadership skill of helping them figure out how to solve the problem, not solving the problem for them.

Back when I was doing knitting instruction, one of the things people would say is, “They’re a really good knitter. They should be a teacher.” I would watch them, and the difference is did they took the work out of someone’s hands and did it, or were they able to talk them through how to do it themselves? To me, that’s the difference between a good teacher and a bad teacher. Every once in a while, I would teach teachers, and some of them would say, “There’s no way I can teach more than eight people.”

Without even seeing them, I knew because they were having to do it for them and show each person individually. It’s like, “You’re right. You never can.” I would teach classes of 20 and 30 people. I’m like, “You cannot do that on some of this stuff.” It’s like, “Nope, I absolutely can, because I didn’t have to show it to them. I was able to let them figure it out, go through the mistakes, help them through their mistakes so that they learned how to do it themselves.”

You’re right. That is a much harder skill if you haven’t done it before. It definitely takes some time and practice, and it requires patience.

Patience of, “I could have had this done an hour ago,” is really where most of the entrepreneurs lose it, quite honestly.

I was going to say it’s two places, I think. There’s the patience piece. I could have done this so much faster on my own with fewer mistakes, got it done right the first time. Also, what I see is lead time. See, an entrepreneur is used to having an idea and it’s implementing that idea today. When you have a team, and I know this because I’m oftentimes like the first non-VA-level team member that a business will hire. It’s like, “You cannot have the idea at 8:00 AM and expect me to turn it around as a fractional contractor by 5:00 PM.”

It doesn’t work that way. Like, “I need you to have the idea today and be okay with implementation in 2 to 4 weeks, and sometimes, depending on how big the idea is. It’s 2 to 4 months. I think sometimes the entrepreneur gets frustrated by that and they think, “That’s ridiculous. It shouldn’t take that long.” What they don’t realize is that it would take them the same amount of time. It’s just because all the ideas are in their head. They haven’t set the clock.

They didn’t start the clock until they were 90% done.

I think that’s the other piece. I can speak for myself when I started hiring people that I very quickly recognized that I needed to get my stuff in order. If I ever wanted to feel like I had hired somebody who had their stuff in order, because it’s not their business, it’s not their baby. They don’t have the vision, they don’t have the heart for the industry or for the customer. They need to get all of that from me. They need me to tell them what’s important and why, and then they can carry it out, but I’ve got to think ahead. I have to have some foresight for all of that. That was uncomfortable for me.

Communicating boundaries with your clients is important. Explain to them why they positively affect your business. Share on X

I think the other piece that’s related to this is owning which part of the problem is actually you’re CEO’s problem. I think we often make the problem about how they’re doing it, the timeline, all of those things, their problem, whoever they are, whether they’re an employee, a contractor, a fractional, I don’t care who it is, instead of saying, “No, this is my problem.” We went through this fairly recently as we were trying to plan for our most recent in-person retreat that we’ve had, which we’ve done several times.

This time, there were a lot of other things going on, and it was the first time that one of our team was trying to help with it. I realized a whole lot of things got missed. Whose fault was that? I could say it was hers, but it was not hers. It was mine because I hadn’t identified in plenty of time for her to be able to get prepped in plenty of time to be able to do the steps that I needed her to help me do, and remind me to do in plenty of time. Now, did it work out fine? Of course, it worked out fine because we all came together and we made it happen, and all of those things.

It would have been really easy to say, “I cannot believe you’re doing this. Why is this not there?” The reason it’s not there is that I didn’t give enough information. I didn’t give enough space. I didn’t give enough time to make that happen. Luckily, I’ve gone through this enough and I’m self-reflective enough, and I have you to help me self-reflect on some of these things to say, “This is not her issue, this is my issue.” The default is to say, “They s***, why can’t they do the work? Why can’t I find good people?” Sometimes they’re not good people, sometimes maybe we’re not good people.

I remember when I hired Sheena, who was one of my first, like, grown-up business owner hires. I had hired like three or four people before her. When I hired her, I was like, “Here’s the deal. I cannot find anybody to do this role reliably. I like that they end up ghosting me. They do this.” The fact that four people have done that and I’m the common denominator is not lost on me. Let’s just really put that out there, and then I gave her permission. I said, “I need you to tell me when you notice that I am doing something that prevents you from delivering on our agreement.” Obviously, I don’t see it because I keep rinsing and repeating this whole problem over and over again. I had to listen when she came to me and told me those things.

Which are usually pretty hard things to hear.

Yes, they are very hard things to hear, because why should I do everything? That’s what she told me. You’re not going to be surprised by this, Gwen. She’s like, “It’s really hard to have the standardized process because nothing in the delivery is standardized.” She’s like, “I’ve worked with you on eight projects now. Every single one is unique and built from the ground up.”

Setting The Most Personal And Team Boundaries

I’m like, “Yeah.” She’s like, “Yeah, so it’s really hard for me to give you a process and to have benchmarks and milestones if that’s how you’re doing things.” I come by all my understanding and empathy for our reader, honestly, because part of it is some self-compassion here. There’s something else that I feel like we need to transition into, I think, in fairness to the reader.

We’ve talked about that identity crisis that makes it really tough to go from acting like a solopreneur to thinking and acting like a CEO. We don’t need you to just think like a CEO. Your business needs you to act like one. There’s that identity crisis. Who am I if I’m not doing things all the time? Do I have any value if I’m not coming in at the eleventh hour and saving the day? The other piece, though, is boundaries.

Its boundaries are on all sides. It’s not just your boundaries, but it’s also honoring the other’s boundaries and being clear about where all of those are and being okay with it, actually, really truly being okay with it, not saying, “Uh-huh,” when we’re saying, “Uh-huh.” It cannot be a head shake, no, when we’re saying yes, it has to be that we are going to honor that boundary.

I think part of that is realizing that you’ve got to set the boundaries to say, “I’m not going to just jump in unless I’m asked.” That could be a boundary, but it also has to be clear on their side that they cannot let it go past X without asking you. It was quite a while back now, but I remember that we realized that folks were struggling with things for hours without actually reaching out to the tech support on a particular SAS tool that we’re using.

Businesses hire people to give leaders more time to become visionaries who can think ahead of the market trends. Share on X

The problem is that if you’re trying to fix something that’s broken on their end, you’re going to spend days because you don’t have the ability or the tools to be able to fix it. This isn’t actually about your knowledge. It’s about the tool itself. If we only focus on one piece and we say, “I’m going to fix it, I’m responsible for fixing it,” we have to say, “You can spend 30 minutes. After that point, you have to put in a tech support ticket.”

Either they have the answer and they’ll find it for you, or they will say, “We did an upgrade that actually broke that. Thank you for letting us know. We’ll have it fixed in the next day, 12 hours, 2 hours,” whatever the thing is. Its boundaries are on both sides. It’s not just your boundaries, but it’s

their boundaries, and being clear about what those pieces and processes are. That is starting to think like a CEO.

It’s still some bit of it is management, but it’s also being closer to leadership, saying, “This is how we behave. This is how we think.” Getting that down through the organization, not just for yourself. That becomes another piece of the transition of what these boundaries are that we have to set. As an example, we don’t have an agency, but if we had an agency, we’d have friends and clients who have agencies.

In an agency situation, if your rule has been, for example, we don’t work after normal business hours, knowing that some people’s business hours are earlier in the day if they’re on the East Coast and they’re later in the day if they’re on the West Coast. We have a general rule there about what business hours are.

We need to make sure that those boundaries stay in place with our clients, even when we bring other people who say, “I’m okay working at midnight.” It’s like, “I don’t care that you’re okay working at midnight. You’re going to schedule that email to go out during normal business hours because we’re not establishing the precedent that we’re available at midnight.”

It’s boundaries for you individually, what should I be doing, what shouldn’t I be doing? It’s boundaries for the people you’re working with. What are the guidelines that they need to work in? It’s still boundaries for the organization. What are we okay with as an organization? What are we not okay with as an organization? I don’t care if you personally are okay with it as an organization. You don’t get to do it.

That can be challenging, I think, when you’re hiring other entrepreneurs. When you’re hiring freelancers because they’re like, “This is my best time.” You’re like, “Yes, but you are training my clients that this is my best time and it is not my best time.” Please stop doing that. I think also that since I mentioned clients, I mean, I think we need to talk about the there is a boundary that you have to establish with your clients if you’re a service provider. As you’re making this transition, you’re going to have clients who want you to be the doer. It is so much easier for you to just answer that call. How would you approach setting that boundary, Gwen?

I think the first thing is being clear about why that is changing. It’s explaining the why. There are all sorts of reasons that are right why reason. I’m not going to give like necessarily, the wine, because there can be lots of reasons. Sometimes it’s so that I’m able to provide this important service to more people because when you’re only one, you’re only one. That’s the reality.

Sometimes it’s because I need to be able to do other things that require my unique ability, but I have people who can do this as well, often better than I can do it, so we’re bringing them in to be able to support. The list can go on and on, but I think communicating that with your clients and helping them understand why this is important to your business, but also doesn’t negatively affect their business.

Thinking usually takes multiple times before you get an ROI. Share on X

In some cases, actually positively affects their business because now, instead of having to wait three weeks to get on my schedule, you can get on the person’s schedule, whoever else is on the team, within a week. Now you aren’t having to wait three weeks. See how much better this is for you? That’s legitimately true. You cannot do it with a lie. It needs to be a legitimately true reason why it’s working for them.

Figuring out where those pieces are and how it can be done is, I think, how you’re able to start moving it away from it being you. Now, the other thing is you can also make it true. We’ve had this with one of our clients where we said, “You can get me, but I’m now three times as much as the next person below me.” “If you really want me, you get me, but you’re going to pay for me,” back to “I only have a limited amount of time that I can be offering my services.”

By the way, a third of my price is also exceedingly excellent at what they do. In some cases, the client that I’m talking about, there are some cases where they’re like, “Nope, we’re going to pay this.” I remember her saying recently that someone called and said, “I need one hour of your time. I realize how much it’s going to be, but I want you for one hour.” She’s like, “No problem. You can pay the rate, and we can do that.”

Other folks are like, “It’s because I know three hours of Sue’s time, making up a name here.” It’s actually probably worth two hours of your time. You may be a little bit better than Sue, but you aren’t that much better than Sue, and not at this particular thing. I’m actually getting a bargain by working with Sue instead of you. Back to focus and all of the other things, it’s about what the reasons are that you’re doing it, and what makes sense. Right now, we’ve been making a transition for you doing a little more hands-on work with our clients.

Part of it is that they’ve seen you consistently. You are not just some new random person who just likes, “Who the heck is Tonya?” They’ve all seen you and interacted with you in some form or capacity over the time that they’ve been working with me, but we also explained why we’re doing it. I’m trying to launch something new, which means I need more time to focus on this. These are some chunks of time that I can easily delegate to you, and you will do an excellent job. It’s not like, “I’m running away and they’re never going to see me again.” They still have access to me, but it’s just a little more limited.

You make a good point because I think sometimes I don’t even know how to articulate this, which I feel like I say those words in every single episode, but it’s because my brain runs faster than my mouth sometimes, and sometimes it works in the opposite as well. In our head, to do that. To hand over fulfillment to somebody else is telling the client that they’re no longer a priority.

Maybe that’s because we felt like that, like we felt like we got moved over to the B team for whatever reason. We feel like we’re telling the client that, but really it comes down to one, like you said, giving a reason, but two, that reason needs to set the other person up for success. One of the things that you did when informing our clients that I would be handling, that it’s actually some very light-level fulfillment stuff. It’s not the high-touch fulfillment stuff you do.

It’s a very light level, but part of it was “I have stepped in that capacity for you over the past couple of years anytime you’ve been traveling or doing anything else. You had seen the quality of the way that I could deliver that service already.” They’ve experienced it, and all you had to do was remind them and say, “This is nothing that most of you haven’t already experienced. It’s just, you’re going to get this now every single week. However, I’m still going to be paying attention. If there’s anything that Tonya feels like is a little bit over her head, she’ll pull me in.” You have let it. Anytime I’ve been like, “Gwen might think something different, but here’s what I think.” You never go in there and go, “Tonya’s off her rocker. Don’t listen to her.”

I would, though, if I thought that was true.

Setting Boundaries Around Strategic Thinking

You might, oftentimes you go, “Yeah, everything Tonya said, I have no notes,” or you’ll say, “Everything Tonya said and maybe this one additional thing.” That’s also part of it is you have to have your boundary with the client, and you have to make your new focus not so much making the client okay with working with the doer, but helping the client to appreciate why they’re in the best possible hands at this time with the doer. Making sure the doer has everything that they need. I want to address something else that you just brought up is the boundaries around strategic thinking, because I think that’s where our solopreneurs really do struggle.

   

The Business You Really Want | Business Problem

   

Say more about where you’re headed with this. I think I know where you’re going.

Part of why we build teams. Part of why we hire people is because we need more time and space to be the visionary that our business needs to figure out what’s next, what trend do we follow? What trend do we need to get ahead of? That requires thinking time, but we don’t like to protect our thinking time, Gwen.

That’s because thinking time doesn’t feel valuable. It’s a weird thing to check off on your to-do list. I spent an hour thinking. Now, interestingly enough, it’s one of the things that I actually have on my quarterly goals is that I spend an hour each week thinking because I realize I need to have more thinking time. I also know that if I don’t set it as a goal, it’s easy for it to get lost in the process.

True thinking time, not thinking while doing something else, but real thinking time and asking yourself the hard questions and saying, “What would I say to myself about this thing?” Whatever it happens to be. One of the most valuable things you can do because nobody else is going to do that for your business but you. You may hire someone like me to help you with that process, but it’s I still cannot do it for you. I can only do it with you.

It’s really important to do that thinking piece, but it doesn’t feel valuable because we cannot show the work. There’s no work to show when we’re done. Maybe the closest thing we can do is show a journal that has several more pages filled out in it. That’s possibly the one thing that we can show out of thinking time. A lot of times, thinking time takes multiple thinking times before you get a result, before you feel any ROI.

We have a process that we use that’s part of Nick Peterson’s philosophy called Open Loops. I have found that I have to leave things open-looped for a long time before I get resolution on it, before I see some ROI from it, where one of our other clients does open loops like, “Man, she’s getting stuff every live long day.” Part of it is that she’s also trained herself for that thinking time.

She’s trained the muse.

She’s trained herself to say, “This is part of my process. This is part of my thinking. I have not yet been that disciplined. I wish I were. I have not been, but I know from having watched others that it will pay off in the end. I’m trying to be very focused on it and not get wound up when my open loop is not solved the next morning, like we’re hoping is supposed to happen.” It’s like, “Nope, it’s going to be okay to keep the same open loop for days on end, if need be. It’ll come when it comes.” That thinking time is a CEO activity. It’s a leadership activity. It’s not a management activity.

The Challenge Of Owning The New Identity

In terms of boundaries, you’ve talked about communication boundaries. About like drawing lines around when we do business, when we don’t do business. It’s okay if you do business at a different time, but you need to make it look like we only do business during these times. Talked about boundaries with the clients who expect you to continue being the direct fulfiller of their work. Talked about the boundaries around your thinking time or your visionary time. Any other boundaries that you think are maybe either critical or easy to overlook, hard to implement as you’re making that shift from solopreneur to CEO thinking?

I don’t know if it’s truly a boundary, but it is owning the new identity. Being okay with what that new identity holds and knowing that means certain things are no longer true. In the example, if you’ve been the expert at the thing that you’re doing and you start bringing in other people so that you are no longer the expert, there’s a point at which you’ve got to be okay with the boundary is I lead the best experts. I am no longer necessarily the best expert.

Business leaders must learn to be comfortable not being the best expert in their team, but leading a team of the best experts. Share on X

I lead a team of the best experts. I am no longer necessarily the best expert in whatever it turns out to be. I remember experiencing this when I led an IT department 20 years ago. I ran an IT department. Somebody said, “If such and such happened, you wouldn’t know how to fix it.” I said, “No, I wouldn’t.”

I said, “It’s because that’s not my job. My job is not to know how to do all of the things. I had a ton of systems and programs, and things.” By the time I was really leading it, I couldn’t have done hardly anything at all. My CIO husband now cracks up because I asked him to help me with IT stuff. He’s like, “You ran a major IT department.” It’s like, “I know. My job wasn’t to know the details. It was not to know the details. It was to understand the strategy and to be okay with not knowing the details.”

That’s a big boundary to be able to hold and say, “No, it’s okay that I don’t know it. That’s not my job. That’s not my job anymore to know that.” It’s a different boundary to be able to be comfortable in this new place. That means that you have to be doing different things that you probably aren’t as good at as you were doing the things before.

I mean that right there, I would say, is the crux of the whole episode.

It is. It’s the hardest piece because moving into this other role means you’re no longer doing the things that you have often identified yourself with.

You need a new identity for your business to have it.

You need a new identity, and you need to be okay with it. Back to using a knitting teaching example, I would often say in class, in various classrooms, it’s like, “I am probably not the best knitter in this classroom.” I was a good knitter. I mean, you cannot just be a total hack, but I was a decent knitter. I know some of my students, and I knew them well to the point that I knew technically they were better knitters than I was.

What I also knew was that I was by far the best instructor in that class. I was able to let go of being the knitter and being the instructor. I knew no one in that class could teach better than I could. They might be able to do better than I could, but they couldn’t teach better than I could. Same thing with the CEO. If you really hire great people, you’re going to have people who are way better than you, but they aren’t going to be able to lead this organization better than you can.

Next Episode’s Discussion And Closing Words

Gwen, thank you for updating thoughts on this conversation because again, there is, I think, plenty of good reason that from solo to CEO, that first episode of the series was our second most or is our second most downloaded episode of our first year as podcasters. What I would encourage readers to do is tune into our next episode, because next week we are going to be talking about our number one most downloaded episode, according to readers who did not even exist. I don’t even know if we had brainstormed it two months ago, but it was our dark horse that came out to the front running. If you are still reading, I would love to hear from you.

What do you think about these top episodes that we are featuring? What has been hard or easy for you as you’re making that transition from solopreneur to entrepreneur? If that’s your experience, you can email me directly at Tonya@everydayeffectiveness.com and tell me where you fall on the scale that Gwen described, from solopreneur to CEO, or what you think about this episode or any others. Whatever it is, I read each and every email, and I will get back to you within about 48 hours because that’s one of our standards of practice around here. We’ll see you next time.

  

Mentioned in This Episode

 

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.