Gwen Bortner and Tonya Kubo tackle a question many people are quietly asking: should you actually be an entrepreneur, or would you be happier (and better supported) as an employee right now? Together, they unpack the cultural myth that entrepreneurship is somehow more honorable than having a job, and how this belief pushes many capable people into building businesses that do not align with their natural abilities or values. Gwen and Tonya also get candid about the ways they have both wrestled with this question themselves, and they break down what tends to separate “true entrepreneurs” from business owners and operator-types. This episode is for anyone who has been feeling the weight of running a business and wondering whether they are doing it wrong – or whether they are simply trying to force a square peg into someone else’s round hole.

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Entrepreneur Or Employee: Which One Fits You Right Now?

It is, if you are tuning in real time, March 3rd, 2026, which means we are at the tail end of Q1. We are in the tail end of Q1 in the year that follows quite the year. Unprecedented is probably the word of the last five years or so. It continues to fit. The topic is a question that Gwen and I are both not hearing people specifically ask the question, but we are seeing people take action. That means that at least they have internally asked the question. That is, are you cut out for this entrepreneur gig?

Hold on, no interrupting, hold your finger because I am turning it over to you in a second. The question of whether you are cut out for this or not is actually a neutral question. If the answer is no, it does not necessarily mean you are a big fat failure. With that, because I think Gwen is going to hyperventilate if I do not turn it over to her shortly, Gwen, why don’t you go ahead and spew what you were about to say before I did not let you interrupt?

What I was going to say is I was in a conversation with several other business owners, most of whom are all focused on the operations topic. This came up because one of the folks was talking about things. I said this. As soon as I got off the call, I got on the call with Tonya, and I said, “We actually need to make a podcast about this because part of the goal of this show is to say the things that we talk about privately that need to be said in public.”

The topic was, do you actually need to be running a business right now, or do you need to do a thing that is allowing you the flexibility and making the money that you need to make, so that you can do whatever this other thing is that you actually want to do instead of trying to force everything into this entrepreneurial box? As we asked the question, I confessed, and then Tonya confessed, so it is going to be a big confession show. I ask myself this question quite often.

Do I actually want to be an entrepreneur? Do I want to be developing, building, and running my own business, or do I want to be an employee? One of the reasons I feel like I am good at being an advisor is that I have played all sides of the equation. I enjoyed them all. It was not like, “Working for corporate was the worst thing ever.” That was not my experience. Real entrepreneurs, in the end, that is almost always how they feel.

They are like, “Corporate is the absolute death knell of my life.” Part of the conversation that I was having in the small group, and that we were having, is that we have made it seem like being an entrepreneur somehow is more honorable. We can put all sorts of adjectives around it, but somehow it is way more honorable than being an employee, than working a job. That is such a lie. There is nothing true about that statement. What I think happens is that a lot of people go down an entrepreneurial path who were not actually cut out to be entrepreneurs.

Some people absolutely are entrepreneurs. Everything about how they approach everything is entrepreneurial. I would put myself in the category of a very official title of, well, sort of. Some aspects are very entrepreneurial about me, but there are many aspects that are what I would call I want to be an employee. I am okay with that. I would not ever hold myself up as an example of a true entrepreneur.

Qualities Of A True Entrepreneur

Why is that? What are those qualities?

First, is that the definition of risk almost does not make sense to most people. I am relatively risk-averse. Real entrepreneurs are zero risk-averse. They are willing to try everything. The next thing, and there are going to be people who want to argue with me about this, and I am okay with that, is that I think real entrepreneurs love the idea of the sales and the marketing aspect of whatever it is that they are doing.

I rarely come across truly successful entrepreneurs who do not love a lot of the sales and marketing aspects of their business, and often it is the place where they want to spend the most time. I am much more likely to see salespeople from a corporate environment become successful entrepreneurs than the admin people, the people like an HR person or an accountant, leaving a corporate environment and becoming successful entrepreneurs, typically, because that is such a huge part of the job for so long, doing the sales and the marketing piece.

You and I have talked about it. It is very clear that I like doing sales, but I do not like doing marketing. I think it is both of those pieces that, as I said, every person I have ever met who is truly an entrepreneur loves that. They never think they are that. Not never, but they often do not think they are that good at it. When you look, it is like, “No, this is what you live, eat, and breathe all the time.” That is also an element of it. The other is the ability for what I am going to call full flexibility. Very few things derail them.

You’re talking about entrepreneurs.

Very few things derail real entrepreneurs. If you look at anybody’s stories that you read and listen to very many times, most of the ones that we know that we have put names to that have success have failed spectacularly. Bankruptcy failed multiple times before it succeeded. All of that is like, “Just another day.” My current favorite, only because he has now been doing this for so long and a lot of people know who he is, is Dan Sullivan, who is the founder of Strategic Coach.

He talks about how he filed his divorce papers and bankruptcy the same day, which was basically before he founded Strategic Coach. Within a year or two, he had Strategic Coach, the basis of what became Strategic Coach, going, and it has now been going for a long time, but he was spectacularly failing. The last one I would say is true ambition. Always growing, always stretching, always challenging.

“I want to be at the top. I want to be the best. I want to be all of those things. I am willing to do all of the things that need to go with it” is also part of entrepreneurship. I was talking with one of our clients who is absolutely an entrepreneur, and she is like, “No, if I sell these two businesses, I am not retiring. I am figuring out what the next 2 or 3 businesses to start and do.” I have zero doubt about it. Dan Sullivan, actually, that is his current thing he is talking a lot about, which is how do you continue to channel your ambition as you get older and older?

Real entrepreneurs will continue to be ambitious, even in their 70s, 80s, and 90s. When you start saying some of those things, and you start thinking to yourself, “Maybe I am not an entrepreneur.” Now, it does not mean you cannot be a business owner. It does not mean that you cannot do this. I think it is also important to say, but maybe you are trying to fit your square peg into someone else’s round hole.

Real entrepreneurs will continue to be ambitious even in their 70s, 80s, and 90s. Share on X

You are going to have to explain to me the difference then, because I think most people equate entrepreneur and business owner as the same. You are saying, “You might not be an entrepreneur, but that does not mean you cannot be a business owner.” Make it make sense, Gwen.

Business owners and/or CEOs are dealing with the ongoing issues of owning a business. In our environment, because a lot of the folks that we talk to are relatively small businesses, it does make sense because they have often started it from scratch. It feels very similar. It is important to realize that maybe you are not an entrepreneur, but you are a business owner. It is the same thing as thinking about CEOs. The person who runs Coca-Cola is not an entrepreneur. They are a CEO.

Their job is to run Coca-Cola. They might take a job elsewhere. If you are a follower of Mike Michalowicz, this is the whole basis of Profit First is that a lot of entrepreneurs do not understand the difference between being a founder, a CEO, a director, and a business owner. They do not know how to pay themselves appropriately or how that should all work out.

Most entrepreneurs do not want to be at all involved in the day-to-day operations in any way, shape, or form.

What do they want? They want to start businesses, and they want to sell and market them?

They want to have ideas. They want to market them. They want to design things. They want to come up with IP, intellectual property. They want to stay at a very high level. They will get into the weeds to get it off the ground. That does not satisfy them for very long. It is one of those things that, as soon as the puzzle piece is figured out, they are ready to move on.

What Makes A True Entrepreneur

We spend a lot of time talking about what makes an entrepreneur. You said in your experience, it sounds to me like they are visionaries. They like to start things. They like to create. They like to get things up off the ground. They are truly flexible. At first, I thought, “What you are seeing is they are resilient,” but it is different because there is resiliency that is required for employees, too. It is that full flexibility, like, “You are going to throw a challenge at me. It is another day that ends in Y. We will figure this out.”

They have that true ambition. Even if they were not doing this, they would be doing something else that would be similar to this. They would not be serving up drinks at the local Starbucks. That is not where they are wired. Employees, so far, what makes an employee’s mindset? You had mentioned being risk-averse. I would say not necessarily risk-averse, but I do think that people who are made to be employees place a high level of value, security, and stability. Where I see an employee struggle as an entrepreneur is the natural roller coaster that comes with business.

It is something that our mutual friend Rachel Allen talks about. If you are in it to make money, if that is why you did that, there are so many easier ways to make a six-figure salary than entrepreneurship. Entrepreneurship is hard. It is a constant rinse and repeat spin cycle thing. You are always having to reinvent yourself as the market does. When you were talking about accountants and bookkeepers, the thing with the employee is that a lot of employees say, “I like change. I like environments.” They also tend to like knowing what they are doing today.

They like knowing how much their paycheck is going to be.

It is like knowing what you are doing and knowing what the price is for that. I always joke that when people ask me if I miss university life, I say, “Miss the people.” When you are talking to anybody who has been in a different field, a lot of times that is the answer. I miss the people. I do not necessarily miss the work. I miss the people. I do not miss the red tape. I miss the people. The other thing I do miss is having a bad day or having a day where I am not firing all cylinders and knowing that I made the same amount of money to stare at the wall for half the day as I did to do my best.

I do not miss making the same amount of money doing my best work as Joe Schmo down the hall, who stared at the wall four out of five days every week. I do not miss that part. There is an amount of stability that is intrinsic to an employee relationship. I am going to get ahead of the letter writers here. You can be laid off at any time. Yes, you can. There is almost always another job where that one came from.

I was going to go to the exact same place that you did because that is my favorite lie that is out there, where people are like, “You have complete control over everything when you have your own business, when you’re an entrepreneur.” That is the biggest lie on the planet because the thing that you have zero control over is how many people are going to actually buy your product or service. You cannot make anybody buy your product or service.

You have way less control over your income than you do as an employee. You could get laid off, but it is easy to say, “I have got 100 clients,” and all of a sudden say, “I have zero clients” because you cannot control whether or not they are going to pay you. You can say, “I have 100 clients, but none of them have paid me on time. I am expecting to get $50,000 in, and I have got none of it.” I cannot make them pay me. You can send letters, and you can do all the things, but you cannot make them.

As a service provider, this is something somebody was asking me, “How has business been?” I was like, “I am a service provider.” My business generally goes well because I provide a good service to people. However, my business success is 100% dependent on my clients’ success, and 2025 was a hard year for a lot of my clients.

It was not like my clients were bailing because they found cheaper, better services elsewhere. My clients were scaling back because their businesses were struggling. That is two entirely different things. My clients were good at the stuff that they did, but the market shifted. That is all. Some of them were faster to respond to the shifts in the market than others.

Dispelling The Fairy Tale Around Entrepreneurship

What I want to talk about, because I think this is great at unpacking, and I think this is what you would rather talk about too, Gwen, is this fairy tale that we have made up about entrepreneurship being somehow more not altruistic, but somehow more pure, more beneficial, better. Let us say entrepreneurship is better than employeeship. I totally made up that word. I know it is not a word, but it works for me. That it is somehow superior to being an employee.

I am going to start with mine, and then I am going to ask you, because we talk about this a lot. One of the things that I see is “I will make sure that I do not do any of the bad things,” whatever we are defining as bad things. That list is long. That happens in corporate America. It is like, “That is true.” There are also a lot of businesses out there that do not do the bad things, whatever you are talking about.

As you become an entrepreneur and a business owner, and if you start bringing in anybody working for you, all of a sudden, you start understanding why some of these “bad things” have to be done. Sometimes it is the law. You’re like, “I do not have to do that,” and it is, “You do now because you actually have an employee.” Because of this, you have to do these things. Sometimes, one of my favorites is when people are like, “I cannot believe this has happened with this company.” It is like, “They brought in investors.”

The investors are all focused on the money. We have given up on the altruistic nature of what we were doing. Sometimes all of these things are true. My answer is that there are enough options out there that you can find things that will meet your criteria of what the culture needs to be like, what the purpose needs to be, and why we’re doing the things that we are doing. That whole idea of “I am doing it because of all of these great reasons” is one issue. I have got several more, but I am curious, give me one of yours, Tonya.

I think there is a lot of pressure to be living out our highest purpose. A belief that you cannot live out your highest purpose as an employee, that being an entrepreneur is the only way to fulfill your highest purpose in life. This could be an age thing. Maybe it is the older I get, the more I see that there is no perfect one-size-fits-all solution. My issue with that is, who is to say that your highest purpose has anything to do with your work?

It is like there is this interesting, I do not know, American like work yourself to the bone value judgment that my work has to be connected to my highest purpose. I tried self-employment for a period of time after I had my first. There is like four and a half years between my first and my second. The idea was I would do the self-employment thing while I had my baby, so I could have as much time off as I wanted.

You do not actually get a ton of time off self-employed when you have kids. When baby number two refused to stinking appear on my timeline, I was like, “Fine, forget it. I will go back to work.” Get all those things that employee life gets you. The 401(k), the 529 plan, and the matching, and all these things. It made sense. When I went back, I remember people from my consulting life who would be like, “Are you enjoying it?”

I would be like, “Yeah, it is okay.” They were like, “This must be what you love.” I was like, “I cannot say that I love it, but I can say I am good at it.” If they are willing to pay me this wage to do something I am naturally good at and they honor their end of the bargain of telling me I only have to work from 8:00 to 5:00, and at that time it was a remote gig, which you could not get back in 2012 in my field, then actually I feel like I am getting the longer end of the stick at this point.

Now, very quickly, because remote gigs were so rare, they very quickly found office space for me and then insisted that I was in the office. First, it was two days a week, and then it was five days a week. My 9:00 to 5:00, I got a new boss who determined loyalty by how many all-nighters you pulled. They were somebody who wanted work to be their hobby and work to be their whole life. They did not have the work-life balance focus that my prior supervisor had. In 2012, that job was 100% fitting what I needed and what I wanted out of life right then and right there.

It did not come in 2019. It was not because I was not necessarily fulfilling my highest purpose. It had to do with what I wanted out of the deal. I was no longer getting out of the deal. Circumstances had changed. Entrepreneurship gave me a better option at getting what I wanted out of the deal. What it comes down to is we are reading all these inspirational motivational quotes that tell us that we need to live out the best, greatest sense of ourselves. They paint an employee relationship as a prison. Those bars are preventing us from getting there.

Many inspirational quotes tell us that we need to live out the greatest sense of ourselves. However, they also paint being an employee as a prison that prevents us from achieving that. Share on X

You whoosh right by it. Another reason people will talk about entrepreneurship being better employment is that you have complete control over all of your time. Of course, there is a meme out there of, “Yeah, you get to work any eighteen hours a day that you want.”

125 hours a week to make money while you sleep.

That is actually truer than what people think it is. That is a piece that we also miss, which is that we believe the only way to have flexibility is to be self-employed, to be entrepreneurial, but that is no longer the case. The right environment will totally allow for the type of flexibility that you want. You may have to look harder for it. It is not just going to be.

  

  

That is the thing. Everything has a trade-off. I will say in my field, because I am somebody who is always looking at who is hiring in my field, partially because I do train people to do what I do. I want to be able to give good advice on whether it makes sense for you to try to be like me and do this hanging out your shingle. Does it make sense for you to spend a few years doing this for somebody else, learning how it works in that environment, and what are the transferable skills?

I am always seeing a very rigid flexibility. Flexibility is that you get one Friday off a month to do whatever you want. For some people, some entrepreneurs have not had a Friday off in ten years. Now they convince themselves they could take every Friday off if they wanted to, so that one Friday off a month does not sound so great to them. One Friday off a month might be nice for you.

I am in a situation where I am the person who takes my kids to and from school. My only employment option would have to make that possible. They are wonky windows of time. It does not mean that there is no employer out there who would not be willing to let me work 9:00 to 2:00 every single day and a Saturday to make up for it and still pay me a full-time salary. In fact, I bet there are several that would be willing to do that, to have a Saturday worker in this line of work, because a lot of people in my line of work do not work Saturdays.

Part of it, though, Gwen, is that first of all, it is very easy to tell yourself that that is impossible. No opportunity like that exists if you are not looking. Can we be blunt and say some people are so scared to look because they think even looking, even entertaining the question, makes them a failure?

Some people are so scared to look because they think even looking or entertaining the question makes them a failure. Share on X

To me, that is the big piece of why that would be a failure. The thing that I talk about a lot is maybe this is the best answer for this season.

You can always make a different decision later. You were the one who taught me that, Gwen.

You can make a different decision later. You and I both have done our own business, entrepreneurial gigs, freelance work, and corporate work at different points in time. As I was saying before we actually got on the show, I actually liked them all for different reasons. If someone says, “You must hate the thought of ever going back to corporate.” “Not necessarily.” There are certain environments that I would absolutely not want to be a part of.

I know that, but it does not mean corporate, working for a larger organization, and being part of a larger team is like, “I could not possibly do that.” It is like, “No, I could totally see that. I could totally see doing that.” Going back to doing freelance for somebody else, “No, I totally see that.” I could see being an independent contractor doing a particular type of work for only one or two clients.

I could totally see that. All of these are possibilities, but it is because I do not hold so tightly to the idea that if I am not an entrepreneur, I am a failure. The bigger issue here is that we get, and I also think this is another United States thing, we get so tied up and associated with whatever work title we have that when that work title changes, we do not have enough self-identity in and of ourselves that is separate from our work identity.

That we are like, “We’re still useful and valuable and all those things, even if we are not doing whatever that work identity is.” We were talking about what defines an entrepreneur. As I say that, I think that is also part of what defines an entrepreneur, that they are not defined by whatever work they are doing at the time. It is at the time.

That is true. We talk about serial entrepreneurs. It has gotten a little messy in later years because of the personal brand aspect. You become like you are the planner expert. In your case, you are the accountability expert. I am the community’s expert. It is funny, I remember somebody reaching out to me, and they were trying to sell me something.

I was picking up a lot of fractional CMO work. People like you are hiring me to be their marketing officer. This person used that because I had introduced myself in a networking group. I said, “At my heart, I am passionate about online communities. I am a communities expert.” I have found myself recently picking up a lot of marketing officer clients.

She used that to reach out to me and say, “I know you’re in the middle of a big pivot. What I do is I specialize in helping people who do not walk their way through pivots.” I was like, “Who said I am in the middle of a pivot?” It said, “You’re moving away from community.” I am like, “No, I will never move away from community.”

If I got a job tomorrow as a school teacher, I would still be designing communities on the side somewhere. I do not care if I have to design them at 2:00 AM. I will never leave that. I am saying that this community focus of mine has actually attracted some very relationship-centered entrepreneurs who have brought me on to support them with their marketing efforts because they do not like funnels and whatever.

  

  

This is not a pivot. I am not moving from one thing to the other. I am doing this other thing, actually, to support my work over here. That is part of the entrepreneur thing. I know a guy who owns a chemical company. He owns a laundromat. He is thinking about buying into this retail shop, but it is because his daughter wants to be a fashion designer.

He was like, “Designing clothes is one thing, selling clothes is another thing. Maybe if we do this retail shop, she can get a sense of what it is like to sell clothes, what people want, because she can design all day in a vacuum. That does not mean anything is ever going to go to market.” He has got his finger in all these pies. At some point in time, he is going to sell all those, and he is going to go buy something else. I cannot tell you what it is. I just know that is what he will do because that is what he always does.

He is not that interested in running any of those businesses.

No, you know what drives him more than anything is optimizing businesses. What he likes to do is he likes to buy these businesses that have a pretty decent profit margin. He likes to figure out how to grow the bottom line. How does he make it bigger without growing the expenses and all of that stuff? He loves to truly scale operations. If, after five or six years, he finds it does not scale, he loses interest, and he moves on to something else.

He is not interested in knowing the name of every driver in the chemical company. He does not care who comes in and uses the laundromat. He is only in the laundromat when something breaks. The general manager in the laundromat loves that Sue comes in every Friday and loves having conversations with Sue about her life as she is washing her clothes. Two entirely different people.

To me, a real entrepreneur is using the term that Mike Michalowicz uses, is a shareholder in the business. They might be the sole shareholder in the business. A lot of us are entrepreneurial, but we’re business runners. We own the business, but what we’re doing is running the business. We like it. There is nothing wrong with that. I am going to use myself as an example. I do not see myself owning eighteen different types of businesses. It has got to be something that I actually understand. I want to be able to think about how I would run it. I have got to be more in it. Am I entrepreneurial? Yes. Am I an entrepreneur as we are defining it? I do not think so.

A lot of people are entrepreneurial, but they are really business runners. There is nothing wrong with that. Share on X

Why Being An Employee Is Not A Brand Of Failure

Why do you think it is such a testament to failure to go from entrepreneurship to becoming an employee, because we’re seeing a lot of people do that? We launched this show because I had been watching people who left entrepreneurship to become employees, only to get laid off and try to resurrect their businesses. Talking about part of resurrecting their business, of course, part of building that personal brand was talking about what led them to leave their business in the first place, and now why they were coming back. Why do you think it is such a mark of failure to say, “I want to be an employee,” or “I want a guaranteed paycheck?”

It’s because it makes it feel like we were not good enough. We were not capable enough. We do not feel any of those kinds of words. Back to that is not true. It is not true. Real entrepreneurs will fail a lot. Things will go disastrously bad. They will go and do something similar, usually something different, but it is similar again and again. We say if we fail and we say, “I do not want to deal with this again,” we are calling it an actual failure. It is like, “No, you learned something new.”

Let us also be honest. A lot of people shift from entrepreneurship to getting a job to bail out their businesses financially. I think that is also why it feels like a failure, because very few people have the six-figure monthly recurring revenue business and then go, “I think I want to go get a job.”

A lot of people shift from entrepreneurship to getting a job to bail out their businesses financially. Share on X

It has usually gone very poorly, and or they have gotten it there, and they have realized, “I do not want to be responsible. These are not actually things that I want to do. Owning that you do not want to do it feels like a failure because it is like, “You should. It means you’re real.” It is like, “No, it means that this is not the thing that you’re actually cut out to do.”

Discussion Wrap-up And Closing Words

What I would say to close us up here is that first things first, if you get nothing else from this episode, get that it is totally fine to be an employee. Making sure that you know where both Gwen and I stand, we think being an employee is as honorable as being an entrepreneur, and being a business owner is as honorable as both. If you are somebody who wants to set your business aside for a while and take some orders for that guaranteed or dedicated paycheck, no harm, no foul.

You do not owe anybody anything. You get to feed your family in whatever way makes sense for you. If you are tuning in and you are like, “I still do not know. Am I an entrepreneur? Am I meant to be an employee? I’m not quite sure where I land,” I think reflection is the best way to figure it out. You know what you could do is you could subscribe to Gwen’s One Good Question email. You do that at www.tonyakubo.com/question. Her Good Question email and answer it from either perspective.

Answer it like, “I’ve got this great question. How do I answer this as an entrepreneur? How would I answer this if I were an employee?” See what comes easier. You might find out that even if you are an entrepreneur, even if you have a responsibility for a team, your default mindset is that of an employee, and that is okay. It is totally okay. The main thing is you can only have the business you want by living a business in alignment with what you want in all aspects of your life. We will see you next time, where we will probably pick at this scab or another scab like it as much, because that is what we do around here.

 

  

Mentioned in This Episode

• Strategic Coach
• Profit First
• Everyday Effectiveness Question
• Gwen Bortner on LinkedIn
• Gwen Bortner on Facebook
• Tonya@EverydayEffectiveness.com

  

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.