Whose Finish Line Are You Running Toward?

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The Business You Really Want | Finish Line

Chasing the wrong finish line can look like success on the outside and feel like emptiness on the inside. In this conversation, Tonya Kubo and Gwen Bortner unpack why so many leaders, especially women entrepreneurs, find themselves pursuing goals that were never truly their own. They explore the emotional cost of inherited definitions of success—from industry standards to old versions of ourselves—and how to recognize when your heart is no longer in the race. Through honest reflections and practical insights, they show how clarity, alignment, and better self-questioning can help you redraw your finish line and run toward what genuinely matters.

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Whose Finish Line Are You Running Toward?

Are You Running Someone Else’s Race?

What if the finish line that you’re crossing or that you’re chasing isn’t yours? That’s a question that stopped both Gwen and me in our tracks when our friends over at the Listening for Questions Podcast started exploring what it means to finish and the important questions to ask about finish lines. It’s a simple question, and yet it unravels so much about how we set goals, how we measure success as business owners, and ultimately, how we decide what is and is not worth our effort.

In this episode, what we are talking about is what happens when we inherit the finish lines we’re chasing, whether we inherit them from mentors, from the industry we’re in, or even from our younger selves. We will also talk about how to know when it’s time to redraw the finish line or put it in an entirely different place. In leadership, crossing the wrong finish line is as pricey as never crossing one at all.

If the conversation hits home, you are going to want to get on our weekly list at EverydayEffectiveness.com/question. Every week, Gwen sends out one good question. She doesn’t give you advice. She doesn’t dump a bunch of insight on you. It’s the kind of question that gets you into your CEO brain and helps you see your business differently.

Let’s talk about finish lines, who draws them, why we chase them, and what it looks like to finally claim ones that we feel ownership over. Gwen, I want you to kick us off because you were the first person who wrapped words around this idea of chasing goals or running after finish lines that aren’t yours. I want you to share with us how you’ve seen this manifest in business, particularly in businesses founded by women.

The Social Media Comparison Trap & The Idol Of 7-Figures

There are so many examples. I don’t even know where to choose from. I blame it, and that’s an oversimplification, on social media and the comparison trap. We have a whole episode on the comparison trap. That is the problem. We see other people’s goals. They appear to be successful and happy. We project a whole lot of things on what we’re seeing on social media, our conversations in networking groups, and the list can go on. We decide that we will have whatever things that we believe they have if we do the same thing that they’re doing, whether it’s a marketing tactic, a financial goal, or a number of hours worked goal. It’s not any particular topic. It can cover all sorts of pieces.

  

The Business You Really Want | Finish Line

  

The first challenge is what I’m always saying. Context matters. Most of the time, we don’t have enough context. Part of it is they’re considering success what you would consider success and how we define success. We get caught seeing consistent examples of success. It used to be that it had to be a 6-figure business, and then it became that you have to have a 7-figure business. We haven’t quite got to if you don’t have an eight-figure business, you’re not successful, but I’m sure we’re going to get there pretty soon because we watched that.

What makes that number successful or not successful? There are so many other things where a 6-figure business could be super successful, and we’ve shared examples of this before, more so than a 7-figure business, depending on how you’re defining success. The problem is that we let other people create this imaginary definition of success, which is a generic definition of success that may or may not apply to us personally. We go chasing after that, whatever that is. That becomes the goal, the finish line, or the thing. If it doesn’t align with our real definition of success, when we get there, it is so empty.

The problem is we let other people create this imaginary definition of success that becomes the finish line. If it doesn't align with our real definition of success, when we get there, it is so empty. Share on X

I’m so glad you brought up the seven-figure and eight-figure business example. I feel like the “seven-figure business” or the million-dollar business has almost become an idol in and of itself. In business, particularly in online business, there’s this myth that online business has no overhead. People like to think it has no fulfillment costs, so everything you do goes straight to your pocket.

You start talking about the 7-figure business, and people genuinely think 7 figures into their household bank account and all that’s going to do for them. They do not realize all the other stuff that comes with the seven-figure business that they may have started their business to get away from. In having a team, not all seven-figure businesses have to have a team. That’s not true that all models go that way, but a lot of times, they do. Maybe they come with a level of fulfillment people don’t want and all of that other stuff.

You start hearing it so often that you feel like you are a phony, or you’re too much of a newbie if you don’t say it. You start saying it so often that it doesn’t even have true meaning for you. I don’t know about you, but nobody has ever asked me. When I’ve shouted a big goal like that, like, “I’m going to have a 7-figure agency,” or, “I’m working toward my first 6 figures,” when I was there, no one person ever questioned me. They go, “Me too.”

There’s never like, “Is that a good idea with this particular business model? Have you thought about the things that that’s going to entail?”

Even, “I’m so happy for you. On the other hand, I am super happy at low six figures. I thought about that seven-figure thing. That’s not for me. That’s for the birds.” Nobody wants to say that. I don’t think you’d get kicked out of a room, but we fear that we would because we’re not playing big enough.

I was going to say that we’re not ambitious enough. That’s the thing. If we aren’t constantly going after this thing, we aren’t ambitious enough, or we aren’t driven enough. There are all sorts of things about that, which could be true, but probably aren’t. It may be true right now. Maybe I’m not ambitious right now because I’ve got a whole lot of other things that are taking my ambition energy and/or that I may be ambitious about. We always assume that if we aren’t doing that, we aren’t the things an entrepreneur is supposed to be.

There’s a lot of imposter syndrome that comes with entrepreneurship. These goals, or what we’re racing toward a lot of times, activate that imposter syndrome. What I love about this question is that we’re not the only ones asking it. The idea of this came from our friends over at Listening for the Questions, which is a brand new podcast. They’ve got five episodes so far.

What I love about the show is that they ask questions and discuss questions, but they don’t answer them. It’s because, like us, they understand that my answer is not the same as yours, and where the transformation happens is when we sit in discomfort and curiosity asking these questions for ourselves. Also, we’re about asking smart questions. That’s something that you have hit on. Most of our clients may be hungry for more information, but they don’t need more information. What they need is to be asking themselves better questions. They need people to ask them harder questions. I know that’s a service that you provide for them, and they appreciate that. I’m curious. Before we get more into the finish line piece, what have you personally discovered about yourself through the exercise of asking deeper, better questions?

Most of our clients may be hungry for more information, but they don't need it. What they really need is to be asking themselves better questions. They need people to ask them harder questions. Share on X

Stop Looking For Answers, Start Asking Better Questions

The first, which isn’t a surprise, is that it’s hard to ask yourself good questions because we self-edit. There are some tools and techniques that I use that make it usually better, but I won’t say that it’s outstanding. Have an outside person ask the question. Often, they’re doing it with curiosity. “Have you considered? What would it look like if?” I’m not saying that necessarily, that’s the right answer, but getting us to consider that other piece.

The other piece that I’ve seen with it is our primary focus at Everyday Effectiveness is accountability. That’s what we’re providing. It’s not accountability, “Did you get the task done?” It’s accountability. That is the way we define accountability, which is reflection. It’s not just, “Did you do it?” but, “What did we learn about doing it?” including, “Was it the right thing to do?” Sometimes, it’s about not only whether it was the right thing to do, but whether the right time to do it was the right order to do it.

I was in conversations where we were talking about whether you’ve got a chain and there are links in the chain. You can see there are six links, all of which have some issues around them. There’s a link that is practically rusted through, but we’re ignoring it. It doesn’t matter that we fix these other links because the chain is still super weak, where the one is practically rusted through. That’s the piece of, “Are we focusing on the right thing?” Asking that question of what is the right thing is a hard question to answer for yourself.

A couple of things that you’ve said in the past, getting back to the topic of finish lines, is that when a leader isn’t defining their own finish line, especially in alignment with their values, their life, and even the season of life. A lot of times, especially the people you work with, they’re bound to be successful no matter what, but the level of success doesn’t feel as fulfilling as they expect. Sometimes, it doesn’t feel sustainable.

We also see that some people inherit goals. I’m going to ask you about that in a second. Those inherited goals sometimes cause burnout and misalignment. If you have a team, your team gets confused because everybody’s running. They’re not necessarily all running in the same direction, and not all running together. It’s like a meme. My ducks are not even in a row. They’re scattered like ferrets. How do we inherit finish lines? When we think of inheritance, we think, “I got this from my parents.”

The Three Ways We Inherit Finish Lines (Absorption, Family, Obligation)

The inherited finish line comes from a lot of places. Sometimes, it’s social media. It’s the things that we’re being bombarded with in the media, TV, or all the places that we’re getting input from the outside. We’re seeing this, and it’s like, “That must be the thing that I’m supposed to go after. Many people are going after that. That must be the thing.”

One of the inheritances is more of an absorption of a finish line or a goal. There are the ones that are truly inherited that are related to our family story, family relationships, and close friendship relationships. It’s like, “This is the way that we measure success.” One of my clients knows this, but she still struggles with it. Her father was an excellent salesman. If he believed in it, he would be able to sell ice cubes to Eskimos at a premium price. That was his mojo.

The way you track sales is money. Did someone buy? Is it a successful sale? Anything else is not necessarily a successful sale. Although money doesn’t drive her at all, she still gets very wound up from time to time, worrying about how much there was. It’s not, “Was I satisfied?” It’s not, “It doesn’t meet my needs.”

That’s an inherited story. She’s self-aware enough to know that. We’ve got enough of a relationship where I can say, “That’s your dad’s voice that you’re hearing.” She’s like, “Yeah.” It’s not that he would put that on her, but she was raised with that. It wasn’t like, “If you’re not making this amount of money, you’re not successful.” That was not the messaging at all. It’s that inherited environment of, “This is what success looks like.”

I also think there is this inheritance of what made sense for us at a time that isn’t necessarily making sense for us anymore. I’ll call that the inheritance of obligation. We’re like, “I said I was going to do this. I’m no longer interested or desirous. It’s no longer appropriate.” The list can go on and on. We’re like, “Since I said I was going to do it, I won’t be a quitter. I’m still going to go after this thing, even though deep in my soul, or maybe not even that deep, I know it’s no longer the right thing.” We continue on with it. When we know that, when we get there, there is zero satisfaction for it. We already knew it wasn’t going to be satisfying before we even got there.

It’s the inability to claim a finish line that’s not a finish line. We’re like, “I finished the swim of the triathlon. I’m going to call it good. I’m not going to do the bike or the run, but I’m still calling it finished. I realized all I cared about was getting the swim done, and I got the swim done. I’m not even getting on the bike.” Many of us are like, “I said I was going to do the triathlon, so I’m getting on the bike.” There’s a lot that falls into obligation as well. It often is self-obligation. We said we were going to do this, so we think we have to do this.

We see that in so many segments of life.

Everywhere.

It’s like students who don’t want to change their major. They have this little kid’s dream of majoring in a certain thing to get into a certain field. They take the first major specific class, and they’re like, “I do not want to do this.” They feel like, “How do I admit that? How do I admit that I got this far not knowing what the actual job was?”

I love that you explained how we inherit finish lines that aren’t ours. We’ve talked a lot about industry norms. As an online business, we’re still at the peak of hustle culture. People are fighting back against it. We still see a lot of that. Many of us who are at this level of business came up under hustle culture. Even if we hated it or we know it’s hogwash, we still have absorbed some of that definition of success that we have to fight. It’s the whole thing of implicit bias. The reason it’s implicit is that you don’t know you have it. There’s that piece where you’re like, “This is what people at this level do.” What I’m wondering is this is what people at this level do. That is hard to know when it’s false and when it’s true.

That’s the place where we have to start digging deeper and checking, for lack of a better term, our sources. This is where we need to get more context. My whole thing is, if you can’t get the context, then don’t assume it’s true. Many people will say, “So-and-so,” enter any big-name online person here, “Says such and such.” Do you know if that statement, as you are defining it in your head, is what’s actually happening? What else is going on behind the scenes that you don’t know that may be making that thing happen in the way that you’re saying, “I should, as an individual, be able to do this.”

If you can't get the context, then don't assume it's true. Share on X

Maybe that’s true, but my guess is, depending on how big the name is, they’ve got a staff of ten that is fulfilling the thing that they’re like, “You should fill in whatever blank.” If you can check and say, “Who are the people that are doing this?” and understand and get into the details. Most of us don’t have the time, the energy, or the relationships, quite honestly, to get to that level of detail to be able to say, “Is this true?”

The bigger question you need to be asking yourself is, “Is this true for me?” Maybe for the five other people, this is what they have to do, but do you have to do it that way? That’s one of the things I say a lot to my clients and other people. For almost anything, there are multiple right answers. The trick is to find what is your best right answer for you.

Maybe this is what we have to do at this level of business. That may be true for a lot of people, but the question is, does it have to be true for you? Are you okay with it being true for you? I don’t think there is an easy answer. Almost always, when you’re sure that to be at this level of business, you must fill in whatever blank you want to fill in, if you look hard enough, you can find someone who’s at that level of business and is not doing that thing. There may be a whole bunch of other things they had to do so that this other is true. This is the place where there’s always a struggle.

I was talking to one of my friends who has at least an eight-figure. It might be a nine-figure business. He’s got a very successful business. He finished taking a year’s sabbatical as the founder, owner, and CEO of this business. There are people who say you can’t possibly do that. I said, “What are you doing now?” He says, “I work about twelve hours a week.” I was like, “Awesome.” He had to do a whole bunch of other things to make that possible. There are a lot of people saying you can’t have an 8 or 9-figure business as a founder-CEO and not be in it.

Other people say, “Pay me $10,000 and I’ll teach you how to have an 8-figure business on a 10-hour work week from day 1.”

I also know that wasn’t true for him either.

3 Critical Markers: How To Know If Your Goal Is Not Yours

If somebody’s reading and they’re like, “I don’t know if I’m chasing a finish line that’s mine or somebody else’s,” what are some symptoms or markers that they could look at to recognize whether they’re chasing their own finish line or somebody else’s?

The first is, are you excited about it, no matter what? When I say excited, I mean motivated, passionate, or whatever the case may be. Are you excited about the journey to it? That’s what I mean by no matter what. No matter where you are in the process, are you excited about it? We’re working on piloting accountability training for businesses instead of using it internally with our clients. Anytime I start talking about it, everyone’s like, “You are so lit up about this.” We are so early. We have so much to figure out. We have made zero money on this at this point. We are so far away from anything that would be called a finish line.

We are so in the cost of fulfillment at its highest.

We are so far away, but I still get lit up about it. Maybe at some point, that’ll change. Maybe something will happen. I don’t think it’s going to. The finish line that I’m trying to go to is a real finish line for me. Interestingly enough, that includes some things that were not on my finish line before. Before, I wouldn’t have wanted to have the employees that this finish line will require. It has changed. I’m also okay and excited about that possibility. We’re not there yet, but when we get there, I’m not worried about it. It’s a very different finish line than I had before, but I can feel the excitement about it all along the journey. If you’re like, “I have to do that,” then this may not be your finish line.

It’s your finish line if you’re feeling excited, no matter where you are on the journey toward it. This goes a little bit farther in the journey. Something else that I’ve heard you talk about is that you get there, and you feel accomplished, like, “I am here,” but then you’re like, “Is this it?”

The Journey Vs. The Destination: Why A Finish Line Is Just A Moment

I was thinking about that as the other half of it. Are you expecting a major change in your feelings, your energy, or fill in whatever blank? It’s emotional stuff, not physical, like, “I expect to have sold $1 million by the time I hit the goal of selling $1 million.” Those two things go together, but emotionally, are you expecting something to be wildly different upon reaching that finish line than what you feel? It’s not that it won’t be somewhat different, but wildly different than where you are.

It’s like a little kid with their birthday. They’re so excited to turn double digits, and then they realize that turning double digits doesn’t automatically make them a different person.

Everything is still pretty much the same. Maybe you can stay up a half an hour later, but pretty much everything else is the same. That, to me, is the other, the other sign. The destination, the finish line, or whatever it is, you’ve got to realize that it is but a moment in time. It’s just a moment in time.

That’s why I said the journey is the critical piece. If you’re miserable all along the journey, there is nothing about that moment, and I don’t care how you define that moment, that’s going to make it worth it if so much of the rest of the journey is miserable. There has to be its own satisfaction along the way. You may expect a high at that point, but it can’t be Mount Everest compared to the ocean shore. It’s not going to happen, and that’s going to be so disappointing.

What else? What other markers are there that it’s not your finish line?

The last marker is when you know in your soul. We discount our own intuition so much so often. When people say, “My heart’s not in it,” that’s probably true. Your heart’s not in it. Your heart needs to be in it. All of this is hard. None of this is easy. You don’t need to add complexity. You don’t need to add difficulty to your score. You might as well be going after the things that your heart is in. It’s not that your heart is going to be in every moment of every second of every part of the journey because that isn’t the way that it works either. When you’re thinking about the goal and those bigger finish lines, is your heart in it?

All of this is hard. None of this is easy. You don't need to add complexity and difficulty. So you might as well be going after the things that your heart is in. Share on X

The last one, which we’ve talked about multiple times, comes from our friend Nick Peterson. The idea of the thing that you want, is that goal in line with that? We’ve used this before. I see it happen a lot in the world of women, particularly entrepreneurial women or professional women, who say, “I want to achieve this thing so I have more time and freedom to be with my children, but to get to having more time and freedom with my children, I spend less time with my children.” It’s never going to get you what you need if the path that you’re taking is going in the opposite direction of the thing that you should be headed toward. Maybe it’s not a direct line to the thing you’re headed toward, but it can’t be going completely in the wrong direction.

  

The Business You Really Want | Finish Line

  

Working a 40-hour week is not going to get you to a 20-hour week by the end of the year, usually. That’s a big cut.

The only way it’s going to happen is if you know exactly what you’re doing. You’d have to be very precise about, “How is this thing producing that thing in a very short-term way?” It’s not, “When I get promoted, I will have more freedom to be able to go to more soccer games.” It’s like, “Do you know that? Will they still be playing soccer then? I don’t know.” Being in alignment with what you think the goal is going to deliver is another huge one.

What about the leadership cost for those who have teams?

Leadership Clarity: The Cost Of Misalignment On Your Team

When we’re not in alignment, it’s way easier to get distracted. That’s one of the things. The squirrel factor becomes high. The shiny object factor becomes high because we’re not that focused on the goal. It becomes way easier to be caught by all sorts of other things. When we are not focused on the goal, that means we’re probably giving all sorts of mixed messages to our team. When we get there, if we’re not enthusiastic, then they’re not enthusiastic. This is a trickle-down theory in practice. What the energy is at the top is what gets translated down through anyone else that you’re working with.

I’ll give a converse example. I can’t remember the gal’s name, but she was the former owner and founder of Spanx. When she sold it, that was a thing. Everybody felt it. It was where they were going. They were building this thing to be a big thing. This was her mission. It showed that it played out throughout a lot of aspects of it because she wasn’t just celebrating for herself. She was celebrating with the whole team. The whole team was celebrating with her.

That’s the thing. When you get to the goal, is the team also going to be excited about it? At the point that I get the goal that I’m working on with this account, I know you, Sophia, Rachel, and anyone else who’s working is also going to be excited about it because we can see what that impact is. It’s not just about, “We’re going here because that’s the random goal that we’ve set.”

It’s also easier for me to direct the kind of work that I need the team to do because it’s also super focused and aligned. I can feel when it feels like it’s starting to shift. I say, “This doesn’t feel like this is in alignment. Let’s get back into it,” as opposed to letting my team also get distracted by the shiny object. I work with all subcontractors who are, in and of themselves, entrepreneurs. It’s easy for them to do the same thing.

I love that you use the example of selling a business because that’s one, especially when people are starting out, that they don’t think about. If you have said that the eventual goal is to sell the business, if your team is doing their job correctly, they are going to be building out a system that can run without you, especially once you start bringing on key leaders.

If that’s what you’re saying, and internally, you’re like, “I don’t know if this is sellable. Maybe I’ll close it because I don’t want to hand this off to anybody else,” then you’re going to fight them at every turn because you don’t want the business to go on without you. What that does is people are confused, like, “Why am I getting pulled back or redirected when what I’m trying to do is get this business to a sellable place faster?” They get tired of spinning their wheels, so they start to disengage.

One of the things that I’ve always heard you talk about is that a leader’s clarity is what defines the organizational energy. The team can get energized when they feel like the leader is clear and they’re all going in the same direction. That’s the issue that it causes from a leadership perspective when you’re chasing the wrong finish line. At this point, people should be aware they’re either chasing the finish line that’s theirs or they’re not. If they’re going, “Maybe this isn’t what I want to do. Maybe this isn’t where I want to be,” how do you redraw the line?

A leader's clarity is what defines the organizational energy. Share on X

“I’m Done With That”: How To Redraw Your Finish Line

It’s the easiest and hardest thing in the world. All it is is saying, “I’m done with that. I’m going to do something else.”

I love that. It’s the easiest and hardest thing in the world. There’s your answer right there. It’s as simple as saying, “I’m going to do something else.”

That’s easy because all you have to do is say, “I’m going to do something else.” It’s hard because, for many of us, that makes us feel like we were a failure. Often, we don’t know what the next thing is. If we don’t know what the next thing is, saying, “I’m not doing this, but I don’t know what the next thing is,” makes that even harder because we feel like a failure. Sometimes, it’s as simple as saying, “Instead of going 3 degrees to the left, we’re going to go 4 degrees to the right.” Sometimes, it’s not that big of a deal, but it’s getting clear on it and saying, “We’re done with this for whatever reason.”

One of the things we talk about in our Quarterly Planning Process, the QPU, pretty much every time is that sometimes, we don’t know the finish line isn’t our finish line until we’ve started toward it. It’s like, “I want that finish line,” and we start working toward it. At some point, it’s like, “I am now far enough in to see all the other things that go along with this particular finish line, and I do not want those.”

It’s as easy as saying, “I don’t want those,” and it’s as hard as saying, “Then what?” It’s super easy and super hard all at the same time, but it is about being decisive. For a lot of folks, that is the hard piece. Even if it’s not externally perceived in any way whatsoever, internally, we see it as a failure. It’s just data. It’s information.

I’ve known this in my own life as well. Sometimes, you don’t know you’re chasing the wrong line until you’ve started the journey. Part of what we have to do is recognize that the finish line isn’t necessarily a point of completion. Sometimes, it’s figuring out what’s most fulfilling for us.

Also, back to super easy and super hard, both at the same time.

We can’t prescribe the right finish line to anybody who’s reading, for sure, because we’re not having a two-way conversation. Second, it’s one of those certain things in life where you’ll know it when you see it or when you get to it. What we can leave our audience is the comforting thought that not every finish line deserves to be crossed. Sometimes, the bravest thing that you can do as a leader or the most authentic thing that you can do as an entrepreneur is to stop running towards something as soon as you realize it no longer fits who you are, where your business is headed, or where you want to take your business.

Not every finish line deserves to be crossed. Sometimes, the bravest or most authentic thing you can do is to stop running towards something as soon as you realize it no longer fits who you are. Share on X

The finish lines that we inherit, whether it’s from mentors, industry norms, or our past goals, often look super impressive on paper, but that is what keeps us trapped in living out other people’s definitions of success. What you have said in the past is that you have to pause long enough to ask, “Is this finish line or goal still mine?” That’s where you start to create the space where you can see a new goal or a new finish line to move you forward, not faster. Although sometimes, it does end up being faster. That’s one thing that we’ve talked about a lot. It’s faster, but with a clearer purpose.

To bring us full circle, if the question has stirred something for you, then you want the questions that Gwen sends out every week. She’s not going to give you advice. They’re not big insights. It’s one good question designed to help you think differently about your business. It’s the kind of question that will shift perspective, spark clarity, and help you start intentionally moving toward a goal that feels more in alignment with everything that you do. You can go to EverydayEffectiveness.com/question to sign up. Make it part of your week. The emails come out on Fridays. Who knows? By Monday, you may already experience a shift in how you lead and how you’re working.

  

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.