Effective entrepreneurial goal setting requires stepping back to celebrate wins before chasing the next objective. In this episode, host Tonya Kubo and strategic business consultant Gwen Bortner explore why high-achieving founders constantly move their finish lines. They discuss the psychological differences between business owners and true entrepreneurs, revealing how unmanaged ambition can turn growth into an exhausting cycle. Learn how reflecting on your progress fosters satisfaction and keeps your business healthy. Plus, they break down a practical tool called WRAP (Weekly Review and Action Plan) to help you acknowledge your achievements while scaling effectively.

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Why Does Success Keep Moving The Finish Line?

Recognizing The Entrepreneurial Goalpost Trap

If you’re in business, you have had that moment. I know that you’ve had that moment because I’ve had that moment. You finally accomplish something that you have been working toward for months, maybe even years. You land the dream client. You hit that revenue goal, which is the magical 6 figures or the magical 7 figures. You hire team members. You have people. It’s no longer just you and the mouse in your pocket. You open a new location. Almost before you’ve even had the chance to celebrate, your brain is already onto the next thing.

If you’ve ever wondered why success never seems to feel quite as satisfying as you expect it to, this episode is for you. Gwen, something that you have told me in the past, in fact, when we first started working together, and you talked about your proprietary way of assisting clients with goal setting, is that entrepreneurs are good at setting goals, but they’re not so good at noting when they achieve them or giving themselves credit for how far they’ve come. Where do you think that comes from?

Defining The True Entrepreneurial Mindset

I’m going to define what I call a true entrepreneur. It is someone who sees everything as an opportunity. There are business owners. I consider myself not an entrepreneur. I consider myself a business owner. A true entrepreneur sees a problem and knows how to solve it. They will occasionally see an opportunity, but not everything on the planet is an opportunity.

 

 

If you’re dealing with a real entrepreneur who sees all the opportunities, part of the problem is that. In their mind, if they’ve started addressing it, it’s probably, in their mind, solved, so they’re on to the next thing. What it looks like is that we move the goalpost before we get there. We’re running down the field. We’re down to the twenty-yard mark. We don’t have that much further to go to get our touchdown, but we say, “We’re supposed to go to the other goalpost,” which is 80 yards away.

We start going in that direction. What happens is, usually, we achieve the goal and blow past it because we’re already on to the next thing. We’re already seeing the next thing. Moving the goalposts, to me, is one of the things. If we’re getting close, there is this assumption that we will achieve it, so in our minds, it’s done before it’s done. When it happens, it’s like, “Six figures. Seven figures.” We don’t think about it because we’re already, in our minds, past six figures. We want to be mid-six figures. It’s like, “Six figures is nothing.”

Our mind has gone past the thing sometimes before we get there. The other thing is that’s also why we’re able to do what we’re able to do. There is always another goalpost. There’s always something else. I’ve been listening to some conversations with Dan Sullivan, who’s the owner of Strategic Coach, and Joe Polish. Dan talks about how long he wants to live. I think it’s 140. He’s in his 80s, I’m pretty sure, at this point. I may be wrong on the details here.

They’ve been having conversations, and one of his things is that he feels he’s more ambitious now in his 80s than he was in his 70s. He anticipates he’ll be yet more ambitious in his 90s than he is in his 80s. Dan is a true entrepreneur-minded person. I’m giving the Reader’s Digest version. I would encourage you to go listen to some of the 10xTalks. You’ll find value in them.

His thing is, “Once I know that I can do this hard thing, then I assume that I can do the next harder thing.” His whole thing is, “Now that I’m in my 80s, I can see all of the hard things I’ve done. This next thing can’t be that much harder than all of those things. I’m going to keep pushing that limit.” That is the natural entrepreneurial mind. Therefore, we don’t necessarily take time to acknowledge the success because we are only looking out in the future all the time.

I feel like this is what you said, but I want to make sure that I’m understanding it correctly. Entrepreneurs are naturally wired to look ahead. That is the difference between the entrepreneur and the business owner.

It’s a piece. There’s lots of research that says that capacity is a natural tendency. That’s a little more DNA-based. I’m not sure that’s truly true. That is a limited amount of the population that will do that in that kind of way. It is also what makes them successful because they also treat failure in a similar way.

Tell me what you mean by that.

It’s like, “I hit six figures, but now my mind is already into the middle six figures.” When the thing doesn’t work, it’s like, “We’re going to do the next thing.” They don’t necessarily dwell on it, circle on it, and spend lots of time on it. Not that they won’t spend some time on it, but they also don’t get stuck there, like, “That failed, so that means I can’t do anything.” It’s much more like, “That way doesn’t work,” and they keep going.

 

 

You look at many of the folks that are held up as very successful entrepreneurs. A lot of them have gone through at least one, if not multiple bankruptcies. They tend to be boys, not girls, when that’s the case. It is one of the things. I’ve heard folks say, “I can’t possibly go bankrupt. It’s going to ruin my life.” A lot of that’s mythology.

When you talk to people who’ve gone through bankruptcies, they’re able to move on, make things happen, and keep going when it needs to happen. It goes back to how they aren’t like, “I went bankrupt, which means I suck as an entrepreneur, and I’m never going to be able to do this again.” They’re like, “I made some bad choices. Let’s not make that again,” and away they go.

You were talking about Dan Sullivan’s ambition. I’m wondering. More power to him wanting to live until he’s 140. That is not an aspiration I have. Is there a point where an ambition like that stops serving you?

I think if it’s being destructive or it’s causing you harm in any way. In Dan’s case, I don’t see any evidence of that. I see him saying, “How can I make this better? How can I do this next thing? What is the next opportunity?” That comes a lot from your own personality. It can be destructive where there is no satisfaction. That’s also not the case with Dan. One of the things that Dan Sullivan talks about is, “What do I want?” It’s not, “What do I need?” but, “What do I want for the sake of wanting it?” He pays attention to achieving his wants, which means he also has a level of satisfaction with what he’s doing.

Understanding The Limits Of Unmanaged Ambition

Ambition is not out of a negative mindset. It’s out of a positive mindset. That’s where it can be detrimental if it’s not managed well. You’re like, “I suck. I never achieve any of my goals.” Is that true? Maybe not. Maybe what’s true is you don’t move the goalpost before you hit the goal. Part of this is how we approach it. Do we use ambition as a way to continue to grow, improve, and see the value of it, or do we use ambition as a way to demean ourselves and be frustrated with lack of progress?

Sometimes, we use ambition under the guise of ambition.

True entrepreneurs treat failure as a strategic iteration rather than a personal setback. Share on X

We see that a lot.

It’s like, “I won’t do this until I hit six figures. I’m not going to do this thing until I hit $500,000. I won’t sell my business until it’s a $500,000 business.”

Demystifying Revenue Milestones And Business Realities

Somehow, that’s going to be a panacea. One of the things that we have to remember is that the moment that you hit whatever that measurable goal is, it is truly a moment in time. The minute before and the minute afterwards are not going to be that different because that’s not the way life works. The moment you hire someone, that is a moment.

It isn’t going to instantly completely change. It’s not like you’re going to transport and appear at a completely different timeline because you hired someone. You’re still going to go through a linear process of what all of those things are and what all of that means. When we put so much weight on it producing an emotional or physical result for us, it’s always going to fail us. The moment that we hit six figures, we don’t magically have a new house. We don’t magically have all these things. It’s not the way it works.

The moment before we had 6 figures, we had $99,500. It wasn’t that it landed. It was probably an additional $500. People are like, “When I start getting a $100,000 client.” You didn’t go from a $0 to a $100,000 client. You had a $500, a $5,000, a $25,000, a $50,000, and a $75,000 client, then, you had $100,000. It’s not this big jump that we think it is.

We haven’t talked about this in a long time, but one of the things that you have brought up a lot of times, especially around ambition that is tied to revenue goals, is that a $100,000 business has problems and challenges that a $50,000 business doesn’t have. Likewise, a $500,000 business has issues that a $100,000 business doesn’t have. When you get to seven figures, it doesn’t solve all of the issues. It opens the door to some new ones.

Ambition should fuel your business expansion, not become a weapon you use to demean your current progress. Share on X

Bigger versions of the old ones.

Sometimes, things that you could get away with ignoring or overlooking at $100,000 are deal breakers at $500,000 because they get so much bigger with everything else. It reminds me of when I worked with somebody several years ago. We had launched a thing, and it was a $180,000 launch. There was a client who was like, “What I wouldn’t give for a $180,000 launch. That would do this, and that would do that.”

The owner said, “You have to realize that you’re a solopreneur. A $180,000 launch would be huge for you. For us, we have a much higher threshold for success. I’ve got 14 staffers, and quite honestly, $180,000 doesn’t even cover payroll for the year. I get why you think that was a successful launch, but for us, it was a failure.”

What I’m hearing so far in this conversation is that while ambition isn’t bad, it doesn’t serve us if we’re constantly thinking that we have to cross this line in order to be satisfied with our business. It’s like, “I’ll have the business I want in the somewhat foreseeable future.” If that isn’t a good measurement of success, my question for you is what is.

It’s one of the things that we focus on when we do our quarterly planning. We wrapped one up not long ago. It’s looking back and saying, “How far did I come from where I was? What progress did I make? Am I seeing a difference from where I was to where I am?” Entrepreneurs are horrible about that because we don’t take time to look back. That is why we make a very focused part of our quarterly process to take time and say, “Before we start looking to the future and do the planning piece, we want to first say what got accomplished. Where did we move from and to?”

We typically look at it as a quarter, but because we do this with our clients quarter after quarter, from time to time, the client will say, “I can’t even fathom how far I’ve come in the last eighteen months.” If they hadn’t been doing that, they would still say, “I’m not successful,” because they’ve moved the goalpost, they’ve changed the direction, and they’ve done the things that entrepreneurs will do that aren’t necessarily bad. I’m not saying that these are bad behaviors, but they don’t see progress.

A seven-figure business doesn't solve your problems. It gives you bigger versions of your old ones. Share on X

Measuring Real Progress By Looking Backward

The only way to see progress is to look behind you. The horizon is always the horizon. If you’re looking at the horizon and heading toward the horizon, it always looks forever away because it is. It’s the nature of it. You never get to the horizon. It’s that backwards look. Back to Dan Sullivan, that’s one of the books he wrote. The Gap and the Gain. That’s what that book is about. Are you looking only at the gap, the horizon, or how far you have yet to go, or are you occasionally looking backwards at the gain of what you’ve done? When I read that book, and I’d been talking about it for years, it was like, “That’s my whole review process.” You have to look backwards.

These aren’t the exact questions that we have our clients reflect on during quarterly planning, but it gets to the questions of, “Is this business healthier than last year’s last quarters? Are decisions getting easier?” That’s one that a lot of our clients will spend some time with. Looking at whether you’re a better leader, and if you feel like you’re a better leader in what areas.

If there are areas where you feel like you’re a better leader, there are probably areas where you’d like to improve. A lot of times, all we think about is, “I still struggle with performance evaluations,” whereas before, you wouldn’t have performance evaluations because you didn’t want to have difficult conversations. At least now, you’re having them.

That’s a perfect example of you may not have achieved the ultimate goal that you think you want to have achieved, but have we taken steps there? It goes back to how no one magically appears at the final destination. It is a process. It’s always a process for everybody.

This reminds me of a new client. There are a lot of outcomes with business. There’s revenue. There are all the different things that revenue can get you. Also, there is the personal growth.

That is it. Being an entrepreneur is more about a self-improvement exercise than anything else because we’re having to learn about ourselves. We’re having to learn to adapt to all sorts of environments and situations that we wouldn’t necessarily have chosen on our own. We’re going to be encountering people, some of whom we do choose, and some of whom we don’t choose. If you talk to anybody who is a long-time or serial entrepreneur, they will tell you they have learned more about themselves in the process than anything else. It becomes a huge element of it. If it’s not, it’s something to consider.

Taking 15 minutes a week for strategic reflection changes how you make operational decisions. Share on X

The question you can say is, “Who is the business helping you to become?” If you don’t like that person, then that’s important to explore.

That is also the beauty of it being your own business. If it’s helping you become someone that’s not making you happy, then change. You get to drive this bus. You’re the one that’s in the driver’s seat. If you figure out how to minimize, eliminate, or delegate that aspect of it, that is the true entrepreneur. They are not replicating what already exists. They are creating something that is uniquely theirs.

If somebody reading realizes that they’re spending so much time chasing the finish line without ever acknowledging which ones they’ve crossed, what is one thing you would encourage them to do differently?

Implementing Weekly Reflection Systems

We use a tool that we call the WRAP, the Weekly Review and Action Plan, with our clients. Part of that process specifically is the R, the Review piece. When we onboard people into the WRAP process, the first couple of questions are way more tactical questions. They’re like, “What are you doing? What are you planning on doing?” They’re pretty tactical questions. The third question is where the meat of the question is, which is, “What did you observe about the prior week, the week that you completed?”

You’ve been reviewing WRAPs with me for years as well. It’s interesting. When people first start, it’s still very tactical what they observe. It starts out tactical, and at some point, there is some switch that flips or a thing that happens. All of a sudden, they’re reflecting and paying attention to that bigger impact. That’s often when they start seeing, “I moved the goalpost on myself. I didn’t let myself celebrate this thing.” They start seeing those pieces.

This is not something that we’re asking them to spend hours doing either a day or even a week. Most of them only take 15 to 30 minutes for the entire full process once a week. We use it within our own business as well. I can do the first couple of questions fast. The third question is always where my time is invested. I spend time thinking about, “What did I observe? What did I learn?”

Outside perspective helps you realize when you've successfully hit the goals you set months ago. Share on X

When the switch flips, everything in their whole world flips as well because they start paying attention to the fact that, “I did cross that finish line. I am moving the goalpost. I celebrated for about half a second and then quickly moved on to all the things that I’m failing at instead of saying, ‘That was pretty darn impressive.’”

Getting into that habit would be the thing that makes the biggest difference. I’ve seen it for myself. You’ve seen it for yourself. We’ve seen it for our clients. Sometimes, you need someone to help you in that process, and that’s something that we’re happy to work with people on, but you don’t necessarily need somebody else.

I’m going to have to disagree with you there. I’m listening to what you’re saying, but I’m also thinking through what I have observed. What I see is a lot of times, they’ll leave that question blank at the beginning because they’ve got nothing.

That’s true, too.

We’ll prompt them. A lot of times, I’ll start documenting what I’ve observed on their behalf. Then, they’ll go more tactical, like, “The fifth Saturday of every month is always slow. Maybe we should consider closing early.” They go to something tactical like that. Oftentimes, the shift comes as a result of the perspective that we call out.

I’m going to point out one client who has been a long-time client. She predates me. For two years, she has had a goal every quarter for more time for play. It’s some version of that. It’s not always that specifically. It’s either like, “I want more dedicated personal creative time,” or, “I want to have more fun,” or whatever.

It was a couple of quarters ago that she recognized that she’d done that. Her recognition came after going, “I feel like I’m stuck. I feel like I’m stagnating. I’m not doing this forward, and I’m not doing that forward. My weeks are so compressed.” I was like, “One of the goals that you’ve had for so long is more time for creativity.

Now you’ve got yourself in a situation where you’ve set aside a full day every single week in this pursuit for creativity. You’re taking a class, and it takes a whole day. You’re driving there and driving back.” She was like, “You’re right. I have.” My thing was like, you’re acting like you have five full days in the office. You don’t. You only have four. Having four isn’t because you’re bad. It’s because you prioritize this one thing that was so important to you.

That’s the trade-off. You can’t have that and then have this. She recognized she is more productive the other four days a week than she had been when she was working a five-day workweek because of having this creative outlet, but she was still beating herself up every single week until we were able to surface that observation for her. That flipped the switch. Now, she’s observing all the different ways that having that creative time set aside has benefited her.

You’re right. That often is the issue. If you don’t have someone outside helping you observe, then it is easy to get in our own heads. That does become a challenge.

Leveraging External Perspective For True Growth

What this episode is about is that it is always going to be easier for us to see how far we have left to go because we live with our vision every single day. It does take somebody else to bring our attention to how far we’ve come.

Both things are true.

One of the things that I love most about these conversations with you is that they don’t end when we stop recording. They don’t end for our audience. We get emails, or at least I get emails, all the time that’s like, “You derailed my whole day because I tuned in to the episode. That got me thinking about this.” If that’s you, and this conversation has gotten you thinking about how you define success in your own business, we have a way to keep that conversation going.

It’s this email that Gwen sends out every single Friday called One Really Good Question. It is one thoughtful question. It’s one opportunity to spend five minutes reflecting on your week and how far you’ve come so that you can move forward with greater intention. To sign up for that, you don’t even have to talk to us. You go to www.tonyakubo.com/Question. There is a quick little form. You do your name and your email address. Nothing big there.

On Friday, the email drops in your box. If you want to reply to it, awesome. Either me or Gwen will respond right back to you. If you don’t, that’s okay. Another email comes the following Friday. We will see you next time. In the meantime, even if you don’t sign up for One Really Good Question, I would encourage you to be thinking about the intersection of your ambition, what that says about the business you want, and if that ambition is ever going to let you enjoy the business that you have.

 

 

Mentioned in This Episode

• One Really Good Question
• The Business You Really Want on Apple Podcasts
• The Gap and the Gain

 

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.