When you’re a new business owner, a quick Google search can solve 80% of your problems. But as you grow, the stakes get higher and the decisions get more complex—making it perfectly normal to feel stuck. But are you truly overthinking, or is your gut trying to tell you something you aren’t seeing? We’re breaking down why successful founders struggle with indecision and how to change your perspective to gain the clarity you need to push forward. Ready to get unstuck? Join us as we explore the path to making confident, strategic moves.
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The Real Reason You Don’t Trust Your Next Move
Defining The Clarity Problem Over The Confidence Problem
There is a specific moment that happens as you grow your business. It happens to all of us. You are faced with a decision that you should feel ready to make but you don’t. It’s not because you lack experience because honestly, you wouldn’t have gotten this far without some experience. It’s not because you don’t have options.
You don’t feel backed into a corner. It’s because something about the decision doesn’t quite feel clear. You feel like you’re missing something, so you pause and you think. You think some more. I would argue that you probably overthink it. You second-guess after you thought you made a decision. This decision that should feel simple suddenly becomes an albatross hanging around your neck.
If you’re reading and thinking, “It sounds awfully familiar. In fact, that’s where I’m at now. I don’t know what the right move is. I don’t want to get this wrong.” The whole purpose of this episode is to help you reframe that. I would argue and Gwen will agree with me, that hesitation isn’t insecurity in the traditional sense. You don’t have a confidence problem. You don’t even have a knowledge problem.
What you have is a clarity problem. Gwen, I want to start here because I just think it gets mislabeled way too often. Somebody gets stuck on the decision and you know because you’ve been stuck on decisions. I’ve come to you because I’ve been stuck on the decision. The default assumption is, “You’re thinking on this too much. Make a decision. Move forward. Trust yourself it will all work out.” I have heard you tell people, “That’s not always the case.”
I will say, sometimes it is the case.
There are exceptions to every rule. Rule to every exception.
Sometimes that is the case. The thing is we assume that’s the issue 90% of the time. With what you’re saying, “I’m overthinking. I need to make a decision.” That is true only 5% or 10% at a time. We waited at exactly the opposite likelihood of what it is because sometimes that is the case. That is so much more rare. That hesitation is probably trying to tell us something different and this is the place where I often will talk about instinct or gut reaction or any of those kinds of kinds of things.
That indecision is saying, “I’m missing something here.” That missing something could be all sorts of things. Since we often don’t trust our gut, although we should. Let’s just be honest, we should. We put it to these other things. I’m overthinking. I’m not confident about it. That’s that 5% or 10% piece that we put it to. We’re not saying, “My gut is telling me I’m not ready to make this decision.”
It’s trying to tell us something there that there is some hesitation for a reason. Now, the hesitation can come from lots of different things. Sometimes, it’s because the hesitation is, “What I want is A and I want is B. In my mind, I have no idea how to make A and B both be true.” There’s a hesitation there. It’s like, because if I choose A, then that means I’m not choosing B. If I choose B, that means I’m not choosing A.
In my mind, they are of equal priority.
They may be completely related to different things but sometimes, we say it all the time. When you say yes to something, you are often saying no to something else. You may be very fully aware that that’s what’s going on in your world. You’ve got an A and B in your world. If I say yes to A, I’m saying no to B and I don’t want to say no to B either. Sometimes, that’s the piece of it. That’s where the hesitation is coming from. That’s good data. That’s good to know that. Sometimes, it’s because we don’t have quite enough data to make the decision. We haven’t got the pieces that need to be in place. Nick Peterson talks about, are you making new data and different decisions? The same situation, different decision based on new data.
Every time you say yes to something, you're also saying no to something else. Share on XDistinguishing Between Early-Stage And Advanced Business Decisions
Sometimes, what’s happening is like, “This situation is happening and I’m going to make the same decision but sometimes we have new data.” Sometimes, we don’t have data. It can be either side of that equation but it’s like an instinctive thing. There’s something not going on here that we need to do. I was in another Mastermind conversation and we were talking about this. Sometimes the thing is like, “This situation feels exactly like that situation so I need to make this decision. The reality was, this situation that you’re aligning with, was when you were at a $50,000 business. The decision you’re making now feels the same but, “I have a $200,000 business now.”
I want to pause there because this is where the real issue lies. This is why successful business owners struggle so much. It’s because what it feels like to them is, “I used to make decisions so easily. I used to be so decisive. What happened? Now I feel like I can’t cross the street without a frozen cons list.”
I just want to spend a little bit of extra time on what you just said because it’s important for the readers to hear. In the early stage of business, first of all, the reason we think 80% of the time we’re overthinking is because 80% of the time when you’re a brand-new business owner, you are overthinking. The answers you need are there. Your decisions as an early-stage business owner, “What should my logo look like? What are my brand colors? What is my offer suite?”
Asana versus Monday.
Do I do invoice? Do I do auto payment? Do I let them pay automatically? It’s very brass tacks things that a Google search can get you 3/4 of the way there then you ask a couple of people and it’s like good enough for government work. Once you get more advanced in business, we are beyond logo colors. We are beyond, “Do I hire this person for $20 an hour or that person for $25 an hour?” It becomes questions like, do I hire for experience or do I hire for fit? Deeper questions. I love that you’re pointing out that it is perfectly normal to struggle more with decision-making as you get to a higher level of business.
It absolutely is because as I said, often, it feels like the same decision. I’m going to pick on the Asana or Monday decision like when you’re first starting out. We’ve all had to make those early software decisions. We say, “Do I want to use Asana or do I want to use Monday.com?” I’m not recommending or de-recommending either. They were the two that popped into my head. You choose one and they’re relatively similar. They’re relatively similar in price depending on what you’re doing.
At some point, you’re much further on in your business and the question is, “Do we go ClickUp? Do we go GoHighLevel? Do we make the change at all?” This feels like the exact same decision that we made back at the beginning but it’s not. It’s not only the cost of the software but it’s the time and effort to move all of the data and do all of the migration and all of the pieces that go along with that. We now have more likely either more complicated or at least more well-documented and complete processes than we did way back when. We’re thinking about which of these tools will maximize.
There’s all a whole lot more in this simple software decision this further along than there was at the beginning. If you look at it at the surface, it was like, “That wasn’t that big of a decision. I ended up choosing such and such. It was fine. Why am I stuck?” It’s not just a software decision. It’s about the resources, the time and the effort and all the other things. We get caught in our minds saying, it’s exactly the same. It’s not the same because we’re at a very different point in the journey. Does it feel like a good tangent?
No, exactly. I’m just going to sum it up right here towards your readers. Instead of assuming something is wrong with you. Recognize that your brain, your psyche, something is recognizing that everything is not adding up in this situation. Let’s carry this project management tool example forward mainly because every business has to make that decision at some point. Even if they’re going from using no tool to suddenly, they realize with five employees they need a tool. People get stuck because they think they have information. They think everything because Google solved their problems before. They think Google can solve their problems again.
In this case, we’re talking about Google Search. Not the tool itself or what I found on YouTube or whatever.
What my Mastermind said. Gwen, every Mastermind I’ve ever been to has had somebody telling me that whatever problem I came to the table would be solved. That’s if I use the same project management system that they use or if I use the same software that they use. If they’ve looked at everything, in the case of the project management system. I’ve done my cost comparison. I know that all things are equal here. I’ve done my features and benefits comparison. I know you’ve said part of it is because there’s layers, cost of acquisition and all of that. Why does that not appear clear?
There’s lots of reasons why it might not appear. One is you may instinctively realize there’s something more complicated about this that you may not understand what’s more complicated about it. I feel like we talked and we’ve done enough for episodes. All the podcasts are the same. We may have talked about this in the last episode. It may have been like 6 episodes or 8 episodes ago. I’m just going to put that little disclaimer. One of the things that happens as we do these situations is we think we may have the information. As I said, instinctively it’s going, “No. There’s something here.”
Understanding The “Black Hole” Of Intuitive Hesitation
The problem is, we don’t have anyone around us who can point that out. At that point, we feel like we’re overthinking because we’re circling. It’s one of those things like, “I’m circling around this big black hole. I keep circling around this big black hole.” There’s no one to help you go down that big black hole to figure out what’s down there. It’s like, “I have a feeling this big black hole means something.” There’s this layer there that becomes problematic. I’m going to use that term a little bit loosely. We’ve got data. There’s a big black hole but that data isn’t useful yet.
Also, going back to something you said before our mutual example of the project management system. People will say, “You have this problem. Here is everything it does.” You walk away going, “Tell us all those things,” but does it do all those things? Does it do things this way? You know the inside of your business and they don’t. They only know what you’ve told them.
What they’ve likely heard is likely all the ways that your business is similar to theirs or their desires are similar to yours. They’re putting all this intent that they had onto what you are objectively describing. I feel like there’s the information thing. That’s facts, data, and objective but the black hole piece is the context, that matters piece. I was trying to avoid saying that, Gwen. That’s why I’m a hem and haw because you always say it, “It’s the concept.”
I love it that I’ve got you say that all the time because it does. Context does matter.
It’s the context that gets to the root.
That’s the thing. The black hole is, there’s a root cause problem here. I’ve been working around it and I don’t know how to get to it. It can’t identify it in real practical situations. It’s when we’re doing tactical symptom fixes and not figuring out what is the real root cause. Sticking with our project management automation organization system thing. Often, we find people are trying to change their automation process by getting a new software but it’s not even the process or the software. It’s the person who’s implementing it.
They’re not looking at the person who’s implementing it. There could be 1,000 reasons why they’re not. It can be because they helped me get started and they’ve been so critical. They know everything about the business and it’s like, “That’s part of the problem.” They still want to do it their way, which doesn’t work at this size of business. I’m making up two or three examples but the thing is like, “I’m going to fix this by putting in a new automation software.” It’s like, “You’re not because that’s not the problem.” This is back to that root cause piece that was missing. Back to, there’s this instinct of, “I’m missing some critical piece of information.”
Where and how you get the data becomes the question. How do I get the information that I need to understand, “This is a software problem. This software isn’t designed to do the type of things that we’re doing now in the business. We now need to move to ClickUp or GoHighLevel.” The list goes on and on, or not. That becomes the issue because maybe you do. Maybe you do need to upgrade your software. Maybe there’s this thing. I’m like, “I don’t think I want to do this because I don’t think it’s actually the problem.”
Since we’ve done these upgrades before. Maybe what the problem is the software does a whole lot more than we’ve ever used it for. The people who use it learn to use it from the predecessor and they don’t know. I feel like we’ve done a good job of agitating the problem and as you said, the question then becomes, what do I do next? Before we get there, I want to flip it because I want you to draw or paint me a picture of what it looks like when somebody does have clarity on their real problem. That’s the other thing. Somebody’s reading and they’re like, “Is this me? Is this not me? I don’t know.” They started thinking that they’re overthinking that.
That might be the 10%.
What happens when somebody does have clarity on the real problem? What does that look like? What does that feel like? How does the decision-making change?
We finished Savvy Syndicate, which is our very small, intimate Mastermind retreat. There’s only a few people there. It maxes out at four people, plus me. It’s very intimate, which allows us to have great conversations and deep vulnerability and all of those things. It’s because of that, one of the things that I will say is when you have clarity, there is an emotional release and/or it doesn’t feel hard. Now, sometimes it’s an emotional release, but it still feels hard because it’s like, “I know what I need to do. Oh, crap. That’s going to be hard to do that thing.”
Recognizing The Signs Of True Clarity
Using these examples that we were just talking about, “I don’t need to change my software. Crap. I need to let Kelly go.” There’s this emotional release on the decision but it could still be hard. I’m not saying it’s absolute but other times, it is about, “I can see how to do this.” It’s like, this makes perfect sense. I know where to go. I know this is the right thing. I know how it’s going to get me to where I want to go.” Which usually also has an emotional release. We had lots of conversations. One of that kept coming up was like, “Gwen, you just broke my brain.”
I’m glad because you break my brain all the time, Gwen, in a good way. It’s in the best way possible.
All of a sudden, this tension that was being held. It was that. A lot of times, it was like, “The reason all of this feels so hard is I haven’t been looking at the full picture of something. I haven’t realized what all of the data was. I didn’t see the black hole.” As soon as I say, “I’ve already been down that black hole. What’s at the bottom is blah, blah, blah.” They’re like, “Oh.” All of a sudden, it changes everything. That’s the piece. The decision becomes, I’m not going to say easy because, as I said, sometimes it’s like, “This makes sense. This is going to be hard.” It becomes more obvious.
That’s where the ease comes in. If you hadn’t said, I was going to say, what comes easier? That’s a marker, too. That’s a symptom of, “I’ve got the clarity I need.”
The thing I watched was energy and we talked about it all the time here. Energy is an important thing to stay aware of and it’s hard for us to do because we don’t have any super easy access, ready-made tools to help us track energy.
What do you think changes or shifts in how they evaluate their options? Coming off of Savvy Syndicate, you could see visibly how the energy shifted. You had a lot of benefits there being in person. What shifted and how did they evaluate their options?
It became so easy. That was the thing. There were things that they were like, “I don’t know if I should do A or B.” As soon as there was clarity on whatever the missing piece of data was, it was like, “I do A or I do B,” or it became very obvious for them, “I can do A and B. I was thinking these were in conflict but I just need to do A for a bit and then B for a bit and then A for a bit. Obvious is the right word. It becomes obvious. Even if they still don’t completely know, it’s obvious what their next step is. They may not know what the actual final-final decision is but it’s like, “The next thing I need to do is, blah.”
Speaking from personal experience, part of what makes a decision obvious is fewer options seem relevant.
That’s back to having that missing piece of data, which sometimes it’s actual data. We talked about a whole lot of things. We’ve got two full days. There’s a lot of time to cover a lot of things. One of them was, “This is the situation. This is hard. Their argument is X. Go check the data to see if what they’re assuming is true is actually true.” They don’t even have access to the real data so they don’t know. They’re just doing enough of their own feelings and I said, “It could be right. I don’t know but it could be completely wrong.”
Sometimes, it’s about getting the data. The actual tangible data but sometimes it’s about getting clarity. I think the term we like to use is a diagnostic saying, “I’ve been looking at it through this narrow lens. I just need to do this.” As soon as I change the lens by a few degrees and that’s that diagnostic piece. It’s like, “Everything becomes so much more clearer on what’s going on.”
Here’s what I think we all do. Founders do us a disservice if we think success comes from becoming a better decision maker. We say, “If you become a better decision maker, you make faster decisions. You make more right decisions. You did all of this stuff. It’s not so much about your becoming a better decision maker. It’s that you see everything, the situation clearly enough that the decision makes itself back to its obvious. Back to, you now have that clarity.
Again, going back to our readers. Here’s where you come in. If you’re reading and you’re realizing like, “I don’t think I’m clear on what I’m deciding.” The unpopular truth is that you can’t push through it. You cannot force your way through clarity. You have to step back and to your point, Gwen, change the perspective that you’re looking through so that you see it differently. As you mentioned earlier in the episode, the higher you go, the higher the cost of making the wrong decision. The cost of delaying your decisions is just as high. Sitting on the fence going, “We don’t want to do that because we might change our system.” That is expensive, too.
Addressing Indecision And Seeking External Perspective
My mom, who’s extremely wise, said this to me. It’s when I was being very indecisive, which is very highly unusual for me. She said, “You need to realize that not making a decision is also a decision.” Not that that’s a wrong decision. Sometimes, not making the decision is the right decision because maybe we don’t have enough data. Maybe there’s not enough things. In this case, she knew I wasn’t going to get any new data in another day, week, month or year than what I already had. There was no more new data to come in.
I had all of the information I needed to have. In this case, that piece was but holding off and circling the black hole using that thing won’t necessarily get us where we need. We need someone who can help us see into the black hole. Get us down on the black hole and help us figure out what that is. Sometimes, it’s not the people who are around you because back to often what’s in the black hole are your assumptions and your blind spots.
A lot of times, your assumptions in your blind spots is the whole confirmation bias that we’re seeing in social media and all of all of those things. They’re just going to keep seeing the exact same thing. Anyone you talk to. Be it your spouse, your best friend, your mastermind, or whoever. They’re often the ones seeing the exact same things but it is a confirmation bias. That’s one of the pieces. It’s to say, “Are the people that I’m working with or the things that I’m doing actually filling in this gap that we’re looking for to fill in to be able to make the decision.
Confirmation bias thrives in our blind spots. Social media—and even the people closest to us—can reinforce the same assumptions instead of helping us see what we're missing. Share on XThat’s the important piece. Honestly, usually the answer is no because if they were, you wouldn’t have that intuitive hesitation or intuition-driven hesitation. We are out of time. I’m just going to cut to the chase. I am going to say that if you want help getting clear on what’s going on before you make your next move because you just can’t push play.
There’s something holding you back. Hop on a call with Gwen. You can book your Clarity Call with her by going to www.tonyakubo.com/Clarity. It’ll be a 30-minute call. Tell her what you’re ruminating over and she will summarize the situation from her perspective. Let you know if there’s anything she sees that you haven’t considered. You’ll talk it through and then chances are you’ll know what your next step is.
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.
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