Episode 118: Overcoming Self-Doubt, With Brett Gilliland

When your business is growing at a rapid pace, you may feel like you’re barely hanging on. Although you’re on the path to taking your company to the next level, you question if you have what it takes to get it there. In this solo episode of the Elite Entrepreneurs podcast, you’ll learn strategies to help you reduce your self-doubt and become a better leader.


Trying to find the time to develop your leadership skills can be frustrating when you’re also trying to run a successful business, but the payoff is worth the effort. Learn how even a few minutes of leadership development work each day can make a dramatic difference in your relationships and your success as a business leader.

What You Will Learn:

  • What to do if you have self-doubt about your ability to lead
  • How to remove any negative labels you’ve placed on yourself
  • What statements help you rewrite the script in your head
  • What 3 strategies can you implement to become a better leader
  • Why you shouldn’t expect to be the leader your business needs next year

About Brett Gilliland
Brett Gilliland is Founder and CEO of Elite Entrepreneurs, a company that specializes in giving $1M+ business owners the knowledge, processes, and tools to grow to $10M and beyond. Brett is an expert in organization development, leadership, and strategy and spent 10 years helping Infusionsoft grow from $7M in revenue to over $100M. Brett was involved in the foundational work of Purpose, Values, and Mission at Infusionsoft and facilitated the strategic planning process for many years.

One of Brett’s favorite professional accomplishments is co-creating Infusionsoft’s Elite Forum along with Clate Mask and building the Elite business inside of Infusionsoft. As the leader of the Elite business, Brett has helped hundreds of struggling seven-figure business owners overcome their biggest challenges and achieve new levels of success. He also played a central role in the development of Infusionsoft’s Leadership Model and was serving as the VP of Leadership Development when the decision was made to spin the Elite business out of Infusionsoft. As the new owner of Elite Entrepreneurs, Brett can’t think of anything else he’d rather be doing professionally. When Brett isn’t busy helping $1M+ businesses succeed, he is a family man who enjoys spending time with his beautiful wife, Sharon, and their 8 children.


Listen to the podcast here

In this episode, I have the opportunity to share what I call a solocast. I get to share with you some of my thoughts, some things that have been present for me, and that I think will be helpful for you as a seven-figure business owner. Here are my thoughts on this episode. This starts with a conversation that I had. I talked with a good friend who’s a business owner and he used a phrase that triggered a question in me.

Here’s the phrase. “How are things going,” is what I asked him and he said something like, “I feel like I’m hanging on by my fingernails.” If you picture it with me, somebody who might be hanging on the edge of a cliff by his or her fingernails, that’s the image that came to mind for me when my friend said that. Naturally, I was curious and I wanted to dig in a little bit. I said, “Tell me more about that. Why are you feeling that way?”

What he went on to describe was that his team was larger than it had ever been. They are now up to twenty people. He hired two people that maybe were a little higher in salary than previous hires had been. He was starting to feel like things were changing. “The business is growing, and I’m not sure if I’m a good enough leader to lead this business where it feels like it’s going or where it could go.”

He didn’t use those words specifically but that was the feeling of it as we were unpacking that together. It was like, “I don’t know that I have what it takes or I’m not confident that I am who I need to be in order to lead this thing to where I see it going or where it could go if I were a better leader.” There’s a lot of there was a lot of self-doubt in there. There was wondering in my enough of a leader. There was concern about the growth overtaking his ability to lead.

We talked about that a little bit, and I tried to give him some help. I felt like this was not a unique occurrence among business owners that I have worked with now for the past several years. I often come across this sentiment that I don’t know what I’m doing. I have never done this before. I think every business owner knows to some extent we are making it up. We are figuring it out as we go, but the stakes grow larger. The stakes get higher and higher as the business grows.

Every business owner knows to some extent, we're making it up, we're figuring it out as we go. But the stakes get higher and higher as the business grows. Share on X

We then start to feel this mounting pressure like, “If I didn’t know how to be a good leader at $500,000 in revenue and a few people, I certainly don’t know how to be a good leader now that we are at $1 million and we have 8 or 10 people. Maybe we have stretched that to $2 million and we have got 15 or 18 people. I don’t know what it’s like to lead a growing team. I have never done that before.”

It starts to feel unfamiliar, and our brain is warning us, “Danger. This is unsafe. We have never been in this territory. You don’t know what you are doing,” and the little voices of doubt start to creep in and not at you. A lot of times, it feels like a weight on you. It’s not just a little noise or chatter in your brain but some actual physical heaviness on you, on your shoulders, or your chest, or specifically, on your heart. You feel the weight of it all and the uncertainty of how to lead confidently as this thing is growing beyond what you feel are your natural abilities.

I want to emphasize this. If you felt anything like that before, that’s completely normal and understandable. You haven’t been there before. Our brain is wired to protect us from new things or things that might be perceived as scary. That’s normal. You are in a normal place. However, what I want to talk about in this episode is how to overcome that self-doubt. How to be moving in a direction of more confidence, more security, and more feet planted squarely on a solid foundation.

I want to talk about the effect of what I will call head trash. We used to joke about that as the term when we talked about this at a fast-growing software company where I worked for several years. We grew fast and many of us had never been where we had grown the thing. How do you lead and organize work at that level? We grew to $100 million. It was different at $10 million and it was different at $30 million.

All along the way as we were moving through the stages of small business growth, the landscape was shifting or the size and scale of the ship we were steering was getting out of our control, or at least it felt that way at times. We had to continually level up our leadership. We had to get some help from the outside. We had to continue to push ourselves to be able to continue on that growth path.

What I want to talk about is the nagging and ever-present doubts that can be in the back of our minds. If we are not careful, we are not aware of them, they will keep us back. Here are some things that I would recommend you can consider doing if you have any of those thoughts of, “I’m not enough,” self-doubt, or whatever you want to label them. The thoughts that say, “I don’t know what I’m doing,” or, “You don’t deserve to be here,” or you can’t figure out how to keep going forward.

If we're not careful, the nagging ever-present doubts that can be in the back of our mind will keep us back. Share on X

If you have any of those thoughts, first, we need to be aware of them. We need to be clear that those are labels that we are using on ourselves and those labels are shaping the way we show up. I will give you another very real-time example. This conversation spawned out of the conversation I had with my friend. I also had another conversation with a valued resource in our life. My wife and I have a parenting coach. We have several children and some of them have unique needs. Even if they didn’t have some unique needs, we are not perfect parents. We have a parenting coach and it’s awesome.

This parenting coach is good at helping us see some of our labels about our parenting, some of the unhealthy, or unproductive thoughts, and negative things that go on in our brain about our parenting. One of those for me that we talked about was, “I’m not a fun dad.” The coach said, “Tell me about that. What does it mean to you to be a fun dad?” I tried to describe it. “I think that means I do fun things that I’m spontaneous that maybe it bleeds over into how affectionate I am or do I cuddle with my kids and show hugs and physical affection to them.”

I’m using all of these descriptors in my mind about what I think is or is not what a fun dad is like. I went through those descriptions and then the coach very competently asked me to talk about times when I feel like I have been a fun dad in the past. “Tell me about a time when you were fun.” I told her about something that I had done. She said, “That sounds like that was fun.” I told her about something else. She was like, “That sounds like that was fun.”

She methodically shot holes in a fundamental belief that I have in the back of my head that’s not a very conscious belief where I go around saying, “I’m not a fun dad,” but I do have that thought back in my mind. Guess how I show up with my kids most of the time when I’m coming from a place of, “I’m not a fun dad.” You guessed it. I do things that aren’t that fun. I might see some of their childish or young people’s behavior as being annoying like leaving stuff out or doing something to a sibling.

They do things all the time that are “childish” but they are children. That’s what children do but I might view that as more annoying if I’m coming from a place of, “I’m not a fun dad.” Whereas, if I’m coming from the place of, “I’m a fun dad. I know how to be fun.” I would turn those same circumstances into very different outcomes by the way that I show up, the things that I do, and the things that I say.

Our thoughts are very powerful and if you are thinking in yourself and your mind, “I’m uncertain. I don’t know how to lead from here. I don’t know that I can do this. I have never done this before. I’m an imposter.” With all these types of thoughts, then you are going to show up that way in your leadership and you are going to artificially constrain what you could do if you would get rid of some of those things.

EEP 118 | Self Doubt

Self Doubt: Our thoughts are very powerful. If you doubt yourself, then you’re going to show up that way in your leadership and you’re going to artificially constrain what you could do.


What are some ways we can overcome this? The problem is pretty clear that most of us, not many of us have some of those challenges. What can we do to change that? First of all, we can employ something that a coach taught me. His name is Steve Hardison. He’s The Ultimate Coach. He is an amazing human being and fantastic at his craft. He taught me this concept of the presidential pardon.

He said, “The president of the United States has the ability to pardon criminals to set them free. They could be guilty of the most heinous crimes sitting on death row at some state penitentiary or state prison, and be pardoned by the president of the United States and they would walk free.” That’s a powerful pardon. He said, “Use the presidential pardon on some of these self-imposed labels, some of these labels that you have created for yourself over time. It doesn’t matter how long they have been there. If they are unproductive labels that you have about yourself, identify them and then let them go. Presidential pardon them.”

“I forgive myself for judging myself as being a no-fun dad.” We rescripted. He taught me this way to rescript. He said, “For the new truth is, I am a fun dad. I do things that my kids enjoy. I make my kids laugh.” Whatever the new label needs to be, we have full power to rewrite that script. “I forgive myself for judging myself as, fill in the blank, of the unproductive thought or label that you have for yourself.” That’s the presidential pardon. It’s gone. You never have to bring it back. “For the new truth is,” and the rescripted new truth. It’s the thing that you want to write about yourself.

I’m not naive enough to think that one presidential pardon makes that long-formed habit or that bad thought in your mind go away that easily. The job from then on is a little vigilance. If you ever notice that thought coming back, you say, “I forgive myself for judging myself as being a bad dad or an unfun dad, but the new truth is.” We are rescripting over and over and over. The other related concept to this is a concept of creating I am statements where you intentionally say, “I am a fun dad. I am that I have a personal meaningful relationship with each of my precious children and they know that I love them unconditionally.”

That is one of my I ams that I have said to myself once a day in at least the last few years. That is one of my lengthy, but true I am statements. I say that every single day. What you will notice in that I am statement is it doesn’t say, “I’m fun.” I have got to work on that one myself but this is something we can all utilize. At the same business, I referenced where we grew fast over several years. We kept growing.

I worked with an amazing human being who’s the one that introduced me to this coach who was coached by Steve Hardison many times. His name is Clate Mask. Many of you have heard me talk about Clate. You have also probably heard me say this, but I’m going to say it again because it’s very relevant to this conversation. Clate would go around saying, “I am not the CEO. This business needs me to be twelve months from now. On this day, I’m not the CEO the business needs me to be twelve months from now because we are growing fast and twelve months from now, we will be at a new place.”

He would then go on and say, “You can count on the fact that I will be when we get there. I may not be the CEO today that the business needs me to be twelve months from now, but by the time we get there, I will be.” That was his public declaration of a personal commitment to continue to grow himself. What does that look like? How do you become more confident in your leadership?

I’m going to share three ways, three precious resources or strategies that you can employ to become a better leader. The first one has to do with how you spend the precious asset of time. If you are a go, go, react, react, respond, respond, and do, do throughout the day, all day every day seven days a week, you are never going to become the leader that you need to become.

You are going to be good at getting a lot of stuff done and your set of leadership capabilities. If you want to keep growing, you have to carve out some time on a consistent basis to do things like read a book, listen to a podcast, read some articles, or go to a CEO group. Become a member of a CEO group like Elite Entrepreneurs. That’s one of the things we do. If you are looking for a group like that, you should come to check us out at GrowWithElite.com.

EEP 118 | Self Doubt

Self Doubt: If you want to keep growing, you have to carve out some time on a consistent basis to do things.


You can join a group. You can go to events. There are ways you can use some of your precious time to intentionally invest in your development as a leader so you can get rid of some of those thoughts that might be holding you back in your mind. The second strategy or resource you have to employ to become better in your leadership is money. Are you spending money on books? Are you spending money on CEO or leadership membership groups? Are you spending money on events? Are you spending money on coaching? How are you employing the valuable resource of money to work on your leadership development?

The last thing that you can do is ensure that you hang around and that you surround yourself with great people who can help you get where you want to go. These might be mentors. They might be coaches like we have already talked about. Maybe it’s hanging out with peers in a community like our Elite Momentum Community here at Elite Entrepreneurs.

Whatever it is, you can find people who are in a similar space as you in terms of their development and their company growth and/or preferably 1 or 2 steps ahead of you. You do not want to be the smartest person in the room. You don’t want to have the biggest business in the room if you join CEO groups or masterminds or leadership development programs. You want to be around some sharp peers.

Some people in your shoes will put together what’s called a Little Advisory Board where you get people who are 1 or 2 steps ahead of you. Maybe you give them a little bit of equity in your business or the opportunity for some equity in your business if they help you grow over the next few years. You assemble a group of 3 or 4 key advisors like that. There are lots of ways to do it. You can be creative around it but who are the people you are surrounding yourself with?

You are the average of the five people you hang out with the most. I paraphrased it. I didn’t give an exact quote. There are a lot of people who have said something similar to that truth and that is true. If you hang out with people who are going to push your thinking and your ability as a leader, you are more likely to get there but if you hang out with people who aren’t looking to become better leaders. Maybe they are not even leaders at all.

If you hang out with people who are going to push your thinking and your ability as a leader, you're more likely to get there. Share on X

You need to be looking to hang out with other business owners who are working through similar challenges or preferably have gone through similar things that you can learn from. In summary, you are capable of doing what you are doing. You wouldn’t be in the spot that you are at right now if you aren’t capable. You have built something amazing. Seven-figure business owners are elite. You represent the top 3% to 5% of business owners that ever started a business.

If you have gotten to $1 million or more in revenue, you are elite. You are doing something right. You got to be not so hard on yourself. Also remember, if you have some of that head trash going on, it’s time to take out the trash. It’s time to give some presidential pardons. It’s time to rescript some of that and then it’s time to get to work. It’s time to work on yourself as a leader. It’s time to surround yourself with other people. It’s time to carve out time in your calendar and to dedicate some budget to this, and make sure that you are getting the help that you need so you can feel confident to lead your business into the future.

EEP 118 | Self Doubt

Self Doubt: If you have some of that head trash going on, time to take out the trash time, to give some presidential parties. It’s time to restrict some of that. And then it’s time to work on yourself as a leader.


I hope that’s been helpful to you. I mentioned it a couple of times. This is what we do at Elite Entrepreneurs. We help business owners like you make that seven-figure mark and then start to bump into some walls. Whether that’s a growth ceiling or that’s a confidence feeling in your abilities to keep going, that’s what we do. We help you with not only the methods, some of the mindset, and we give you the tools and the examples to be able to do the business-building work that will allow you to move forward as a capable and confident business building business owner or CEO. We want to take you from a $1 million entrepreneur to a $10 million CEO and it’s less about the revenue. It’s more about the mindset, the confidence, and the ability as a leader to lead a growing group of people to take targeted and coordinated action to achieve some cool and big things together.

I hope that you will keep reading our episodes. We are fully dedicated to helping as many seven-figure business owners as possible do this business-building journey and your mindset about your abilities plays a huge role in how you show up. Please keep reading. Share, review, or like. Do all the things that help us reach as many business owners as possible, and we will see you next time.


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