Episode 072

CEO Mindset vs. CEO Entitlement

I’m currently in the midst of my launch for my nine-month group program Wired for Wealth, so this is the perfect time to bring you two important concepts that I share with my clients. I call them the CEO Mindset and CEO Entitlement, and fully understanding them both is in service of the future of your business. 

When you started your business, you likely thought of yourself what you do. You were a Coach, a Copywriter, a Photographer, or anything else. That is the employee mindset, and most people are used to wearing that hat. However, if you want excel as the CEO, founder, and owner of your business, you need to also put on your CEO hat and elevate yourself as such.

Tune in this week to discover how to step into the role of CEO of your business. I’m showing you what your role should involve as a CEO and how to adopt the mindset required to be an effective CEO, without falling into a state of CEO entitlement.

What You’ll Learn from this Episode:

  • The difference between the employee mindset and the CEO mindset.
  • How we’ve gone through life with other people telling us what to do, but that needs to change when you build your own business.
  • The roles you need to take on as the CEO of your business.
  • What you can do to see where you’re stuck in the employee mindset, and how to elevate yourself to the CEO.
  • Why, as a CEO, you aren’t entitled to feel good about your business all the time.
  • How to stay out of CEO entitlement as you manage and grow your business.


  • If there is something specific that you want to hear or learn about money, business, marketing, or selling, send me an email!
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  • Irit Levi

Read the full transcript now

You’re listening to the Mastering Money in Midlife podcast with Debbie Sassen, Episode 72.

Welcome to Mastering Money in Midlife, a podcast for midlife women in business to overcome financial anxiety and make more money without burning out or sacrificing their families. Join Certified Life and Money Coach Debbie Sassen, as she shares practical business strategies and mindset shifts that help you dissolve the money blocks that keep you stuck in a cycle of underearning and undersaving, sabotage the growth of your business, and prevent you from building the wealth that you desire.

Hello, my friends, and welcome back to the podcast. I am, right now, as I record this, in the middle of my launch for my nine-month group coaching program, Wired for Wealth. And as I’m going through the process of my launch, and also some things that have come up with my clients in the past few weeks, I thought that this would be the perfect time to speak with you about two different concepts that I share with my clients.

One is the CEO mindset, and one is the CEO entitlement. I think that I’m going to start by defining the difference between what a CEO mindset is versus an employee mindset. Then I’m going to skip over and talk about CEO entitlement. And then, I’m going to speak about the higher-level CEO mindset. So, let’s jump in, first of all, discussing the difference between CEO and employee mindset.

Most of us have gone through our lives, until we become the CEOs of our business… I know for many people starting in business, and depending on where you are in your journey of growing your business, you very likely think of yourself as an employee, in the beginning of your business. And you think about yourself as the thing that you do.

You are a coach like me, or you’re a copywriter, a web designer. You can be a photographer, an author, a book publicist. There are titles that we give ourselves that sort of define who we are and what we do; more what we do, than who we are. We use those titles, and don’t elevate ourselves to becoming the founder and CEO and owner of our business. And, there’s a difference.

We have gone through life doing things that other people tell us to do. We are growing up in homes where our parents tell us to make our bed, to clean up after ourselves, put our dishes in the sink, put our dishes in the dishwasher, fold the laundry, walk the dog, do all the things.

And then we go to school and our teachers sit in front of the classroom, teach us our times tables, we learn history, we study for our English tests. And again, the teacher is telling us what to do, when the tests are, when we’re doing our homework. And then maybe we go to college, and we have a little bit more independence and authority over our own time. But still, someone else is telling us what to do.

And then you go into the job market. And again, someone is telling you what to do. They are setting the expectations and you show up. And if you want to advance in your career, make more money, earn a bonus, get commissions, whatever it is, then you work hard. And generally, you are satisfying somebody who is on top of you.

When you are building your business, you are on top of you. It sounds a little bit like you have to wear two hats, which you really do. I like to say you are the CEO of your business and you are the star employee. But most of us stay stuck into the employee mindset. We never elevate ourselves, or it takes time before we elevate ourselves to the CEO.

The CEO is the one who has the strategic thinking. Thinks about, what am I going to accomplish in my business in 2023? What are my goals? How much money do I want to make? This is why there are several podcasts, and you can look at the history of this podcast on setting goals, setting income goals.

You want to think about what you want to achieve this year, next year, three years out. I think it’s a little bit challenging to stretch our minds into five or 10 years with our businesses. You can definitely put a five- or 10-year plan into place. You can put a money goal in place, and I think that that’s a really good thing to do.

I think about my $10 million business, and it just lets my brain marinate overnight and months and think about you know how I’m going to get to that goal, but I don’t spend time in the moment thinking about how I’m going to create $10 million. But it’s definitely a target out there. It elevates my self-concept into someone who is thinking bigger.

When you start thinking about your business more strategically, you put plans in place. I share with my clients, the ones who work with me one-on-one and my clients who work with me in my program, Wired for Wealth, that we plan, in our businesses, with a long-term vision. And then we put foundational pieces in place every quarter.

You can be focusing in Q2, as this podcast releases, we’re just stepping into the second quarter of 2023, you can think about what business foundations you need to put in place now. Do you need to improve your marketing system? Do you need to improve your customer journey? Is there something that you need to work on for a sales page or a website? What are the foundational pieces that will make your business growth and scalability smoother?

You can then follow them up, get yourself out of the day-to-day running of the business, and again, go back to focusing on who your clients are, how you can serve them better, and your business growth.

The CEO always has that sort of 30,000ft view, right? You’re looking at the entire picture. And with that entire picture, you’re putting plans in place. Also, as the CEO, you are the one, especially when your business is smaller, you maybe have one employee, three employees, five employees, even I think when you have 25 employees, the buck still stops with you as the CEO.

But when you have, let’s say 25 employees, you’re going to have some managers underneath you who are managing the people below them. But until you get to that stage, as the CEO, you are also one who’s doing, for lack of a better word, the dirty work underneath, right? You’re the one who’s taking out the garbage. You’re the one who is cleaning your computer. Maybe you have a cleaning lady, but you’re the one who’s doing the practical pieces of the business.

This is where I want to take a break, and I want to move over to the CEO entitlement. If you are in business, and you are at the stage where you have already hired people to work for you. Maybe you have a virtual assistant, you have somebody doing social media for you, you have people who are doing some of the work for you. Maybe you have even made orders for some of your clients.

This happened to one of my clients who made an order on behalf of one of his clients and that order got stuck in a warehouse. What happens when you’re in CEO entitlement is that you’re expecting that things will happen, and you’ve sort of outsourced it without taking responsibility for what is happening to your end-user. Meaning, to your client or to your customer.

And if things aren’t going smoothly and going your way you spend your time spinning in frustration and annoyance. This shouldn’t be happening. Why is everything falling apart? Why isn’t the tech working? This actually happened to me in my launch for Wired for Wealth.

I had a signup page for Money School. You might remember that a few weeks ago, I did a three-day training called Money School and I had a signup page on my website. But people were signing up and those signups were not going automatically into my email system. I wasn’t able to capture all the names and send them the Zoom link for the three-day training.

There was a tech hiccup, and I’m not a tech person. My VA was off because she’s in the United States, I’m in Israel, our hours are different. And I knew that it was a problem that I needed to solve. She was unavailable, and I think that it might have been just a little bit above her technology.

But I quickly reached out to someone, one of my clients, Irit Levi, who is a tech expert and a systems strategist. And I asked her to help me figure it out. I took responsibility for this tech hiccup and got the problem solved.

When you are operating from entitlement, you are expecting everything to happen without you taking responsibility, without you taking charge. And I’ve seen this with a couple of my clients recently, with their employees. It could be a virtual assistant who got sick. People get sick, this is something that happens in life. But spending time being annoyed and frustrated that every week she had another doctor’s note and another doctor’s note and another doctor’s note and things weren’t getting done. It was frustrating.

My comment to my client was, “Hey, as the CEO of your business, you are not entitled to feel good about your business.” I left it there, full stop. I could maybe soften that by saying, “You’re not entitled to feel good about your business all the time.” Because sometimes in our business, I do believe that we feel good, and we feel excited, and we like the work that we’re doing, and we enjoy working with our clients.

But there are the times that we have tech hiccups, or we’re expecting someone to do something in our business, and they’re just not happening. When you have a bigger business, with more employees, you can make sure that there’s an overlap between your employees. So, if somebody has an emergency medical issue, or you have an employee who is off on maternity leave, or just life happens, then there is somebody who can fill in the blanks and get things done.

But unless you are really, really strapped for time… Let’s say your assistant can’t work, and you also have a medical issue or a family emergency or something like that, right? That could be the perfect storm. You, as the CEO of your business, are not entitled to feel good and to get frustrated when other people are not doing their jobs.

First of all, you’re doing the hiring, and you’re doing the firing. And we can talk about hiring and firing in another episode. But really, you always have to remember that the buck stops with you. Your responsibility is to make sure that your clients get serviced, that whatever you promised them gets delivered on time. And sometimes that means we have to make tough choices in our business.

If there is a pet project that you would like to do, and I have this with one of my current clients in Wired for Wealth. She has a pet project that she wants to grow and develop. She knows that the long-term profitability of this product is very, very positive. And at the same time, she has a lot of client deliverables that needed to be fulfilled before the Passover holidays. So, there was this sort of rush energy inside of her. And this product would be also perfect to sell before Passover.

My coaching to her was, “Yes, if you think about the long term of your business, this product will also be available after Passover. The next time there are Jewish holidays, you will be able to sell it. The summer holidays are just coming up, it will be valuable then. Just look at your clients that you have right now, who are waiting for you and waiting for their deliverables. If you want people to love you, to recommend you, to refer out business, take care of your current clients now and make sure they get serviced.”

That’s where we’re going to talk about the CEO mindset. The CEO remembers that she or he is the one in charge. That you have to make sure that your systems and processes are moving smoothly; that was my hiccup with my tech. You have to make sure that your customers are getting serviced. That you’re maintaining communication with your customers. That if you go away for three weeks on holiday, your clients know ahead of time; you send them emails. You’re allowed to go on holiday.

I had this last summer, with some of my clients. I’m like, make sure that your clients know that you’re going to be away. If you’re going to be available to take care of emergency situations, let them know. If you’re traveling abroad, let them know that there might be a time gap. If somebody is filling in for you, give them the email of your assistant or the second-in-command.

Maintain communication with your clients, it is the most important thing. Because your clients today are your ambassadors for tomorrow. That is the way a CEO thinks.

Again, you are not entitled to feel good in your business all the time. It might feel uncomfortable to tell your clients that you’re going away on holiday for three weeks. I don’t know why it would feel uncomfortable. But some people do feel uncomfortable, as if, as the CEO, we think that we have to show up and serve our clients 24/7.

They’re allowed to go on holiday. They’re allowed to not respond to us right away when they’re away. But for some reason, we have this thought error, “No, no, no. I have to be available to service my clients all the time.” Boundaries are very important. You are not available 24/7. You’re not available even 26, if you are offline on the Sabbath like I am.

You are available during normal business hours. And as the CEO, you manage your clients’ expectations, and you let them know what’s happening. That means also, if you’re working on a longer-term project; and some client projects can be a six-month project, a nine-month project. One of my clients is an interior designer and she has multi-year projects.

You want to make sure that your clients are always kept in the loop. That they don’t think that you’ve ghosted them, you disappeared, and they haven’t heard from you for four or five or six months. Stay in touch with your clients. They are your best ambassadors for all of your future clients.

Back to the CEO mindset. When you’re thinking about your business long term and the strategy and the planning for your business, now you see how satisfying your customer, how your clients’ journey and the way they interact with you, how that is also a part of your long-term strategy.

We will all continue to market our businesses. Let people in the world know that we’re open for business, and we have something beautiful and wonderful to share. Just think about, part of your marketing strategy is satisfying today’s clients, because they will go and do all the marketing for you, no cost. You don’t even know where it’s going to end up.

But also think of them, besides wanting to satisfy them and make them happy, but they’re also part of your long-term planning. So, take care of your current business, in service of your future business.

And remember that sometimes, as CEOs and business owners, we do uncomfortable things. Things that we thought we outsourced to someone who’s better suited to do our graphic design or to be a social media manager or to be a virtual assistant, because that’s not our unique genius in the world. That’s not our creative genius in the world.

So, you either have to figure it out yourself, or you have to hire somebody quickly, to get the job done. And I will just make a point that if you have to hire someone quickly, it’s an emergency hire to get something done, like I had to do with my tech, it will almost always be more expensive. People pay for speed.

Just think about wanting to send a letter from A to B. You can send it by the regular postal service, and it’s going to cost you a dollar or two. If you want to send that same document by FedEx or DHL, it’s going to cost you multiples of what it would cost by sending it through the post office. You’re guaranteed quick delivery.

And you’re guaranteed that under normal circumstances, not national disasters, under normal circumstances, your package will arrive with FedEx, where it might not always arrive with the postal service, especially in Israel. Sometimes we have issues with their postal service, but we’re not going to be talking about that today.

That is what I would like to leave you with today. Look at yourself in your business. How are you managing your business? Are you in a frustrated, annoyed, ‘woe is me’ situation, where you’re thinking that everybody around you should be taking care of certain bits of the business and you’re just spending your time spinning in frustration and annoyance? That is not very useful. It’s not very efficient. It doesn’t have a great return on investment of your time.

Or are you saying to yourself, “Yeah, this is uncomfortable. I wish it weren’t like that. I’m the CEO. I’m in charge. And I’m going to go pull up my bootstraps and I’m going to get it done.” That’s what a CEO does; a CEO gets the job done.

Thank you for listening in my friends. I wish you a beautiful day. I will see you next week. Bye for now.

Thanks for listening to Mastering Money in Midlife. If you want more information on Debbie Sassen or the resources from the podcast, visit MasteringMoneyInMidlife.com.

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