Growing Your Entrepreneurial Mindset with Jeannie Andresen

Hey goal achievers, Kristin here. Recently, I was fired up to connect with Jeannie Andresen on the Elite Achievement podcast. Jeannie is a coach who grew up in the Chicago suburbs. She spent nine years in the financial services industry and was a sales coach for interns and recent college graduates for six of those years. That is where she first fell in love with coaching! While she was in the industry, she grew her leadership skills and went from an intern herself to a coordinator, to a campus recruiter, to an associate director, and then finally, director! Jeannie attributes her success to always having an entrepreneurial mindset. Even when she was an employee, she rarely felt like she worked for anyone but herself. Jeannie felt like she needed to make a change in her career and transitioned companies right before the pandemic. However, as the pandemic hit, she lost her job, turned inward, and ultimately thought maybe this was meant to happen!

I start our conversation by asking Jeannie to share more about her business and how she got started.

“I run a coaching business,” says Jeannie. “I help women take action on the dream businesses that have been on their hearts for years, and just need the courage and the guidance to do it! I was with my former company for nine years, and it happened to be the company that connected you and I. We both worked there, but of course, you over in California and I was in Chicago. I really loved leading my team, and I worked my way up. I was committed to what I was doing, but there was a point where I had recognized that I needed to make a change. I had been there for enough time, and I didn’t feel myself following my heart anymore. I knew that I needed to get uncomfortable and experience something new to figure out who I am and what I wanted next. The best way to do that was to make a career transition, and so I did! I transitioned industries from financial services to tech, and I made that transition on March 13th of 2020, which happened to be a Friday the 13th, which also happened to be doomsday when we recognized that this pandemic was hitting and everyone was going remote! Within one month, I had lost my job. I went from being with a company that loved me, who I loved as well, for nine years with a very, very secure position to taking a leap of faith, joining a new company, and losing my job one month later due to unforeseen circumstances.”

Jeannie continues, “In that moment, for a day, I was in a little bit of shock and mourning, and the next day I said, ‘This is for a reason, and I’m going to figure out what that reason is!’ I spent a couple of months not jumping into anything else and instead focusing on myself and what I wanted. What I wanted more than anything was to start a coaching business – I wanted to help women develop their entrepreneurial mindsets. With my background in sales coaching and essentially helping small business owners start their businesses, I realized I wanted to help women specifically start their businesses and recognize their power.”

Listening to Jeannie’s story prompts several questions. First, she made a courageous career transition leaving a company after nine years. She probably had thoughts of, ‘What if it doesn’t work out?,’ and yet she worked through that fear, made the leap, and then the worst came true. I ask Jeannie how she found the courage to persevere and pivot after being let go from the tech company.

Working through Fear: What to Do When the “Worst” Comes True

“It’s a fantastic question,” Jeannie responds. “Here’s my answer – and it’s twofold. To be honest, I’m grateful to be blessed with confidence. I really didn’t think it wasn’t going to work out – I have always had the mindset that I will figure out something new when it comes my way. So, when I made that transition into the tech industry, I only went into it intending to grow in a new industry. I never really made that decision with fear in mind. I made it with my best intentions to get uncomfortable by switching industries and growing an entirely new skill set. It’s obviously where our world is going, and I was very excited about learning tech. It’s funny that it didn’t work out, but I wasn’t really afraid of that. When it didn’t work out, that was definitely a surprise, but I always channel my favorite book when something doesn’t go according to plan.”

Jeannie pauses then shares, “My favorite book I’ve ever read in my life is called The Power of Now, by Eckhart Tolle. In it, Eckhart states and educates the reader that whenever something happens in life that is unexpected in a bad way – really difficult circumstances – the best way to deal with that is to accept it as though you have chosen it yourself. And then, all of a sudden, the universe will work for you and not against you. I encourage anybody dealing with something tough to hear that and feel that because ever since I adopted it about three or four years ago when I first read it, really wonderful things have come my way just from accepting the bad things that have occurred. I say to myself, ‘How can I accept this as though I chose it myself?’ because that way, things will begin to work for me and not against me. So, the next day, I said to myself, ‘Okay, I am grateful that this has happened. I will figure out why.’ And that led me to start a business much, much sooner than it would have if I would have resisted it and pushed it away. The faster that you can get over something by accepting that it has happened, the faster you will get to beautiful things that are coming your way.”

I heard Jeannie say that she didn’t go into the career transition from a position of fear, which is incredibly powerful because I know many people make decisions from fear. I also heard her say that The Power of Now changed her life because it provided a perspective and way to process the bad things that happened. Because let’s be honest, bad things are going to happen – unpredictable things are going to happen. I think 2020 taught us all that we have far less control than we thought we did. I’m curious, is it really that simple? Can we simply say to ourselves, ‘I accept this?’ and ‘What am I going to do about it?’ 

Jeannie jumps in, “Oh my gosh, I feel like we need another podcast about this. But to sum this up in a couple of minutes, it is an elevated version of mindfulness to accept things that happened to you sooner. It takes meditation and affirmations to rewire your brain to recognize the good that is happening, bring you back to the present moment, and recognize what’s actually happening versus fear. It takes practice. It really takes practice. And you have to want it too. Eckhart has another great book called A New Earth, and I would recommend that one too. But what happens is, our egos get in the way. And our egos are saying, ‘How could this happen to me? Why me? This isn’t happening. I deserve better. I deserve more.’ And that doesn’t make any sense. Who are you to say something should or should not happen to you? Or that something should happen to other people? It’s recognizing that all of that comes from our egos in a different sense than the traditional usage. Once you recognize that a lot of these things are thoughts going on in your head and not reality, you can tackle them with much more clarity. If I could add one more thing, I would say that to get to a place to make a decision courageously and not with fear, it took affirmations when I switched companies. I reminded myself daily that I wanted to live my life based on curiosity and courage rather than fear. And when I recited that to myself – daily during my career exploration – it made it much easier to decide to move forward because I want to be somebody that is courageous.”

I appreciate that answer so much because it connects back to the power of a morning routine. We don’t know when we are going to be called to lean on this mindset. And that’s why we need to focus daily on our affirmations, vision statements, gratitude, meditation, whatever it is, that gets us in the right mindset. 

As we are thinking about mindset, the entrepreneurial mindset comes to my mind. I ask Jeannie to share how she defines an entrepreneurial mindset and how we can grow our entrepreneurial mindsets. 

The Benefits of an Entrepreneurial Mindset

“In my nine years with the company I was with and beyond,” says Jeannie, “I attribute my success to always having an entrepreneurial mindset from the beginning. Even when I worked under ten people, I never was truly concerned about that. I never showed up as an employee. I showed up the best that I possibly could because of this mindset that I had of being a business owner. And as I grew in that company and started leading a team, I just saw a difference in my team members and how they showed up, as opposed to other people who showed up as employees. That is why I love leading, and I love leading women, because when someone has this type of mindset, they show up differently. Having an entrepreneurial mindset as an employee matters. An employee might be listening to this thinking, ‘But I work for somebody else. I am not in control of my schedule or what I do on a day-to-day basis. And you know what, I am salaried. I don’t get to choose my income either. So how in the world can I show up as an entrepreneur?’ And here’s what I would say back to that – sure, that might be the case on paper. But if you show up feeling as though things are in your control, with confidence, and with a mindset that you are a business owner, all of a sudden, you begin to make decisions with more confidence. You begin to come up with solutions versus look at problems and wonder how in the world these are going to get solved and give them to somebody else. You become experimental because you are figuring out what’s going on and what works for your business. And yes, I’m saying your business even though you’re an employee because I really believe that every single person out there who is an employee – they are the owner of their freaking business of whatever their title is. It’s also studying your area. It’s saying, how can I get even better at what I am doing so that I have more control and more confidence to make decisions?” 

Jeannie goes on to share what she has found when people show up with an entrepreneurial mindset. “What often happens is this person recognizes whether or not this is a business that they want to be showing up for day after day after day. And you and I both know, Kristin, given that we are business owners, if you don’t love what you are doing, it’s never going to work. And the reason why I always empowered my team to adopt an entrepreneurial mindset is because I wanted people on my team that loved what they did and who felt that they were in control, not that they were employees. So, what that caused my team to do was either grow in their role and become even better leaders themselves. Or, I would coach them – I guess you could say coach them out sooner – which allowed me to find that person who was showing up as a business owner every day. So, when you show up with an entrepreneurial mindset every day, you all of a sudden recognize if you love what you’re doing. ‘Is this something that feeds me, is this something that I’m growing in, even just in myself – in my own mind and body?’ Or, ‘What’s another job that I can feel that way about?’ And that’s how an employee can have an entrepreneurial mindset and how it can really transform them. Because I am telling you right now, I wanted the people on my team that had this mindset because they just showed up differently.”

This is such a powerful discussion for anyone that is working for someone else. One of the lessons I learned early in my career was from when my leader would tell me, “Kristin, don’t just come to me with a problem. Come with a problem and a couple of ideas on how to solve it.”

“Yes,” Jeannie agrees. “You get creative and bring solutions to the table, and all of a sudden, when you start doing that, you are more empowered to make these decisions sooner. Especially with time in your career and job and with more trust from your boss. I’m telling you right now, every single boss/manager/leader out there wants a team that can make all of the decisions without them. Every good leader wants that sometimes. I think that employees – people who think of themselves as employees – don’t recognize all we want as leaders is for them to step into their power and be the best that they can be, and the only way you will get there is by starting here. And by gaining more confidence from the solution you brought to the table. When your leader says, “I think that’s fantastic, I would have loved for you to have just run with that,” once you hear that a couple of times, you will start gaining confidence to start running, and it is incredible for your growth as an employee who may one day be an entrepreneur.”

I ask Jeannie to share a couple of things an employee can start doing to grow an entrepreneurial mindset.

How to Grow Your Entrepreneurial Mindset

“Great question,” Jeannie begins. “The first thing is to step into the control that they have. A lot of people lean on things being out of their power, and that is a crutch. Everything is out of my control, sure, but what is IN your control? Is everything going on inside your head? And how do you show up day after day after day? If you begin to show up thinking, I have the power to make decisions, come up with solutions, and have confidence in what I have already brought to the table – in my experience, you are choosing to show up differently. Truly, you have to decide if this is something that you want or like to do. Do you just want to show up, clock in and clock out, and in that time feel like everything is happening to you? Or, do you want to show up feeling like you’ve chosen to show up that day and that when things come your way, you will take care of them? That you are the best that you can be in that role and that you are committed to what you’re doing? If you choose that, then it is a mindset thing – it’s showing up and saying I have control over how I show up. Life is about showing up.”

When I was an employee, I heard “successful” people. And as I look back, everyone has their own definition of success and how they perceive success. But, at the time, these people were very successful in my mind, and I always heard them talking about reading or having a personal development plan. So, I leaned into those recommendations and became a very avid reader and now always have a list of books to read. I think the Power of Now will go on my list to read based on our conversation, but that’s another way that employees can take control. You have the opportunity to control your personal growth and development. And because of that, you are going to find yourself in a wildly different position several years later, which is where we both found ourselves – now running businesses. I ask Jeannie to tell me more about the company that she launched last year and the work she is doing to help women grow their courage.

Launching a Business: From Employee to Entrepreneur

“What made my transition easier going from employed to unemployed to business owner,” says Jeannie, “was this mindset that I was always a business owner. I always created my schedule, focused on my priorities, and followed my heart. And for the most part, that is what I would say helped make some of these decisions. The other part was on my heart for years, and that was becoming some sort of professional coach. I aspired to be more of a life coach early on. And I say that with a little bit of hesitancy. Because I also feel, even though I am helping women start businesses, my life coaching comes in almost more than my business coaching because so much of what holds us back is our mindsets. It is a limited belief, thinking it is avoidance of making mistakes or getting uncomfortable. But we don’t know that. I hired a coach when I was making this career transition a year and a half ago because I recognized that I didn’t love where I was. I had just turned 31, and I hired a coach. And my exact words to her were, ‘I want a different life by the time I’m 40.’ And I invested in a coach because it was more important to me to put money in and to invest in myself in that way to change my trajectory, to break through any avoidance and unexamined fears that I didn’t even know I had. All I know is I wasn’t taking action because I didn’t know what action to take. And it was invaluable to make that decision to invest in myself in that way. Because what happens is you start recognizing what truly is holding you back. And you recognize that it is a lot of things that are only existing in your head. And once you get clear on that, you can find out what things to tackle, but we don’t know what those things are until we’re talking about them. So that would be the other thing that helped make that transition to business ownership and helping women start businesses.”

Jeannie continues, “The issues we deal with internally come up almost more than my business coaching expertise and tactical next steps to get started. It is all about mindset because anytime we’re talking about the next steps, something is holding somebody back. And it’s examining what that is and knowing the right questions to ask to get them to talk about it. And that is how I help women to break free of comfort and fear.”

I remember I hired a coach a couple of years ago to grow my confidence because I knew that the stories I was telling myself and how I was ruminating and weaving things together were not helping me grow and get to that next level. What was also really helpful in my own journey was learning that I wasn’t alone. Sometimes as women, we think we’re the only ones having these crazy thoughts or the only ones who are really mean to ourselves, and that’s not true. That’s where investing in yourself and having the opportunity to have conversations with professionals like a coach can be absolutely game-changing. I’m curious as Jeannie is working with women and helping them launch a business; what she would say are some ways to grow our courage.

Grow Your Courage: It Starts with Mindset and a Plan

“The first one,” Jeannie starts, “is again going to be mindset, because when somebody wants to launch a business, usually, they have been thinking about it for forever, and something has held them back from starting. And they might say it’s the fact that they are a wife and a mom. And that comes first. They might say the money aspect has held them back. I will tell you; we never know what is holding us back until we are talking about it. So, the first thing that I help people with is their mindset that they are ready to do this, that their idea is a great one if they’re passionate enough about it, that I absolutely am too, and that they can have all the success in the world. I’m also just a huge fan of abundance. Every single thing is available to us, all of the money, the clients, the joyful life that we all want to live, it exists – it totally exists. And you have to believe that if you are starting a business, because you can’t say you’re starting a business, and one week later call me and be like, ‘I’m out, I haven’t made a sale.’ No, you’re not going to make a sale for some time. You have to believe you’ve been making sales for years if you start a business because when you’re in that headspace, you don’t worry – you know what’s coming. So, the first step is mindset.”

Jeannie continued, saying the second step is a plan. “What is their business? What does this look like from an investment standpoint, from an income standpoint? I don’t want people going into debt creating this business. Debt means very different things to everybody. But my philosophy is, don’t invest everything in this business if you don’t have it. So, what does this look like from an investment standpoint? What are the absolute musts that you need to invest in to get this started? Because everything does take an investment. And then, when should you be obtaining clients or customers or whatever that looks like for you in terms of an income? Is it three months? Is it six months? Will you map it out? When really should you be gaining traction? When should you be starting to create an income for yourself? Who’s your ideal client? And do you have a good product? It’s the plan and the mindset that leads everything else. Because what happens if you don’t have a plan is you start a business and within a month, you’re like – ‘I’m out, I’m going broke, I’ve put five grand into this, nothing’s coming back, I’m so worried.’ But if we would have laid out the plan, we would have anticipated that you will not receive the income until month three, let’s say. If that’s the case, then you’re looking at it, and you’re able to say, ‘I expected this, I’m right where I’m supposed to be, I just have to keep going.’ It’s a mindset and a plan.”

“Mindset and plan,” I repeat. And I think back to my early days when I launched my business. I brought on my first clients without a website. I brought on my first clients with willpower.

Jeannie explains, “We’re saying that people are looking for a way to show up perfectly and to avoid starting. And that includes thoughts like, ‘I need a website, I need business cards, I need all of these things’ that you actually don’t need. When you get started, you just need to show up. The other thing that I will add to what makes a successful business owner, in addition to mindset and a plan, is recognizing that you are going to have to get uncomfortable. You are going to have to show up as though you’ve been doing this for years, even if you’re brand new at it. So, you’re going to be doing things that you never expected to do. And you will absolutely at times have a bit of an identity crisis and experience imposter syndrome. And you have to recognize that if you do what you always do, you get what you always got. If you want a radically different life, then that means you are going to have to show up radically different – you have to be ready for that.”

Jeannie explains that this shift is why it’s important to have a coach that can remind you of these things and bring you back to the present moment. A coach can get you back to why you started and back to reality. “When you show up differently, and you’re thinking everyone is judging you, then we have a five-minute conversation to recognize that no one’s judging you and the people that are don’t matter at all. That is how you will keep going.”

Jeannie talked about continuing to grow and have courage, and I think that’s such an important point to hear because if you are going to be successful as an entrepreneur, there isn’t some magic day where you have it all figured out. Or, you no longer have to do scary things. The scary things get bigger and get different, but you become more equipped to handle those scary things. Throughout our conversation, it’s become incredibly clear that mindset, whether you are an employee or an entrepreneur, is absolutely critical for success. To be on a journey to grow that entrepreneurial mindset can benefit you greatly as an employee and, obviously, as an entrepreneur. We also talked through things such as affirmations, investing in a coach, and reading different books. It’s a very intentional practice to grow the right mindset. As we wrap up our conversation, I’m curious what is giving Jeannie energy in her business now and ask her to share.  

“I’ve been in business for eight months or so at this point, and what has been very fun for me is bringing on new clients that are ready to start their businesses and recognizing that we’re following the same steps to get them there consistently,” says Jeannie. “So, I have launched a new offering on my website, www.jeannieandresen.com. It is a six-step program to get a woman started on her business that she has been thinking about and dreaming about for years. The six steps include identifying your business, your ideal client, what you’re registering your business as, how your clients will find you, how you are going to find them, and of course, mindset comes up constantly. It has been so successful in terms of getting women to feel that they are supported. I have two coaching certifications, one through my former company when I first became a coach and another that I obtained when I first started my business because I wanted to make sure I’m offering a great product. Along with addressing a business’s tactical aspects, I am trained to ask the right questions to identify what’s going on. Those two things together provide a ton of support for a woman to get started.”

I am so appreciative of Jeannie’s conversation and ask her to share her contact information for anyone who wants to connect with her. She suggests her website, Instagram and LinkedIn.

With that goal achievers, keep focusing on your wins, learning from your lessons and identifying those key priorities so you can consistently progress in the direction of your goals.