UFYB 278: CULTIVATING A CEO MINDSET AND DEBUNKING ENTREPRENEURSHIP MYTHS: A CONVERSATION WITH AMY PORTERFIELD

Welcome to Unf*ck Your Brain, the only podcast that teaches you how to use psychology, feminism, and coaching, to rewire your brain and get what you want in life. And now here’s your host, Harvard Law School grad, feminist rockstar, and master coach, Kara Loewentheil.

Hello, my chickens. I am so excited to talk to today’s guest. In fact we just started blah, blah, blah chatting immediately as soon as we got on and then we were like, “Maybe we should record this and back up so people know what’s happening.” So if you are in the online business space at all you for sure know the name, Amy Porterfield. She is a little bit of a legend I would say in our own day and age. And she can tell you much better than I do all of her accomplishments and accolades and what she does.

But I know Amy as the person who I think I first started following to learn how to grow and scale an online business. And since then we have talked about a lot of stuff. I went on a podcast she was doing about body image. So it all comes together. We have talked about a lot of different things and she has an exciting new book out that she’s going to tell us about. So we’re going to be talking about her journey, the book, just give us the overview, tell us all the things.

Amy: Oh my goodness. I’m so excited to be here. So first of all thank you. And so I’ll just kind of tell everyone just a little bit about who I am?

Kara: Yes, please. Yeah, sorry, when I said all the things, I just meant introduce yourself, not give us a lecture.

Amy: I was like, “Well, where do I start?”

Kara: No, I’m sorry, introduce yourself, yes.

Amy: I always say I’m an ex corporate girl turned accidental entrepreneur. I never really sought out to have my own business or be an entrepreneur but here’s what happened. Got out of college, started taking all of the corporate jobs. Had jobs with Harley Davidson and publishing and sales and all these different things. But my last nine to five job was with peak performance coach, Tony Robbins and I was the director of content development. That meant that I got to travel the world and work on content that Tony did on stage, like Unleash the Power Within and Date With Destiny.

If you know Tony you know those events. And it was a really good job. I got paid well, I got to travel. I got to work with a legend. It was good. However, there was this one meeting where Tony brought in a bunch of internet marketer online business entrepreneurs and they talked about their businesses. And for the first time ever I thought there’s a whole other world out there that I know nothing about but they kept talking about the freedom they had, lifestyle freedom and financial freedom and I thought I want that.

I’ve never really had freedom. I’ve always had a boss from my first boss, my dad, a really strict guy. I mean we won’t get into daddy issues but there’s some there.

Kara: We’ll do a different podcast about that. I feel a lot of successful women entrepreneurs have daddy issues.

Amy: Yes, I think we need it. You’re just the perfect person to get it out of us. And then fast forward to having a bunch of male bosses and I realized I want to call the shots. I want to say what I do, when I do it or how I do it. So that was the first time I ever thought I want freedom really bad. So it was about a year after that that I went through this whole transition of how I’m going to start my own business. So I put together a roadmap to get out of my nine to five job and start my own business.

Fast forward 14 years later, I have a business that I have generated over $80 million, helped over 50,000 students and I have a life that I never ever freaking believed was possible. So I want to help more women discover how to make that transition so I’m on a mission.

Kara: I love that so much because I think that women generally aren’t taught to see themselves as entrepreneurs. Women, they might be like, “I’m going to have a small business.” I’ve talked about on the podcast before that when I left my job to again, unexpectedly decide to become an entrepreneur, my big goal was okay, in three years I’m going to make $150,000 to replace my salary. And I’m not at all shitting on 150 grand. Making that first 100 grand is the hardest in some ways and that’s an amazing accomplishment.

But it’s only funny in retrospect just to see where the business is now. And my business is not your level but now we’re doing $5.5 million a year and I thought that 150 was so impossible because of what I had been taught my vision for myself could be. And one of the things I want to talk to you about and I’d love to hear kind of how this played into the decision to quit and the mindset work you had to do, is that I think part of the – I teach this feminist business mastermind.

And one of the things I see in my students is they can already be making multiple six figures and yet they don’t think of themselves as good decision-makers or good with money or as having the authority to make those decisions. So I call it that CEO mindset thing. So I’d love to hear what came up for you as you were thinking about quitting and how do you think that kind of programming played into it?

Amy: Okay. Played big time into it because I talk about this concept in the book called un-bossing. And it’s believing that you have the ability to lead yourself and you don’t need anyone to lead you. But because we’ve had bosses all our lives to the point that we become our own boss, un-bossing doesn’t just happen overnight. And so when I first went out on my own I did social media for small businesses so I had clients. And I had eight clients, I literally let them all treat me like they were my boss. I was like, “Yes, sir, yes, ma’am, whatever you need.”

But it gets worse than that. I’ve got to tell you a quick story. Talking about thinking that you can’t lead yourself and that you need somebody else to boss you around kind of thing. Well, I went out on my own and I was about four years in and I had hit my first million dollar year which is a really big deal for entrepreneurs, so 950,000, so close. So I was doing really well but at the time I was in a mastermind with a bunch of people and there was this guy younger than me that was just killing it in his own business doing something similar.

And I said, “Hey, come help me. How did you do that ad strategy? Or could you get in my business and show me this?” And he said, “I could do you one better, let me be a 50/50 partner in your business and we together could explode this thing.” Now, I would like to tell you that I took weeks to decide, that I went to my lawyer and said, “Let’s draw up a contract. What would this look like?” I crunched the numbers. I did none of that. One sleep, I woke up the next morning and said yes to him because I didn’t believe I could do this on my own because I felt I wasn’t good enough.

That I had almost made a million dollars but I still didn’t really know what I was doing and this is all a fluke so I said yes. And for the next few years we crushed it together. We did really big things. It really helped my business grow. And then one morning I woke up and I was miserable and realized I literally am this guy’s employee. Something goes wrong, I look to him like, “Are we going to be okay? What should I do? Do you think I should do this or should I do that?” We get on a meeting and I get off the call with 20 action items, he’d have zero.

Kara: Wait, just pause. That is the story of so many women and so many even high level roles. And if you’re listening to this and you’re not an entrepreneur, it almost doesn’t matter. People are doing that in their day job also if you take all the action items and the dude gets off the call and it’s just, okay, well, back to my work day.

Amy: Why did I let that happen? It blows my mind. But I went back into employee mode like that. And I tell this story and this is the one story I didn’t want to tell because I actually, when I told him I wanted out I almost lost my business because we could not agree on what I’d have to pay him to get my freaking business back. So was disastrous for a year. But I tell this story because you do not need to give up that power and it is so quick that I did it that I want women to know to slow down a little bit.

That you have the ability to do this on your own but we for some reason have been programmed to think that we need somebody else to help us and that is not true.

Kara: Well, especially a man.

Amy: A man, I always thought I needed a man to help me, absolutely.

Kara: Right, especially if it’s like math or finance or strategy, those are all these things that we think, I was just coaching a woman in my mastermind who makes $300,000 a year which isn’t fucking nothing.

Amy: That is a lot of money.

Kara: Right. And she kept telling me how she wasn’t strategic. And I was like, “Where do you think the money came from, you just stumbled on a pot of gold and like a leprechaun, what are you talking about?” But that’s how women are socialized to think. And that bossing, one of the things we talked about at that meeting was I was like, “Okay, if you were an employee who had been hired to do your job, would you be doing it any differently?” And they were all like, “Oh my God, yeah, I would be doing this job so much better.”

Because if I had to report to someone else and that responsibility can be so paralyzing because we’re not socialized to believe that we can make the good decisions. I mean I still do it. I often will type something up to my mastermind and then I’ll be like, “Why am I fucking asking them this? Delete this and make this decision. What are you doing? You don’t need their opinion on this.” Obviously it’s great to have colleagues and there’s nothing wrong with having a business partner when you’ve thought it through the right way. As always it’s not the action, it’s the mindset.

Amy: I love that you just brought this up. I have a team of 20 full-time employees, 18 are women, two are men, they’re gay. So I don’t even have a straight man on my team. And not that I don’t want to, it just hasn’t worked out that way.

Kara: Of course, of course.

Amy: And with that I am constantly telling the women on my team, they’ll draft something up to send to an outside contractor who is a male or someone we’re working with and they ask permission or should we do this? And I keep saying, “We’re not asking you guys or women, we’re not asking. Let’s just do it and tell them what we’re doing.” But it’s so easy, even my team, to ask for permission even when we’re killing it. So I see it a lot. I see it in myself. I love that you admitted, wait, hold on, why am I doing that. It still comes up but the ticket is to catch it. That’s all we’ve got to do, we’ve got to catch it.

Kara: Yeah. And practice, the whole reason we don’t want to make the decision is that then when we think that we’ll blame ourselves if it doesn’t go well, and I’m sure you see that with people who are thinking about leaving their job. That decision paralysis where we’re afraid to take a chance because we think we’re afraid of what will happen, really we’re afraid of how we’ll feel, what we then tell ourselves like, see, you can do it. Your father was right or whatnot. My father he was an entrepreneur too.

So we kind of sort of talked about the mindset hurdle for you it sounds like that un-bossing which is such a great term of claiming that for yourself. You wrote this thing in the book that I just love because I’m a big sticky note proponent also for thought work about how you’d quit your job and put it on your bathroom mirror. So I’m just curious, what do you think that did? I’m constantly telling my students, write their thoughts on post-it notes and put them up around the house. So I’m always glad when somebody else is into sticky notes.

Amy: Okay, I love that you do that as well. This was a big one for me. Number one, I had golden handcuffs meaning I had a really good job where I could make a lot of excuses why I should stay. And I knew I didn’t want to stay but I could easily. It was a sexy job to get me back into. So I set the date, put it on a post-it, put it on a mirror where I saw it every day. But then one thing I didn’t write in the book that I should have is when I would look at that post-it note I would say, “What’s one thing I need to do today to move me closer to that?”

The six months of when I decided okay, I’m actually leaving on this date to when I actually left was six months. And I knew I had some mental work to do and some strategy to do during that time. So here’s an example. There was this woman online that had a business exactly like the business I wanted to create. She had digital courses and she was doing a little one-on-one coaching. And she had this awesome website. She had a blog and everything I wanted. It was probably the most simple business but it looked like Disneyland to me, it was huge.

And so I sent her an email and I said, “I know you don’t offer this on your website, this is not the kind of business you’re in but can I pay you to tell me how you built your business? Can I have one hour of your time? I want a business like yours and I will pay you for your time.” And she said, yes. This was a woman I did not even know.

And so at my lunch hour when I was still in the office, we had really thin walls. I hid under my desk because I had a little office and I’m whispering to her, “Okay, so how did you get started? Did you have money? What did it look like? How did you get your first client?” And she told me everything. This is why I love women. She was like, “Here you go.” And she was so gracious with her time which is why I wanted to write a book, to be gracious with all the strategies I know work so I can map them out for a woman that comes after me.

And so I did things like that every day. I listened to podcasts, bought courses, watched YouTube videos because I wanted to be prepared when I left. The secret is you’re never really prepared but I wanted to do as much as I could.

Kara: Yeah. So let’s talk about some of the – we did talk about one of your big pitfalls you experienced but let’s back it up and talk about that first year which I think is so – I so often have students where I’m just like, “They’re in so much drama and suffering about a business that’s actually going okay.” I’m just like, “Just hold on.” It’s like watching a kid get really frustrated when they fall down and can’t walk, something or they’ll learn to tie their shoes. And you just know, you are actually where you need to be and in six months it’s going to be fine and in a year it’s going to be amazing.

But it’s so hard because I think we all did, you look at the people who are succeeding and then you look at where you are in the beginning and you’re just like, “I don’t know, it’s supposed to look like that. Somehow I’m supposed to make $20 million overnight. I don’t know how.” And I think it really normalizes when we talk about failure.

So I’d love to hear, what do you think was the biggest mistake you made in your first year of business and how you handled that without letting it – some people make one mistake and then they’re derailed for the next five years and you just were able to keep going, what was that like?

Amy: I think my biggest mistake that I made in my first year of business was comparing myself to everybody else and we all know that when you compare yourself to someone on Instagram, you’re comparing the backend messiness of your business to the front-end shininess of theirs. It’s not true. And so at the time when I came on the scene everyone seemed to be making tons of money, $100,000 a launch, 200, 300, a million. So I thought, I could at least make $100,000 in my first launch. Looking back now I’m like, “That’s so cute. That’s so cute.”

Kara: Sweet Amy, that’s not how it works.

Amy: I was so sweet. I really believed it. So with a list of 600 people that I never emailed so I don’t know really how I thought I was going to do it.

Kara: You were like, “I don’t need to do the math. I have faith this is just going to somehow [crosstalk].

Amy: It’s going to happen, we’ll sprinkle a little magic dust on, it’s going to happen. So I did my first launch and made $267. That’s how much I made. The product was 297, but when you factored out my expenses, which was a few thousand dollars, I didn’t sell that many, a few thousand dollars in expenses, I made $267. I cried for an entire week, every day I got up and started crying. I thought I am worthless. I am not cut out to be an entrepreneur. I was crazy thinking that I could leave that job and do something else.

And now I’m going to have to grovel back for my nine to five. I was convinced. And the saddest part is that everybody new in business is going to crash and burn in that first year. There’s no way you’re not going to have a crash and burn. Now, if you fast forward to the end of that year, I made just as much as I made in my corporate job that first year. That’s a huge fete just to cover your salary but you’re right, in my head I was a total loser. I was not doing well, it was a mess but it wasn’t. I was just trying to figure out my way.

Kara: Yeah, I love that. The first thing I did, I mean I started with one-to-one coaching and I think if you are a life coach there’s a good reason to start with that. But the first thing I tried to do beyond that was a body image retreat that I did with this friend of mine and complete flop. I think we sold two spots and then one person canceled and wanted their money back. I think we sold three spots, two people canceled and wanted their money back. And then we just had to cancel the retreat, we lost a few grand. One person, we converted to one-to-one coaching.

Amy: What did you do with that? How did you handle that?

Kara: I think because I have an entrepreneur in the family maybe I just was more – not that my father, I don’t remember, he didn’t talk to us about like, “Well, this catalog didn’t sell this week”, or whatever. I think I just didn’t make that mean anything, even at the time I was disappointed and I’m sure I had a little drama but I kind of think there’s superficial level and existential drama level.

Amy: I had existential drama.

Kara: Yeah, you could be sulky on the surface. And then I had a lot of existential drama about other shit. But just was like, “Oh yeah.” I remember that I did it with somebody else and it definitely felt like her brain had a much harder time with it and making it mean something. Maybe it helped that I had started being able to sell one-on-one coaching so it wasn’t literally the first thing I did. And I think the other premise people have, so people have two premises. One is successful people have never failed.

And then other people who think they’re being more realistic are like, “I’m sure successful people failed at the beginning but then they stopped failing.” So I would love to hear about that because I launched three things this past year that didn’t sell that I had to, one we just canceled, one we got it over the finish line but it was a grind. This shit happens all the time all along the way.

Amy: Okay. So I’m 14 years in at the time of this recording early 2023, however in 2021 which essentially feels like just a year ago.

Kara: And also 100 years ago somehow at this point in time.

Amy: Exactly, 100 years ago or yesterday, I don’t know.

Kara: Yeah, one of those two.

Amy: One of the worst years. I always say the worst year of my business was when I got out of the partnership and thought I was going to lose my business because we couldn’t agree. The second worst time was 2021. I would do launches and everything that had been working before was not working anymore. And I felt I had lost my edge and I’m in my 40s so I thought I’m too old for this. These girls are coming up, they’re young.

Kara: Yeah. That is socialization also, men in their 40s are never like, “I’m too old to be valuable.” Women are programmed to think in their 40s, you’re as good as dead.

Amy: Yes. I started thinking, I’m a has-been, my strategies don’t work anymore and these things aren’t going to sell. It was one launch after another, I was not hitting goals. And I really did, I have to be careful, I work with a good friend of yours who’s a coach of mine. I can quickly go to, “I’m a loser, I am not cut out to do this.” And I just thought, okay, this is going to be the end of me. Thank God I get the support I need. I have a therapist, I have a coach, I have great peers in my life. And I had to finally reach out to them and say, “I am having a year, I am stuck.”

So yes, this was 13 years in and I had one of the worst years of my business. 2022 though, because I did the work on myself mentally and physically, got my body in a good place for energy and my mind in the right place, I had an amazing year. So it’s not the end all be all, but yes, I still have those challenges. I still have failures.

Kara: Yeah. And that’s so important for people to hear because I think what paralyzes people so much from making any big decision like quitting your job. Their thought is what if I fail? And your thought just seems to be, for sure I’m going to fail some of the time, for sure it’s going to happen. Let me prepare for how I’m going to handle that when it does happen. It’s definitely going to happen. If you look at one myth from this podcast, let go of the myth that there is any scenario in which you quit your job, start a business and you never have to feel bad and it works out perfectly forever. That’s never going to happen.

Amy: If someone believes that, our work here is done. And I love that you work with women who are building businesses and doing all these things because that’s another thing I would change in my early years. I wish I had a coach. I was in masterminds and I always had a guide but I never had someone to talk to personally. That would have changed everything for me. I would have believed in myself in a whole different way.

Kara: Oh my God, if I wasn’t being aggressively coached by Brooke during the first two years I was doing my business, coach training and master coach training. I mean I think everything would have taken 10 times as long. I just had so much bullshit. I had this whole insane thing where I refused to call myself a businesswoman.

Amy: Why?

Kara: Because my brain was a total mess. Brooke’s always like, “She wants to be an example of what’s possible.” And I’m like, “I want to be an example of what’s possible with a half managed mind.” That’s my goal is to be you don’t need to get it all figured out. I came from the nonprofit world. I had this whole thing about business is bad. I was like, “I’m going to start a business but keep all my thoughts about how business people are bad.” I thought that was a good plan and I just did not, yeah, I had a whole, I was like, “Business women wear great pant suits.” That was some idea I had.

Amy: [Crosstalk] when I think of a businesswoman.

Kara: Yeah. I mean we don’t call ourselves that so much. I guess Corrinne has no BS businesswoman but I’m curious to hear because you obviously have so many people come through your programs who are getting ready to quit their job or trying to quit their job or working up to quit their job. But what are the common mindset challenges you see in kind of your people when they are considering leaving their current job to create their own business, which is what your book is all about, how to do that, what are the most common things you see come up?

Amy: So the number one thing I see come up is a little bit what we already touched on, this idea that they need someone else to lead them or to step right back into being an employee even when they get out in their own business. I have a lot of coaches, consultants in my world and I see that happen a lot. Another thing I see happen is superwoman syndrome where they think I have to do it all alone. They’ll say, “I don’t have any money to hire anyone. I don’t have the resource to do so. I’ve got to do it all alone.”

And I always say, “There is no badge of honor in doing it alone.” So of course, in the very early stages it’s just you. But the first thing I want people to do as soon as they can is let’s hire a virtual assistant. Let’s get you a little help because another challenge I see is instant burnout. That first year they have hit it so hard, they’ve said yes to everything due to FOMO or desperation. I hate to say this but we all have a little desperation in our first few years of being on our own and so we start saying yes to things we shouldn’t.

We kind of lose ourselves in all of that, come up for air and realize you haven’t showered in three days and you literally, your business feels like it’s on fire. Burnout is very real in the very beginning stages of entrepreneurship but it doesn’t have to be. So looking to say, “Who can I hire? Who can I make a trade with?” And my first assistant was five hours a week. I wasn’t sure if I could even afford that but I was desperate and I waited too long.

So that’s another thing, the superwoman syndrome and this idea that you are an employee even when you are on your own I think shows up a lot.

Kara: I don’t think I’ve put this together this way before but from what you’re saying, one of the things that I teach about in my – I do this advanced certification in feminist coaching to teach people how to coach from this perspective. And one of the things that I talk about a lot in there is this idea that women are socialized to believe that their value comes from, kind of that they’re workhorses, their value comes from the effort and the time and the work, not from the brilliant ideas or strategy.

And I hadn’t put this together but I think maybe that’s also part of why women resist hiring in some ways is they don’t accept this. The whole point is if you free up your time you can use your brain for bigger things. But if you don’t think that your brain is good at bigger things or is strategic, if you don’t believe that part of your value comes from higher level thinking and you’ve been socialized to think that’s not what you can offer, that’s what men do.

Then of course you’re going to see no point in hiring or even actively resist it because you’re scared to have to sit with your brain and try to do that kind of thinking.

Amy: I never really made that connection and that feels very true for where I was and for many of my students as well, I really do believe. And so also we’re conditioned, how we were raised, our values of how we were raised will play a huge part in how you navigate entrepreneurship. There was a lot that I needed to unlearn in the beginning.

So this is going to sound wild but my dad, he’s blue collar to the bone, he’s a firefighter and he used to tell me when I was young, “Hard work is work that you’re doing that you don’t want to do. So if you’re doing work you don’t want to do, you’re doing it well, you are a hard worker.” And there was a badge of honor in my family to be a hard worker.

Kara: That is so common, the idea that work only counts if you hate it.

Amy: Yes. What is that? That is the saddest thing I’ve ever heard. I didn’t even know I believed it until I started working really hard and was proud of myself and hated the business I created. Yeah, that’s great, yes.

Kara: Yeah. That’s such a thing. I don’t get credit for working hard unless I’m miserable and I hate what I’m doing. And women also are socialized, I think to see anything that comes to them easily is somehow not valuable or doesn’t count. And only the things that are hard for them count as work which is also so bizarre because we’re like, “I want to be an entrepreneur to do the things that I like doing.” And then we’re like, “No, none of those count, [crosstalk] count.”

Amy: I mean come on. And I have to admit, you know that saying, let it be easy? I have a good friend, Susie Moore, who has a podcast and a book called Let it Be Easy. And I hear it and I want to believe it. And I tell myself it all the time but you just hit it on the head that if it’s too easy I should be finding something else to do. It should be hard for me, that means it matters. That is such bullshit. It is not true whatsoever.

And here’s the thing, if I could go back 14 years and I was just starting my business, this is for anyone just getting started. First of all, if you let it be easy you will literally be winning the game over so many of us who think we need to trudge through these first few years. And the second thing is, set up your life and priorities before you set up your business. What do you want your life to look like? What are your priorities? What comes number one, two and three to you? And where does your business fit in?

I let my business be number one for many, many years until I realized, wait a second, there’s a whole other life out there that I want with my husband and my son. And I want to live life and I want to travel. I kind of forgot all about that. So in the book I talk about not losing yourself in this whole process of building a business, that you’re supposed to be building a life and a business by your own design. But then sometimes we lose the life part and go all in with the business. It doesn’t have to be that hard.

Kara: Yeah, there’s definitely an irony circle that I got trapped in that was, I started my own business, and even before I started my own business I knew I couldn’t work a nine to five in an office so I’d become an academic which is more you work 13 hours a day but from different places but at least you don’t need to go to an office. So I already knew that I could not work a nine to five but yet I was basically telling myself that if I wasn’t working a nine to five in my business or if I wasn’t working the same hours as my employees that that was a problem.

So I’d done all this fucking work to create the freedom to have a different schedule and then I was just imposing on myself the same norms of the corporate world which I see happening a lot. So one of the other things that you say that I love because we’re sort of talking about this perfectionism that keeps women from quitting their jobs basically. And you talk about how you don’t think that you need to have a completely detailed business plan all laid out.

And I feel this is also a thing that women do because we don’t trust ourselves. We have to have the whole plan mapped out and have a council of 12 people approve it. And then I can quit my job because we don’t trust ourselves to figure shit out on the fly or whatever else. So can you let them hear it from a business expert, why is it not important to have a fully detailed business plan?

Amy: First of all, I have never ever seen a business plan in my life so I am proof that you absolutely do…

Kara: We’re like, “We actually don’t know if you need one because we don’t know what they look like and we didn’t have one.”

Amy: Yeah, I don’t know what it looks like but I sure as heck know I didn’t have one and so many of my peers, when I wrote the book I called many like, “Did you have a business plan when you started?” No one did. Now, of course you want to plan. Who do you want to serve? How do you want to serve them? But I promise you, the business you create in the beginning will look dramatically different in five years from now. You’re going to find your way because action creates clarity.

All I want you to do is get into action and do something and then the action you take will lead you, no, that didn’t work or that works really well, let’s go down that road even more. And people will share with you what they love and it will morph into something else. So let me give you an example. I started out with doing social media for small businesses, hated it. Hated having all those clients. Hated doing the work for them. So I decided I’m going to create a digital course. I created a digital course and I made $267 so that worked really well.

At that point I could have said either I’m not cut out for this or I’d better go back to just doing all my clients. But instead I said, “That didn’t work but I’ve seen it work from a lot of other people. I’m going to try it again.” The next time I did it I made $10,000, not huge but enough to keep me going.

Kara: On the right momentum.

Amy: On the right momentum. And the course was about social media but then I launched one more course, did really well, I hit $30,000 in one launch, my whole life was changed. I wanted to roll around naked in all that money because it was the most money I’d ever made. And that’s when people started saying, “You do these courses really well. How are you doing this? Would you teach me how to do a course?” Fast forward and that is my bread and butter, that’s how I’ve made as much money as I’ve made.

I teach people how to create digital courses. I would have never landed there if I didn’t just start somewhere. So that’s the one thing. You’ve just got to get started, your business will look dramatically different. So I always bank on that, is that action creates clarity.

Kara: Well, it’s like parenting. You can think you have a whole theory about how it’s going to work and then you start interacting with an actual human child and you’re like, “Well, that was a lot of nice theory I had that doesn’t work at all or doesn’t fit this child”, or whatever else.” Yeah, I mean I thought I was going to be a coach for lawyers and then I was going to do a lot of work with law schools and law firms. And then I did one thing with a law firm and I was like, “That was terrible, I definitely don’t ever want to do that again.”

Amy: Exactly. So you had to do it. You just don’t even know. So you’ve got to leave a lot of room for experimentation in the first few years. And a lot of women will say, “If you’re experimenting and it’s not working you’re failing.” So we really quick go to this didn’t work for me but that’s how it’s supposed to work. It’s giving you answers to what’s your next move. It’s giving you feedback. So look at all of that as feedback in the first few years. You will get a whole lot farther.

Kara: Totally. I’m always telling my students, “Think about those guys who get $20 million in venture capital funding without even having a revenue plan.”

Amy: Yeah. So that’s right, we were talking about the business plan so let’s talk about a little bit more. All you need to do is think about how you’re going to get started and what that might look like but the business plan is the big excuse for not getting started because it’s like, I’ve got to work on this, I’ve got to do more research. What happens when you’re researching, working on it, calling friends? You’re staying comfortable. And we all know that growth does not happen when you’re comfy.

And so staying comfortable keeps you playing small. That’s why we’re going to go out without a business plan, we’re going to have to somewhat of a plan kind of formulated, maybe you’ve written a few things down but we’re just going to get started and see what works because it’s just a big fat excuse. I promise you, you don’t need that. You don’t need a fancy website. That’s another one. So many of my students will not launch courses until they have a website. And I keep telling them, “You don’t need a website, I promise.”

Kara: You’re like, “Teachable exists, there are things that will just do this for you.”

Amy: Overnight, you could literally get a website, a simple website up overnight. I always say, “I made my first million with the ugliest website on the web, I promise you.”

Kara: We always talk about the Fly Lady, have you looked her up?

Amy: No. Who is she?

Kara: There is this woman who teaches you how to, I think it’s how to clean your house bit by bit but her website is from not even 1997, 1897. It’s the jankiest thing you’ve ever seen but she makes at least a million dollars a year. So whenever we’re getting, in my mastermind, Brooke, showed it to us. We’re getting perfectionistic about it, we’re just like, “Remember the Fly Lady, if she can.” I’m always saying to my students, “People made money before there were Instagram accounts.” Whatever it is that you are telling yourself you have to have perfect.

People made money when all you could do was go to the market and be like, “Here’s these pears I have, let me see if I can trade them for something.”

Amy: Amen. And I think here’s a way to check yourself. When you find yourself saying, “I can’t get started until”, and that until things are kind of dragging on, that is your red flag to say, “I’ve got an issue here.” This is an excuse. This is not a strategy because there’s too much proof of people just getting started and putting themselves out there.

Kara: And no one else can tell you if it’s going to work. People want to find, I also say this to people, I mean people do hire me for business coaching so maybe I’m part of the problem. But my business coaching, it’s always like, “I don’t know what the fuck you should do. I’m just here to teach you to think differently about yourself as a woman, as a CEO.” And I have seen even just people that I have worked with for years, nobody knows what’s going to work, nobody can tell you. You can’t outsource that. We want that authority and approval like you had with that partner.

You want the approval from an authority figure, usually a man, occasionally a woman who’s made enough money to tell you that this is a good idea, it’s going to work. And here’s the pro tip, we don’t fucking know. I can tell you if you come to me and you’re like, “I just think I’ll help people with things.” I can be like, “That’s not specific enough, we need to dial it in.” But do I know what opt in is going to work the best for your course for stay at home moms who have this problem? I don’t know, you’ve got to go test it.

I think part of perfectionism is this idea that if you think about it enough you’ll come up with a perfect solution that’s unassailable that can be guaranteed to work. And there’s just no such thing. You can’t develop it in a vacuum like you’re saying. You have to go out and try it. That’s where you get the information and the feedback you need.

Amy: Absolutely. And I think that’s where a good side hustle could come in. I started with a side hustle. So one of the things I talk about in the book is how to put together a runway, exactly what to do so you leave with full integrity and you feel good and you’re successful on your way out. One of the things I say is you could start a side hustle. So if you just get going with something to make a little extra money but really the goal is to think like an entrepreneur. How might I think different while you’re still in your nine to five job, I want you to start thinking like an entrepreneur.

Start doing something on the side to bring in a little money, but more so test out some ideas. That’s going to give you some more confidence to keep going. So you don’t have to go all in. I’m not telling people to quit tomorrow. My book might be called Two Weeks Notice. But I have a ramp up because before this Two Weeks Notice happened. There’s so much you could do before you take the leap but here’s what I don’t want women doing. Don’t just think about this. Don’t just get my book and put it on a shelf and think, one day I’m going to get to that.

Because Carolynn is talked about in my book. I write a story about her. She always thought about being an entrepreneur. What might I do? I could take my skills in my job and be a consultant. There’s so many different things I want to do. Thought about it, thought about, did nothing about it. And then one day she woke up and she got laid off, lost her job and had nothing set up, although she’d been talking about it for years. She could have started her runway. And I think that’s what’s most important.

1.4 million women left the workforce during COVID which makes me so pissed because we know why they left, childcare. They went home to take care of their families, it kills me that it was the women that did that. But now they’re looking around thinking, well, do I need to go back to work because things are getting freaking expensive, the cost of eggs is out of this world right now? The world is expensive right now. Do I go back to my J-O-B or do I do what I’ve been thinking about forever which is my own thing.

But that leads me to one thing that I think you’d have a really good opinion about. Actually there’s a controversy that I’ve kind of started, I’d love your opinion. Are you ready?

Kara: I’m ready to give you my hot take, okay.

Amy: Alright, so these women that are thinking about going back to the workforce or starting their own thing, what’s coming up for some of them and I’ve talked to many is that their partner does not want them to start a business. Let it be a hobby. Do a little side hustle or don’t do it at all. Stay at home with my kids. They need their mom at home or whatever it is, or get a job because we need more money. But they don’t like, start your own business because we know that takes a little while to get up and running.

And so in my book I talk about the fact that if you go to your partner and you tell them, “I want to do this. This is my dream. Here’s why. This is what it means for me, the family, for us.” And your partner says, “Don’t do it. I don’t want you to do it.” I tell the women in my book, “You have to find a way to do it anyway even if your spouse doesn’t want you to do it.” What do you think when I say that?

Kara: Why the fuck is this controversial?

Amy: It’s a big deal. Thank you. So I’ve been on other podcasts and even women are like, “I’m not going to do something that my husband doesn’t support.” And I said, “Okay, so you’re going to lay in bed every night starting to hate him.”

Kara: I would just constantly be like, “Really, does your husband not do anything that you don’t support?” 100% does.

Amy: That’s good, I knew I’d get some good soundbites from you.

Kara: Those husbands, listen, obviously, yes, I have a lot of thoughts about this and most of them are that that’s ridiculous.

Amy: What if you really love your husband though and you really do have a good relationship, what do you do then?

Kara: Of course, here’s not what I’m saying. I’m not saying, you said, “I’d like to refinance the house to do my business.” And your husband said, “I don’t consent.” And so you go to the bank and forge his signature. I don’t think any of us are saying you should do that, don’t commit fraud. But I think this really gets to something that is so important when you’re trying to leave a job which is I saw this in myself so much where I was rejecting the norms of my family and the people around me but I wanted them to approve of my decision and support it and understand it.

Which is completely irrational. You can’t be, I’m going to law professors being like, “So I really hate this thing that you do and love and I think I’m going to leave it to start a business as a life coach.” And then want them to be like, “What a great idea.” What am I talking about? The same thing with my family, I mean my father is an entrepreneur and they are very supportive now. But even at the time because I have done so much thought work, I really was not upset that they weren’t supportive of the idea because why the fuck would they be supportive of this idea? It sounded insane.

I went to law school, I went to Yale and Harvard, they luckily were able to pay for my law school education so I didn’t have to worry about loans. I’ve invested all this time in this career. I come from this Jewish family where everybody’s a doctor or a lawyer or an entrepreneur but it’s always different when you’re an entrepreneur versus your kid is. And I was saying, “Hey, I’m running a think tank at Columbia Law School and I think I should quit that.” I’m not even saying I’m going to be an entrepreneur. I’m saying I’m going to be a life coach on the internet.

Amy: That would seem wild.

Kara: Why would they have been like, “Yeah, good plan. I don’t see any pitfalls with this at all, this sounds brilliant.” But that’s the thing, women aren’t socialized to believe in themselves and their vision. And so to me if your partner or your parents or your kids or your best friend or your boss, whoever, saying somebody doesn’t support you, I mean for me with the mindset work I’m always like, “What does that mean?” What you’re saying is they’ve said words to you that were different than the words you wanted to hear.

First of all, what did they actually say? Because of the way that we interpret things, somebody might say, “Well, I want you to be happy but I’m concerned about the financial impacts.” And what you hear is, “You’ll always be a failure, don’t do it.” So what are the actual circumstances? What are they actually saying? And also it’s your life. So I don’t think there’s a blanket rule, you have to decide that and figure it out for yourselves as a couple. But for me, for women being financially dependent on a partner especially a male partner is a high risk endeavor.

Studies show that divorce is financially beneficial for men and financially disadvantageous for women and their children. And so yes, I think you should, again, don’t mortgage the house without your partner’s opinion of any gender. But I think that if somebody is ‘not supportive’, first of all you’ve got to get really specific of what that means. And then second of all, maybe you’re going to do it a different way.

Maybe it will be partly a side hustle. Maybe you are going to be like, “Okay, I understand, I will keep my job but I’d like you to agree to take the kids every other Saturday instead of playing golf every Saturday so that I can spend eight hours working in my business.” Whatever it is, I just think a lot of people who say, “I can’t do something my husband doesn’t want me to do.” Their husband’s probably do shit they don’t want them to do and that they think it’s fine.

Amy: Yes. Amen to that.

Kara: Sorry, that was a rant, I had a lot of feelings about that.

Amy: No, I wanted a rant. I needed to hear. I’ve had enough people tell me, “Whoa, that’s dicey.” That I wanted, I knew you’d be on my side.

Kara: It’s crazy. Yeah, you’re not saying, they said you can’t borrow the car so you steal the car. You’re saying your partner doesn’t think it’s a good idea and I think you should find a way to do it anyway. I mean find a way doesn’t mean, again, quit your whatever. But this all comes back to the same thing to me which is if you really believe in yourself and in your vision then you will want to figure out a way to do it and you will be okay with the fact. A marriage is a long thing. There are going to be times that one of you doesn’t like what the other person’s doing and you have to work that out.

But I mean honestly, to me, if you have a dream like this and you have come up with some kind of plan that makes sense, and your partner is like, “No, I think you should be a stay at home mom” and you don’t want to. Then I’m like, “I’m sorry, why are we staying married to this person?”

Amy: That was another thing that if they’re going to not want you to follow your dreams here, you do want to look around and say, “Is there any other places this is coming up in our marriage where I want to go for something or I want to do something that the idea has been squashed.” But let me tell you, I love your example because your example of going from something very prestigious to something people don’t understand, you making that happen shows other women they can do that.

And I’ve got to tell you real quick about one of my students, Rachel. She was a pharmacist, her family always wanted her to be a doctor or a pharmacist or something like that so she did it. And she did really, really well but then started to get burned out and started to hate her job especially during COVID. That was when she was like, “I’m out.” But she couldn’t just jump ship so she started to buy real estate and do luxury B&Bs and it started out really slow. She did it on the side.

When it started to take off she told her husband, “I want to do this full-time.” He’s like, “No way, you are making bank as a pharmacist, you are solid, you’re in a foundational job. You’ve got this.” He thought she had lost her mind. But I love Rachel, she did it anyway. She’s making 10 times more than she ever made as a pharmacist and he loves her job now. He thinks she’s a baller and she throws it in his face sometimes, “Remember when you told me not to do this.” But thank God she didn’t listen to him.

Kara: Oh my God, my parents would think it was a brilliant idea that I did this thing, totally think it was their idea. I love that. I think your point of look at the relationship as a whole and is this equal? To me that would be the question. If your husband doesn’t make job or career decisions without asking you for permission first, okay, fine, you have an equal arrangement. That’s who you want to run your marriage, figure out something on the side. But if it’s unequal where your husband makes career decisions without asking you your opinion or asking permission.

The idea that women are in this mindset of I have to ask my husband if it’s okay for me to start a business. I’m not here for that.

Amy: No. And I really hope someone who’s listening right now, that’s exactly what she needed to hear. She needed to get the permission to do it anyway, figure it out. Life is too short. And I’ll tell you this. The worst day as an entrepreneur, the day I literally thought I would lose my multimillion dollar business to this guy who wouldn’t let me out of the contract kind of thing. The worst day as an entrepreneur is still better than the best day in a nine to five job. I could say that all day long because you still have freedom, you’re still calling the shots. It’s a different kind of life.

Kara: Yeah, I think that’s so true if it’s for you. And I know you don’t think this either but just since this is a business podcast lots of people listen to it. Neither of us are saying being an entrepreneur is categorically better for everyone than being an employee.

Amy: Great point. Some people aren’t meant to be entrepreneurs.

Kara: Yeah, or don’t want to be and that’s totally fine, but if you feel that calling to it, yes, I could never, if my business – I don’t know, if the internet disappeared and it was Armageddon, I’d be like, “Well, I’ve got to figure out how to sell life coaching to zombies.” I would never go back. And it’s not better or worse but it’s just if that is who you are, if you’re drawn to this too then your hard has to be worth it. You have to know your why. If this is what you are drawn to do then all the hard is worth it for you.

When you’re in something, when you’re in a job when you truly want to be an entrepreneur the hard doesn’t feel worth it because it’s not what you’re supposed to be doing.

Amy: I’ve never heard that and I like that, the hard has to be worth it. And I love that you said that. It’s a good reminder for me. Not everybody wants to be an entrepreneur. Not everybody wants to do this. My sister is a second grade teacher, she would never be an entrepreneur. Quite honestly she looks at my life and thinks it’s insane how busy I am and all the stuff that goes along with it wants nothing to do with it. And I love her for that. So you’ve just got to know what you want but get clear about what you want.

I did this thing with Mel Robbins where every day I had to write down five things I wanted every day. And you were supposed to kind of change them up. It was very hard to think about what I really wanted. I hadn’t done that in so long. So I think some people listening really get clear what you want. Ultimately what do you want? And that might mean that entrepreneurship is the way to go to get what you want and maybe not but I love that you brought that up.

Kara: Yeah. It’s again, it always for me comes back to the socialization. Women don’t know what they want because they’re so busy doing it based on what other people think they should do. And both of the things are true. If all your friends are entrepreneurs and you’re like, “Well, maybe it’s cool to be an entrepreneur.” No, that’s not a good reason. It’s okay to like your job and also if you want to be one, your parents don’t have to approve, your partner doesn’t have to approve, your friends don’t have to get it.

If you can quit an ivy league thinktank to become a life coach on the internet, then people don’t have to understand what you’re doing. Tell people quickly please how can they find your book? Guys, you’ve got to buy Amy’s book, pre-orders are very important. You’re going to be hearing me talk about that quite a lot as my book starts getting to come out. Go pre-order Amy’s book or order it. This podcast might come out the week, it’s the week before but go buy the book. Tell people where they can get it.

Amy: So you can get it anywhere where you buy books online but also if you go to twoweeksnoticebook.com I’ve got bonuses because pre-orders and orders during the week of pub means everything to authors. I put together some juicy bonuses to help you make that transition and start an online business. So twoweeksnoticebook.com.

Kara: Go do it and if you love your job and you don’t want to leave it you know you’ve got a friend who’s miserable who doesn’t like their job, go buy them a copy.

Amy: Yes. Amen.

Kara: Go buy Amy’s book. Thank you for coming on my friend.

Amy: Thanks my friend, I loved every minute of it. Talk soon.

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