Measuring Growth

When to Quit and When to Persevere in Your Business with Margo Aaron

Margo and I have both quit businesses. And in this interview that we originally recorded in September of 2019, we explore what it meant to quit and how we each realized it was time to let go.

Susan Boles
June 22, 2021
"Why Margo believes that self-awareness is necessary to figure out whether the hard part is a sign to quit or a sign to double down and persevere."

It's ok to quit.

Consistency can be critical to success, but knowing when to quit is an equally valuable skill.

So, how do you know when to quit and when to just push through the hard parts?

You've heard me talking to business owners who credit being consistent as the key to their success.

But failure is also a part of being an entrepreneur and one we talk about a lot less because it's not as pretty. Most successful business owners have at least a few failures in their rearview mirror.

I had 2 businesses that were marketing and branding successes and abject financial failures before I started ScaleSpark.

Failing sucks, there's no doubt about that. But those failures are a big part of what motivates me to teach financial skills and why I believe that your numbers tell you a story about what to do next in your business.

Deciding to quit something is so hard and emotionally wrenching. I also wish I'd listened to the story my numbers were telling me on both those businesses and quit earlier.

But you don't always know if you're failing. Maybe you're just stuck in what Seth Godin calls "The Dip:" that point in every project where you have to figure out if something is genuinely not working or if you have to push through.

Today my guest and I are talking about how to know when you should quit.

Margo Aaron is the cohost of the YouTube show Hillary and Margo Yell at Websites and the author behind That Seems Important. She's a psychologist turned accidental marketer and she's fantastic at getting to the heart of the entrepreneurial mindset. Her email newsletter consistently gets right to whatever mindset fog I'm in at that point in time and always manages to encourage me to keep going.

Margo and I have both quit businesses. And in this interview that we originally recorded in September of 2019, we explore what it meant to quit and how we each realized it was time to let go.

Listen to the full episode to hear:

  • The client call that made Margo realize she had a major disconnect between what she was getting paid to do and what she wanted to be doing
  • What questions to ask yourself to assess if you’re in “the Dip” or if it’s time to let go
  • Why product-founder fit is as important as product-market fit
  • How to build a business that aligns with your values and defines success on your terms
  • Why you need creativity, intuition, and experimentation in your business, not dogmatic models and rules

Learn more about Margo Aaron:

Learn more about Susan:

Episode Transcript

Margo Aaron (00:00):

There's the business you could run, and there's the business you should run. And they're not the same. And I think that that is one of the hardest things for founders who are ambitious and smart is that there are a lot of things we could do. And we can put a round peg in a square hole all day long.

Susan Boles (00:22):

It's okay to quit. Consistency is important. It can be a critical component of success. But knowing when to quit something is an equally valuable skill. So how do you know when to quit and when to just push through the hard parts? I'm Susan Boles, and you're listening to Break the Ceiling, the show where we break down unconventional strategies you can use to save time, boost your profit, and increase your operational capacity.

Susan Boles (00:52):

Throughout this series, you've heard me talking to business owners who credit being consistent as the key to their success. Pushing through and doing the thing over and over, putting in every single rep. That's the way they built successful businesses.

Susan Boles (01:08):

Failure is also part of being an entrepreneur. And it's a part we talk about a lot less because it's not as pretty. But most successful business owners have at least a few failures in their rearview mirror. And those failures also led to success.

Susan Boles (01:25):

I had two businesses that were marketing and branding successes, and really just abject financial failures before I started ScaleSpark. Failing sucks. There's no doubt about that. But those failures are a big part of what motivates me to teach financial skills. It's why I believe that your numbers tell you a story about what to do next in your business. And deciding to quit something is so hard and so emotionally wrenching. But I also wish I listened to the story my numbers were telling me on both those businesses and quit a whole lot earlier.

Susan Boles (02:01):

But you don't always know if you're failing. Maybe you're just stuck in what Seth Godin calls the dip, that point in every project where it gets really hard to keep going and to figure out if something is genuinely not working, or if you just have to push through.

Susan Boles (02:18):

But how do you know when you're just in the dip and you need to keep pushing, where focusing on consistency is the key? Or if what you're doing is legitimately not working, and you need to pivot or to quit.

Susan Boles (02:33):

That's what my guest and I are talking about today. How to know when you should quit. Margo Aaron is the cohost of YouTube show Hillary and Margo Yell at Websites. And she's the author behind That Seems Important. She's a psychologist turned accidental marketer, and she's fantastic at getting to the heart of the entrepreneurial mindset. Her email newsletter consistently gets right to whatever mindset fog I'm in at that point in time. And it always manages to encourage me to keep going.

Susan Boles (03:06):

But Margo and I have something in common. We've both quit businesses. And in this interview that we originally recorded in September of 2019, we explore what it meant to quit, and how we each realized it was time to let go.

Susan Boles (03:22):

Why don't you tell me a little bit about your previous businesses and how those businesses have kind of evolved into what you're doing now?

Margo Aaron (03:31):

Oh my goodness. How much time do we have? So I started in my entrepreneurial journey as a consultant. I was a marketing consultant specifically for, and here's where it gets complicated, who knows? When I first started, I was in that stage of business where I didn't feel like I had the privilege of saying no. So while I was trained as a strategic planner, so if anyone's an agency person, they know that I was basically working in between the people who were managing clients and the people producing creative collateral. Taking data and insights, and turning it into actionable ideas and strategy.

Margo Aaron (04:11):

Then when I started freelancing which turned into consulting, I was just taking every single referral I could possibly get. I wanted to get so much under my belt because I didn't feel like I was in a position where I could really say no. And I wanted to learn. Everything was a learning experience. I started Susan where I was so nervous to write my first contract for $1,000. I'm not even kidding. I remember being petrified that I was not worth $1,000. And by the end, I was doing contracts for 96,000. It was unbelievable the growth that happened in that time. But I needed that experience to really help me understand was I niching my services, was I niching the market? Was I focusing on a specific sector of marketing? What kind of strategy was I doing? It was sort of like a trial by fire because something that I learned pretty quickly is that people don't pay for strategy. They pay for outcomes, they pay for results. And that was a very painful lesson to find out.

Susan Boles (05:15):

Especially when they should pay for strategy.

Margo Aaron (05:18):

Yes. Well, because no one believes they have a strategy problem. And I had to learn that by going in and talking to them. It would be clear to me that they didn't have strategy. But to them, they thought they did. And it was a very humbling lesson to recognize that you have to meet people where they are in the process. So it wasn't my job to tell them, "Here's what you really have." It was my job to come in and say, "Okay, so you think you have a Facebook problem. Talk to me about that. Why do you think you need to be on Facebook?" And we'd go deeper, and deeper, and deeper until they realized that none of their marketing with adding up.

Margo Aaron (05:49):

So I had started off where we were doing branding. And that sort of evolved into my interests, which was more conversion rate optimization and copywriting. So it was kind of fusing the two at the same time. But really what was making me the most money, and this is what was so confusing was these bespoke custom contracts. So I would come in and I would get an introduction from a word of mouth referral. and someone would say, "Hey, Margo is really, really great for X, Y, Z." And I'd be like, "Oh I am? Okay, great." And we'd sit down and we'd talk. And I'm like, "I don't know if I could do that, but I will figure out."

Margo Aaron (06:27):

And then I would go into the depths of what they needed and create a custom proposal. So sometimes, my proposals were 30, 40 pages. They were really, really, really detailed. And we got to be pretty great at what we did. The problem was we couldn't really define what we did cause it kept changing. So aside from some amorphous it's a marketing strategy, we didn't do a good job of articulating what problem we solved for people. And my problem was the things that were making me money didn't add up with what brand I needed to build in a scalable way.

Margo Aaron (07:01):

And reconciling that was also difficult because there was what makes you money, and what you wanted to do. And that's when I discovered that there was a disconnect for the first time.

Susan Boles (07:11):

What did you do when you realized that?

Margo Aaron (07:16):

There was a very sobering moment. I'll never forget I was in San Francisco visiting my sister, and I was taking one of those emergency client calls that's not a real emergency. And she was listening in on the conversation and she looked at me afterwards and she goes, "So is your job managing temper tantrums?" And I was like, "Oh man, I think it is." And I looked at what I was doing, and it became really clear to me that even though I was getting known as a marketing consultant, there wasn't really any marketing happening. When I would go deep into the weeds of a lot of these companies, it was the founder fighting with the board, or the board fighting with the investors, or the marketing department fighting with the sales team, and really having to dig into things that had nothing to do with what I was hired for. So the outcomes were still really positive, but they didn't necessarily lead to increases in the bottom line in the way that I had promised or wanted. And it was driving me insane. It was like a full-time client management position. And one hand, I was bored. I really didn't like client managing. And I realized that that is a dispositional thing.

Margo Aaron (08:30):

I had some friends that really, really didn't like doing marketing. What they wanted to do was biz dev for the rest of their life. And I saw them building companies like mine and doing a really great job because they loved bringing leads in the door. They loved dealing with the complex emotional intricacies of each client, and being a yes person. And I was losing my mind, Susan. It was driving me insane. And I was like, "I don't think I have the disposition for this." Because I missed writing. I also really felt ethically conflicted, because a lot of times, the reason people hired me was different from what they wanted me to do.

Margo Aaron (09:11):

And what I mean by that is I would sit down with a client. I'll give you an example, a prospect who would come to me and say, "Okay, we have a $500,000 budget." This was actually a conversation. They said, "We want to own the LA market." And I said, "Great. So my recommendation is that you don't own the LA market." And they'd be like, "What?" And I'm like, "You need at least $3 million if you want to do that." Because they wanted television. And I was like, "Yeah, that's not happening. Let's pick secondary markets." And they were like, "You know what, Margo? We like you because you're honest. And you tell it like it is. So we're going to hire you to do the thing you just told us we shouldn't do." And I was like, "Ah!"

Margo Aaron (09:55):

So it'd be this dilemma where it's like I could take the money and implement, but then I'm setting myself up. It just kept being a consistent problem over and over again. And in part, it's built into the frustrations with marketing, but also because I failed to specify. I was doing strategy on such a macro level, that it was really, really tough to be responsible for someone's funnel when you're not responsible for their funnel. The better way to have done it would have been to be really explicit like, "We only do Facebook ads," or, "We only manage email," or, "We only do one specific sect of what you're looking for." And the trouble is it's all connected.

Margo Aaron (10:33):

And what started to happen as I did try and specify a few times, I remember a client once got really annoyed. He was like, "Okay, we did everything right. I don't understand why this is not selling." This was months after we had stopped working together. And I went to the website and I looked, and it was all really rigged up beautifully for conversion. And I said, "Well, what are you doing to generate leads?" And the guy looked at me and he's like, "What are you talking about?" And I was like, "Wait, you hired me to do conversion rate optimization. You have to send traffic to the site." Never occurred to him. Literally had never occurred to him. And I was like, "Oh my God, I can't do this anymore."

Susan Boles (11:12):

As a non-marketer before hanging out with you, I'm not sure I would have known either. On the surface, it seems really intuitive that if you're going to optimize conversion, you actually have to have people to convert. But I'm not sure that occurs to non-marketers to be honest.

Margo Aaron (11:31):

But it also made me feel like I should have done my job better then. It was part of my job to educate. And that's actually what created the next pivot is that I discovered that the actual value that I brought to the table for a lot of these companies was I broke down marketing. I sat there and I didn't assume they knew anything when I walked in. And I would sit there and I'd be like, "Listen, I know you know what marketing is, I know you know what branding is. But I just want to make sure so we're all on the same page that this is how we define the difference between marketing, branding, advertising, and PR, just so we're clear." And it allowed them to save face. And it allowed me to set the boundaries for what my role was. And it also helped them discover what they needed to hire for and what their strategies would be.

Margo Aaron (12:16):

Because people really don't understand marketing, in part because marketers do a really bad job of explaining it. And they very, very unethically sell it. A lot of the times, I was walking in the door to people who were dealing with the ghosts of bed marketing agencies past. So they would tell me, they'd be like, "Well, I just spent $14,000 on this and nothing happened." And I'd read the proposal and I'd be like, "Well of course nothing happened. This is a terrible proposal." But they had no idea. They had no idea because it was snake oil. And it's really hard to know the difference between what is a legitimate contract of someone who's going to help you achieve something, and someone who's telling you that they're a panacea for your business. Then they can't be.

Susan Boles (12:58):

Particularly because I think you have to have at least a fundamental understanding of what you're hiring for in order to accurately hire. I don't think I could have hired a copywriter before I had a really good understanding of what the hell copywriting was, and what it did, and how powerful it could be.

Margo Aaron (13:14):

Exactly. And why you even need it. I mean, there are some companies that I worked with, I say with all due respect, you don't need a website, you're a word of mouth business. You need a reference site. You don't need conversions.

Margo Aaron (13:23):

Yeah. So that sort of led the pivot to me teaching and speaking, which ended up being a much better fit for my personality, and much better fit for what was helpful to the clients.

Susan Boles (13:34):

Okay. That totally makes sense. And you're a wonderful teacher because you're basically the person that taught me about marketing. So if you can get it through my head, I think you can teach it to anybody. So how did you get from consulting, and then teaching, and speaking, to coming up with the idea for The Arena?

Margo Aaron (13:55):

Okay. Well we skipped steps. Arena came first, actually. So around the time when I was still consulting, I was frustrated, and I wanted to do some of the marketing that I knew how to do for myself. And at the time, I didn't have a website and I had a colleague call me from London actually. And she said, "Margo, I love you. And you do great work, but I'm not referring to you anymore until you build a website because you're sketchy." So I said, "Fine, I'll put a website together." And that's what launched That Seems Important, which is my website. And it was in the beginning really stressful because I was being perceived as a expert in my field, but I didn't really know what my website was for. And without being able to answer that, you cannot optimize it. And it made me very nervous that clients were going to come and see something that was incongruent with their impression of me and the fees that I was charging.

Margo Aaron (14:48):

So it took months to not years for me to really feel comfortable writing in the tone that I wanted to write and being clear about why I was starting a website. But the very honest truth was I wanted to play. I needed a place that I could play. I wanted to play with pop-ups. I wanted to play with headlines. I wanted to play with copy. I wanted to grow an audience. I wanted to know if I could actually do the things I was hired to do, and do them for myself. Plus I really enjoy writing, which I think is an important theme that we should talk about. Just knowing the parts of your job that light you up. I had spent so much time ghostwriting for clients, that I had forgotten how much I enjoyed writing for myself. So that was just therapeutic for me.

Margo Aaron (15:35):

So I set this up. I did not promote it. I was just having fun. And I started building a following of founders, which was a little bit different than my consulting clients, which tended to be, sometimes they were founders and sometimes it was other consulting firms or agencies, or someone in the middle who would bring me in. This was people who were creating their own businesses, and a lot of solopreneurs and entrepreneurs.

Margo Aaron (16:00):

So they would reach out to me with email because I was emailing weekly, I think at this point. And they would say, "Listen, I have a marketing problem. Can I talk to you? Can I hire you?" I said, "Sure, let's get on the call." And this happened a whole bunch of times where we'd get on the call and I'd start asking questions about where they're struggling with marketing. And it became really clear to me that people didn't have a marketing problem. Because in my head I was like, "Okay, I can build a course. I can write a book. I can do all these things to help solve your marketing problem." But as I was talking to them, I was like, "You don't have a marketing problem. What you have is a self-doubt problem." And I thought how do you solve self-doubt? And also, how does the self-doubt get so bad?

Margo Aaron (16:40):

It started to emerge this pattern that a lot of founders and entrepreneurs feel really alone. And they don't have anyone on their level to talk to. And one of the advantages I always felt like I had was I found a tribe of people that I could talk to about what it's like to build a company, which is a very difficult and isolating thing. And a very, very uncomfortable thing to talk about publicly, because you want to present yourself in a way that people think you're successful. Because if you don't, then you're probably not going to get business. So it makes sense, but there's a thin line between putting on errors and perpetuating a fraud, and really feeling vulnerable and having a safe space to talk about your doubts.

Margo Aaron (17:21):

And I found that a lot of the people that I was speaking to really were struggling to trust their own intuitions about what their company needed. In part, because they were getting sold this idea that marketing worked as a template, and there was a very specific way to do it, and they need to follow so-and-so's templates. So they'd been a little bit brainwashed by marketers unfortunately.

Susan Boles (17:45):

I think we've been brainwashed by marketers about ... well honestly, isn't that the point?

Margo Aaron (17:50):

It shouldn't be. It should be actually to help match make people's problems with your solution. But unfortunately, I think we get obsessed with selling certainty when we feel insecure. So we pray off of people's fears, which shouldn't happen. That's the wrong way to do it.

Margo Aaron (18:05):

So I really felt for a lot of the people I spoke to. And I thought, "You know what? I have an idea. I have an idea that if I put everyone in a community of some sort online, that they will start to connect with each other and be able to solve their own problems. They'll have the confidence they need to fix this on their own and grow." And that was the first inkling of an idea I had for what became The Arena, which is how you and I met. Which was my virtual coworking space. And I branded it that way because I was living right outside New York at the time. And I felt like I had great access to lots of entrepreneurs. And when I went to visit family that lived in Kansas City and Houston, I remember feeling like, "Oh my God, where is the community here? How do you meet people?"

Margo Aaron (18:54):

It was so crazy when people would ask me what I do. And I would tell them a little bit about my life and how I worked from home. And their brains would explode because they were looking for a label or a name that they could understand. And they were like, "I don't understand. So do you wear a suit? Can I have your business card?" And I'm like, "Those are weird questions." I was always surprised at how confusing the fact that I worked from home was for people.

Susan Boles (19:17):

Well, and they also just assume that you're not really doing anything.

Margo Aaron (19:21):

Right. You're not doing anything. You're just fucking around. And that was problematic too. Which sometimes is true. There are people who do that. That was not me. That is not every business.

Susan Boles (19:33):

Certainly not me.

Margo Aaron (19:34):

It's like actually no, we're working three times as hard. It's because most of us are obsessed with efficiency. And if you have a 'proper' office job, you have to do your hair for 45 minutes in the morning, and then spend an hour in the car. It's not a really great way to maximize efficiency here, but I digress.

Margo Aaron (19:51):

So I wanted to connect people who didn't have access to communities that had great and strong entrepreneurial tribes. So that was the goal that created what became a product, a hybrid product service that was my next business.

Susan Boles (20:08):

From the outside, The Arena ended up being pretty much a textbook, profitable, recurring revenue, kind of subscription type business model that it seems like a lot of people are out there actually trying to build. And you did build it. And I can speak from experience. It was an amazing customer experience. You did actually create the tribe that you initially set out to build. We were talking about before the call that I think everybody that I've met in The Arena I've either hired, or has hired me, or has referred people to me. They literally have become my tribe online. And I don't think that I would have gotten ... I got really, and you created The Arena right about the time that I needed it. And I don't know that I would've been able to make the transition from having had brick and mortar businesses, to online businesses, to where I am now in as short a time period without that try, without that resource. So I mean, you succeeded, but you ultimately chose not to continue it. So can you tell me a little bit about why? What was going on for you and what was going on behind the scenes?

Margo Aaron (21:20):

It still stings when I hear that-

Susan Boles (21:22):

I know. I know it hurts. I've been there.

Margo Aaron (21:25):

We should resuscitate. It was so hard, Susan. The first problem was that I started to plateau in numbers. And the story I was telling myself first was that I wasn't doing the marketing right. So that was the first story. I was like, "Okay, if I could just get the marketing engine back up and focus on promotion, we can do this."

Margo Aaron (21:46):

And I ended up hiring some help, which was awesome. Building things out to where it needs to be. And then I would launch, and the numbers weren't hitting what they needed to hit. And in part, it was because I was very, very discerning with who we allowed in because I was so protective of the community. And I think one of the flaws of the model, but also the bread and butter of the model was that I was the gatekeeper. And I was so deliberate with the type of person that I wanted in, and that I felt like could contribute to the group, that I ended up choosing smaller numbers. And it was making it more and more difficult to find those people. We had a top-of-the-funnel problem if you will.

Margo Aaron (22:29):

So that was one that I couldn't solve. And when I looked at the competitive landscape in the market, there were two models. It was let anyone in for 49 to $99 a month, or have it be a 10 to $25,000 a year, really exclusive mastermind. Those were just the two buckets. And I was sort of meeting in the middle.

Susan Boles (22:50):

It was very much in the middle.

Margo Aaron (22:52):

Yeah, very much in the middle. And I had made some mistakes. When I let in someone too beginner, too advanced, I could see the effect that had on the community and the atmosphere that I was trying to create. So I wanted people with a certain mindset and at a certain level. And finding them was very difficult at scale. So that was one.

Margo Aaron (23:11):

The other problem that I ignored was that I happened to get pregnant and have a child. I was like, "This is no big deal. Everyone else grows a business while they have kids. It's not a big deal. And you're going to be fine." And I had-

Susan Boles (23:27):

It's totally a big deal.

Margo Aaron (23:28):

It was like nothing will fit.

Susan Boles (23:30):

And I say that as somebody who ran a guest ranch when my son was one.

Margo Aaron (23:33):

I know you get it. I was sitting there barfing my brains out in the first trimester being like, "I am fine. I will do all of the work." So the next story that I was telling myself was this thing will grow once you got this motherhood thing down, and then you can really spend time on this business. Now, you need to just give birth. And then it was like okay, you've given birth. So now you just need to sleep a little. There was always a thing. There was always something [inaudible 00:24:01]. And of course, while this was all going on, there was churn. And there was both employee churn, which was its own set of issues that I messed up. And there was churn with members. That was also hard. We had flatlined. I couldn't quite get us to where we were growing. And I felt like I was putting water in a leaky bucket. And I felt like I was at that what they call in the startup world the trough of shit, or it's the trough of sorrow. Where you have to decide do we kill it, or do we wait this out because this is normal? It's what Godin calls the dip.

Margo Aaron (24:36):

And it was really difficult to me because it was something I loved so much. But when I looked at how I was spending my time and what my strengths were as an operator, it became really, really clear that even though this was a great and viable idea, it was also true that I was probably not the right person to run it.

Susan Boles (24:56):

So how do you think you can tell when it's actually the business itself, the business model that needs to change or pivot versus you, and your skills, and where that fits in?

Margo Aaron (25:10):

I think you're looking at how you're spending your time and what you're investing in, and how you're investing in it. So as the owner/operator, I was spending a lot of time growing my personal email list, for example, and writing, and maintaining that. And not focusing on for example, promoting and doing PR for The Arena. Or I was getting really caught in the weeds of operations.

Margo Aaron (25:35):

You need self-awareness, which is something you don't have in the moment. I was privileged enough to have ... or maybe it's not a privilege. I chose it. I had people in my life who were uncomfortably honest with me and said ... I had an employee who turned around and was like, "Margo, you are focusing on features that don't matter." We had built out a membership portal. And Susan, you were one of the other people who mentioned it to me later. But I don't think I heard it in the moment. I was just blind to it because I was so afraid of not producing something high quality and disappointing members that it didn't occur to me until someone hit me over the head with it that I was tweaking features of the product that really didn't matter in the custom portal. That our actual value was in the Slack channel and in the people's relationships with each other. And I had felt very much like it was contingent on me.

Margo Aaron (26:29):

So a lot of these were me issues. And I think that it took someone pointing it out to me, and also me just being honest with myself about what kind of things were a little self-sabotaging. I think some founders never get there to be honest. They just lose the money. [inaudible 00:26:44].

Susan Boles (26:46):

No, absolutely. Do you think there is a distinction I guess in the business that you can run verse the business that you want to run? And that it's a trough of sorrow if it's something that ultimately you do want to do versus just something that you ... it's a great idea that you came up with, that you want to see through.

Margo Aaron (27:07):

Yeah. I think that's a really good point. There's a great quote from Liz Gilbert when she was like, "Listen, everything has a shit sandwich. The question is what flavor is your favorite flavor of shit sandwich?" So I love that because I feel like when people tell me, like when it comes to writing, where they quit, or where they've stopped, or where it gets really hard, I have all of those things, but it never occurs to me that those are reasons to stop. I remember even on days where my kids slept maybe two hours and I was like a zombie, I still somehow made time to write. Because it was like if I didn't, I couldn't breathe. Whereas with The Arena, there were things that were so frustrating that I couldn't get through, that I was like, "Oh fuck it." It's a different sort of internal energy that pushes you through when it's the right thing.

Susan Boles (28:02):

I agree with that, because that's definitely reflective of my experience with both the guest ranch and the running store. We built something that was, on the surface, it was working. We had brand awareness nationwide. You would see our hats in pictures on Instagram in other countries. We were doing on the surface, a really good job. But in the background, it was just something that we could see the path forward of where that business should go. We could see the growth plan. But ultimately, it came down to something where we honestly probably just didn't want it bad enough. That wasn't the thing that we wanted. Whereas with ScaleSpark, that is the thing. There's nothing else. You can just feel it I think. It wouldn't occur to me to give up ScaleSpark in the same way that I was willing to ... it was emotionally very difficult when we give up those businesses. Because it's something that you've built from the ground up, and you have all of this, they're sort of like babies. You built it. It's really hard to let it go. I think a lot of the times, we push ourselves further, because we're attached to it. We've got some investment.

Margo Aaron (29:14):

Well, that's just it.

Susan Boles (29:15):

That it makes it hard to just let it go.

Margo Aaron (29:17):

That's it. So there's a great, great lesson in, I took the altMBA during this time. And there was a great lesson on not letting your decisions be driven by sunk costs. And that really stuck with me. And I've thought about it ever since. It's been years now, but every time I sit in a decision, I think, am I making this because this feels like I don't want to waste all that I've put into it, or is this actually what I want to do? And I don't think you can answer that honestly unless you've done some self-work and you know how to read your own signals. Because I don't know about you, but I'm really good at lying to myself about what I want.

Susan Boles (29:56):

Yes, yes. I'm getting better at it or getting better at not doing that, I guess.

Margo Aaron (30:02):

Exactly. So there was a point where I was being driven by sunk costs. I'd put in all this time, and I was doing it for the wrong reasons. And I knew that once I thought about putting it away, that it felt like an exhale. And that's really different.

Susan Boles (30:21):

[inaudible 00:30:21] that it's the right decision, but it feels good.

Margo Aaron (30:23):

When I think about not writing my book, I go into a panic attack. I feel so anxious and sad. Because that's something that I want so badly that I will do anything for it. So I think you do need a little bit of that, a lot of that irrational faith in your own idea, but without it clouding your vision and ability to pivot and actually read the market.

Margo Aaron (30:47):

Because that's the other thing. When you say, "Is it you or is it the market?" I think sometimes, the question doesn't matter if it's not the right fit for you. It's very possible that The Arena was the market, and it doesn't matter because I shouldn't have been running it anyway. It's a moot point.

Susan Boles (31:04):

I actually think that's probably true. I think a lot of The Arena was you and the cultivation, the amount of selection process that you put in to making sure that the right people were in there and the right, that makes it sound bad. But that they were a good fit for the community and the goals that you were trying to accomplish in the community. So I think on one level, there is an aspect of I'm not sure that anybody else could have pulled it off because of that piece, the curation piece that was such a big part of it. But I think the concept itself, and we're seeing a lot more of that now with larger communities. I think it probably was just something that wasn't the right fit for you.

Susan Boles (31:49):

And I think that's okay to say. I had to accept that too, you know? We decided to shut down the guest ranch because ultimately, I didn't want to be running a business where somebody was going to walk into my living room at 6:00 in the morning while I was there in my pajamas. We didn't want to be running a bar when my son was two and waking up at 4:00 in the morning. It just wasn't the choice that we wanted for our lives. Not that it wasn't a business that we actually could run, that we were good at, we had the skillset to run. But ultimately, it came down to that's not the choice that we wanted for our lives and not the business. Even though on the surface, we had talked about running a B&B for years. It seemed like the right choice. But the reality of running that business wasn't right for us.

Margo Aaron (32:40):

Now you're getting exactly into product founder fit, which is ... my dad said to me once there's the business you could run, and there's the business you should run. And they're not the same. And I think that that is one of the hardest things for founders who are ambitious and smart is that there are a lot of things we could do. And we can put a round peg in a square hole all day long.

Susan Boles (33:06):

Ultimately, we're problem solvers.

Margo Aaron (33:08):

That's exactly right. And that's where it gets confusing. That's why I think there's so much self-work that needs to go into these decisions. Because my biggest fear and one of the things that was really sobering for me when I made these calls was I was actually looking at other parents who were waking up at 45, 55 with regret. And I was looking at my daughter and I was like, "This is not worth it. There's a choice that I could make here that if I'm going to miss part of your childhood, I got to miss it for something else." Or there has to be a version where I have to understand that maybe, I need to take a financial hit for a little bit in order to be present. Or maybe I'm the type of person who doesn't want to be present and wants to throw myself into my work. I mean, they're all totally fine options.

Margo Aaron (33:55):

But the point is that you need to know yourself, and you need to find that intersection between the business model and your personal disposition. And I think that's how I define product founder fit. We talk so much about product market fit, which obviously is very, very important. But if you don't have the right person running the right company, then product market fit doesn't even matter because they're going to run it into the ground.

Susan Boles (34:20):

Yeah, absolutely. There's tons of stories about that.

Margo Aaron (34:22):

Because you will lose your mind. It's so hard. And it's not about gaining more mental toughness. I think that we come to the world with certain dispositions. My husband has never met a spreadsheet he couldn't make sense of. He is so amazing with pivot tables and being able to take data. He's like you. And can take systems and make them talk to each other. And he is a great brain to put into operations, or senior management roles, or CEO roles.

Margo Aaron (34:55):

I am not great for that. I have a bootstrappers mentality. I figure shit out and I break shit. And I never think the rules apply to me. So I am a terrible person for that role. Terrible. I jury rig everything. And that's good to a certain point, right? There comes a certain point where I'd be the type of founder where I'm good at the bootstrapping, then I'd need to hire a CEO. and you have to know that about yourself I think going in, before you start your next venture.

Susan Boles (35:22):

And I think that's totally true. And I think there are certain types of businesses and certain stages of businesses that are right for certain personalities. I'm a fixer. I come in and I love fixing the problems. That's the part that's fun for me is figuring out the puzzle, figuring out the challenge. But I am not the person that when it's just on autopilot, I'm not the person to keep it on autopilot. Because I'm always going to be pushing for it to be better. And there are some personalities that doesn't work for. I think finding the right person, at the right stage, with the right skills, and the right business model is all a part of that.

Susan Boles (36:08):

So for you, how have your experiences with The Arena and with consulting kind of impacted your choices about how to structure your business or your life now?

Margo Aaron (36:18):

So first, I had to come face-to-face with how much I was measuring my worth based on other people's benchmarks for success. So an example of that is I had built something that I could scale, because that was kind of the gold standard. You want something scalable. It shouldn't be reliant on you. That's a huge mistake. And it actually was a mistake for The Arena for the reasons that you explained. It was way too reliant on me. And that was also a problem with my consultancy and scaling it, which I didn't get into. But I had a team of contractors under me. And every time I had them do something that I should have been doing, it was very difficult. Or they would disappear because they're freelancers. Right? So I thought that scalability was the thing. And it occurred to me that I have an option to reject that if I want. I actually really, really hate managing people. I like having a small, small team. I like being the sole decision-maker. I hate having to explain why I made a decision that's irrational. I like to just make it.

Margo Aaron (37:20):

So knowing those things about myself, it opened me up to not feel the shame that comes with feeling like my business should look different than it does. So knowing that I get paid to speak, and I get paid to do workshops. I'm writing books. And I have courses. There are certain things that they're still pretty reliant on me, but in ways that leverage and scale me in a way that I'm comfortable. Like speaking, it's technically not scalable, but it is scalable in the sense that I am in front of an audience. I'm in front of lots of people. So it's one me and lots of them, but it's still reliant on me. It is scalable in the way that I'm comfortable. And that has to matter.

Margo Aaron (38:04):

I feel like in the way that I have judged myself in the past, it's like what I wanted for my business and for my life was not a consideration. It was simply maximizing shareholder value, or increasing profit margins, or these really, really, for lack of a better term, practical ways of looking at business. And I felt like I went into business, well one, I can't not do it. So I'm probably the worst employee ever. So there's that. I feel like if I could do something else, I would.

Margo Aaron (38:35):

It was also because I wanted a lifestyle that was built around my value system. So part of that was having a flexible schedule so I could see my kid. And part of that was so I didn't have to deal with some health stuff. And part of that was so I didn't have to spend time commuting all the time or I could travel and see family. There are a lot of different things that matter to me, that the way the world talks about what you're allowed to value, they devalued it. Especially in the context of business. You're not allowed to care about those things.

Susan Boles (39:12):

Talking about a lifestyle business, and it's almost-

Margo Aaron (39:15):

A black sheep.

Susan Boles (39:16):


Margo Aaron (39:17):

I think Paul Graham has essays about how terrible they are. And in fairness, he's not wrong because we've all met those people who are like, "I'm moving to Bali to go do this thing." And they're just lying. They're not doing that. They just got laid off from IBM, and they have a severance. And then they're just going to burn it for six months and end up back somewhere else. And God bless, that's fine. But don't call that lifestyle entrepreneurship. Call it taking a break.

Margo Aaron (39:41):

So there cannot be shame in how you choose to deploy business principles in your life. I think that we have put on a pedestal the types of businesses that break people down. We praise people who value all of the wrong things. You can berate your employees. You can be an absentee father. You can cheat all the time. You can lie about your taxes. You can create loopholes. There are all of these things that people, are just part of the foundations for what we build. But it's not okay to say, "Hey, I'm okay with making X amount per year."

Margo Aaron (40:14):

And it's different for everyone. I talk to people who are like, "I only want to make $250,000 a year." Other people, that number is 75. Other people, that's 750. Whatever your number is, we have to stop feeling so much shame if it's fitting within the lifestyle that we wanted for ourselves in the first place. That was what kept me going when I considered what the next pivot was going to be for me, and why I was here to begin with.

Susan Boles (40:38):

I love that, because I think that's true. I think especially in the world of online entrepreneurship, it's drilled into our head the types of business that we're supposed to build. And whether you're doing the VC I'm going to build a giant company route, or you are doing the lifestyle business, even though the lifestyle business even in The Arena where you are talking lifestyle businesses, they're talking you have to build a course, and your business has to look like this. And you need a funnel, and you need all of these things. Where I think a lot of those are just misconceptions. They're marketing that is trying to take advantage of you, or trying to eliminate your choices. Or make you feel like you don't have a choice when in reality, choosing a very conscious choice to design your business or to design your life in a particular way is both valid. And at least for me, very empowering.

Susan Boles (41:40):

I designed my business consciously in a very specific way to allow me to live a life, not the other way around. And I think that's a valid, but I also think it's still kind of a difficult choice to be the person out there saying, "This is why I did this." And I'm choosing not to grow, or I am choosing the growth path that I've picked. And I'm okay with that. But I think it's hard because there's a lot of people out there that will shame you or judge you for whatever choices that you've made.

Margo Aaron (42:15):

Absolutely. Society too. And the thing to remember, it's so hard for me to keep this in check, but it's always true, is that that shame is a reflection of their own insecurities. It has almost nothing to do with you. And the more you live according to what your value system is, and judge yourself based on how you define success, the more those people will start to envy what you have in a beautiful way. And you empower them to do the same. So the people who shame you, you end up emancipating by just living your life on your terms.

Susan Boles (42:47):

I love that. So you have written a lot lately about not doing things perfectly or not letting imperfections stop you from moving forward. And I know that's something that's resonated a lot for me, particularly as I launched this podcast, which is something that's completely new for me kind of stepping out in the world. But putting anything creative out in the world, it was always a little terrifying. So can you tell me a little bit more about why that's what you're focusing on right now?

Margo Aaron (43:16):

So I've had the privilege of being behind a lot of businesses. And one of the patterns I see over, and over, and over again in the successful ones versus the ones that flounder is this mindset of just playing and trusting yourself. Looking at things almost experimentally like, "Let's try this. Let's try that." And not having these strict definitions for what their business is supposed to look like, and sort of taking it as it goes. And I found that a lot of the entrepreneurs, myself included here, we tend to look for a model, a template, a system, a framework that we can take and copy. And I think a big problem that we're seeing in today's online business world and just the entrepreneurship world in general is people failing to trust themselves as creators, and understanding that part of entrepreneurship is making things up. You are bringing something into the world that didn't exist before. And when you try and fit that into a prescribed model, you lose everything that's great about what you've created.

Margo Aaron (44:28):

And sometimes, the rules are not set in stone. Sometimes, the rules are really malleable, and especially when it comes to marketing. I get asked a lot, and this is part of why I'm writing about it a lot is I get asked so many times what's the right brand voice for my emails, or what should I capitalize, or what color should I make this button? And all of these really tactical details that really don't matter if you know who you are and what you're trying to do. And if you are more open to playing with it. One of our mutual friends [Talia 00:44:59] created I think, what is her account at now Susan? Do you know?

Susan Boles (45:04):

I don't know. I lost track over 100,000.

Margo Aaron (45:06):

It's way over that. Now. It's like 250, she might've broken three. She was in the New York Times this week. So Susan and I have a friend, and she's a perfect example of this, who started building an Instagram following. And she was like, "I'm not going to do it the cheating way where you buy followers, I'm just going to play around." And that was her mindset. She's like, "I am just going to play." And she played, she played, and she played. And it started working. And it wasn't that she followed a prescribed model. She started to just understand intuitively what worked. And that's why she's winning in my opinion, is that-

Susan Boles (45:38):

Talia is a perfect example of somebody who just experiments. Everything is just, "I'm just going to go test this and see what happens."

Margo Aaron (45:46):


Susan Boles (45:47):

And she can just throw herself out there.

Margo Aaron (45:48):

We have a fear that we're going to do things wrong. And that's what I'm trying to launch a revolution against is that this is business, and this is creativity, and this is entrepreneurship. You're not going to get it wrong. And the consequences for getting something 'wrong' are really not that big. No one's dying if you tweeted wrong. But it feels so heavy. And we're so-

Susan Boles (46:11):

Every decision feels so crucial.

Margo Aaron (46:13):

Yes. And that's part of what I'm trying to rally against is people feel ... listen, I'm a marketer. I am a copywriter. I want to sit here and tell you that the headline on your website makes a really big difference. But unless you are getting hundreds of thousands of leads to your site, traffic to your site a day, it really isn't going to make that big of a difference in the beginning. It's okay if it's not right. And what's even more interesting and part of why I brought up Talia is that when you do it good enough, it works. Her very first sales page was fine. There was a lot of problems with it, but was good enough. It converted. It did just fine. And what I want people to know is that you can trust yourself. You can trust yourself to figure out these patterns. Because ultimately, business is about dealing with people. It's about understanding people. and lucky for you, we are born pattern recognizing machines. That's part of our wiring.

Margo Aaron (47:04):

So the more we put ourselves in situations to go, "Okay, what worked about this? What didn't? How can I change my approach? What should I do differently?" The more we're going to finally get to those conclusions that we believe are hiding in books, and hiding in courses. And the answers that we're looking for, you can arrive at them on your own without feeling that fear, and without feeling like someone needs to give you the answer. And that's part of what I want people to recognize. It doesn't need to be this scary.

Susan Boles (47:33):

I love that, because that's something that I've tried. I am susceptible to that. I always want a framework. I want somebody to have done it. I want to learn from previous experience. But I think there's a point at which you can learn from previous experience. But ultimately, it has to be personable to you, and your business. And the templates, and the checklists, and the models just ultimately aren't going to give you the answer. You need real actual data.

Susan Boles (48:04):

I mean, I very clearly remember when I started talking about my pivot from projects type work to retainer work, and I had had all these kind of mindset around I don't want to work in a retainer model. And trying to figure out what a new model could be for a retainer. And you said something that was really, really simple. But you're like, "Just go talk to people." I was like, "What do you mean just go talk to people." "Just go talk to people. Go call people up and just go talk to people. How many people have you talked to?" "I've not talked to anybody. What do you mean talk to people?"

Susan Boles (48:39):

And now, I think it's so funny because that's become my go-to now is I'm just going to go talk to people. But it was such a hard mindset for me to get over, getting into that just go test something. Put something out there, see what it works. Maybe it won't, maybe it will. And just have fun with it. And I think that's been a really big mindset shift for me. And it ended up being reflected in my business. The more fun I have with it, the more successful the business gets. I love the idea of just trusting yourself and just putting yourself out there that it doesn't have to be as terrifying as sometimes it feels.

Margo Aaron (49:18):

And let me be clear here. This doesn't mean it's going to work, right? There's still a lot of things that could go wrong, but that is the point is that it could go wrong either way.

Susan Boles (49:28):

It's just going wrong in the real world and not wrong in your head.

Margo Aaron (49:30):

Exactly. That's exactly right. You want to be in The Arena. But that's exactly the point is that you want to be getting real feedback from real data, and you don't want to be ignoring your instincts and ignoring what you're seeing.

Margo Aaron (49:44):

There is a friend of mine who ran a style business. And I remember we were having a conversation on price. And the running prevailing wisdom and best practices said you got to be a high price point if you want to be in the premium market. And he sort of looked at his market and he was like, "No one is spending more than $300. I know I need a $2,000 thing, but it's not happening." And it finally took him a lot of courage to say it's not my copy that's the problem. The market will only bear so much. So he tried a lower price point, and it sold. So it shifted what he focused on. And he couldn't have come to that if he was just blindly listening to the mantra. He needed to pay attention to the market.

Susan Boles (50:30):

Giving something a shot and failing isn't bad. To me, failure is just data. It tells you what didn't work. And now, you have better information for when you try again. I like to think of owning a business as an interactive experiment. I'm always trying stuff to see if it works, and collecting data about my experiments along the way. Because better data leads to better decisions. That's true in finances, and true about just about every decision you can make. And sometimes, the only way to get the data you need to make a good decision is to try something and fail. And that's okay. That data will help you build something better the next time around.

Susan Boles (51:15):

Sometimes, the key to success is consistency. It's about pushing through. Sometimes, it's about quitting what's not working so that you can make space for something better and stronger. If you're interested in hearing more from Margo, you can find her on YouTube @hamyaw. That's H-A-M-Y-A-W. Or at And if you liked this episode, I'd really appreciate it if you shared it with someone you think would enjoy it.

Susan Boles (51:44):

Break the Ceiling is produced by Yellow House Media. Our executive producer is Sean McMullin. Our production coordinator is Lou Blaser.


Measuring Growth