773 Sara Roach Lewis: 7-Figure Confidence

What holds women back in business? What stops us from tackling ambitious moonshots or aiming for billion-dollar success?  Entrepreneur and feminist business strategist Sara Roach Lewis says the masculine “winner take all” “win at any cost” war-like structure of business saps women of ambition and confidence – so today we talk about how to rewrite the rules.

MELINDA

Hi, I’m Melinda Wittstock and welcome to Wings of Inspired Business, where we share the inspiring entrepreneurial journeys, epiphanies, and practical advice from successful female founders … so you have everything you need at your fingertips to build the business and life of your dreams. I’m a 5-time serial entrepreneur and founder CEO of the interactive podcast app Podopolo. Wherever you are listening to this, take a moment and join the Wings community over on Podopolo, where we can take the conversation further with your questions, perspectives, experiences, and advice for other female founders at whatever stage of the journey you’re at! Because together we’re stronger, and we soar higher when we fly together.

Today we meet an inspiring entrepreneur who is on a mission to help ambitious women build scalable businesses that support their busy lives.

Sara Roach Lewis is the CEO of SRL Solutions, creator of the 7-Figure Confidence Program, and author of She Rules, What You Didn’t Know is Holding You Back in Business. Today on Wings, Sara shares her strategies for exponential business growth, achieving laser- focus while moving through resistance, rebranding self-care as an important business practice, and how to turn your imposter syndrome into 7-figure confidence.

Ever felt judged by another woman – or a man – for being “too ambitious”? Ever felt like an imposter in your own business because the people around you make you question your dreams? Or simply felt alienated by the “winner take all” strategies, tactics, and language of business? There are many ways in which the underlying beliefs of our society, including the masculine often militaristic structure of business which rewards profits at all costs, can undermine women’s confidence as entrepreneurs. It’s hard to feel confident in a structure that doesn’t feel natural to us or aligned with our more collaborative natures. And it might be why less than 2% of women owned businesses make more than $1 million a year, and 86% make less than $100,000 – even though women are starting businesses three times as often as men.

Sara Roach Lewis says it’s time to shift the paradigm that keeps women stuck in the hardest phase of business, and her book She Rules: What You Didn’t Know is Holding You Back in Business, Sara shares how best to leverage our feminine power to feel more confident, be in control, and make more money. With her 7-figure confidence program, she coaches women to build scalable businesses, turn imposter syndrome into exponential business growth, achieve laser-like focus while moving through any resistance, and prioritizing selfcare as a vital business practice.

Today Sara shares her strategies, plus why she believes that gender equality can solve all of the world’s problems and that by advancing more women we’ll make a better world for everyone.

Let’s put on our wings with the inspiring Sara Roach Lewis and be sure to download the podcast app Podopolo so we can keep the conversation going after the episode.

Melinda Wittstock:

Sara, welcome to Wings.

Sara Roach Lewis:

Well, thank you so much for having me.

Melinda Wittstock:

I’m excited to talk to you in this new year about how women in business can really grow their confidence. What’s the main reason, do you think, that women suffer from lack of confidence?

Sara Roach Lewis:

I think it’s a multitude of things, Melinda. And when we look at women in business in particular, a couple of years ago, I was really struck by conversation, after conversation, after conversation with women business owners and entrepreneurs about how they didn’t always feel comfortable or confident in their business even though it’s theirs, and in many cases they were the ones who created it. And so I really started thinking about that. And as someone who has a deep background in strategy, as well as understanding women’s experience, I worked for a feminist organization for almost a decade. I really want… I pulled a super big picture. And so when we think about business, historically business was designed for men, inspired by military strategy and supported by a woman at home doing everything else. And so when we think about business from that context, it’s no wonder that we don’t always feel comfortable or confident in our skin in this game.

Melinda Wittstock:

Because it’s a structure that’s imposed on us rather than us organically creating it.

Sara Roach Lewis:

And it’s a structure that wasn’t designed for us. We all live within systems and structures, and the structure of business was designed for men. And when we go back to that military strategy, it was really built on that. And when you think about the art of war is really considered the Bible of business strategy. And when you read it makes sense why. And really, we see that in our business language all of the time in terms of what is the chain of command and what’s your tactics and your strategies.

It’s the language, but it’s also the permutations of military strategy is designed for winning at all cost. And when we translate that to business, that translates to profits at all costs. And that strategy doesn’t work for any of us anymore. And it certainly doesn’t work for the women that I work with and thousands of women that I’ve worked with over the years. We tend to be more collaborative. We tend to want to do things a little bit differently. The structure sometimes, it plays a role in our lack of confidence.

Melinda Wittstock:

Sara, that military analogy, oh gosh, it makes total sense to me because even though women now do go fight in wars and whatnot, we are wired differently in business. And I think some of the interesting research that’s coming out now is that we actually outperform men in business Because that collaborative ability means better teams, better aligned teams. It’s better in a marketing sense too because we’re really creating community. Our customers feel part of something bigger than just a transaction. We’re better at risk. We’re actually better as long as we’re doing it, I guess on our own terms.

Sara Roach Lewis:

Our way. And so I think that’s part of the challenge is that we couple the system and structure that wasn’t really created for us. We’re trying to fit ourselves into that with another system and structure that really encourages us to not live our full self. And so if we think about from the time that women or from the time that people are sorted into their pink and blue onesies, women are socialized to look after everyone else first and put everyone else’s needs ahead of our own. And so we are told over and over again to play that supporting role. And then we add that into this idea that we are told over and over and over again that we’re not confident.

I think about part of the reason why we’re told and that message is reinforced is because it encourages the patriarchal system in which we live to continue to operate as it does. Our world is built and lives on the unpaid labor of women, whether that is emotional or physical. And so continuing this narrative that women aren’t comfortable and confident allows the world to continue to exist the way that it does right now.

Melinda Wittstock:

I think it’s really interesting in the context too of women founders of businesses such as my own, which is technology business, needs venture capital. But it’s very, very difficult for female founders to raise money from primarily white men. I mean 98% decisions are made there. And I have often wondered whether… it always goes unspoken, whether they think, “Oh gosh, a female founder, she’s not going to, I don’t know, win at all cost,” which is what the VC is looking for. It’s unspoken in the conversation, but it’s probably there and they’re looking at it in those terms.

Sara Roach Lewis:

Well, and I think the VC is a really interesting space to consider in all of this because it is an odd space. There’s this intense competition and there’s also this… part of what you just talked about, women are really good at what they do. And part of what makes us good at what we do is that we’re realistic and that we think things through. And part of that VC world is the bravado, is the like, “Yeah, absolutely. I can do this thing. I have no idea how I’m going to accomplish it.” But there is that selling and selling into… and I think women are very good at selling. It’s that system is one that is more uncomfortable for women.

Melinda Wittstock:

It’s interesting because say if I use my own business as a lens, when you come up with your numbers or your forecast for your investment round, VC is automatically going to discount it. And what happens is women are realistic going into that conversation.

Sara Roach Lewis:

Exactly.

Melinda Wittstock:

Whereas men are just the hockey stick or whatever. And then when women, even when you actually say what you believe you’re going to do, they’re just going to discount it anyway and then just doesn’t look as interesting to them. And then they think, “Oh, aren’t you being aggressive?” Whereas they would not ask a man the same question.

Sara Roach Lewis:

And I also think in that particular world, there is this whole idea about solving problems that we have that potentially men don’t have. They don’t necessarily see that there’s a market for that. I think there’s a whole lot going on there. There’s a woman who lives close to where I live and she’s working on this amazing business where she is creating a better prosthetic breast that you use after you’ve had breast cancer. And so she’s talking about the challenges. We had a conversation last week. She was talking about the challenges of having these kinds of conversations with investors who, as you say, are overwhelmingly men and can’t even begin to wrap their head around what her experience is except in the, I mean luckily… I guess that’s not the right way to say that, because I was going to say luckily most of these men know someone who’s experienced breast cancer, but they don’t have that same experience of what that’s like.

In that context there’s part of it is they don’t understand the product that she’s creating. And the other piece to it that we see often is it’s really emotional for her and it’s often really emotional for us as business owners. And that makes men uncomfortable. Whereas if we can just lean into, business is emotional.

Melinda Wittstock:

Yeah. It’s about relationships, it’s about people today.

Sara Roach Lewis:

When you said at the beginning, we’re very successful at it when we lean into the whole of who we are. And that’s when we look at confidence, when we look at what I would call a feminist business strategy that is about leaning into the whole of who we are.

Melinda Wittstock:

And so I think a lot of this is the underlying root then is the fear, what’s the fear of leaning in entirely to who we are? Because that’s a journey. Because we’re all swimming in the same primordial soup in the sense of the collective unconscious or our own subconscious beliefs. 80% of our decisions are basically ruled by our subconscious minds. As we’ve all been socialized in this same way, I think it can be really fearful for women sometimes to play a bigger game. I know so many female entrepreneurs who start like, “I’m just going to start this small business,” as opposed to saying I’m going to build a billion-dollar business. Whether we are able to think in terms of leverage and scale and some of these things which are potentially foreign, I think women are so used to doing everything. They think, “Oh man, if I have a really big business, I’m going to be doing more than I can do.” Which shows to me a lack of understanding of leverage, which men seem to naturally possess.

Sara Roach Lewis:

Exactly. And I think that’s the thing, is that there’s a lot of the things that we can learn from men that we do need to learn. And part of that is we are so used to playing that supporting role that men naturally understand leverage, they naturally understand, “I’m going to do this one thing and I’m going to do it well.” Whereas women are very much used to and socialized and encouraged to keep all of the balls in the air and do all of the things so that it does feel overwhelming when you imagine growing this big business. I also think there’s a whole piece too, in my book, I talk about ambition and I work with ambitious women entrepreneurs. Ambition is one of those words that for women when I use that word, will wonder whether that-

Melinda Wittstock:

[inaudible 00:12:58]. And I’ve never understood that. Why should that be?

Sara Roach Lewis:

Because it’s one of those coded words that if a woman is ambitious, it’s a code for selfish or thinks that they’re better than other people and all of these kinds of things which we value in men, but we don’t necessarily value the same way in women. I think again, when we look at how do we address this fear, how do we address these confidence issues? Part of it is understanding what is yours to own and what is society for you to reject. Like, “You know what? That is an old narrative. I am not living by those rules anymore, so I am rejecting that.” There’s a part of this, it’s for us and there’s for us to work through and there’s a part of it for us to just say, “Nope, I don’t live that way anymore.”

Melinda Wittstock:

Yes, 100%. because women I think really seek the approval of other women. We’re so relational. When we dare to,  stand in our full light or be the lighthouse, really double down in something that’s ambitious, you get a lot of side eyed glances from other women. I think that really holds us back. How can we change that? Because I think it keeps us playing smaller and it keeps women from really stepping into who they are and building amazing businesses where we’re I think naturally wired to be great at business.

Sara Roach Lewis:

I would agree. I think we’re naturally wired to be good at business and great at business as well. There are lots of things that we can do. And part of it is just having the awareness and the recognition that the patriarchy is sneaky and it gets us to do the work for it. What you’re talking about there is it’s good old-fashioned, lateral oppression, internalized sexism, whatever you want to call it. We are very good at doing that work of society to make sure that we don’t get too big for our britches and therefore stop doing all of the unpaid labor that needs to be done. How we overcome that partially and first starts with awareness and first starts with what are the stories that we tell ourselves about ourselves and about other people? And women in general we are really hard on ourselves and we’re hard on each other. Step one is awareness, and then step two is just making that decision to be radically supportive of yourself and your ambitions and those of other women as well.

Melinda Wittstock:

100%. On this podcast, we always say we all soar higher when we fly together.

Sara Roach Lewis:

Absolutely.

Melinda Wittstock:

What does it look like for women to consciously support each other, mentor each other, buy each other’s products, promote each other, actually invest in each other. And I find that a lot of women are still trapped in a bit of scarcity. This is underlying idea that there’s only room at the top for a few women, not all women. And so we’re competing with each other in that kind of scarcity mind mindset rather than being in a more abundant one where another woman does well that paves the way for all other women. This is a mindset shift.

Sara Roach Lewis:

Yeah. And I think right now we do need that mindset shift. And I believe that mindset shift is happening with podcasts. I know that’s even hard to say. With podcasts like yours and these kinds of conversations, the reality is about 2% of women owned businesses make more than seven figures, a million dollars a year in annual revenues. And probably even more stunning is 86% of women owned businesses make less than a hundred thousand dollars a year.

So when we think about where does that scarcity mindset come from? The scarcity mindset comes from businesses that are not making enough money and that that’s part of it. For me, I really encourage women move through those early stages of business as quickly as you possibly can because we want to be doing is creating… right now, if you’re in that 2%, you’re a trailblazer. Well, we want to make that trail to seven figures and a wider path, and then eventually we want that to be a superhighway where there are entry points all along the way so that anyone who wants to jump on that superhighway and find their way to wealth and abundance and the freedom that comes from that has the ability to do that.

Melinda Wittstock:

Yes, 100%. It’s very interesting too in the context of hiring. My business is just closing a venture round. And I find that the men applying for C level or VP level or director level jobs tend to apply, and the research bears this out, even when they don’t have all the qualifications on the job description. Whereas women tend to rule themselves out.dd So it’s hard to hire, even when you’re actively looking to hire and promote women, it’s so hard to find them. This is what’s me flirting at the moment? I’m like, “How is this possible?”

Sara Roach Lewis:

It’s amazing, isn’t it? And I see it all the time. I see it all the time with entrepreneurs with friends of mine who are in business. And a woman sent me a message the other day, there was a role came up and we had talked about it in person and she sent me a message and said exactly what you just said, “I don’t have all of the qualifications.” You have 85% of them just apply and in your cover letter tell them that you don’t have all of the qualifications. I think you’re right there’s that, and it really is how do we encourage every step of the way, both other people and ourselves to step out and do the thing that potentially means we’re going to get rejected, potentially means that we’re going to have our worst fears realized, but also more than likely means that we’re going to get the job, or we’re going to get the contract, or we’re going to get the client that is going to make the difference for us because we can do it, we just sometimes get lost along the way.

Melinda Wittstock:

That’s so easy to do, especially if you’re not surrounded by people that truly have your back. Say for instance, I think part of the context of women as well, if for any reason their husband or partner or their in-laws or their friends or just the people around them are saying things like, what makes you think you can do that? Or often they’re coming from a well-meaning place because their own fears are projected on that. They don’t want that person to be hurt, or they’re actually threatened if the woman’s going to make more than the man or whatever. And I think women have internalized that so much too that they’re afraid of rocking the boat. They say that you’re really the song, you’re probably the median of the five closest people you hang around with. If you’re hanging around with people that are limiting you, you’re going to be limited.

Sara Roach Lewis:

And I think that’s the thing is if you’re listening to this and you’re thinking, “Okay, this is all well and good, whether it’s the patriarchy or society or whatever, that is part of why I am not feeling confident, how do I actually feel more confident?” And some of the things that we can look at are exactly what you’re talking about. If we are that median of the five people we hang around with, look at who you’re hanging around with. And maybe that needs to have a bit of an edit, maybe you need to continue to look to see where are those business besties? Where are those people that I can find who will be confident in me when I am not confident in myself?

Melinda Wittstock:

Right, right, right. Yes, exactly. specifically built an advisory board, mostly composed of super strong women who have built major things. Because I know it can be done, and whatever I’m going through or whatever fear I’m having or whatever it is that I have to overcome or whatever, I know I can call them up and they will talk me through it. They’ve probably experienced exactly what I’m going through ahead of me. And so having those mentors actually really seeking them out.

And I find that women who are really strong and very accomplished are much more generous as well. They’ve done it and they get to this place where you want to give back, it’s why I do this podcast as well. Because you’re just like, “Okay, I’ve gone through all of this.” All the ups and downs and all the things, like I say on the introduction to this podcast, they’re very, very real. Moments like, “Oh my God, how am I going to make payroll?” Or like, “Oh,” all the things. And there’s always a new challenge in entrepreneurship. There’s always stuff that you don’t see coming, and it’s just, you got to take it in the spirit of this is not happening to me, it’s happening for me, and I’m just getting stronger through this process. And by the way, all these lessons and all these learnings can be passed along. We don’t have to keep reinventing the wheel.

Sara Roach Lewis:

Exactly.

Melinda Wittstock:

When people are in your confidence program and you’re teaching them about this, talk to me about your process of how you get women into their full feminine power, their full sense of confidence in themselves, really valuing themselves deep down.

Sara Roach Lewis:

Well, what I do is pretty practical, I think. When I work with women, I have a program that I work women through in terms of, I generally work with service-based business owners. And so when you want to take your business to that next level, and you’re not really sure how to do that, often service-based business owners are in business because of their expertise, but they don’t actually have the business experience. And so what I really focus on is teaching people how to do entrepreneurial planning in their business. And so how does that connect to confidence? Much of when we look at confidence, there are things that we can do to build our confidence. One of the things that we can do is what we just talked about. Find people who are going to be supportive of you when you don’t feel supportive of yourself.

Finding ways to reframe that language. Rather than saying, I don’t have confidence to I am experiencing a crisis of confidence. That when we use the language that is easier for us to move through crisis rather than something as absolute as I don’t have confidence. We do things like that. But then another key thing that we need to do when we’re building our confidence is building our skills. And so generally speaking, when we’re looking at business owners who are in those early stages, whether they’re at 50,000 and they want to get to 100,000, they’re at 250,000 and they want to get to 500,000, whatever that path, I’m always thinking about that path to seven figures. Every step of the way there are different challenges, there are different things that open up and there are different challenges.

What I do is I help discover how to solve those problems along the way. And that is such a key piece of building confidence. I have a whole section that I do around money management, and first we talk about mindset, but then we actually dig into how do you do financial projections that are going to be super helpful for you in terms of making business decisions? And man, there’s nothing that builds people’s confidence more than, here’s how to use a spreadsheet that’s going to give you really good information.

Melinda Wittstock:

Right, right. Right, right. Knowing your numbers.

Melinda Wittstock:

Numbers tell a story. Business, it’s about relationships. It’s also about numbers. How are you doing? What was your cost of user acquisition? What was your this? What was your that? How can you do better? But if you’re not looking at those, or just in a funnel, if someone says, I want to make a million dollars, or what’s your price point?

Sara Roach Lewis:

What are all the inputs? Yeah.

Melinda Wittstock:

How many people do you have to reach? What’s your conversion rate thinking in a funnel? Some of these things. I’ve found with other women that I’ve mentored over the years and just my own experiences, is once you just dig into that and they’re like, “Oh, that wasn’t that hard.” It’s just understanding those systems, just doing it as Nike says.

Sara Roach Lewis:

Well, and it really is. Action is the only antidote to a lack of confidence.

Melinda Wittstock:

Yeah, exactly. That’s all you can really, really do. Sara, in your own journey as an entrepreneur, I mean were these things that you learned through your own experience or how did you come to these insights?

Sara Roach Lewis:

Yes. My entrepreneurial journey is a funny one I suppose. I spent most of my career working in the not-for-profit sector, and I at 45 decided that I was ready for a change. And So it was almost a process of elimination that I landed on entrepreneurship in starting my own business. And I experienced the most massive crisis of confidence in that first 18 months of being in business. I was the executive director for a feminist organization. I was often sought out for my experience and my expertise, and people would come and ask me questions and our organization would help government inform public policy. And so I had this really great job and I supported women in a variety of stages, ages, careers, not careers.

And what I saw over all of that was all of those experiences helped me see that it doesn’t matter who you are, every woman has a story that will break your heart. And every woman has amazing potential that often hasn’t been allowed to open up. That’s what I brought to this whole experience. And that first 18 months was brutal. It was very out of character for me to be that paralyzed. Part of what I do with my clients is very much based on all those years of working with women all those years of running a small not-for-profit, which is very similar to running a business. And that my own experience of having these challenges around confidence, and I mean, we all still have them, we just find new and different things to not be confident about. That’s all. We’re able to move through it more quickly, but that’s really where it came from.

Melinda Wittstock:

Yeah, it really does come from that. I mean, if you look back on your life and you really honestly assess where did I grow the most? It was from those sort of failures. It’s from having being in a difficult situation and overcoming it. And I think that’s the root of real confidence as opposed to just sort of bravado or pasting confident veneer over subconsciously lack of confidence. It’s earned experience in a way. Entrepreneurship, I think is the surest fastest way to do that because it’s just going to put things in your way that you have to overcome. So if you go into it again without right mindset, you’re going to grow your confidence faster than probably any other path, maybe becoming an athlete or there’s certain other professions that require that, an actor or whatever, where you’re just up against constant challenge.

Sara Roach Lewis:

Because I think where it comes to is that… because it goes back to that, the antidote to a lack of confidence is action. And as entrepreneurs, we have to act. There is no time for inaction because when we don’t act, we don’t get paid and we don’t make any money and then we have to find a job. That to me is where there’s this such great joy is in figuring out that done is better than perfect, that I will do something, I’ll learn from it, I will iterate that process and I’ll do it again. And that is really the only thing we need to do as entrepreneurs is to keep moving forward.

Melinda Wittstock:

Yes, exactly. 100%. Sara, I want to make sure everyone knows how to find you and work with you. What’s the best way?

Sara Roach Lewis:

The best way to find me, I love to hang out on Instagram. I think it’s a fun place to hang out. So I’m sroachlewis on Instagram, and then my website, you can go and find me there. And it is sherules.biz.

Melinda Wittstock:

And also, I’ll make sure that everybody has all the details of how to get your book in the show notes and all the ways to contact you as well.

Sara Roach Lewis:

That would be wonderful. Well, thank you so much. This has been a real pleasure.

Melinda Wittstock:

100%. Thank you for putting on your wings and flying with us.