Emma Isaacs: The Art of Winging It

Tami Simon: Welcome to Insights at the Edge, produced by Sounds True. My name is Tami Simon, I’m the founder of Sounds True, and I’d love to take a moment to introduce you to the new Sounds True Foundation. The Sounds True Foundation is dedicated to creating a wiser and kinder world by making transformational education widely available. We want everyone to have access to transformational tools such as mindfulness, emotional awareness, and self-compassion, regardless of financial, social, or physical challenges.

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Emma Isaacs is a remarkable person. She has six young children and at the same time is the CEO of a global membership organization that has half a million members. She’s such an impressive person, but to me, not primarily because of what she’s accomplished in the external world, but because of how straightforward, heartful, grounded, and committed she is to being a role model for women in business. Here’s my conversation with Emma Isaacs:

Emma, as the global CEO of Business Chicks, Australia’s largest community for women that now has a Los Angeles branch, and the mother of six children, I have to ask the question that I think would be on anyone’s mind hearing that your sixth child is ten weeks old, which is, like, how do you do it? How are you doing?


Emma Isaacs: As the words come out of your mouth, Tami, I can realize how crazy that sounds. And to anyone who asked me how many kids I have, I can now proudly say I have half a dozen kids. It’s insane.

And listen, it’s been very challenging these past few months having them all at home and four of my kids are school-aged. So doing homeschooling, running from room to room and working out all the different software programs and trying to manage all that comes with that has been fun and games, let me tell you, but, I mean, there’s no intelligent answer as to why we had six kids.

My husband and I have always said we wanted to live a really big life and we sort of accidentally had the first and then accidentally had the second. And after six, I can assure you that we’re going to stop now. I think we’ve worked out how it happens, and that it’s a beautiful blessing. It’s a beautiful, beautiful blessing. We had our sixth child just ten weeks ago as you said, and he was born on the first day of summer as the sun was rising here in Los Angeles, and we were in lockdown, obviously, due to the pandemic and also under a curfew.

We had protests in our street for the Black Lives Matter Movement. So we had helicopters whirring above us, we had police out front and it was a really beautiful, I suppose, contrast to bring him into the world with what was going on in the world. So we’re very, very blessed to have him and yes, we’re going to stop there. Six is enough. Let me tell you.


TS: OK. Now, I’ve heard it said many times to people the saying, “You can have it all.” And I can imagine someone from the outside saying, “Look, Emma Isaacs, she has it all. She has half a dozen kids, and a business that supports women, a global business based in Australia and the United States. She just wrote a new book.”

And I know when I hear that statement, “You can have it all,” I think to myself, “Well, you don’t know all the things I don’t have, actually, that I’ve given up to have what I do have.” And I wonder what your comment is about that statement. “You can have it all, women.”


EI: You cannot have it all, women. That’s my response to that. It’s been said that you can have it all, but you can’t have it all at the same time. And I’m a massive advocate for that. I actually write about this in my new book Winging It and there’s this theory that’s called The Four Burners Theory.

And it has you imagine your life as a cooktop stove. So you have these four burners going at any one time, and those four burners represent your family, they represent your friends, they represent your health, and they represent your social life. And it’s been said to be successful, you have to have at least two of those burners, sorry, three of those burners switched off.

And to be highly, highly successful, you need to have at least two of them switched off. So for me, my version of doing it all is really dialing up the burner of work and the burner of families.

So I’m not out there running triathlons. I’m not out there building a beautiful garden in the backyard. I leave that to my husband. I’m really just focused on the two things that I can do really well, and that for me has always been choosing my business and choosing my family, and everything else sort of pales into significance.

So yes, I’d say that to women, it’s just not possible to be a really amazing leader, to run a not-for-profit, to exercise every single day, to grow the world’s best herb garden. You have to choose a couple of things and do them really, really, really well and what that’s meant for me in my career in my life so far is saying no. It’s meant saying no to so many different opportunities. And I’ve done that because when your why is so clear, and when you’re focused on the two priorities you have in your life, decision making becomes really, really easy.

It’s easy to say no to the things that you’re not focused on. So for me, I’d really encourage any women out there, any people out there—it’s for the dads, and men out there as well—just to choose two things to do really well and focus all of your energy on those two.


TS: Do you ever feel a sense of emptiness about what you haven’t chosen?


EI: I don’t. I don’t because this is a moment in time. I’m knee-deep in parenting, and parenting, no matter how many kids you have is a high-contact sport.

It requires all of your energy, it’s up and down. It truly is a roller coaster ride, and I’m so in it and I’ve got to remember I chose it, right? I can’t be a victim over something that I chose.

So I never have that feeling of, “Oh, I wish I could.” Because if I wished I could, I would choose that. So there’s not an emptiness, because I’m in a moment of time of parenting. And it’s going to be like this, probably that for the next 20 years. And when 20 years passes, I can choose another priority and that might be triathlons or being a world-class gardener. I don’t know. I don’t know what’s in store, but no, you can’t regret what you choose. You can’t regret what you choose.


TS: Now, I wanted to talk to you about something else because you’re very clear in your new book < Winging It that you don’t believe in work-life balance. And first, why don’t you explain what do you mean by that? You don’t believe in work-life balance?


EI: Yes, I mean, my career story is that I started my first business when I was 18 years old. So I look at your story, Tami, and there’s so many different parallels and we’ve worked a very, very similar career path. And when you are so clear on what you want to do with your life, and when you find what I call a good addiction, a passion, my business has always been a really great addiction for me.

I don’t really feel like I need to build something to escape from, Seth Godin says that, we’ve had Seth speak for us at Business Chicks in the past, and he says that when you find… I’m paraphrasing here, but when you find what you’re made to do, you don’t want to set up a life that you have to escape from. So for me, I’ve never seen work as work, and home time as life, it’s just one big challenge that we take on, the lines are very, very blurred, I don’t have set hours that I keep.

And yes, for me, it’s just one big happy life and it all blends in. So I really encourage people to try — and obviously it’s something we’re told all the time — but to find something that we love doing so that we don’t have to feel like we have to escape from it all the time and have that balance. And for me, the concept of work-life balance, you get this vision of someone standing there with two scales in both their hands, right? And you’ve got to have the scales perfectly-tipped every single day. And that’s hard work. It’s really, really, really difficult to get those scales in this perfect equilibrium every single day, it’s never going to be like that.

Sometimes your work calls you to work 14, 15 hours a day and sometimes, you have to be on the Zoom calls with your kids or with your partner at home, whatever situation you have at home. So I think when we chase this perfect kind of construct of having this balance, we just constantly feel less than. We constantly feel like we’re failing at one thing.

So I just like to see it as do your best in both. And that might sound a little utopian, but for me, it’s just manifested in one big life where I am going to have to work more on some days and I am going to have to be in my personal life and at home on other days, and that’s, that’s perfectly acceptable.

And I think if you can relax into that, and I think if you can lose your expectations of yourself and just try and enjoy the ride a little bit more, and try and bring more fun and lightheartedness into your work and into your home life, then the work-life balance thing, it becomes a lot easier, it becomes a lot easier.


TS: I need to dig in a little deeper here because this is a question that’s personally quite important to me because I’m with you. As you mentioned, there are some parallels in our life stories, of course of many things that are different. I have not a number of kids, but zero children. But that aside, in this notion of work-life balance, I’m a very passionate person about the work I do, that issue never comes up for me.

But what I have found is that the people who work at Sounds True, the 125 or so employees who work at Sounds True, this is a really important issue to a lot of the people who work at Sounds True. And I’ve gotten feedback from people, “Tami, I’m glad you’re so passionate. We want work-life balance.” So I’m curious what you think about that.


EI: Let’s not confuse work-life balance with passion. So you and I have found something that drives us, we’re happy to do it probably 20 hours a day, perhaps a little bit less now, I’m not getting much sleep with a newborn. So I do appreciate my sleep a little bit more.

And our situations are unique and I’m in the same situation with my workforce, we employ about 40 people, they’re actually all women in Business Chicks right now. We have had some men in the company in the past, but right now, I’m employing approximately 40 women, and they come to me with the same challenges as well. And I encourage them, the rules are the same, though it really comes back to how you look at your work and how you see your work.

And we’re in the perfect storm right now to talk about work-life balance with working remotely and working from home, and I know it’s important for our employees to have boundaries. And I know it is important for them to switch off, but we also have to ask our team members to find their passion and love their work and if they’re not finding that, and if they’re finding that they want to be away from the office, if they’re finding that they want to run away from their work, if they’re finding that they have anxiety, or they’re stressed about their work, perhaps they’re not as passionate as they need to be. And perhaps it is time to have a hard conversation and say, “You know what? Maybe this isn’t the place for you,” because, again, your work is meant to be enjoyable. It’s meant to be fulfilling, it’s meant to be challenging, you’re meant to wake up each day and look forward to going to work.

And for a lot of people, they lose sight of that conversation, they lose sight of the choice that they have, and they feel trapped into having to do something when they don’t have to.

So I suppose my advice to people if they’re dreading getting up to work and wanting to only work a couple of hours a day, is to really question and dig deep, really ask that question of yourself and say, “Is this what I’m made to be doing? Is this what I’m put on the planet to do?”

And I know a lot about your culture, Tami. Well, not a lot, but I know a little about your culture and it, again, has parallels with ours at Business Chicks. And I think what’s really important for us as leaders is to build cultures where people want to come to work, and they don’t see it as being trapped or something that they have to do. So for us, that’s meant experimenting with a whole heap of different, what we call work perks. We have done, we’ve experimented with all the different types of work perks over the years from having a chef come into the office, from having a massage therapist come into the office.

I mean, we can’t do any of that now that we’re not going to offices, and we’re not allowed to touch people. But I’ve really tried to run my companies and businesses to emulate an environment where people want to come in and they want to enjoy their work, and they see it as part of their life as opposed to something they have to do.


TS: Yes. OK. And I’m going to ask you a couple more questions about being a mother of six and the CEO of a global company, which as I read in Winging It that you’re very intentional in how you explain to your children, why you choose to work as much as you do. So how do you explain it when one of your kids tugs on your shirt and says, “Mom, why do you work so much?”


EI: Yes, and this is, I mean, my eldest is 11. So we’ve been having this conversation for the past nine or ten years with all of my children.

And a wise woman once said to me when I had my first child, she said, “As much as you look down into that little bundle in your arms, you look at that new baby, and you look into their eyes and you say, ‘I wonder what you’re going to make of yourself? What are you going to make of this one wild and precious life? What are you going to get up to? What are you going to achieve? What are you going to impact?’” As much as you’re asking that question of your little babies and your children as they grow, they’re looking at you and asking the exact same questions.”

So I’ve always been really inspired by that. My kids, whether they know it or not, they’re looking at me and they’re thinking, “What is my mum getting up to? Who is my mum inspiring? What impact is she making in the world?” So I’m very, very clear that I want to be a role model for women. I want to be a role model for my kids and it really circles back to what we said before, Tami, it’s about being so clear about why you’re put on the planet, and I’m put on this planet to inspire people. I want to make life better for women. And if I keep coming back to, that’s my why, and that’s why I’m here, I can answer my kids honestly and I’m not sure that they completely understand it yet, but it’s my hope that as they grow, and they find their careers and their passions, they’ll look back and think, “OK, my mum had it figured out. She had it sorted.”


TS: And Emma, here’s my last question in this vein, which is, in Winging It, you call guilt a wasted emotion, that it’s not useful to spend time feeling guilty, but I’m curious if there are times when you feel guilty that your children need you and you’re unavailable or they express that they need you. What do you do when you feel guilty? I mean, it’s simple to have this idea. It’s a wasted emotion. But what do you do internally when you feel that way?


EI: Yes. Of course, I feel guilty. I mean, I have chosen a career where I have to travel all the time and that means that I’m away from my kids. I mean, I often try and bring them on trips with me, which has been really great, but of course, I feel guilt. I mean, I don’t think there’s a mother or a father on the planet that hasn’t experienced guilt hundreds of times and regularly, and I do as well.

I think the thing for me is working out how to manage that state and how to get out of it as quickly as possible. So it’s completely acceptable to say, “Oh, this isn’t working. I feel bad about this. I feel guilty.” But we need to let those feelings inform the decisions we make, right? So it’s about exploring that and thinking, “Do I want to change things? Am I traveling too much? Do my kids really need me more, or is just an outburst that’s going to pass in two minutes’ time?”

So it’s completely acceptable and I feel guilty all the time, but I just really try and stay, get out of that state as quickly as possible and move on and, but also, have some introspection about it and ask myself, “Do I really… What’s important here? Am I working too much? Do I need to pull back? Am I getting it right?” And I think that constant questioning and that constant curiosity is what helps parents lose the guilt and move forward. And again, it’s coming back to why they’re doing what they’re doing and if they’re very, very clear on that, then I’ve always found the guilt is a little bit soothed, if you like.


TS: Yes. Now, your new book, Emma, is called Winging It. What do you mean by that title? Winging It?


EI: Well, I mean, I spent the past 15 years talking with thousands and thousands of women in my role at Business Chicks and it’s been a really, really beautiful journey to uncover what holds them back and what propels them forward. And it really led me to write this book, because the collective wisdom of these thousands of women is truly sacred. And unfortunately, it’s still women who are plagued with quite a unique set of challenges.

We often wait for permission, we often wait to be tapped on the shoulder, we’re not always the best at asking for what we want. I mean, you just have to look at we’ve all heard the story about there’ll be a job available, and there are ten criteria, and a woman will look at that application and say, “Oh, I’ve only got seven or eight of the qualifying criteria, so I won’t go ahead for it.”

But a guy will look at that job and think, “I’ve got four or five, I’m going to apply and I’m going to go for it.” So really, for women, the one lesson I want to share is that no one truly deeply knows exactly what they’re doing at all times.

I mean, definitely not at the start anyway, and that everyone is winging it to some point. So I set out to write that book to encourage people, but particularly women, to back themselves, to have a go, to try and to move past the uncertainty, to really just step into “I don’t know what’s going to happen here, I don’t have all the answers, but I’m willing to step into that uncertainty and give it a go.”

And when I first started out in business when I was 18 years old, I read so many books and I read so many books about goal setting, and planning, and every management textbook and I listen to all the amazing teachers, people like Tony Robbins and Kawasaki and Napoleon Hill, and they all taught us how to plan and how to set goals and no one had written a book on how to wing it.

So I set out to write the Bible on winging it and yes, it’s been a beautiful journey sharing those stories and sharing that philosophy.


TS: I want to go deeper into these two things you mentioned, your discovery of what holds us back, from working with the Business Chicks community of women, and your discovery of what propels us forward. If you were to try to distill this down into the key ideas, Business Chicks is about helping women play a bigger game. That’s the way you describe it, helping us play a bigger game. So what holds us back from playing a bigger game and what propels us forward to actually go do it?


EI: Yes, I love it. Great question. So firstly, let’s clarify. I mean, people think that winging it is about being completely reckless, and they think it’s about not having any plan at all. So we need to really define that more clearly. I’m never going to tell you just to jump off a cliff, I’m going to tell you to remember your parachute, because we have to do winging it responsibly and there’s definitely an art to winging it and I’ve discovered nine key rules to winging it, but you’re going to have to read the book, Tami, for all of them, but let’s talk about the… Let’s choose maybe three of them.

So in terms of propelling people forward, I think the first rule is definitely to say yes and figure the rest out later. I mean, you did that with Sounds True, right? You made a decision. “I’m going to start this business, I’m going to figure it out as we go.” And I’m seeing … Even my eldest daughter recently, she wanted to start a slime store. Do you know what a slime is? It’s that thing that people are… All the kids are playing with these days. Have you heard of slime, Tami?


TS: Well, no, but I’m imagining it as you’re describing it. It’s like jello or something?


EI: You got it. You got it ,and it drives me crazy because it sticks to everything in the house. And I’m constantly walking around and there’s slime in the rugs and on the walls, and they take all the toiletries from the bathrooms and they make this slime, they make it with shaving cream and laundry detergent.

Anyway, all the kids are doing it, all the cool kids are doing it. So she’s decided she wants to start a store and she has no idea how to do this, and I’ve been encouraging her through this saying, “Let’s just make a decision. Let’s say yes and figure out the rest as we go.” And I think that’s a really key thing. People can get really, really stuck in the decision making to start something, they can get stuck in inertia, they can get stuck in fear, they can get stuck in fear of failure.

So I think the biggest thing that we have to encourage people to do as they propel forward and get out of their stuckness is really just to start. And I love this quote from Karen Lamb, and it’s, “A year from now you’ll wish you’d started today.”

So I think that’s a really, really key rule for winging it. I think the next one, what would I say? I think the next one is to learn how to be flexible. And I think it’s about not being so set in a plan that you can’t duck and weave and pivot. I mean, it’s impossible to talk about this time without using the word pivot, but to change it up when you need and we’ve been served up the biggest learnings this year with the turbulence of COVID, right?

I mean, this is a perfect storm for being flexible and trying to work it out on the fly. I had this big vision for my year this year, it involved a big live book tour with hundreds of live events plus lots of travel. And I even had a vision for my kids going to school, which now it seems like a wild kind of vision, but we’ve all been called to be flexible and to really step into that uncertainty.

And I know when COVID hit, our business at Business Chicks, we drive about probably 80% of our revenue from live events. So we had to really sit down and make a plan for how we were going to be flexible, and how we were going to pivot. And we’re able to do that really, really quickly because we all have the mindset of saying, “OK, we’ve been dealt these cards, but we have to play these cards now.”

And yes, so being flexible, I’d say is a really, really key point for getting ahead. And I think the next and final one I would draw upon the rule of winging it is really about believing in yourself.

It’s about believing in yourself enough to give your dreams a go. About 15 years ago now, I was invited to an event and it was an event called Business Chicks and I remember saying to the girl who invited me, “I would never go to any event that calls themselves anything chicks.

I mean, that’s just so derogatory to women. It’s insulting, that’s a terrible name. I’m a serious entrepreneur.” And she said, “Look Em, get over yourself and just come along to this event, you’re going to love it.” And I remember walking in that room and seeing, the music was playing and there were hundreds of women there and they were high-fiving and they were giving each other hugs and it was just the most electric atmosphere and I remembered walking and thinking, “What do we have here?”

And I went back to my office, I was running a recruitment company at that time, and I pass around my credit card to the 25 or so women sitting there and I said, “Every single person in this office become a member of this organization, and let’s really get behind it.” So we bought three tables to the next event, and we all became members, and at that next event, I learned that the business was for sale.

And my general manager of the recruitment company, she leaned into me and she said, “You’re going to buy it, aren’t you Em?” And I just had this experience of… it was almost an out-of-body experience. Every single cell in my body became activated, I felt more alive, I started … I sat up straighter. I just knew in my heart of hearts that I had to have this conversation to buy this business.

Now, if you’d looked at my situation back then, you probably would have said to me, “Emma, don’t do this. You’ve got a strong successful business in your recruitment company. You’re making profits, you’ve got… Your life is cruising, you’re doing really well. Don’t even consider doing this.” And I remember when I was considering buying Business Chicks, I even went out to a couple of management consultants and had them run the numbers and they both came back and said to me, “There’s no way you should buy this business. It’s not even really a business. Just forget about it.”

And they also told me I had no experience to run an events business and a membership organization. So, but I believed in myself and I knew, because my body was giving me all these cues, that I had to go for it. And we’ve been able to grow that organization from 200 members to now having a global reach of just under 500,000 women. And that was because I backed myself, I believed in myself enough to give that dream a go. And so I’d say that’s the next biggest thing.


TS: Yes.


EI: A crucial rule for winging it.


TS: Yes. OK, 500,000 women, that’s a large organization, but the number that is really sticking with me is that 80% of your revenue came from in-person events when the pandemic hit.



EI: It’s huge.


TS: And it’s fine for people to say, “Oh, we’ve had to pivot and it’s a small little thing, maybe 10% of their revenue, 15%. They have to figure out how to change things.” But 80% of your revenue!


EI: Up and gone!


TS: So, Emma. How have you managed this without freaking out?


EI: Yes. There’s been a few freakouts. We have had moments of definitely freaking out and having to sit back and take a deep breath and draw upon strength that we didn’t know we had. Listen, I think the way that we conduct not only business, but our lives, and I talked about this in the book, is to be pragmatic and not dramatic.

So what that means is it’s all well and good to throw things up against a wall, or curse, or have a little meltdown. Ultimately, being successful is about getting into action, and it’s about finding a state and a mindset that brings you into calmness. And I know that all sounds a little bit woo-woo and you’re probably thinking, “Yes, that’s all well and good for you to do.” So what do we actually do?

So firstly, we obviously got the team together. I have a CEO in my Australian business and we talk ten times a day. So we got everyone together and we said, “Listen, we don’t know what we have ahead, we don’t know what it looks like. We can promise you that we will communicate as best we can, we’ll promise you that we’ll communicate at every turn, we’ll promise you we will involve you in decision making, but we are going to have to work out how to run a very, very different business.”

So there was some rationalization at the start. Unfortunately, we had to make a few layoffs, which is never ever fun for any business person or leader to make, but we’re just, we’re looking down the barrel of… And who knows how long this is going to go on for me, at the start, we were planning for six months and we sat down with our accountants and said, “OK, give it to a straight. How many months of cash do we have left before this becomes a real thing?”

So we definitely got into the numbers and tried to look at a really real picture. So at first, we had to make some layoffs, which was not fun, as I said, and then we had to look at how can we take our magic or our secret sauce and turn it into something else that we can make money off of. And of course, the natural decision there is to take the events online and have digital events. So we did that. And we did it very, very, very, very quickly.

And it’s interesting because for the past 15 years that I’ve had the business, we’ve been saying we should do more online events, we should do … We should be able to do these things so we can serve more people, because we understand that most of our events are in the big cities, in LA and New York and across Australia.

So people can’t always get to these big events, and we need to be able to have a solution for them and serve them online. So it’s been interesting how this time has forced innovation. It’s forced us to turn our hand at trying new things. It’s forced our hand at learning new technologies. Even, Tami, recording the audio book for Winging It was a really funny time because, originally, we’re going to come to your studios in Colorado, but then we couldn’t travel. And then we thought the solution would be to record the audio in Los Angeles where I live, and then the studios here closed, so we had to wing it and I had to set up a makeshift studio in my closet with seven mattresses and 17 pillows.

And we got it done because ultimately, this time is all about finding solutions. And this time is about having the right mindset and really, it’s easy for me to say, and it’s easy for you to say because we are tremendously privileged and we have roofs over our heads and we have strong businesses that we’ve been building for many, many years, but I don’t want to trivialize this time for people who are doing it really, really, really, really tough.

And I definitely come back to being grateful for the opportunities that I’ve had that show me that this too shall pass, and I know we’ll have a strong business when we emerge from it. But for us, it’s meant, yes, going online, it’s meant unfortunately, making some layoffs, it’s meant communicating at every single turn. And believing it’s going to be OK because ultimately, that’s what we’ve all got to be doing in this time.



TS: Well, I love this teaching about being pragmatic and not dramatic, very memorable. And I’m curious when you find yourself in a drama, you feel this drama inside that clearly I’m being dramatic here, I’m going on and on, just inside yourself in your own head with yourself.


EI: Yes.


TS: How do you get out of that and find your pragmatic voice?


EI: I talk about this a little bit in the book as well, because I think it’s a muscle that needs to be flexed. It’s not like you just wake up one day and say, “Hey, I’m going to be calm and all Yoda-like and suddenly I have all this.” Yes, I don’t know. I guess calmness is the word and we talk about it in the book about calmness is a superpower, but it is a skill that can be cultivated, and for me, I mean, people are always saying to me, “Em, if you were any more calm, you’d be dead.” I think that’s a compliment, I think that’s a compliment.


TS: It is. It is. Yes.


EI: But I mean, I have spent the last … I’m 41, I just turned 41 and I really have spent most of my adult life trying to explore ways to control my emotions and funnel them in the right way. So I don’t want to at all tell you I’m a world-class meditator, I’m not, but I have really tried to practice techniques that are bringing calmness to each situation.

And I think if you can helicopter up a little bit and try and look at your life from a really high vantage point, and you can see that any drama that comes along is only going to be a moment in time. If you can have that outlook or that philosophy that in ten years’ time, is this really going to matter? In ten years’ time, is this really going to matter that my business lost 80% of my revenue, its revenue? In ten years’ time, is it really going to matter that my kid was sick and had to miss school for a month or so? So really just trying to have that long-term view of your life and seeing everything is just a moment in time.

And yes, it’s been my philosophy. I mean, I’m not for one that of course, you’ve got to vent when things don’t go your way. Of course, you’ve got to vent and everyone’s got to find their version of venting and for me, it might be about pouring a glass of wine and just taking a moment.

It might be about getting on a call to my best friend and having it out, and allowing myself some moments to say, “Oh, woe is me.” And, “Why me?” And, “This is terrible.” And, “Why do these things always happen?”

But it’s similar to the guilt thing, if we can try and work out how to make that time shorter, and we can get into action after the drama has just happened. I’ve always found that’s the best method for being pragmatic and not dramatic.


TS: Yes. Now you shared a little bit with us Emma about the origin story for you with Business Chicks, how you purchased that company at a young age. Tell us a little bit about your decision to move Business Chicks from Australia to opening a Los Angeles branch. I imagine that’s a big, huge deal. You’re a big fish there in Australia, you have a successful company. You have a whole life there. Really, you’re going to take this big risk and bring Business Chicks to the United States?


EI: Yes. I will never forget the day that we packed up our lives and we were on the sidewalk at Sydney Airport and we had our 17 suitcases. And at that time, I had four kids and it was such a whirlwind that we were all there, and we’d forgotten to dress the babies.

So we had our 17 suitcases, the little naked three-month-old baby that we’d forgotten to dress because it was just so fast and so turbulent, the decision that we made, but really, the origin for that story, and I’m going to name drop here and I don’t feel bad about it at all.

But one of the best perks or parts of my job is I get to go to Necker Island in the Caribbean every single year and we run this beautiful leadership gathering for leaders there and Richard Branson owns that island and generously hosts us, each week we go there and I remember one morning we were up at the breakfast table and it happened to be a bunch of Aussies, Australian women there.

And he was asking one of the women about their business and she was explaining what she did and how she did it and he paused and he looked at her and he said, “Is it even possible to make money in Australia?” And he didn’t mean that to be rude, or he wasn’t trying to put her down in any way, but it just, we all looked at him. And it was like one of those moments of the mic dropped and we all and for me, certainly, it was an “Aha!” moment.

I thought, “He’s a guy, he’s a self-made billionaire and he has businesses all around the world and for him, Australia is just this little … It’s a little island that we dropped in the ocean, which it kind of is, and is it even possible to make money there?” And that that just one little throwaway line sort of opened my thinking. And I’ve always been a huge traveler, I always seek information from other places, it’s not as if I just have only lived in a bubble in Australia. But that line had me think, “Wow, OK, we really need to step it up here. We really need to have a more global outlook, we really need to as I said before, play a bigger game and if I’m trying to encourage my community of half a million women to play a bigger game, then I have got to be that person for them.”

So we started going back and forth between Australia and the US and we eventually did a series of launch events that were fabulous. We had filled ballrooms in New York and San Francisco and Los Angeles, and it was exactly like it was in Australia as I described before. You walk into that room, the music is pumping, everyone is high fiving each other, everyone is hugging each other, and it’s just the sisterhood on steroids. And it was exactly like that in America, but with American accents, which was kind of cool. And I remember going back to Australia and my husband had seen it all play out on social media and seeing the photos. And I’d obviously been calling home and telling him all about it and he said, “That looked amazing. I mean, would you ever consider moving to the States?” And I just looked at him and went, “That really scares me. So, let’s do it.” The thought of doing that terrifies me. So I know I’ve got to make that happen.

So yes, in six months, we packed up our house and found ourselves on the sidewalk of Sydney Airport with a naked child and 17 suitcases and we relocated to LA. And I mean, that in itself was, I suppose, winging it in action. I remember landing here and unpacking the 17 suitcases and opening up my computer and thinking, “OK, now what?”

I mean, that’s truly, you might think that’s just beyond reckless, but that’s almost as far as I had gotten with my thinking and I don’t regret that for a minute because if I had thought too much about it, if I had known what was to come, if I had known how hard it was going to be, would I have made that decision? Absolutely not. I would have talked myself out of that decision, yes, many, many months before.


TS: Have you ever jumped into a mountain lake or taken a plunge into cold water? Maybe you noticed a change, a feeling of invigoration? Suddenly, perhaps even, feeling more in love with life? Maybe even sensed feeling healthier?

You may not be aware that there’s a method created by a Dutch phenomenon Wim Hof, known as The Iceman, who gained world acclaim for feats like running a half marathon in the Arctic Circle — barefoot! Here at Sounds True, our staff has been experimenting with the Wim Hof Method and we found pretty remarkable results. We’d love to share the method with you. You can find out more about Wim Hof and his method at findyourcold.com.

Now Emma, clearly you embody Winging It. No one I think would question that you are an embodiment of Winging It and that story illustrates it. Now, what’s really interesting to me is that you had this thought, “That really scares me, so I know I need to do it.” I can imagine a different person saying, “That really scares me, so I’m going to do a lot of research and I’m going to reflect on this, and maybe my fear is trying to tell me something important.” And I could imagine a different kind of logic. So how did you get to this place? That really scares me so I know I need to do it.


EI: It’s been something that I’ve … A guiding philosophy I’ve had my entire life. I think when you do the thing that scares you, I think when you step into fear, I think no one would argue, but that’s where the growth happens, right? So we have choices, we can live a very cozy life, we can live a very, very comfortable life, we can stay within the confines of comfort, or we can make very, very, very clear decisions to step out of that.

And for me, I’ve always found I’m at my best when I have something in my future that scares me a little bit, that I think I might not be qualified to do, or I might not have the information to do. And for me, and it’s perhaps not for everyone, perhaps not for everyone, perhaps you are someone that thinks, “I’m very, very content in my life, I’m happy with my lot, I’m happy with my family, I’m happy with the work I do, I’m happy with the income I make.”

And that’s fantastic. And in some ways, I envy people who have found that contentment and just happy to sit and be in that space, but for me, I want to live this big life, I want to challenge myself, I want to push the boundaries of what’s possible, I want to inspire others to do more. And for me, that’s really been about getting clear on my relationship with fear and really just dancing in that relationship and experimenting with it.

And for me, in my experiences, I found that the more things you do that scare you, the bigger life becomes, the more life opens up, the more opportunities present themselves. And it’s fun as well. I mean, yes, I find there’s a liberation in doing the things that scare you. And I think we live in a culture that is so, what I said, attached to the outcome, we’re so attached to the outcome, we’re so driven by, “What if I fail?”

This notion of, “I don’t want to be seen to be a failure. I don’t want to be seen as someone who tried and it didn’t work out.” And I’ve just tried to be someone who lightens up and experiments with that, and I don’t mind if I look like I’m a failure.

I mean, I have many, many, many times in my life, but for me, it’s just that experimentation with, “Let’s try something new. Let’s give it a go. If it doesn’t work out, there’ll be some growth along the way, and we will have learned something.” And I think that’s a really, really beautiful rule to live by.


TS:  Yes. You mentioned Richard Branson and in the book Winging It, you talk about how he really has been a mentor in some ways to you. And specifically when it comes to this notion of risk and failure, what did you learn from Richard Branson about risk and failure?


EI: Yes, I mean, I think if anyone’s familiar with his story, you’d know that Richard’s probably had as many business failures as he has successes, right? And that’s been probably the number-one teaching or learning that I’ve had from him. He is just so comfortable in his failure and there have been, I don’t know if it’s hundreds, but certainly tens and tens of businesses that haven’t worked out. He had Virgin Cola, he had Virgin Cars, he had Virgin Brides. I mean, he’s doing really phenomenally well right now with his Virgin Galactic business, but he was due to launch his cruise liners and that hasn’t happened because obviously it was … The launch was due at the same time the pandemic hit, but he’s just someone who says, “I’m going to give this a try. I don’t know if it’s going to work out.”

And he just has zero fear of failure. He just doesn’t mind what you think of him and he doesn’t mind. Again, I get it, he’s a billionaire with deep pockets, and for a lot of people, that’s completely inaccessible, for me, it’s inaccessible, we do have to go forth and wing it responsibly.

But for him, he’s just gotten really, really clear on the fact that, “This may not work and I’m totally cool with that.” So I think that’s been a huge lesson for me that he’s taught me I think.

Another thing is taught me is just to have fun in business. He’s always the first one on the dance floor whenever we get to go to Necker Island, he’s the first one to dress up, he’s the first one to play pranks on his team. He just doesn’t take himself too seriously and I really admire that about him and I try and take that into my work as well. I’m always the one who’s jumping out behind the desk to scare people or I’ll… Early in my career, when we had to make cold calls in the recruitment company, I put on big funny sunglasses and stand up and because I was scared of calling people I didn’t know. So just trying to bring a lightness and fun to your work I think is … It can add an extra layer and people are drawn to that, people are drawn to people who want to have fun and don’t take themselves too seriously, and want to have a laugh. And I’ve always found that’s a really great way to run your businesses and to attract people to your mission, or to your company.


TS:  Yes. Now, I want to address that person who’s listening who says, “I would like to have a higher tolerance for failure, but truth be told, I don’t. I actually don’t have a very high tolerance for failure. It makes me feel terrible about myself, and that’s what’s keeping me from playing big.”


EI: And I understand that. I mean, I think being an Australian living in the US now, I’ve got a unique perspective on failure and there’s a cultural, more of a cultural acceptance, I would say, in the US for failure, than there is in Australia. And even in Silicon Valley, there are a lot of investors who won’t invest in your business unless you can show them that you’ve had two or three failures in business, which I find super-cool.

And I suppose what I’d say to that person out there is it’s about practicing and if you’re putting yourselves into a position where you’re not allowing yourself to fail, then you’re not getting better at it. And you can start out small, you can start out with it might be for you, and I know we’re addressing people here that aren’t all business owners or business leaders. It might be just trying to write that first chapter of your novel, or it might be if you have a passion for a social cause, it might be trying to start a little not-for-profit and raising your first hundred dollars.

I’m not saying you have to move countries, or buy businesses, or hang out with Richard Branson to be able to get ahead. I think practicing with failure and practicing with small acts and small little challenges will only help improve your tolerance for failure. And the more and more we can do that, I think the easier it becomes. So I’d say that to people: just start small, but you’ve got to start. You’ve got to give it a go, you can’t hide behind the excuse that “I’m scared,” you’ve got to dip your toe into that water and at least have a go no matter how small.


TS: Now you mentioned that when you were first introduced to Business Chicks, you had this negative response to the word “chicks” and that was at the very beginning.

And then you write in Winging It about bringing the company to the United States and going through a whole set of discovery exercises to see if perhaps there was a better name for the network and yet, you’re still here with Business Chicks. So tell me a little bit about how does it feel to you now?


EI: Oh, I mean, if you could be a fly on the wall of our marketing meetings in our boardroom, you would… Yes, I have paid witness to some pretty lively conversations over the years. So I mean, again, culturally, the name Business Chicks doesn’t work as well as it does in Australia. I mean, there we have 15 years of legacy. We are a great brand, we’ve brought speakers to the stage there as diverse as Arianna Huffington, Richard Branson’s spoken for us six or seven times, we’ve had Seth Godin, Kate Hudson, Nicole Kidman, Brené Brown, Elizabeth Gilbert.

I mean, all the greats, and so we’ve built a really, really successful and beautiful business in Australia with that name, and so the connotation with Business Chicks or the brand surrounding that name is positive. There’s not a negativity around it, as there was in the States when we first started. I think I can’t remember who said this to me, but I can’t labor the point enough: in business and in life, you’re not going to be for everyone.

I mean, Steve Jobs had said, “If you want to be liked, go sell ice cream. Don’t be a leader.” Don’t you think it’s true? I mean, we just cannot be for everyone. Not everyone is going to love the philosophies of Sounds True. I mean, I can’t believe that myself, but you’re not for everyone. Not everyone is going to love the philosophies that I talk about, it’s not for everyone.

Not everyone is going to love the name Business Chicks, and that’s OK. It’s about finding your people, it’s about finding your community, it’s about finding the people who jell with your ideals and your mission, and it’s about being that and dialing that up for the people who believe in it as well. So we have come 360 when I first moved to the States, everyone said to me … Not everyone, there were people who said, “That’s a great name, it’s memorable, it sticks… I can attach to it, I get it, it’s fun.”

We even had Diane Von Furstenberg speak for Business Chicks a few years ago, and we had this moment where she was up on stage and she said, “Where am I? What is this?” And my head went to my hands and I went, “Oh my gosh, her people haven’t briefed her. This is terrible.” I wanted to sink into my seat. It was just terrible.

And the emcee said, “What do you mean Diane? You’re at Business Chicks. It’s this community for women, we’re all around the globe and it’s an amazing thing.” She goes, “No, no, no.” She said, “I know that. I know where I am.” She said, I just want to say, “I love it. It’s special. I get it. We can be in business, we can be chicks. I love it.” And she got it. So I think you’ve got to just dial up your uniqueness, right? You’ve got to dial up what makes you special, and while I used to be ashamed of the name at times, and while I used to think, “Oh, how is this going to be received?”

I think if you’re so sure of yourself, and if you’re sure of your name, and if you can step into that and really own it, you’re not going to be for everyone, and you’re going to find the people who are attracted to it, and that’s who you’re for. You’ve got to focus on those people, not spend your time looking sideways, not worrying about what people are saying about you, not worrying about the people you’re not for. You’ve got to be there for those who get it, and you’re not going to be for everyone.


TS: I want to be a Business Chick.


EI: You are a Business Chick.


TS: Am I? OK, good. It makes me kind of want to shake my booty.


EI: You can do that. You can just shake your booty.


TS: Yes, that’s what comes up for me.


EI: That’s good.


TS: OK. OK, now in Winging It, you talk about swimming two and a half miles when you were at Necker Island on one of these retreats as an allegory for the entrepreneurial journey. And I was really moved by this and I want to ask you a couple questions about it, but before I do, just share the story of this two-and-a-half-mile swim, and how you see it as an allegory for the entrepreneurial journey.


EI: Yes, it was, and it remains a huge lesson and driver for me in my career. So as I said to you, I get the tough gig of going to Necker Island each year and each trip that we do, Richard says, “OK, we’re going to go across to …” I mean, he owns another island, two and a half miles across the way, which tells you something about the guy. But he says, “We’re going to have our sessions on the other island tomorrow morning. So there are a lot of ways you can go there. You can stand-up paddleboard across to the island, you can kayak across to the island, you can sail, you can get in one of the little motor boats and go across the island, or…” and he has a big laugh, “ha ha ha ha, you can swim.”

And the first time he said that, I thought, “Oh no, I’m going to have to do it. I’m going to have to do it.” Because here I am, again, a leader who says you’ve got to do the thing that scares you, I’m a leader who says you’ve got to try new things, I’m a leader that says you’ve got to jump even though you’re not prepared.

And I’m not a swimmer, Tami. I mean, I’m from Australia so I’m a fish and I can swim, but I am not a long-distance swimmer by any means, but I knew as soon as the words were out of his mouth that I had to, I would have to try and attempt this damn swim. So I got into the water early that morning and Richard was there, and there’s nothing like swimming two and a half miles next to Richard Branson to make you want to get going, right? But there’s a group of I think four or five of us attempting the swim on that morning.

And inevitably, there’s much stronger swimmers than I am so they went ahead. And I started out and I remember thinking, “I can do this, I’ve got this. Here I am beside Richard Branson. I’m just going to get this swim done.” And I started out and I had all the enthusiasm and it was exciting, it was exhilarating, it was joyous and I got on my way and then I swam a bit further, and a couple of swimmers broke off from the group and they were quite a ways in front of me. So I started to think, “Oh gosh, this is actually quite hard. This is really, really tough. They’re better than me. What was I thinking? I’m not a swimmer. I don’t know why I’m even attempting this.”

So I started to have that self-doubt and those negative thoughts, but I thought, “You’ve just got to keep going, Em.” So I kept on swimming, and I kept on going, and I started to find my groove.

And then halfway into the swim, the sailboat came up beside me and they started to cheer me on and say, “You’ve got this, Em.” And, “You’re doing it.” And I felt really buoyed by their enthusiasm and really encouraged by their support so that got me to the next stage if you like, and I got probably three-quarters of the way into the swim and I started to feel really, really, really tired again.

I started to feel like I just couldn’t do it anymore. I started to think, “I don’t have this. Why did I try this?” And it was about that point that a guy that I was swimming with, he had enough.

He put up his hand, and a boat came in to pick him up and collect him and take him to the island, and I thought, “Maybe I should do that.” But I dug deep and I found a voice that said, “Just keep swimming, just keep swimming.”

And so I focused on the end goal, I focused on the island, I made like Dory and I told myself, “Just keep swimming, just keep swimming.” And I did it until I got to the shores of that island and somehow, I found the confidence to step onto that sand. And they’re all there, and they gave me high fives, and that was the story of swimming two and a half miles of which I was completely unprepared and unqualified for, and I’ve done it twice now, Tami.

When I did the first time, I remember saying to myself, “I will never do that again. That was so hard.” But I’ve done it. I’ve gone back and done it again, and it’s yes, it’s something I encourage anyone to do.


TS: I think the core question I have is when you talk about Winging It and you talked about saying, “Yes, we’ll figure it out later. Being flexible, believing in yourself.” But this quality that got you those two and a half miles is something like will, not giving up, grit, something like that. Like tremendous, I would use the word grit, tremendous grit and I wonder what you have to say about that?


EI: It is. I mean, like in that little story, that anecdote about swimming from one island to another, it has huge parallels with running a business and having a long-term view for your life and exploring those things, like we did before, Tami, of seeing every single situation in your life is just a moment in time that you have to dig deep for and you have to get through.

I think understanding that there are going to be times when you have to really find your grit, find your determination, find your own recipe for getting through the tough times, because that’s going to be different for you as it is for me. And I think we’ve all got to find what lifts us from those moments of self-doubt and not thinking we’re going to be able to achieve something.

And it is, I mean, you said it beautifully yourself. It’s about having a grit, it’s about having a determination, it is ultimately about knowing that every single situation in your life has a start, it has a middle and it has an end and finding what works for you, being able to move through those stages and get to the end is what’s ultimately going to have you land on those shores or emerge onto the sand and get to that beach. I think just knowing that and working out what works for you is the key there.


TS: OK, I just have two final questions for you, Emma. The first one is you mentioned that part of your why, part of what’s important to you, is to be a role model for women. What do you want to be a role model of? When people say, “Oh, she was a role model of…”


EI: I don’t know that I’ve got it that well, beautifully articulated. I mean, I think against the parallels to your story of mine, Tami, I started out in business so, so early, and I had my first company when I was 18 years old, but even winding the clock back further than when I was in my teenage years, my dad got laid off from his work, and he decided he wanted to become an entrepreneur.

So our whole household was filled with cassettes of, you know, and we’d be driving from a basketball game to another, to home, and we’ll be listening to Tony Robbins, and we’d be listening to all these people that I had talked about before. And I really learned something from them, but what struck me at the time and still surprised me to this day is that none of those teachers were women or very, very, very, very, very few of them are women.

They were all men. And I remember thinking, “This is kind of strange.” And it just sparked something in me to say, I don’t know, it just planted a little seed in the back of my mind that maybe one day, I could be someone who could be a teacher and could be a role model and could be that person for women. And obviously, as the decade, the years and the decades have passed, we’ve uncovered and discovered so many incredible female role models, and I’ve been very, very blessed to get to know these women.

But I think that’s what really was the key source of the motivation. So to finish that sentence, what do you want to be a role model for? I think it’s a very, very broad thing, but I want to be a role model for women. I want to be a role model for having people believe that anything is possible. I came from a family that was very lower middle class, we didn’t have any money. We had a beautiful, beautiful, beautiful childhood, but there was nothing in my childhood that left clues to say that I could be a successful entrepreneur.

There was nothing in there that would have you think that my life could turn out as it has and hopefully how it will do. So I want to be a role model to say you don’t need to have a huge amount of money to get ahead, you don’t need to have exemplary education. I dropped out of university after six months, and I still got to where I am today. You don’t need to have a rule book to get to where you want to go. So I want to be a role model for women to show them that anything is possible.


TS:  Yes. I love it. And then my final question, this podcast series is called Insights at the Edge and I’m curious, often, what people’s growing edges like, “Right now in my life, this is the challenge I’m working with, this is my growing edge.” What would you say?


EI: My growing edge… and I love this concept of living at the edge because it’s where I spend most of my time, let me tell you. I spend most of my time either on the edge or flying off of it. My growing edge is around grace. It’s around doing things gracefully. It’s about spending time in as much grace as possible. It’s really about how we all move forward together in uncertainty, and it’s about how we graciously share, and it’s about how we support one another and it’s about how kind we can be to one another. So I’d say my growing edge is how to spend more time in grace, how to be… Wake up in gratitude, end the day in gratitude, but for me, it all comes back to this notion of grace.


TS: What a beautiful answer. Emma Isaacs, I’ve enjoyed talking to you so much, you are so inspiring, what an incredible human being.


EI: Oh, thank you so much for having me on the show, Tami, it was an absolute privilege and an honor, so thank you so much for your time.


TS: Emma Isaacs, the author of the new book Winging It: Stop Thinking, Start Doing. Thank you for listening to Insights at the Edge. You can read a full transcript of today’s interview at SoundsTrue.com/podcast. And if you’re interested, hit the Subscribe button in your podcast app. And also, if you feel inspired, head to iTunes and leave Insights at the Edge a review.

I love getting your feedback, being in connection with you and learning how we can continue to evolve and improve our program. Working together, I believe we can create a kinder and wiser world. SoundsTrue.com, waking up the world.