day one: Overcome your fear of failure

Challenge of the day: What's the worst that could happen? Write out the possible scenarios and brainstorm a solution.


Welcome to Day One of our 5-day challenge, Confidence to Quit. Over the next five days, I am going to be sharing the five different ways, five different problems that I overcame to get the confidence to quit my job and start my own business. So the first one today is the fear of failure - so everybody comment, let me know that you’re here, let’s see who’s on the line and then we can get started.

While everyone is jumping on and commenting, I’m going to let you know how this works basically, so if you’re joining me on the line GREAT. I am going to be Periscoping everyday at 1:30 UK time so that’s now – or five minutes ago. If you can’t make one session live or whatever, don’t worry at all because I’m filming every single one, so you’ll be getting them - if you’re on the list, you’ll be getting them on your email.

And if you’re not yet on the list – if for some reason you’ve missed that – you can join us at And I’ll be putting that in the Facebook group and things as well, so the hashtag is #confidencetoquit. So if you’re on Twitter, on Facebook, whatever – leave some comments, join me and leave a hashtag there so I can find you. If you’ve not yet joined the Living Rosy Facebook group, join us there as well. You can just search Living Rosy on Facebook, we’re on there, and we can comment and have a bit of fun with the challenge as well.

So I’m going to give you my side of the story, the way that I dealt with every problem that I came up with, and I’m going to actually give you a little mini challenge to do every single day. Don’t worry: it’s not going to take masses of time, but it will just help you really get your head around all the different things you’ve got to think about when you’re wanting to quit your job and start your own business.

So watch out for the challenges there, and I’d love for you to let me know how you’re doing with them each day. If you have questions or whatever, join us in the Facebook group and ask away there. You are more than welcome – the Facebook group again is called Living Rosy, you can search for that on Facebook itself.

What are the number one problems that we think about when we are thinking about quitting our jobs?


Fear #1: Losing our income

I know for me, personally, I was just this hot mess of worry. I was like “But what if this happens? What if that happens?” – and it was spinning out of control. Obviously, there’s the first sort of major question, which is “How would I pay my rent next month?” That’s obviously a real fear to have, but then I was spinning out of control, like, “What if I go totally bankrupt? What if I can never buy a house in the future? What if I do this? What if I do that?” Etc. etc. etc. “How is it going to affect every part of my life, you know: love relationships – everything.”

And I was just spinning and spinning and spinning, and the fear was just sort of swirling and swirling and just getting bigger and bigger and bigger. And at some point, you have to just check yourself and be like, “Um, wait a second, you know – is this actually likely to happen? Is it worth me actually spending my time worrying about and trying to solve the problem of this particular fear?”

So we spin and we spin, and we get more and more and more worked up. And society kind of allows this to happen almost; it’s like “the only thing you can have is to be in your corporate job or your 9-5 or whatever job it is you have. It’s 40+ hours a week, and that’s the way you live your life.” And anything else is like this gaping hole of just drama that we’re just wondering, “what on earth is going on?”

And you know what? It’s totally ridiculous that you would think that you cannot replace your income – and I don’t care what your income is, whether you’re earning six figures as an investment banker: I was. I did it. I don’t care how big your income is, it’s ridiculous that you could not replace your income with a business. Why is that even a thing? You know?

Whatever other fears you have, you know, imagine that you wouldn’t enjoy yourself, or you wouldn’t this, you wouldn’t that – and all these things that spiral out of control if you were to quit your job. The most important thing to think about is…is this actually likely to happen?

And I’ll talk about money more later on, but you know this is something that is so, so key is how much of our fears are actually real? Like actually could happen, actually likely, actually probable. And how many are us just spinning and finding a reason to be scared? So this is something that is really key.

how will i make enough Money?

So here is problem number one that I’ve thought about all the time and that my clients come to me and really are worried about all the time as well. And the first one is: “I’m not going to make money.” So like I said, it is totally ridiculous that you would not be able to make your income, whatever it is that you’re currently on now in your business.

The reason I’m saying this is because it’s not difficult to make a corporate salary. Ok, if you are the CEO of Coca Cola, it’s still totally possible to make your $5million salary a year or whatever, but it might take you a little longer to get there. I’m talking about the normal worker, so whether you’re earning $20K/year or $200K/year, you could make that in the first year of your business if you do it properly.

How do you do it properly? Obviously, this is my entire life’s work, and the basis for that is that you take on a premium brand. You take on clients where you’re giving them a whole load of value, so you’re working with them live, 1:1, whether it’s coaching, whether it’s teaching, consulting. You’re offering them a service as opposed to manufacturing a product. And you are solving a problem that’s really really, really important to them, creating some kind of transformation in their lives – whether that is being like a sales consultant for businesses, whether that is being some kind of coach, like a life coach or a health coach or something like that. But you are really creating key, transformative change in your client’s lives.

And you’re also dealing with a very small group of clients, a very niche market, so that the way that you communicate with them is very, very targeted and they really, really resonate with everything that you say.

So let’s just do the maths a little bit. Let’s say you earn $100K/year right now. Ok? That’s quite a high salary. You’ve got to earn a little bit less than $10K/month. If you earn $10K/month, you’d be earning $120K, so let’s just keep it at $10K for now. Remember as well that, depending on your tax jurisdiction, you can actually pay less tax as a business owner than you do as an employee – because obviously business owners take more risk.

So your net income may be higher or lower, but let’s just make it super easy with super easy round numbers - $10K/month, that would be $120K gross a year. If you were to work with clients 1:1, say like a 3-month programme, you could be charging them the average going rate for beginners – not beginners, but, you know, you’re new to this and haven’t really got a huge reputation already, so about kind of 2K - 2.5K – pounds or dollars, let’s forget about the currency, that’s irrelevant right now. So imagine you got four clients – that would be your $10K.

So over the course of twelve months, you’d need 48 people. So someone explain to me how it’s possible that you couldn’t find 48 people in the course of a year who might want to buy your thing? And we’re not talking about you revolutionising the world and coming up with the world’s weirdest and wildest and wackiest and most amazing form of coaching or consulting or whatever it is you want to do. I’m talking about you becoming like a weight loss health coach, you know – plenty of people out there need weight loss. Or you becoming a sales consultant for businesses. Or let’s say you already have a skill, let’s say you’re an architect or a designer, so you go freelance and you help people with designs for their new properties. You know? 48 people – this is without doing any kind of internet marketing, or all the new weird and wonderful and amazing things that I can teach you – all that sort of leveraging your time and not having to get out there – but we’re talking about 48 people over the course of 12 months. And that’s earning you $120K.

You could walk into starbucks...

So then imagine your salary right now is like $30K pounds or dollars, I mean, how many clients would you need then? You’d need like ten to replace that salary. You could literally – as my coach always says – you could literally walk into Starbucks and find those people!

So get it out of your head that it’s this sort of magic lottery whether you make it in business or not. You make it in business when you actually do the right stuff, and you learn what to do, and you create an interesting product that people actually want to buy.

You don’t need be the world’s most original person. You don’t need to be the best and the only one in the market. You can be selling something that, on the surface of it, it’s pretty much the same thing. There’s plenty of health coaches out there in the world, but you do it in such a way and you sort of infuse your brand with your personality in such a way that you actually capture a small portion of that market, and this is called really niching into your market. So let’s say you only deal with mothers whose kids are at school, or new mothers, or just something like that, you kind of narrow down on your market that way. So that was the first part – not making money.

First up, it’s a totally viable fear. I totally get that because I live in London, it’s crazy what rents are here, and I was totally terrified! And I remember going around to everyone when I was at all these networking events, and I was still in my job, and I was desperate to become an entrepreneur, and I’m like “but how do you do it?" Like, “Well, it’s okay for her because she has a husband who can pay the bills,” or “It’s okay for her because she could save.” You know, I had someone in my group the other day say, “Well, it’s okay for them because they earn six figures already.”

If you earn six figures in London, chances are you’re not saving masses of it. You’re not going to become a millionaire in the next five years or anything like that. So I actually made a really conscious decision whenever I wanted to start my business, and I was extremely lucky that I was in the position of earning a little bit more than I needed to pay my basic bills. And I saved like crazy: I stopped going out, I made it happen that I had a small bundle of cash when I wanted to start my business.

You don't need to quit

But the reason why you don’t need to worry about this particular fear quite so much is because, number one – you don’t need to quit your job before you start your business. Did you actually know that? You actually do not need to quit your job before you start your business. You can start your business on the side. And this is how I teach all of my entrepreneurship coaching programmes, because quitting your job immediately – although it’s extremely freeing, and it’s amazing and if it’s the right thing to do and you have the sort of savings or whatever to do it – like good on you. But it actually puts quite a bit of pressure on you because you feel like you need to actually make some money really quickly. And watching your savings deplete can be really scary, no matter how many savings you have.

So actually you can start a business in anything from – I would say the bare, bare minimum of five hours a week. Ideally, you’d be looking at more like ten. If you could possibly handle twenty hours, that would be awesome. But to put that into perspective, let’s say you were working ten hours on your business as a side gig – that’s like 2 hours a night every weekday evening. Or that is like both mornings of the weekend. Or that is one hour before work, and then a half-day on the weekend. That’s really, really doable, you know?

So no one is making you quit your job before you start your business, you can totally start your business first. And then, when you’re making money in your business, it’s a really easy decision to quit your job. So that’s number one.


FEar #2: I won't Ever find another job if i quit

Number two: You could quit your job, and things aren’t happening quite as quickly as you want in your business – you could go and get another job, you know? We have this thing in the corporate world where we need to grab onto this job, and hold on to it with everything we’ve got. But the reality is that you can get another job.

I remember when I was in my first banking job and I was a graduate and they were like, “If you ever leave investment banking, you’re never going to get back in. It’s going to be impossible to leave.” And I was like, “Oh, but I really hate it here, but I’m scared to give it up…” And eventually, I got so sick that I had to take six months off work, and I was actually made redundant at the end of that. I basically totally collapsed and died, and was basically chucked out with the rubbish – which was amazing because I was too blooming terrified to actually quit myself.

So eventually I took six months out, I really healed my body because I was totally broken. I’d ended up with a chronic disease – long, long story which I’ll tell you another day. But, you know, I eventually got out of banking, and I was like “thank god for that,” you know? Because it was awful.

And then I started working for a startup, because working for a startup is a really dynamic industry – it’s going to be amazing. And it was fine – except that it was still a job. You know, I wasn’t working 7am-9pm, but I was working 9am-6pm, and 9-6 is still quite a big chunk of your day. And I didn’t have the creative freedom I wanted, it just wasn’t gelling, I mean, every core of my being was still saying “Rosie, you need to become an entrepreneur” – I still wasn’t quite listening to that.

But do you know what happened when I decided that I really, really wanted to become an entrepreneur? I decided that “this is not working. I need to become an entrepreneur. How on earth do I actually make the money to be an entrepreneur when I’m going to have to quit my job and everything else?” Because I had all these stories still going on in my head, and do you know what happened?

Do you know what happened?

I got a call from an investment bank, saying “Hey, we noticed your CV randomly on Linkedin. We’d like you to come and do the exact job you used to do, but it’s a maternity contract, so it’s temporary. And because it’s temporary, we’re going to pay you about three times what you would have earned had you been full time.”

So I was like “okay, that sounds awesome,” and I was like, “well, it’s going to be an investment bank.” And I called my mom, and I was like “What if I burn out and die again?” And she was like “Well, you know what? You’ve quit once before, you could quit again.” And I was like “you know, that’s actually really true.”

So actually I took the job, actually it was amazing: the people were super, super nice – way nicer than the first place. And it wasn’t what I wanted to do with my life: I still worked pretty long hours. It was like 8am to 6/6:30/7pm, but you know what, I did the work, I got the pay, I managed to save up money. And eventually I quit because I was just bored of the job or whatever, and I had the financial means to do so.

I didn’t have to do it that way around, but because I had made that decision, I got – I mean, you know me and mindset and everything else if you’ve been listening to me before – but the Universe literally gave me that opportunity on a plate. They came to me; I did not apply for that job; I got back into investment banking like that (snap!).

So anyone who is worried that they’re never going to get a job again…there are always jobs out there for smart people. You know, it’s not that tough to get a job – people get jobs all the time. So don’t worry about the fact that you’re giving something up that you’ll never, never, never get back again. There’s always a way back, there’s always a kind of a back door into everything. So don’t freak about that so much.

So that’s really the whole money issue. So I’d love for you to comment on any sort of money worries that you have, or sort of the biggest things that are holding you back in your business. And we’re going to do a proper Q+A at the end, so definitely hold your questions for there, but just to get a sort of a feeling if this is a problem that you’re facing as well.


Fear #3: What will people think of you

So while you’re doing that, I’ll move on to the next one. So the next biggest fear that my people have is – and I did as well, even though I’m a pretty outgoing person, mine was sort of really deep within me, but it was still there – is this fear of what other people are going to think of you. So especially for me, much as I hated investment banking, it’s still in our society, it’s still something that kind of ‘proves your smart’. And to be honest, I don’t necessarily think investment bankers are necessarily that smart, but it’s the hardest thing to get into, etc., and I’d done the degree, and it was almost like a social status that I didn’t really buy into, but I still sort of subscribed to it subconsciously.

And you probably have this thing as well; you have an identity around your career. The first thing anyone ever asks you is “What do you do?” So I would be at parties and things when I’d first left investment banking, and they’d be like “so what do you do?” And I’d be like – I didn’t know what to say. And I’d be like, “Well, I was an investment banker, but now I’m not and like I’m not really sure.” It was really difficult for me to say anything other than I’m a banker – and I wasn’t a banker.

And it was this total identity shift. You know, when I first created my first ever email list, I basically copy/pasted all the connections that I had on Linkedin – 75 or 80% of whom were 50yr old, male senior bankers. And I have this pink Living Rosy brand, I sign off my emails with “With love, Rosy”, I have exclamation points and hearts and everything else going on – and I was thinking everyone is going to laugh. And I felt so scared about announcing my new move to everybody.

I felt so scared...

And do you know what happened? I announced the big announcement like “hey guys, I’ve left banking and this is my new thing” – expecting everyone to unsubscribe, to get loads of hate mail, everyone to be really mean about it. And do you know what happened? Every single email replay was super nice. They were like, “Wow, that’s amazing you’ve escaped! That’s so fantastic! I’m sending this to my wife, my daughter, my sister, my niece, my whoever, who sounds like she really, really needs your help.”

And I was like WOW you know, people really stood behind me. So often these fears you have about people laughing about you, people worrying about what you’re going to say…number one, people are way more supportive than they are anything else. I run huge ad campaigns now, my ads get out to nearly 200,000 people at a time, and I might get two weirdish comments, but I’ve never had a really mean comment. I’ve never had someone like deliberately be awful to me. I’ve had a couple people like, “I don’t believe in this,” or “this sounds silly, ”or whatever, but you know, you can get rid of that. But I’ve never had someone deliberately go out of their way to be really, really awful to me. And I’ve probably reached – I don’t know – but over a million people with those ad campaigns.

So when you’re freaking out about somebody being mean to you, remember that, first of all, your reach when you’re brand new isn’t that big. And secondly, people are actually quite nice at their core. I really believe that people are actually genuinely nice. And the third thing is that most people don’t even notice you! They’re too busy wrapped up in their own thing, and their own problems, and their boyfriend breaking up with them, and what they want to eat for dinner, you know – they don’t care!

So do not ever let that be a problem because it’s so in your head. Just ignore that, cancel that, delete that immediately – because it’s just ego/mind/drama nonsense, which we spin around in. And there is zero reason to worry about that one.

How do you define failure anyway?

So the last thing I want to say is this thing about failure, you know, we’re so scared to fail. We’re so scared of everything else, but how do you actually define failure?...Is that like not hitting a sort of income target? Is that like not getting enough clients? You know, like what is enough? What is failure? Is failure like being homeless? At what point have you failed?

And the reason I ask this is because failure is the opposite of success, obviously, but success is totally subjective. You know? I’m not a millionaire yet, to some people that might not make me a success. To me, I’m growing my business! From January to September, I grew my business like 633% - as in my September revenue was 633 times more than my January revenue. To me, that’s pretty damn good, you know? But I’m not a millionaire yet.

And that’s just a monetary figure – I am so happy nowadays. I’m like radiant and beaming when I wake up in the morning because I love what I’m doing. And I work from home, and I’m sitting on my sofa right now – you can’t quite see that because I’m zoomed in – but I spend my first hour or two every morning in a coffee shop, drinking a cappuccino and just chilling out. And the dad from Harry Potter is in there every single day, and the other random BBC celebrities, and it’s just this kind of surreal experience considering that at 8:30am on any other morning when I was in investment banking, I would have been in my third hour of work. You know? I’m super happy!

My income is still growing, I still have targets. I still really want to grow, and I’m super motivated to really bring Living Rosy to more and more and more people. My big target is to bring freedom entrepreneurship to 1 million women over the course of my career, but I’m so happy! That for me is a huge, huge win.

What is success to you?

So what is success to you, and what is failure? Make sure that you are using things that are relevant to you and not relevant to what you think you should do, and what somebody else thinks that you should do. If you can’t really define failure, then you can’t really fail! That’s number one. 

And secondly, failure has to be on a time limit. If you’re thinking, “If I don’t make $100,000 by December 2016, I will be a failure.” But what if you made $100,000 in January 2017? Would that still be a failure?

So that’s just something to think about: you can only create failure when you give it parameters. So if you just keep going – it might take you four months to get your first client, it might take you nine months – but ten years down the line, when you have a seven figure business, will you really care that it took you a couple of extra months? Probably not.

So always remember that failure is totally subjective, as is success. So if you can’t really define it, and if you can’t really imagine a time limit for it, then it almost doesn’t really exist. So stop worrying about ‘failing’ because ‘failing’ doesn’t really mean anything when you don’t let it mean anything. Focus on succeeding instead; focus on all the different things you need to do to succeed.


Questions and Recap

So I’ve talked a little bit about me, and the main sort of things that my people really, really worry about….

What I would love to know now is what are you afraid of, and how can we get you past that?...When do you want to quit your job? How much do you want to earn in your business? What are the things that are holding you back, and keeping you afraid in your business, and keeping you in that corporate job all the time? So comment away.

If you’re watching the replay, join us in the Facebook group to ask questions. This is for you. The Facebook group is called Living Rosy, and it’s on Facebook.

If you’re not yet signed up to actually receive this challenge, and you want to hear the rest of the videos, etc., then join me on You can sign up there, you’ll get access to all of the replays, etc.

So if you want to watch the replays, that’s the only way you can access them. So I will see you all tomorrow at 1:30pm, where we’re going to talk about how to actually get your business ideas out of your head and into action, because action is the most important thing to starting a business. And if you don’t have a business, then you can’t quit your job, so that’s really, really, really important.

So I will see you all tomorrow guys! See you later!

What questions do you have? Ask away in the Living Rosy Facebook Community! What fears do you suffer from? Let us know!

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