It was 4 pm on a weekday afternoon and I was sitting on my parents' kitchen floor, surrounded by books, papers and guides to choosing my university degree. My close friend Fiona was leaning over the kitchen counter urging me to make a decision.

I had just 30 minutes to submit my final university preferences for what felt like the beginning of a very specific path I'd have to take for the rest of my life. I'd auditioned to get into a dance course and been told to simply put it as my first preference to get in. And that's what I'd selected. However, I also knew I would likely get a high school finishing score that would be good enough to get into a dual degree of law and international business. I was torn. And it was down to the wire.

The pressure around this decision was all of my own doing. My parents were the most supportive parents imaginable. Both had grown up in poor families descended from even poorer families. Each generation had dedicated their energy to building a better set of opportunities for their children, and particularly with respect to education.

My Nonna (my Italian grandmother) had reached a mid-primary school level of education in a rural town in Sicily. My perception of her mother is that she was a harsh woman who saw more value in my Nonna doing physical labour than in attending school. This was likely born of a situation in which labour supported the family financially, whereas school came at a cost.

My mother got to mid-high school, and my father got to complete high school. He had excellent grades but couldn't afford to put them to use by attending university. Both of my parents prized education highly and, as I was part of the first generation of the family able to choose a tertiary future, I felt both the weight of responsibility and the overwhelming feeling that comes with uncharted territory.

While my father didn't have practical advice for me on tertiary education, he had given me something arguably more valuable: he'd fostered in me an awe and excitement around the potential the world held. When I was little he continually encouraged me to keep speaking Italian with Mum — if I spoke two languages I could be a diplomat, or an international businessperson, he told me. He gently encouraged me to picture an adulthood of travelling and working in a high-flying executive role.

He may have got more than he bargained for. As a child I broke down in tears at the suggestion of leaving Lismore for university in Sydney, a 12-hour drive away, telling my dad I would never ever want to leave Lismore, because I would never ever want to be away from my mum and dad. Now I've been living abroad for years and when my mother asks me when I'm moving back to Australia, I'm not sure what to say.

Alongside seeding these images of my professional life, Dad would remind me that getting good marks would give me the freedom to choose a career like that. And if I saved my pocket money and, later, earnings from my part-time jobs, I would have the freedom to choose my quality of life.

The idea of the ‘freedom to choose' became the heart of my motivation and still is today. Even at a young age I was strangely cognisant of this, choosing to study instead of going out, choosing to do fitness conditioning on a daily basis, choosing my high school electives to play to my strengths to get the highest finishing score I could.

‘Freedom to choose' also went hand in hand with a strong sense of independence, which in my memory is best demonstrated by the time I announced to my mum and dad, at about eight years old, that I was ready to move out. I was moving into the cubby house. With gentle and intelligent questions (‘Where will you go to the bathroom?' ‘What about all the spiders?' etc.) they managed to negotiate me out of the idea, but nonetheless, the flame was lit, and there was no turning back.

I was not, however, totally free-spirited. As a child I worried incessantly. I was terrified when I first came to understand the concept of death, and would find myself in a panic lying in my bed thinking about it. This worrying expanded into other areas, of course, and I have vague recollections of child psychologists, flipping dreary monotone meditation cassette tapes over in my white and purple Walkman, and Mum's well-meaning dousing of my pillow in lavender oil each night.

This incessant fear made me shy and, even though I didn't know it yet, depressed. But my shyness was single-handedly eradicated by my year 12 drama teacher, Peter Derrett. An unapologetic, hyper-intelligent disrupter, Mr Derrett taught me lessons and principles I still carry with me today. He didn't soften the world for the classroom. He didn't just walk through the syllabus. He evoked imagination, passion and joie de vivre. He pushed me into a baptism of fire by casting me as Juliet in a school play, and through that tough love taught me:

• You will never be embarrassed or foolish if you truly put everything into what you are doing.
• Always get back up and try again (i.e., reboot).
• The happiest people follow their heart.

Another influential teacher at high school was Mr Quigly, who taught commerce. Commerce just made sense to me. I loved it. But, the subject was only available for a short time, so I didn't revisit this again for many years.

All of this weighed on me in that moment on the kitchen floor. It was my first true experience of a very pivotal moment. The real rite of passage into adulthood — the making of a big decision that only you can make. With few metrics to guide me for such a big decision, I found myself scrambling for reasons to choose one or the other. On the next page is what I wrote down as I looked for pros and cons.

• Dancers were lucky to be able to perform for a living, or even to teach for a living.
• In either of those scenarios, the pay would be low. How could I build the next generation on such a low salary?
• My guess is that, like in many sports, dancers had an early expiry date.
• I wasn't a top-of-the-class amazing dancer.
• I loved dance. My drama teacher, Mr Derrett, taught me ‘the happiest people follow their heart'.
• A law degree meant a good base of knowledge that I could leverage in lots of industries.
• I'd spent my time in high school focused on the arts (dance, drama . . . ) and I knew I didn't properly understand how the world worked. If I took law, while it wouldn't be a natural fit, it would teach me the world in a way that would be to my advantage.
• An international business degree would surely be a step in the right direction to achieve a life that looked like the pictures my dad had painted with me as a little girl.
• And ultimately, if I really didn't like law, surely I could change my career? Go back to dance?

Fiona stared at me, gobsmacked that I would even consider law over dance. She knew me well and in that moment, could probably see more clearly than I could.

I chose law.

Six cups a day

My first year of law and business school was brutal, haunted by a feeling of regret for the path not chosen. I found myself at each semester break on the phone with my old dance teacher, in tears, looking for some guiding light, some comfort that I'd made the right choice. I tried continuing dance training at a local studio, but, without being able to dedicate the same number of hours as I had previously, it was a frustrating exercise in thinking my body could move like it used to, and finding with each step that it could not. Eventually I stopped attending class and stopped my daily dance exercises.

During these days I fell into a weird routine that showed me exactly what happens when you do something that your heart isn't in. I would regularly sleep until 2 pm, then buzz into lectures fuelled with six cups of coffee in a bid to keep my brain switched on to engage with the content. I scraped through exams and assignments with the lowest effort possible, which resulted in the lowest passing marks possible. My essays were an embarrassment, my energy entirely devoted to trying to keep myself moving forward day by day, rather than actually learning. I found it impossible to concentrate on the long passages of legal language and hated myself for my poor marks. It felt like my brain was in molasses.

I wondered how I would ever make it through the full five years. But the idea of dropping out was impossible. To not keep my promise to myself to learn this, not keep my promise to my parents that I had truly made my mind up on my path in life? I had mentally constructed for myself just one viable path to follow, and that was to finish my dual degrees in law and international business.

Painstakingly, I stuck with it. It felt like a cage. But it didn't have to be that way. In hindsight, the best piece of advice I could have given myself would be to look for ways to enjoy it. To get curious about law in a way that really meant something to me, that fit with my passions, values and beliefs. Reflecting on this now, it's possible that I didn't even understand what those beliefs and values were then. Today I am clearer about this, and conscious that these will continue to grow and evolve too.

I am also very aware of how glossy and perfectly impossible that piece of advice to my younger self is — to look for ways to enjoy something I was hating. It's easy to know better more than a decade down the track, with what feels like many lifetimes more experience of the world and myself since then. Interestingly, that lesson is still worth reminding myself of today, on those mornings when I pad around doing tasks that are the least important because I am avoiding the big scary task that I don't know how to do. Yet as soon as I sit down and let myself focus on it, it's absorbing, it's interesting, and it's ultimately very rewarding to crack something entirely new.

During my third year of university, one of the major law firms' local offices had a huge litigation on and my flatmate, Peta, had heard they needed a small army of paralegals to work through the due diligence. Somehow I managed to snag one of the positions. (I put it down to their desperation for able people, not anything to do with my talent, given my middling grades.) This blossomed into a summer clerkship, which turned into a job in the mailroom, which turned into a job offer on graduation.

I felt like a fraud. Had I tricked the system to somehow land this role in a top-tier firm? How long till someone figured me out?

During graduate lawyer orientation and training sessions I was constantly watching my graduate colleagues, wondering if they'd spotted the cracks in my capacity or qualification to be there alongside them. They never mentioned it, but I still wonder if they knew. This sense of fraudulence grew into an accepted self-perception for me. A habit, if you will. And some habits never die.

I found my niche very quickly in banking law. It was one of the few subjects I'd enjoyed at uni (alongside jurisprudence, and in particular a class called ‘legal fictions' where we dissected pop culture against jurisprudential theory, but I hadn't found a way to weave that into a career). And the people around me were incredible. It turned out that the years I'd done in the mailroom served me well, having given me a practical application of the processes that surrounded banking. It would take me many more years to understand that I learned by doing.

Within my 2.5 years of banking law I tried insolvency litigation, banking, finance and securitisation. Immersed in interesting work, surrounded by incredible minds, my attention was held but my heart was not. I was demotivated yet again. I wanted to shine at my work but I was failing to engage with the papers in front of me. I started making simple errors and, while none ultimately slipped through the net, that, alongside my mood dropping further and further, showed me something had to give. And so came that inevitable moment.

‘I had an awesome day!'

I was at dinner with my friends Matt and Jess Newell. Matt, who worked in advertising, asked me how my day had been. It had been the worst. I was working through an insolvency case that I was finding personally challenging. I gave a short version of the overly long day, and then asked Matt, ‘How was yours?'

‘I had an awesome day!' he replied.

When he said that, something just clicked. I hated law. I had to get out. To do that, I had to finally face what I'd been avoiding since my first day at law school. I had to make some clear decisions and take action.

In hindsight, this was another important lesson that I can only today articulate succinctly. Sometimes, the momentum of life that we build for ourselves simply becomes our life. We forget to keep making conscious decisions. We forget to keep checking in with the life we want for ourselves, our values, our vision. I had gone to law school not to become a lawyer, but to learn a new way of thinking. To qualify myself for other dreams. But, here I was, a lawyer. Not looking at any path other than becoming a partner or in-house counsel. It had to stop.

While today I can tell you with clarity how I figured myself out, rest assured, at the time it was messy, frustrating, exhausting and emotional. It felt like it might take forever to get an answer — or that the answer might never come. And even when I did come up with an answer, I didn't know for quite some time whether it was the right call or not.

In many ways, even as I write this book, I am in that place again. I'm asking myself really messy questions like ‘Was that a fluke?' and ‘Have I peaked?' The mind is a brutal companion. We will come back to that later. For now, here are the steps I took.

I came to a realisation that when I chose to study law, I had not known what law was in the day-to-day sense, as an industry: what a good day looked like, what the bugbears were — and what I could and could not live with. And now that I was thinking of changing careers, I didn't want to leap from the frying pan into the fire.

So I began to quiz every person in my life about their career. From close friends to acquaintances at events, I'd eagerly enquire about how their day had been, if that was usual, what kind of tasks they'd done, what success looks like, what the industry was like. The questions went on and on. And as I climbed into that research rabbit hole I realised that I would need to marry up these findings against the things I wanted out of my career. Otherwise, I'd risk choosing something that one of my interviewees loved, not something I loved.

My list was an uncensored mix of work and personal life values, applied to career. It was something like this:

• Whatever it is, my life must incorporate creativity.
• I need to be in an industry that is about creating something, not taking it apart.
• To have the opportunity to really be thoughtful in my work rather than simply having it be a means to an end.
• Yet it does have to have an end! It needs to have a good degree of commerciality for me to work with.
• I desperately want to be in an industry that is less rigid in its regulation and processes, and instead more intuitive.
• Ideally, I want to be in fashion or beauty.
• I want to work in a team, to learn from people who are great at what they do.
• To travel with my work.

As I read this list again today, not much has changed.

In the end, advertising was the industry that piqued my interest. It seemed to have most of my list neatly tied in a bundle. And Matt Newell mostly had good days at work, so there had to be something to it.

I researched agencies and met with as many people as I could. But the truth was I'd already fallen in love with an agency I wanted to join: The Campaign Palace. They had a page on their website dedicated to their values. As I read them I felt like I'd found my tribe. The values, the people, the work. Everything I read told me that this was not just a fit for the kind of career I wanted, but would also serve what I believed in too.

One morning, amid all this personal discovery, the partner at my law firm walked in with about 27 folders of due diligence and had them set up in my office. My heart sank, but my stomach felt very grounded. I knew what I had to do. I closed the glass door and cold called The Campaign Palace. The next day I interviewed with Sasha Firth, the head of account management and group account director, and, a few days later, resigned from law to move into advertising (taking a 50 per cent pay cut along the way).

As I spoke to each of the partners to say goodbye, one in particular will always stick in my mind. He said to me, ‘Ah you're going to do something creative. Of course. I mean — look at your shoes!' That day I was wearing a pair of cobalt-blue fish-skin kitten heels. I smiled, said thank you and walked out the door.

It was the summer of 2008. In Australia summer means long days stretched out on the sand at the beach, salty hair, the smell of sunscreen, and my favourite — the feeling of a warm breeze around bare shoulders.

At that time I had been working in advertising for just over a year. The Campaign Palace operated in a very flat corporate structure, so in a short time I'd had exposure to all parts of the brand-building process — brand strategy development, media-buying strategy, the creative process and, finally, execution. There was a lighthearted sense of quirky fun that permeated the workplace and a lot of learning on the job that I loved. I was finally starting to understand that I learned best by doing and I started to feel at home.

Michael Fox and I had married in September 2006 and moved to Sydney in 2007. He'd started out with a graduate stint in law at Clayton Utz, another major law firm, followed by a graduate role at Super Cheap Auto. At that time, it was the fastest growing retail business in Australia. Michael was the first graduate they'd taken on, and under the wing of the CEO he was given an in-depth operational experience of the entire business, alongside him doing his MBA. The program shifted significantly after his first year and he went on to Google, at the urging of his best friend and a groomsman at our wedding, Mike Knapp.

Mike had worked at Google from very early on in the establishment of the Australian office. He'd graduated law and IT, and was now working as a software engineer at Google's headquarters in Silicon Valley. (To minimise confusion, I'll only refer to Michael Fox as Michael, and Mike Knapp as Mike.)

Finding our Purple Cow

We had all ended up at Broadbeach on the Gold Coast that summer, a beautiful, long sandy beach on the east coast of Australia.

We were lying on the sand kicking around ideas. Mike and Michael had both recently read Seth Godin's book The Purple Cow and had been watching clients at Google achieve stratospheric success thanks to growing consumer confidence in buying online.

The premise of The Purple Cow is to develop a concept so interesting that people cannot resist sharing it with others. Imagine driving past a field and seeing a purple cow in it. Now tell me you wouldn't share that on social media.

We kicked around ideas from ugly sweater kits, to — well, to be honest, I don't remember all of the ideas. But we fell upon shoes at some point.

I had recently made a stopover in Hong Kong after learning from Michael's mother, Jenny, about a store there where she had designed her own shoes. I loved the idea and desperately wanted to try it out.

I had dashed from the airport to Hong Kong Island, winding my way through a cramped street market before finally finding myself in a shoe store roughly the size of a small market stall.

The warm lighting and neat beige shelves with gold finishings were a welcome refuge from the multisensory assault from the alleyway in which the store was located. I glanced dubiously at the rows of shoes, none really to my liking. There was absolutely no hint that I could design my own. Was I in the right place?

An older man came out from the back room and I explained I would like to design a pair of shoes. He nodded and bustled to the back room, returning with piles of swatchbooks and a sketch pad.

This man was Mr Tin, who would become our first supplier.

That day I discovered that designing shoes was a lot of fun. The myriad colours, textures and shapes were incredible. I designed 14 pairs in 1.5 hours — surely I'd broken some kind of record. I returned to the airport elated with excitement.

Ten weeks later the shoes arrived in Sydney. As I wore the shoes I got more and more questions from my girlfriends — largely because the shoes were designs they'd never seen. When I explained I'd designed the shoes myself, they asked if I could have shoes made for them too. The excitement about the prospect of designing shoes was unanimous. The reasons they cited — ‘I can never find shoes in my size', ‘I want to make shoes with a lower heel', ‘I can't find the style of shoes I'm looking for' — would later become key parts of our consumer insights.

Sitting on the beach, we reignited a conversation that Michael and I had with his family the night before — designing your own shoes online. We got talking about how excited every single woman was when we told them about the concept of designing their own shoes. How I had felt when I found out that I could do this. We talked about the shoes I was having made for my friends, how many pairs I'd bought, how much they cost, how long it took for me to receive them, how I'd designed them. It really felt like it could be a Purple Cow idea.

Lying on the beach, feeling the sand shift under my beach towel as I propped myself up on my elbows talking about starting a company — it didn't feel extraordinary. It was a relaxed time of year, heading into holidays and time with family. My mind wasn't racing as it normally did over endless weeks of work; it was relaxed, imaginative and curious. I didn't feel lightning strike. I didn't have a burst of ‘knowing confidence'.

While I knew from my law days about company structures and setting up a business, there was a lot I didn't know about starting a business. I was a good saleswoman (I'm still proud of that time I sold over a thousand dollars of The Body Shop product in one transaction when I was 18), but I didn't have an inside scoop on marketing, PR, financial modelling, fundraising, bootstrapping, conversion rates, manufacturing, making shoes, doing business in China, e-commerce, ROAS, COGS, CAC, LTV, and so on. (Don't worry if you don't know these terms — I'm intentionally doing that so you feel the same discomfort I did at this stage. I'll explain a lot of these later in the book — no need to pull up Google right now!)

And, all that aside, I definitely didn't want to just instantly drop everything.

I did know that I loved designing my own shoes. I loved the idea of everything I'd learned in my career thus far, the skills I'd built and the savings Michael and I had made, providing us with the freedom to explore and potentially choose to start this business. I felt curious enough to explore it a little further.

I admired various businesspeople but I wasn't an avid reader of business biographies and business books. I didn't have a swathe of theories that I was aching to put to use. I just had a curiosity. I know there are many out there who would have had much greater ambitions than I did at that point in the journey, but I didn't. I just looked at the next step, then the one after that and the one after that.

It gave me a sense of comfort that both Michael and Mike had observed this world of entrepreneurship. The fact that they were curious about the idea too validated for me that it was worth exploring. I just felt that there was nothing to lose. And, if this did work out, and we were financially successful — maybe, just maybe — I could take myself and the next generation of my family into even greater freedom of choice.

It was an itch I wanted to scratch. But how to begin?

Going from idea to action

In the weeks and months that followed, we researched. Was anyone else doing this? Were they doing it well?

I pulled out my old university books from my degree in international business and started to think through things. What were the Strengths, Weaknesses, Opportunities and Threats of the idea?

How would the business model work? How would we make money? And then Michael and Mike prompted questions from their fields of expertise — for example, how would people use the website to design shoes?

And, on top of all of that, how on earth would we make shoes? How are shoes made?

When I thought about solving all these problems at once, it felt overwhelming and far too difficult to achieve anything. It was like trying to push a whole pile of boxes through a doorway at once: you're bound to get stuck. But if you take them through the doorway one by one, you'll eventually get everything through.

That is, if you can convince yourself to stop procrastinating. This was my enemy number one, and the beginning of a painful relationship with myself in finding the line between inaction and creating the mental space for creativity and recharging. I knew that I needed down time to really percolate my ideas — to help them take form properly. But how would I know when I'd had enough productive downtime and was now just wasting time? It's not that I wasn't excited about the idea; it was that mentally, I was in a hole that I didn't yet know was depression.

Through our research we found that there was really only one company attempting to do what we wanted to do. And even then, the user experience was poor, the materials were not great, and the designs on offer weren't appealing.

Then there was, of course, NIKEiD, now called Nike By You, that allowed customers to adjust the colours and materials on a limited selection of sneakers. We'd heard that the customisation area of their business had grown to around US$100 million in revenue per annum within a short period of time. This felt validating — we took this to mean that there was a market for customising shoes.

Finding your MVP

If we took the success Nike was having with customisation and put it into a women's fashion shoe label, surely that was a formula worth testing. And so we began the journey to understand what we would need to do to build a ‘Minimum Viable Product' to test this idea. And, yes, this was the first time I'd ever heard the words ‘Minimum Viable Product' or, if you're super hip, ‘MVP'. Mike had experience with this process at Google in building software, so I learned about the concept from him, and it seemed to make sense. Put together the most basic version of your idea, show it to people you think are your target audience, get feedback, and then you know what to invest more time in for the next version of your idea.

Or in more theoretical terms: You need to validate your idea through both qualitative and anecdotal research that provides compelling support for the idea, both for you and the team you hope to build. This is incredibly important because, particularly at the start of a business, the hours are long, the work is difficult and the pay is low. So it's important to do everything you can to show that all of this is worth it.

Here are some of the research questions Michael, Mike and I asked ourselves when we were thinking about our idea and MVP:

• Do people want to buy this product or service?
• Are they looking for it on Google?
• Are they asking about it on forums?
• Are they talking about it on social media?
• Are they trying to use existing products and services in a way that would be better served by a tailor-made solution to that problem?
• Who else is doing this?
• Who are the industry players?
• What do I need to learn from the current industry players?
• How big is the industry?
• Which geography do I want to start in, and end up in?
• How much profit does the industry generate in the market in which I want to play, annually?
• How can I take a share of this?
• How would people find out about my product/service?
• What would the most compelling key message be for customers?
• What's better or worse about the way I think this should be done?
• What's my unique selling point?
• How big can this business be?
• How big do I want my business to be? Do I want to build a large global business, or a lifestyle business for me to run?
• Does this business idea scale efficiently?
• What would the business model be?
• How would I receive payment?
• Are there tax issues I should consider?
• How does this fit with the current regulatory framework for the industry?
• What resources do I need to start my idea? (cash, hires, equipment, etc.)
• How do I rally these resources together?
• Do I need to raise cash? Should I do it through a loan? Venture capital? Friends and family?
• Do I need access to experts in this industry?
• What roles would I need to hire?
• Do I know people I can talk to about this? If not, how do I meet them? Are there networking functions for this industry?
• What would be exciting about this idea for the people I want to work on this with me?
• What would a basic 12-month forecast look like for this?
• Can this business break even? And if so, when?
• If I think this business could be sold to someone, who might that someone be?

Our list kept becoming longer and more detailed, which is exactly the kind of thinking and research that should go into the idea at this moment, before making any significant resource investment.

When we finished our research phase, we took a breath and then set about step two, which was pulling together what we'd need to make it happen.

Just remember — if you also decide to create a list of research questions like we did, I would recommend that you give it parameters. There is a point at which you will learn infinitely more by simply doing rather than planning. So define a limit. Maybe it's a time limit, or maybe it's a milestone limit as to what you need in a minimum viable product to start showing people and get feedback. It can be risky to launch when you know the product isn't perfect, but you can also manage expectations — ‘We're just starting out and we'd love your feedback'.

Just don't get stuck at this stage. You'll never be fully ready, so jump in and start the business before you're ready.