I first took an interest in business when I was 12 years old. I found a copy of Richard Branson’s book Losing My Virginity on my parents’ bookshelf and read it from cover to cover. I was so inspired that I hunted down Branson’s address and wrote him a letter asking for advice about starting up a student magazine. While he didn’t give me advice, his secretary was kind enough to send me an autographed picture, which quickly became my most prized possession.

As the years passed, my interest in business continued to grow. I read and re-read every business-related book I could get my hands on. I wanted to be an entrepreneur. It was all I wanted. I entered high school with a clear goal and had a leg up over my peers. I knew what I wanted to do in life. I had a purpose.

But, nothing happened. I didn’t start a business when I was in high school. There is no backstory where I can pretend that I had a lemonade stand as a child or a lawn mowing business as a teenager. In the days before reliable internet and ecommerce, there was no escaping your reality. My reality was that I had no money and no way of starting anything. I lived in a small city with limited opportunities. My parents were normal, my brother was normal, everyone around me was normal. I was alone in my head.

In the end, my reality wore me down. I gave up on my dream of becoming an entrepreneur. I focused my energies instead on becoming a lawyer. In hindsight, the decision was questionable given that my only touchpoint with law at the time was watching Ally McBeal episodes as a child. Nevertheless, I read one book a week until the end of high school in the hopes that it would improve my written communication skills in preparation for law school.

The next six years of my life can be summed up with one word: disillusionment. Without parental support, I didn’t have the option of going overseas for university or even leaving my home town. I was miserable. Years of my life disappeared and I had nothing to show for it, apart from an ever-increasing student loan. I did an internship at Ernst & Young, which only made things worse; it made me realise that nothing I had learnt at university was in any way useful in the real world.

Despite my reservations, I did well at university and got my pieces of paper. I moved up to Auckland and started work as a Law Clerk in the banking team of a top-tier law firm. My interest in business was alive and well, but I tried to keep it under wraps. I mustn’t have been doing a good job, because during an interview I was asked to put forward a two-minute verbal argument as to why I should be an entrepreneur instead of a lawyer. I interviewed at the top firms in Auckland, but always found the experience to be incredibly disingenuous. “So, why do you want to work at Bell Gully?” This is the answer I wanted to give: “Why do I want to work at Bell Gully? Let’s see: it will look good on my CV and I’m broke after spending six years at university where I received two useless degrees and a crippling student loan.” In the end, I did what everyone else does. I lied. I made up a story about how I identified with the firm’s values and how my limited life experiences and homogenous education would be an asset to the firm. Simple.

At a graduate level, the recruitment process is comical. The goal is to attract candidates that are “partner material,” i.e. those people who will start as graduates, move through the firm, and come out the other end as partners. It’s a dated concept — it is incredibly rare for someone to start at one firm and stay there their entire career. If they did, you would more likely wonder what was wrong with them, rather than rewarding them with a partnership position. If the goal is to ensure that people never leave, the focus should be on recruiting individuals who are the most grateful for the opportunity. That doesn’t mean the best students academically; it means the students who know they are lucky to be there because they would struggle to get a job at another company of similar standing. I wasn’t one of those students.

After starting work as a Law Clerk, I quickly fell into the typical worker-bee routine. Wake up early, have a shower, get dressed, catch the train into work, exchange pleasantries with my unlikable colleagues, and sit at my desk until I was given permission to go home for the day. I really was living the dream. Everyone had their ways of coping with the stresses of the job — usually it involved some combination of cocaine, anxiety medication, and alcohol. I suspect the legal industry would collapse if a prohibition on alcohol was ever introduced. It doesn’t matter if you have to drink half a bottle of whisky each night to get to sleep — the only thing that matters in law is staying in the job and getting enough hours under your belt to progress. The goal for young lawyers in New Zealand is to work for 2-3 years and then head over to London for more of the same. It’s a rite of passage. We would often gather for a drink after work and share war stories about deals we were involved in. As junior lawyers, we all liked to and make out that we played some integral role in the major deals our teams worked on; in reality, we spent most of our time doing photocopying and socialising in the break room. Most of the lawyers I knew spent almost all of their salary going out drinking after work. I suspect there is a direct correlation between how much money we spend on things we don’t need and how unhappy we are in our lives.

I suspect there is a direct correlation between how much money we spend on things we don’t need and how unhappy we are in our lives

To no-one’s surprise, I didn’t last long. I left ten months into my first job after a senior lawyer threatened me and tried to throw a stapler at my head for not meeting an impossible deadline he had set before going out to get drunk with a friend at lunch. My last day of work was October 5, 2011, the day Steve Jobs died. For no particular reason, I took this as a sign. The coincidence was, in my mind, a sign that I was, in some way, like Steve Jobs and destined for great things. So, what happened next? Nothing. Well something, just nothing on the business front. Reality once again set in. I needed money and wound up at another large law firm for the next few years.

One day I was sitting at my desk at 2am on a Friday morning after completing a protracted due diligence and it hit me — I was never going to be anything. I was never going to do anything. I was 25 and had spent the better part of 13 years day-dreaming about becoming an entrepreneur. I spent my spare time reading tech blogs and instruction guides on entrepreneurship, but had no discernible skills. I couldn’t code; I couldn’t make anything; I didn’t know the first thing about marketing or sales. I got so swept up in the idea of being an entrepreneur that I forgot to do any work. I was the business equivalent of an actor in Hollywood waiting tables and preparing for my big break by watching movies rather than going to auditions and putting in work. I knew I had to do something drastic if my situation was ever going to change.

So, I quit. At 2.15am I wrote my resignation letter and sent it to HR via the internal mail system, along with my Practicing Certificate. By the time I got to work at 7am, it was sitting on the desk of the head of HR. I had a meeting with HR at 10am to discuss my exit from the firm. It was an awkward encounter. The woman handling the meeting had just come back from maternity leave. Shortly after the meeting commenced, it became apparent that she was upset by something I had written in her going-away card one year earlier: “enjoy labour, I hear it’s a breeze.” She evidently didn’t have a sense of humour about the matter. I knew enough about exit interviews to not give anything away. Rather than calling out my partner for not bringing in enough work and being an inadequate manager, I simply said that I was looking for a new challenge and wished everyone at the firm the best of luck for the future. I didn’t mean it of course.

My managing partner was livid. She refused to speak to me that day and was so angry that she didn’t want me to serve out my notice period. At the time, I didn’t care. I was coming off the back of an 8-week discovery process where I had to work at least 18 hours a day, 6 days a week, which was quickly followed by a due diligence where I got 3-4 hours of sleep a night. I was so sleep deprived that I could no longer drive because I couldn’t trust myself to keep my eyes open behind the wheel. When I walked out of the building for the last time, I didn’t feel relieved, I didn’t feel happy, I felt empty. I got into the nearest taxi and fell asleep in the back seat.

I stayed in bed the entire weekend. By Monday, my mental haze began to lift. Sometimes when you are living in moments, you can’t fully comprehend the gravity of a situation until after the fact. My legal career was over. I sat up in bed and stared at the wall for hours trying to deconstruct what had happened. How can something like a career be so fragile? It was my first real attempt at introspection. I wanted to try my hand at business, sure, but I didn’t want to destroy my legal career in the process. I didn’t know the two were mutually exclusive.

Sitting alone in my room in the weeks following my acrimonious split from the legal profession, it dawned on me how few skills I had. I could tell people how to do things, but I couldn’t actually do anything. As a lawyer, it had been drilled into me how special and smart I was to have beaten out thousands of other candidates for a job at a large law firm. Yet, I didn’t have a single skill that was in any way transferrable to business. I had nothing to offer and no way of starting anything. For whatever reason, I thought I was going to start something that would make me a household name like Warren Buffett or Mark Zuckerberg or Bill Gates. What about a knowledge retention platform for enterprise businesses or a review-based platform where reviewers are ranked based on an algorithmic trust score? Weeks passed.

One day, as I was unconsciously browsing the internet, I came across a short article about a 21-year-old in Australia who claimed to be making A$600,000 a month selling a weight loss tea online. Her wayward attempt to build an online personal profile shined a light on a business that was imitable and an industry that had no barriers to entry. Discretion is almost always worth more to a business than the attention that comes from publically grandstanding and showcasing personal wealth.

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