How I Used 5 Years of Self-Employment to Buy My Creative Freedom

In four weeks, I will reach a significant milestone: 1,825 days of full-time self-employment.

Five years have passed since I decided to leave my 9-5 job working in a retail warehouse. Before that, I’d spent a little over four years jumping from position to position at the same store without any sense of what I was really working towards.

I’d be in the sales department of one section, underperform and miss my KPIs for a few months, before being shuffled into a vacant position within another department. Again, I’d miss the mark.

This pattern repeated until I was relegated to the KPI-free warehouse role to receive parcels, handle repairs and—for lack of a better term—be a stock boy. I was now in my early 30s, and history was repeating itself.

I had ended up right back in the same position I’d spent my teens and 20s in at the local supermarket.

I started to believe that being a stock boy was all I would ever be good at.

What I didn’t know then was that I was stepping into the most focused apprenticeship of my life.

Breaking the old patterns

Looking back, my life has moved in seasons—at times I was a student of the world, and during others I was just stumbling through it.

At first, there was the education season of high school, followed by five years of aimlessly working at the supermarket, without a second thought about my future.

Later, I tried to shake things up by enrolling in a Nutrition degree at the ripe age of 23. I wanted to test myself, and I ended up going through to my Honours year.

That season was lonely and suffocating to say the least, and I was so engrossed in the work that I had little mental capacity to consider any other life.

By 2017, I had the degree, but my momentum and passion for science had evaporated. Feeling lost yet again, I reached for the most convenient option and fell back into the retail cycle for another few years.

I had to face a blunt truth: I was a failed nutritionist, a failed salesman and a failed retail worker. I was a less-than-enthusiastic player in each of those systems.

During that window, something else started to take root. I began watching videos of Gary Vaynerchuk talking about the world of flipping things online for profit, and I started testing the waters (because at this point, I had nothing to lose).

What began as a small side hustle between shifts—selling a few random items here and there—slowly became the only thing I cared about.

For nearly two years, I lived in a split reality. I’d spend my shifts with a notepad tucked into my pocket, running numbers and projections, trying to trick myself into believing I could extrapolate those small wins on eBay into a full-time gig.

I wasn’t just treading water anymore; I was actively plotting a way out.

I was naive enough to think that if I could make a few hundred dollars a week in my spare time, I could just scale that effort to a full forty-hour week and finally take some control of my life.

Learning to handle the silence

By the start of 2021, the distance between the person I was at work and the person I was becoming behind the scenes had just grown too wide to ignore.

On January 25th, I submitted my resignation letter. I knew I needed to put more skin in the game and finally trust that I could handle the pressure of backing myself. I gave them three weeks’ notice, and by early February, I was out there on my own. Like the flick of a light switch, I went from the noise and chaos of a retail store to nothing but complete silence.

For the first time in my working life, I had the white space to think and focus. Having twelve hours a day to yourself is basically a laboratory for self-awareness; it’s where all the realisations I have now actually started.

The first twelve months were a trial. Lockdowns were on and off, and I hadn’t yet found a real direction. I spent my days sourcing underpriced items from garage sales, thrift stores, and Facebook Marketplace, just trying to keep the momentum alive.

Building systems to survive

Halfway through my second year of working for myself, things began to click. I realised that hope is a terrible strategy and simply hunting for anything with a margin was wearing me out fast. I needed to niche down.

I narrowed into the pre-owned clothing category, which brought a more focused approach, with less decision fatigue, and repeatable workflows. This was my turning point, not just in business, but in life.

I became a systems obsessive. I started organising everything—nutrition, workouts, finances, creative projects—into spreadsheets and Notion templates.

If necessity is the mother of all inventions, then I needed order to thrive in the uncertainty.

Throughout the next few years, from 2023 to 2025, the operations became tighter and cleaner. The business stabilised. It wasn’t growing into an empire—nor did I want it to—and I began to feel that old, familiar boredom. This time it wasn’t a lack of direction, but a lack of challenge.

I worried that I’d just traded a corporate warehouse for my own warehouse.

A five-year education

But then I looked closer at what was really happening under the hood. Unlike my university degree, which took up all of my mental space, this work allowed me to kill two birds with one stone.

My hands did the monotonous, repetitive work, while my mind began to dream again with more bandwidth at my disposal. I essentially started attending a digital university of sorts; my days were filled with podcasts, audiobooks, and videos about philosophy, creativity, psychology, and business.

This self-education gave me something a traditional career never could: the daily headspace to finally figure out who I was and what I wanted from life.

It dawned on me that I had compressed twenty years of personal growth into a five-year window.

But even with the stability of the business, I knew deep down that a new season was on the cusp. I just wasn’t sure what it looked like yet. I was eager to move on and try something new, but starting over from zero is a lot to wrap your head around and accept.

I struggled with the pressure of making the “right” choice. Because there are so many directions I could take, I was scared that if I went all-in on one path and it didn’t work out, I’d look back and realise I’d missed my chance at something better.

The audacity to start over

For two years, I dabbled in different projects with short bouts of enthusiasm. I never fully admitted to myself what I really wanted to do.

I had to find the audacity to believe that I deserved to try.

I realised that while my competence in the business had seemingly crept up on me through the daily grind, my next move needed a more intentional plan. I didn’t want a wishy-washy approach; I wanted to commit to the long hours required to truly excel at a new craft.

That’s when everything clicked.

I picked up Mastery by Robert Greene, and the pattern of my life now finally made sense. I saw that I wasn’t just drifting all the time, but I was actually moving through a series of apprenticeships:

• Education (2000–06)
• Science (2011–16)
• Business (2019–25)

The big unlock moment was realising that for the first time, I didn’t have to follow one of these focused periods with another “lost” period of stumbling. I have grown the business to the level that it provides a comfortable lifestyle, and because of that, it now serves as the financial and emotional grounding for what’s next.

The business is in maintenance mode, so my creativity can be in growth mode.

I am finally serious about it. I have stopped looking for the “right” choice and decided to make this choice right.

And so, now begins the next apprenticeship: creativity and writing.

At the start, five years ago, my only consideration was replacing my paycheck. In reality, it has all been about replacing my mindset. I’m no longer the stock boy in the warehouse, or the scientist lost in the data.

I am a writer starting day one of the apprenticeship I was always meant to pursue.

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