'I quit the corporate world to freelance. Here's every mistake I made so you don't have to.'

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2026 marks a whole decade of me as a full-time freelance graphic designer. I still remember standing outside that Melbourne office building in late January 2016 after my final day as an employee, thinking, "well, here goes nothing." I was 26. I had a portfolio that slapped. And as a Virgo, perfectionist, eldest daughter Millennial who grew up thinking if you just worked hard enough, everything would work out, I was absolutely determined to nail this.

Not to spoil the plot, but I did not nail this.

I'd spent six years in corporate design studios designing branding, billboards, signage, swing tags and everything in between across Adelaide and Melbourne. I was objectively good at my job. But I was sick of art directors claiming my ideas and account managers playing Chinese whispers between client problems and my creative genius. I'd conquered the corporate design world. How hard could freelance be? Same skills, just without the office politics, right?

Wrong. So catastrophically wrong.

They say the best way to learn is by making mistakes. Sounds masochistic to me. So here's the second-best way: let me tell you every way I absolutely stacked it so you don't have to.

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I said yes to jobs with only vibes holding it together.

Contracts felt too corporate. Too serious. I wanted to be the 'cool freelancer' who was all, "yeah babe, let's just do this, it'll be great!" So when my Zumba instructor asked for a logo, I designed it. Spent hours on it. Made it perfect. Then invoiced her $500 and she laughed. Literally laughed in my face. "I'm not paying you for that." And because I'd already sent the files (rookie move) and had nothing in writing, I had zero recourse. Hours of work, zero dollars, and a lesson I only needed to learn once.

I priced to be liked rather than hired.

Every single estimate became this anxiety-fuelled, 'Choose Your Own Adventure', where I'd negotiate against myself before the client even saw it. "Maybe if I drop it $50, they'll like me more?" I'd change the number six times before hitting send. Sometimes I'd slash entire line items just to seem "reasonable." All I did was make myself look concerningly cheap and train clients to expect discount-bin pricing for premium work.

I avoided difficult conversations like they were Year 12 maths.

Unexpected costs would crop up mid-project, like a stock photo that cost $400 instead of $40 or a a printer charging rush fees because the client changed their mind last minute. Rather than go back to the client with, "hey, this just became more expensive," I'd swallow it. Pay for it myself. Then quietly resent them for not being grateful for something I never told them I'd done. Main Character Energy, but make it financially catastrophic.

I let boundaries become a theoretical concept.

"I should just be grateful for the work", became my toxic mantra. So I took calls at 9pm. Rearranged my entire weekend because a client "really needed" something. I'll never forget drawing chalkboards in my studio on a Saturday afternoon because a client forgot to brief me until Friday for their Sunday event. My response? "Yeah no worries!" There should have been so many worries.

I convinced myself I needed a studio to be legitimate.

At some point, I decided that working from my Kensington spare bedroom made me look amateur. Real designers had studios, right? So I spent thousands on rent for dingy offices in old buildings that I never brought clients to because, well, they were dingy. Meanwhile, my perfectly functional spare bedroom sat empty. The math was not mathing but I kept paying anyway.

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I treated my business money like it was all just... my money.

For the first two years, everything went into my personal account. Business expenses, invoices, grocery shopping, Friday night drinks = all one big financial soup. Setting up a business bank account felt like admin I'd, "get to eventually." The moment I finally separated them, something shifted. I felt legitimate. Like I'd earned my seat at the 'business owner' table. That confidence showed up in my pricing, my proposals, everything.

I chose fun skills over profitable skills.

I wasn't lazy, I was obsessed with learning. But I prioritised a motion graphics course over understanding profit margins. An illustration workshop, over learning to write proposals that didn't reek of desperation. Then, I'd add all this shiny new value to my services and keep charging the same rates. Congrats Jaz, you just made yourself simultaneously more skilled and more broke.

I became the boss I would've reported to HR.

I'd procrastinate going to the bathroom because I hadn't hit some arbitrary deadline I'd invented in my own head. I'd eat lunch at my desk because taking a break felt "lazy." If I'd treated an actual employee the way I treated myself, I would've been sued. There's discipline, and then there's dictatorship. I chose violence against myself, daily.

I compared myself to peers while doing absolutely nothing to compete.

I'd see other freelancers landing dream clients and get bitter. They were out here living my fantasy while I sat around waiting for my Jedi mind powers to telepathically whisper, "you should definitely hire Jaz", to strangers who didn't know I existed. Turns out they were pitching. Networking. Actually marketing themselves. Revolutionary concept.

I wore "figuring it out alone" like it was a personality trait.

I was drowning in accounting software. Writing proposals that screamed desperation. Googling, "what is a retainer agreement", at 2am like some kind of business martyr. I'd see freelancers in Facebook groups asking basic questions and think, "I should already know that"... so I'd suffer in silence instead. Turns out, every single person I was intimidated by had asked those exact questions. They just weren't too proud to admit they needed help.

Those first five years were basically a masterclass in, Freelance But Not This.

However, here's the thing: mistakes are only failures if you don't learn from them. Every humiliating client interaction, every financial faceplant and every boundary I should've set but didn't. They built the six-figure-profit-while-solo freelance business I run today. The one where I teach other freelancers how to charge properly, set boundaries, and build businesses that don't destroy them in the process.

So no, I didn't get it right the first time. But I got there eventually. And that's what actually counts.

For more from Jasmine, you can find her here. 

Feature Image: Supplied.