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So, you’re thinking about quitting your job and going all in on your own thing? Respect. That mix of “this could be epic” and “what the hell am I doing?” is totally normal.
Loads of Kiwis feel stuck in jobs that drain them, dreaming of self-employment — but making the leap isn’t just about getting a new business card and calling yourself your own boss. It’s scary. It’s risky. And if you don’t plan it right, it can mess with your finances, your sleep, and your confidence.
This isn’t one of those “just believe in yourself” posts. This is the honest guide to making a smart, safe transition from 9–5 to self-employed, based on what actually works here in Aotearoa. We’ll talk money, mindset, safety nets, real risks, and how to set yourself up without burning out or going broke.
Because being your own boss? It can be bloody brilliant — if you do it right.
I remember sitting at my desk one Tuesday afternoon, staring blankly at a spreadsheet and thinking, “I can’t do this for another 30 years.” The idea of working for myself felt like freedom — but also, honestly, terrifying.
Back then, I thought being ready meant having a cool business idea. Turns out, there’s a bit more to it.
If you’re thinking about going self-employed, here are the things I wish I’d asked myself before fantasising about quitting:
And here’s the kicker: if you answered “no” to any of these? That’s not a red light — it’s a yellow one. It just means you’ve got a few gaps to sort before you leap.
I started prepping while still working full-time — dabbling on weekends, testing offers, building confidence. You don’t have to go all-in on day one. In fact, I reckon the slow burn is often safer and smarter.
Side Hustles NZ has a heap of guides, tools, and real stories to help you get started — no guru fluff, just stuff that works. And if you’re genuinely stuck? Flick us a message, buy us a coffee, and have a yarn. Sometimes just talking it through helps.
Alright, so you’re keen — maybe even buzzing with ideas. But before you print your “CEO” mug and tell your boss to get stuffed, let’s talk money.
Because here’s the truth: self-employment looks sexy on Instagram, but behind the scenes? It’s budgeting, invoicing, and hoping someone pays on time. And when you’ve got rent to cover, bills piling up, and maybe even mouths to feed — “just winging it” isn’t a plan. It’s a gamble.
What you need is a runway — enough time and cash to get your business off the ground without crashing by month two. Here’s how I built mine:
I sat down with a pen, a coffee, and my bank statements. Rent, power, groceries, Netflix, Friday night takeaways — it all went on the list. Then I asked: what’s the absolute minimum I need to survive for 3–6 months?
Tools like Sorted.org.nz helped me get a clearer picture. It was sobering, but also motivating.
I treated every extra dollar like fuel for my freedom. I picked up extra shifts, flipped stuff on Trade Me, used ShopBack for cashback, and squirrelled away anything I could.
If you’re looking to stack quick cash, the Fast $500 Challenge has a bunch of ideas that actually work in NZ.
Most people (me included) massively underestimate this. Domain names, software, gear, advertising… it adds up fast. Write down everything you think you’ll need. Then pad it. Because stuff always comes up.
Harsh? Maybe. But realistic. Assume that for the first 2–3 months, you’ll make little to nothing. If things go better than that — awesome. If not, you won’t be blindsided.
I also wrote this article on where to find grants and free money in 2025, which you can check out here.
Let’s be real — no one starts a business thinking it’ll flop. But even the best ideas take time to gain traction. And if you’ve got zero buffer? One slow month can send you spiralling.
That’s where the safety net comes in. Not as a “nice to have” — but as a must-have.
I aimed for six months’ worth of bare-bones living costs. Not luxury-level — just enough to cover rent, food, bills, and life’s basic needs. Some people say three months is fine, but I wanted enough breathing room to ride out the quiet patches.
Did I get to six months before I quit? Nope. But I got close — and even that made a massive difference to my peace of mind.
Leaving a job means waving goodbye to paid sick leave and workplace cover. When you’re self-employed in NZ, you’ll still be covered by ACC — but you’ll need to register and pay levies. And if you want extras like income protection or health insurance? That’s on you now.
I used Sorted’s insurance guide to figure out what made sense for my situation. Not glamorous, but necessary.
Car loans, credit cards, Afterpay — those monthly payments hit harder when your income’s not guaranteed. I tackled my biggest debts while still employed, which gave me way more freedom when I finally went solo.
Even if you can’t clear everything, having a plan — and sticking to it — helps reduce the pressure.
The words “business plan” used to make me break out in a sweat. I pictured those boring uni assignments — spreadsheets, forecasts, 12-point Times New Roman.
But when you’re starting out, it’s not about writing a novel. It’s about getting clear on how you’ll make money, who you’re helping, and how you’ll reach them.
Here’s what worked for me — written on a whiteboard and a couple of sticky notes, not in a binder:
This was game-changing. Not “anyone who needs graphic design” — but “small Kiwi businesses that can’t afford an agency but want pro-looking branding.” Specificity helps you focus your offers and your messaging.
No one cares about your product unless it solves a pain point. If you can finish the sentence “People come to me because…” — you’re already halfway there.
I mapped out my pricing, how many clients I’d need per month, and how much time each job would take. That’s when I realised I couldn’t keep charging mates’ rates and expect to survive.
Website, word of mouth, Facebook groups, Trade Me listings, even flyers in local cafes — figure out your channels. If you need help getting online fast, the free Google Sites guide is a solid start.
Going self-employed can feel like freedom — but also isolation, especially if you’re used to office banter or a team to bounce ideas off.
I didn’t realise how much I’d miss those random kitchen convos until I was working in silence, refreshing my inbox and talking to the cat.
You don’t need a team — but you do need a crew.
People who get it. Who’ve been through the slow months, the awkward first sales calls, the moments of “should I just get a normal job again?”
Here’s where I found mine:
Moral of the story? Don’t go it alone. Self-employment can be lonely, but it doesn’t have to be isolating. The right support makes the wobbles way more manageable.
Transitioning to self-employment comes with financial, legal, and personal risks. It’s crucial to manage these risks in order I’ll be honest — this is the stuff I ignored for way too long. I was so focused on getting clients and making money that I didn’t think about what could go wrong… until it nearly did.
Getting your head around risk doesn’t mean being paranoid — it means being prepared. And trust me, future-you will thank you for it.
When you’re employed, your boss sorts all that behind the scenes. When you’re self-employed? It’s your problem. You’ll still be covered by ACC (if you’re registered and paying levies), but things like public liability, professional indemnity, and contents insurance? That’s on you now.
I used a local broker who explained it in plain English — highly recommend doing the same. Sorted also breaks down what’s worth having.
Even if you’re a one-person show, it pays to separate your accounts. I opened a business bank account, tracked every invoice and receipt, and used a simple accounting tool. Makes tax time way easier — and protects your personal money if anything goes pear-shaped.
In NZ, you can operate as a sole trader, partnership, or company. Each has pros and cons — tax-wise, risk-wise, and paperwork-wise. I started as a sole trader (easy and cheap), but later shifted to a company once things grew. If you’re not sure, have a yarn with an accountant or check IRD’s guide for small business.
If you’re creating content, designing, or selling anything unique — your IP matters. That might mean copyright, trademarks, or just a clear client contract that says “don’t steal my stuff.” I learned this the hard way when a client reused my designs without paying. Contracts are your friend.
Tech breaks. Files get corrupted. Clients ghost. Always have a Plan B — whether that’s a backup laptop, multiple income streams, or a rainy-day fund. It feels paranoid until it saves your butt.
When I first started working for myself, I wrote down this grand plan: “Make $100k in year one.”
Ambitious? Yep. Realistic? Not really.
Helpful? Definitely not — I spent months feeling like I was failing because I wasn’t hitting a goal I’d pulled out of thin air.
So here’s what I learned about goal-setting when you’re going solo:
Forget the big flashy numbers. In the early days, your goals should be about progress, not perfection. Things like:
These kinds of goals build momentum and confidence — way more useful than some random revenue number.
Instead of saying “I want more clients,” try “I want to book 5 new clients by the end of next month.” That way, you know exactly what you’re aiming for — and when.
Stuff will change. Offers won’t land. Clients might disappear. That doesn’t mean you failed — it means you’re learning. Review your goals regularly and be willing to tweak them based on what’s working (or not).
I keep a simple Google Sheet where I jot down weekly wins, income, and goals hit. It helps me see progress over time — even when I feel stuck.
Got your first customer? Amazing. Hit $1k in sales? Even better. Ordered business cards? Still a win. Don’t wait for “making it” to pat yourself on the back. This journey’s full of mini milestones that deserve a cheers.r progress, you can stay motivated and focused as you make the transition to self-employment.
Self-employment isn’t a race — it’s a weird, winding hike. The right goals keep you moving, but let you stop and breathe too.
There’s a weird myth out there that once you go self-employed, everything just clicks. You find your niche, clients roll in, and you spend your days working from sunny cafés feeling smug.
Yeah… nah.
There are high points, absolutely — but there are also wobbles. Big ones. I’ve had days where I’ve questioned everything, from my pricing to whether I should just go back to a “normal job.”
Here are the most common wobbles — and how I got through them:
No team, no office banter, no one to share the wins or vent about the fails. That loneliness can creep in fast. I made it a rule to schedule at least one “biz buddy” coffee a week. And I jump into the Side Hustles NZ Facebook group when I need to connect.
When every hour = potential income, it’s easy to overdo it. I burned out in month three because I didn’t set boundaries. Now I book time off in advance — even if it’s just a half-day in the bush with my phone off.
Feast or famine is real. The key? A buffer, a budget, and more than one income stream. I also track every cent using Pocketsmith — super helpful for forecasting.
Without a boss breathing down your neck, staying motivated can be a mission. That’s why goals, accountability buddies, and small routines matter. Also, some days you just need to rest. That’s not failure — that’s smart.
So many moving parts. Websites, marketing, client work, admin… it’s a lot. I break tasks into chunks, use simple project tools, and sometimes — if the budget allows — I outsource the stuff that fries my brain.
Going self-employed isn’t some magic escape route. It’s messy, humbling, exciting, and wildly empowering — often all on the same day.
But if you do it with your eyes open? With a plan, a buffer, a support crew, and some real talk along the way?
Then yeah — it can be the best damn move you ever make.
So start small. Build your runway. Test your idea. Join a community that gets it. And when you’re ready? Take the leap.
You’ve got this.
Want a free tool to help you kick things off?
Check out our Google Sites website guide — it’s how I got my first clients without spending a cent.
Or better yet — jump into the Side Hustles NZ group and say hi. We’re all figuring it out together.
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Hey, I’m Rachel! I started Side Hustles NZ in 2021 with the goal of helping Kiwi’s start and grow small businesses in New Zealand. During the week you’ll find me discussing side hustle ideas in our Facebook group, working in my website design business, or riding my horses.
