Starting a freelance career today is worlds apart from what it was back in 2009. After over a decade of freelancing, I’ve gathered valuable insights that can save you time, stress, and money. From why you should never work for free to the importance of setting early boundaries and saving a quarter of your income, here are the essential lessons I wish I’d known on day one. Ready to start your freelance journey the right way? Let’s dive in!
Listen to the podcast episode below, watch it on [Youtube], or scroll down for the summary!
Prefer to read it? Here are the main points!
Thinking about going freelance – or still finding your feet? You’re not alone. Whether you’re new to freelancing or years in, there’s always something you’d go back and do differently if you had the chance.
In this post, I’m reflecting on my journey since starting as a freelancer back in 2009 – and sharing the hard-won lessons I wish I’d known from day one.
Things have changed a lot since I first started (no one even used Notion back then!), but the core challenges are surprisingly consistent – pricing, boundaries, comparison, admin, and all the head-fog that can come with being your own boss.
Here are the biggest lessons I’d go back and tell my younger freelancer self – and ones I now pass on to my coaching clients.
1. Stop Working for Free (or for “Exposure”)
Nearly every freelancer makes this mistake – especially at the start. We’re told to “get experience” or “build a portfolio,” often at the expense of fair pay. And sure, there might be rare occasions where a skills swap or portfolio builder is mutually beneficial. But if a client stands to profit and you don’t? It’s not a fair trade.
The clients who expect free or underpaid work are rarely the ones who’ll respect your time and boundaries down the line. Don’t let imposter syndrome convince you otherwise: you deserve to be paid, even when you’re new.
2. Set Boundaries Early – and Stick to Them
Freelance boundaries are like Pokémon – you collect them as you go. But I wish I’d set some non-negotiables much earlier.
For example:
- Charging late payment fees
- Always using a contract or getting written sign-off on terms before starting work
- Protecting myself from scope creep by being crystal clear on deliverables
Waiting until a client crosses the line makes it much harder to reset expectations. Start strong with clear communication, simple contracts (or at least agreed T&Cs in an email), and payment terms that work for you.
3. Stop Comparing Yourself to Everyone Else
This one’s tough. We see the six-figure months, the hustle culture, the TikToks of people working 12-hour days and seemingly loving it. I spent far too long feeling inadequate because I couldn’t match that energy – or didn’t want to.
But here’s the truth: comparison is the thief of clarity.
You don’t know what’s happening behind the scenes of someone else’s business. Maybe they have a team. Maybe they’re burnt out. Maybe they’re just on a completely different journey.
Your only competition is who you were yesterday.
4. Put Aside 25% of Your Income (Yes, Really)
I learned this the hard way. In my first year, I didn’t set anything aside for tax – and the bill hit hard. HMRC doesn’t accept credit cards anymore, but they did back then… and let’s just say I didn’t make the best repayment decisions either.
Nowadays, I use Monzo Pots to squirrel away 25% of all income as it comes in. And trust me – it makes tax season way less scary. Lots of online banks make this super easy to automate now.
5. Track Your Clients from Day One
I wish I’d known what a CRM (Customer Relationship Management) system was when I started. Even a basic spreadsheet with client names, emails, project notes, and follow-up dates would have saved me hours later.
Keeping a record helps you:
- Reconnect with past clients
- Track referrals
- Follow up after a quiet spell
- Spot patterns in your work or pricing
Notion, Trello, or Airtable are great tools now – but honestly, a simple Google Sheet is better than nothing.
6. Don’t Be Afraid to Ask Questions
Freelancing can feel lonely – especially when you’re navigating taxes, contracts, marketing, pricing, and productivity all by yourself. And if you weren’t taught this stuff at school or university (I wasn’t, despite having a business degree!), it can feel overwhelming.
That’s exactly why I created 30 Days to Go Freelance – a step-by-step course to guide you through the basics of going freelance in manageable, bite-sized chunks.
You can take it at your own pace, listen to it as a podcast, and refer back to it any time. It covers everything from legal must-haves and tax to building confidence and finding your first clients – all in a super friendly, non-scary way.
If you’re starting (or restarting) your freelance journey, know this: you don’t have to have it all figured out. The most important thing is to start small, learn as you go, and protect your energy.
I’d love to hear: what would you tell your past freelance self? Or what’s one thing you wish someone had told you before you started?
Ready to Go Freelance with Confidence?
If you’re just starting out – or feeling like you need a reset – my course 30 Days to Go Freelance is the perfect way to feel supported every step of the way: https://freelancelifestyle.podia.com/30-days-to-go-freelance
Follow me on Instagram
Follow me on Bluesky
Email: hello@emmacossey.com
Come join us in the free Freelance Lifestylers Facebook group
Want more support? Check out the Freelance Lifestyle School courses and membership.
Join the Freelance Lifestyle Discord Community: https://discord.gg/RKYkReS5Cz
