Running Your Freelance Business Means Wearing 4 Hats

You've already put in so much work, but this is just the start. Now you have to become a master juggler, a full-fledged freelancer. I think of it as spinning multiple plates while wearing several different hats all at once. The plates represent all the different projects you’re working on, and the hats are the various roles you have to step into, beyond just being the expert at your craft.

As your client list grows, you’ll have more leads in your sales pipeline, more work to deliver, and more invoices to manage. This is when it becomes essential to understand the different hats you need to wear. For anyone serious about that lasts, each role has its own responsibilities. Aside from being the person who makes the coffee, you’ll be playing four key roles: Chief Executive Officer (CEO), Finance Director (FD), Marketing and Sales Director, and Chief Operations Officer (COO).

Let’s break down what each of these really means for your .

Your Role as CEO

When you put on your CEO hat, your job is to work your business, not just it. There’s a quote from that I’ve always loved for its directness:

Cat: Where are you going?Alice: Which way should I go?Cat: That depends on where you are going.Alice: I don’t know.Cat: Then it doesn’t matter which way you go.

Your CEO role is about figuring out your direction. You need to take stock of where you are, where you want to go, and what opportunities are out there. You’re in the driver's seat, and looking down the road helps you target the work you actually want to win.

Are Your Services Hitting the Mark?

If you’re good at landing new clients but struggle to keep them, you have to figure out why. Is it because you offer a one-time service? A dating service is a great example—every success means losing two customers. If that’s the case, you need a constant stream of new clients or a wider range of services.

But if you believe clients come back and just don't, it might be an issue with your process. Ask for feedback to pinpoint where things go wrong. On the other hand, it’s easy to get stuck doing work that clients want but that you don’t enjoy. It pays the bills, and you’re good at it, but it might not be why you went freelance. Consider tweaking your offerings to attract work that makes you happier.

How Do You Grow and Develop?

The work you’re doing now might be fine, but will it still be in three years? I set aside half a day every quarter to review my work and categorize it. It’s easy to skip this, so put a recurring reminder in your calendar.

I try to keep three types of projects going at once:

1. This is the quick, easy-to-get work you can do well. It pays decently and leaves time for other things.
2. These are bigger, more challenging projects you have experience in. They take more time but are more exciting and rewarding when they pay off.
3. These are the dream projects. They take a ton of time and energy just to get started, but they can lead to huge personal and financial rewards. These are the projects that help you build and push you out of your comfort zone. This book, for instance, was my biggest speculative project so far.

If you only focus on the easy stuff, you’ll never reach your dreams. If you only chase the dreams, you might go broke. Balancing all three is key. Try to audit your current projects and see if you have a healthy mix. This is especially important when you’re and trying to grow into something more.

Charting Your Future Course

To figure out where you want to go, try this exercise: Imagine you’re writing a letter to an old friend you haven't seen in years. The catch? The letter is dated ten years from today. You’re writing as your future self, describing what you’ve been up to. This simple act helps you unlock your ambitions and clarify what success looks like to you. From there, you can build a strategy to get there, focusing on the projects that move you in that direction.

As CEO, you also need to stay current with your industry. Read trade publications, go to conferences, and keep your skills sharp. This information helps you set realistic goals and the milestones to reach them.

Your Role as Finance Director

After the CEO hat, the FD hat is probably the most time-consuming. The best way to manage the stress is to stay on top of your finances every single month and know your tax deadlines.

Effective starts with tracking cash flow—the money coming in and going out. Your bank account shows what you have right now, but it doesn't show what you're owed or what you need to pay. You need your own records for that, aligned with your financial year.

Record Keeping is Non-Negotiable

Good records are essential for filing taxes and understanding your business’s health. At a minimum, you need an up-to-date record of all income and expenses. This can be a simple spreadsheet or you can use accounting software like Xero or FreeAgent. Just remember, the software doesn't magically input the data for you. Set aside an hour a week to update everything.

• Every invoice should be logged with the date, amount, invoice number, and payment status. I also like to track potential and confirmed work to get a clear picture of my pipeline. Once an invoice is paid, immediately transfer a portion—a good rule of thumb can be around 25%—into a separate savings account to cover taxes.
• Keep a detailed record of all business expenses: date, vendor, amount, and category (e.g., Travel, Office Costs, Marketing). Using a dedicated business bank account makes this much easier. You can often download statements and quickly organize your spending. Apps like 1tap receipts can even scan receipts for you.

Getting Paid and Paying Your Bills

As the FD, you need to chase down what you’re owed. Build a good relationship with your clients' finance teams and understand their payment process. If an invoice is late, send a polite nudge. If that doesn't work, send a formal reminder that references your terms and conditions. A phone call is often more effective than an email.

When it comes to your own bills, pay them promptly. I try to pay my subcontractors as soon as I receive their invoices. It’s good practice, they appreciate it, and it's one less thing for me to remember.

Finally, don't forget about your pension. Even small, regular contributions can grow significantly over time. It can be tough with an irregular income, but a financial advisor can help you find a plan that works, which is a crucial part of long-term .

Your Role as Marketing & Sales Director

With your marketing hat on, your job is to keep your sales funnel full. If it's looking empty, you need to prospect. If it's full, you need to move clients through it. Don't forget to check in with old clients—not to ask for work, but to share something interesting. It keeps you on their radar.

It’s tempting to stop marketing when you’re busy with paid work, but that’s a mistake. Once that project ends, you’ll find yourself with an empty pipeline. Carving out even 15 minutes a day for marketing can prevent those dry spells and is a vital step in taking your .

Your Role as COO

As the Chief Operating Officer, you’re the scheduler. You make sure client work is delivered on time, but you also schedule time to wear your other hats. The COO looks ahead at the coming days, weeks, and months to manage workload and deadlines.

This is also the part of you that has to assess whether you can take on a new project. A simple calendar with all your key deadlines is a great place to start. Whether you plan your day down to the minute or just use headlines, having a plan makes it easier to keep all your plates spinning.

When things go wrong—and they will—the COO steps in. Honesty is always the best policy. Don't try to hide mistakes. Instead, take stock of the situation, figure out a few possible solutions, and then call your client to explain what happened and how you plan to move forward. Some of my best client relationships were forged in moments of adversity.

Remember to Look After Yourself

is a marathon, not a sprint. You have to pace yourself. Understand your limits and take time for yourself. A 30-minute walk, a trip to the gym, or reading a book can help you relax and recharge. You are your business; if you aren't in good shape, your business won't be either. Schedule real time off—weekends and holidays—to properly disconnect. That's one of the biggest perks of this life, so make sure you enjoy it.