9 bits of advice after 9 years freelancing

9 years ago today was my first day freelancing. I’m not sure how long I expected to be self-employed, but I’m still at it and still enjoying the challenge.

Here are 9 bits of advice I’d share with my younger self if I was to start again.

1. Establish a support/feedback network

Freelancing can be a lonely game. Being part of communities, big or small, is important for your sanity.

While larger communities are great for socialising and learning, smaller groups are better at giving you feedback and support because you can be more honest and vulnerable.

In Creativity, Inc., Ed Catmull talks about the importance of small feedback groups when creating films. Pixar calls this The Braintrust:

The Braintrust, which meets every few months or so to assess each movie we’re making, is our primary delivery system for straight talk. Its premise is simple: Put smart, passionate people in a room together, charge them with identifying and solving problems, and encourage them to be candid with one another.

My equivalent of The Braintrust is my mastermind group (which I’ve written about before: Mastermind groups for freelancers: what and why?).

2. Find your way of working

The internet is full of opinions on the best way to operate as a freelancer. There’s plenty of good advice out there, but don’t just blindly follow that advice.

There are dozens of ways to be a successful freelancer: you have to find your own path. Some people believe hourly billing is nuts, while others thrive billing hourly.

Treat people who talk in absolutes with suspicion. The world is too complex for black-and-white answers.

Listen, read, watch and observe what others do… and then test ideas for yourself. Being open-minded and willing to experiment will help you discover what works for you.

3. Write a blog

I’m not the only one who believes writing and sharing what you do is important. Many of the people who I look up to and admire attribute a portion of their success to blogging (or at least sharing what they’ve learnt in public).

Don’t write a “business blog” – full of stuff you think you should be writing about. Write about what interests you. Make it personal. There’s already too much fluff on the internet and it’s only getting worse with the use of AI. The only way to cut through the noise is to be you.

As David Perell says, “Writing is like weightlifting for the brain”. It helps you work through problems. It helps you understand what you think and why. Writing helps you become better at your craft.

A good place to start, as Chris Coyier says, is to “write the article you wish you found when you googled something”.

4. Get good at communicating

Most of the bad projects I’ve been part of can be traced back to one fundamental problem: poor communication.

Take the time and effort to communicate clearly. Then do what you say you’re going to do.

I’ve heard something along these lines dozens of times: The last developer we worked with was a nice guy but he never responded to emails. It was a nightmare getting hold of him.

Never, ever, have I heard: “The last developer just kept emailing us updates. He over-communicated.”

It would be pretty hard to over-communicate. Keep your clients up-to-date. They will appreciate it.

5. Treat freelancing as a business

If you want freelancing to be sustainable, you need to operate as a business.

Something I learned early on is just how easy it is to focus purely on client work while neglecting things such as sales and marketing.

Michael Gerber, in The E-Myth Revisited, says you should work on your business, not just in your business.

This is something I struggle with. When you’re busy and have a full schedule, how do you find the time and energy to work on your business?

The answer is that you must book the time on your calendar. One of my clients takes every 7th week off from client work and spends the entire week working on his business: improving his website, writing and creating content, streamlining processes, etc.

6. Take control of your calendar

I’ve learnt over time that my calendar is the most important part of my productivity system. Taking your calendar seriously is how you control how you spend your time.

The longer you are a freelancer, the more people you will have vying for your time and attention. This is why, to do good work, you need to protect your calendar.

I use SavvyCal so that clients can book calls on my calendar. The majority of the calls I do are in the afternoon so mornings are reserved for deep work.

A to-do list is a wish list of things you want to get done. If time for those tasks isn’t scheduled on a calendar, they won’t get done. Scheduling time on your calendar is a sign of commitment.

7. Build a financial runway

I can’t stress the importance of building a financial runway: that is, a cash buffer in the bank that’s reserved for when you’re not earning.

The actual runway – whether it’s 3, 6 or 12 months – is up to you. It’s whatever feels right. More than 12 months I’d argue is too much and that money is better invested elsewhere.

One of the primary benefits of having a healthy financial runway, apart from reducing the daily worry of wondering where the next pay cheque will come from, is the confidence it gives you when pitching for new projects. Enter a project negotiation with an empty bank account and you’re more likely to lower your rates or agree to unrealistic deadlines because you need that project. I know because I’ve been there.

8. Know what is enough

One of the many things I’ve struggled with while freelancing is how coupled my time is to how much money I make. Essentially the more you work, the more you earn. There’s always another project you can take on, another hour you can work.

The flip side, of course, is that any time you’re not working, you’re not earning. Go get a coffee with a friend and you earn less. Take a day off and you earn less. Take a holiday and you earn less.

This is why knowing what is enough is so important. There’s an amount per year I like to earn. This gives me enough to pay the bills, travel, enjoy a social life and save and invest a small amount. Earning beyond this is a bonus, not the goal.

I’m not a fan of the term “work/life balance”, but knowing what is enough is the thing that has most helped me keep that in check.

9. Look after yourself

As a freelancer, you are your business. Your primary job is to look after yourself. That means exercising, setting boundaries, not overworking, resting, reading, indulging in hobbies, and enjoying time with friends and family.

If you stop, your business stops. Everything rides on your emotional and mental well-being. You have to put yourself first.

There’s a saying in business: if you don’t run your business, your business will run you.

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