Milestones are funny aren’t they?

The date I sat down at the desk in my dingy London studio for my first day as a full-time freelance copywriter — Monday 2 November 2015 — is etched in my memory.

But don’t ask me what I did that day. I haven’t got the faintest idea. 

What I do remember are the two days that came before it. My last, intensely busy Saturday night shift behind the bar at the Hollywood Bowl in Finchley. And Sunday afternoon at Ikea, debating whether I should spaff some of the little money I had on a pen holder and asking myself: “Will this work out? Or will it fail like my other zillion attempts at starting my own business?” 

Well, five years later, here I am. 

I feel incredibly lucky. I’m consistently busy. I earn more than I did in any of my full-time jobs. And sometimes I still pinch myself when I think this is how I pay my bills. (You’ll also be pleased to know that I bought that pen holder in the end). 

how to become  freelace writer
Absolute scenes of my pen holder in its natural habitat

That’s not to say it’s been easy. I’ve had dizzying highs and rock-bottom lows. And I’ve learned loads along the way. 

To celebrate my five years of freelancing, I thought I’d share the biggest lessons I learned.

Strap in, it’s going to be a long one.

1. If at first you don’t succeed, keep going

Drumming up business is the trickiest bit of starting a business. It’s also a big numbers game. Or at least it was for me, because I had no prior experience and no contacts to lean on.

During the first few months I was in business, I set myself the (admittedly arbitrary) target of sending 10 to 20 cold emails a day. That’s 100 emails a week. But I’d only get one or two replies. Most people I emailed never replied at all. 

But you know what? When it happens, it really happens. 

Hundreds of emails may have gone without a reply. But one single email generated £10K+ in business. 

The lesson here is that persistence is key. You will make it happen eventually. But you need to be consistent, believe in yourself, and keep going. 

Here are some things that helped me stick with it when I got discouraged:

  • Keep tabs on the positives

    I’m a glass half empty kind of guy, but finding ways to stay positive helped immeasurably in keeping me motivated when I felt like I was spinning my wheels.

    Every Friday, I’d make a list of things I’d achieved that week, no matter how insignificant they sounded in my head. It always surprised me how much progress I’d made, even during weeks I thought had been unproductive
  • Don’t count your chickens. In fact, forget they even exist

    Most of the advice out there says you should follow up with prospects, because they’re busy and might need a nudge.

    I disagree. Following up put me in a mindset where I’d keep hoping prospects would get back to me. Or launch my calculator and tot up how life-changing it would be if I won the business. That sort of blue sky thinking isn’t helpful when you’re starting out. You need to stick with the plan and keep doing the work.

    So I stopped following up, and it was fucking liberating, because it allowed me to keep my head down and crack on without getting hung up on what-ifs. I highly recommend the approach:

    1) Research your prospects

    2) Craft a highly personalised email that focuses on what’s in it for them if they work with you

    3) Send it… and then assume they won’t reply. Move on to the next pitch. It’ll help you avoid getting sidetracked and keep you focused on the job at hand
  • Forget the hard sell

    When I started cold-pitching, I viewed it as a zero-sum game. Getting work was a success, while no reply or “let’s keep in touch” was a failure.

    Then, I read Brian Cranston’s memoir A Life in Parts, and it had a passage that stuck with me. Talking about auditions, he said he became much more relaxed when he started viewing them as the start of a conversation, rather than something he’d either succeed or fail at. 

    I started applying this to my cold pitching efforts. Instead of viewing them as an attempt to close a sale, I began viewing them as a simple introduction, an opportunity to sow the seeds of what might become a fruitful relationship down the line.

    The change of mindset helped immensely, and I think it showed, because my efforts became more fruitful. While people might not have had work for me there and then, some did email me down the line. And some even sent lucrative referrals my way.

    That would never have happened if I’d been pushy and got salty when they said they didn’t have anything for me.

2. Spread your risk

If a single client accounts for a big chunk of your revenue, you’re in deep shit. 

I learned this the hard way three months in, when I got dropped by a client who accounted for 50% of my income. I’d just started making ends meet, and this took my back to square one. 

Luckily, things were really starting to happen for me around this time, and I landed my first four figure payday a few weeks later. But I learned my lesson. From that day on, I made sure no single client ever accounted for more than 38% of my total revenue. 

This has paid off. Last year, a major client I’d been working with for 2.5 years got bought out by a megacorp which took all the copywriting work in-house. It could’ve been a disaster. But because I’d made sure they didn’t become too big a source of revenue, I weathered the storm. 

So my advice is, don’t get complacent.

Businesses’ priorities change. Clients go out of business or get bought out. Your contact might leave and the new person in charge might want to bring in their own freelancers on board. 

The beauty of freelancing is that the sky’s the limit when it comes to how much you can diversify your income. Embrace it. 

Besides, if a client is so important you’re scared you’d be utterly fucked if they walked away, that’s not a healthy dynamic. You’ll be much more comfortable charging your worth, managing expectations, and setting boundaries if you’re not entirely dependent on them. 

3. Build your workday around your natural patterns

When I first went freelance, I was institutionalised (9 years of corporate drudgery can do that to you) so I stuck pretty much to a 9 to 5 routine. It didn’t work for me, but it took me three years to start wiggling my way out of it and another year to go all in, because it felt like shirking. 

Two things happened that helped me turn things round. 

First, I heard Annie Browne talk about work-life blend at Freelance Heroes Day in 2019.  

Second, I had an insightful chat with the lovely Megan Rose, who explained to me that working in short bursts takes a lot out of you. This went a long way towards assuaging my guilt over my inability to focus for long periods. 

It all fell into place after that. 

I’ve accepted that I’m useless in the mornings and that my ideal routine is not having a routine — I’m most excited about getting to work when it doesn’t feel like work. 

So mornings are now for lie-ins, family time, household chores, exercise, and the occasional Netflix binge. I get to work sometime between 11:00am and 12:30pm, knock off around 6pm, and, if I’m really slammed, do some catching up after 11:00pm when everyone’s asleep. 

The work gets done, clients are happy, and I feel like I’m living my best life (most of the time). Everybody wins. 

Of course, this won’t work for everyone. But the point isn’t for you to copy my routine. It’s to find out what works for you. 

Freelancing is hard work, but one of the best things about it is that you can keep your most productive hours instead of being forced in a box based on someone else’s requirements. 

4. Put processes in place early on

Ponying up for tools like accounting and project management software might seem like overkill when you’re starting out. As does spending time refining your onboarding sequence or tweaking your workflow. 

But you’ll be glad you did it once your business grows. 

There are two reasons for this.

Firstly, when you’re starting out and work is thin on the ground, you have the luxury of being able to set time aside to research your options and experiment with different setups.

Even if you’re busy, your business doesn’t have much history. And, trust me, it’s much easier to set up your accounting software when you’ve only issued a couple of invoices than when you’re four years in and have to input reams of historical data manually. 

Secondly, while processes might not be so important now that you have one client, they’ll be crucial when you’re juggling four or five. Taking the time to put things in place early on means you’ll be good and ready when this happens.

5. Find your niche

There’s endless debate about whether you should specialise as a freelancer. 

I’m firmly in the yes camp for a simple reason. It makes it much, much easier to market yourself. 

When you become known for doing something, all sorts of doors start opening up for you. It’s easier for people to remember you, hire you, or refer clients to you. It’s also good from an SEO perspective, because you can target less competitive long-tail keywords.

You don’t have to niche right out of the gate, but I’d recommend at least thinking about it and trying it on for size. Pick something that’s in demand and which you’re interested in, have experience with, or are willing to learn about. Or see whether a niche emerges from the work you do. 

6. Get help 

Freelancing isn’t just client work. You wear all the hats: chief executive, chief operations officer, human resources manager, financial controller… hell, tea maker, cleaner, you name it. 

The good news is that you don’t have to do it all by yourself. 

I hired an accountant as soon as I started making some money. It was a great decision, because I got to fob off all the numbers stuff I hate to do, and I got the peace of mind of knowing that if HMRC ever decides to investigate me, they’ll find that all my Is are dotted and my Ts crossed. 

I also hired a designer to fix my website. And, again, he did a far better job than I ever managed to do myself, because I didn’t have the know-how or the patience to learn. 

But when it came to other aspects of my business, I doggedly continued to do everything myself. Until I read Sarah Townsend’s Survival Skills for Freelancers earlier this year. 

Talking about her own struggles, Sarah says:

It was only when my home needed decorating that the penny dropped.

I realised I had a choice: I could spend a lot of time doing a half decent paint job that I’d be semi-satisfied with, or pay a professional decorator to do it perfectly in half the time….

Then it occurred to me.

I didn’t love doing… my admin, or my IT support, either.

Reading that passage, the penny dropped for me too. My inbox was overwhelming me. And I was spending a shit-ton of time doing stuff I hated, like chasing late invoices and setting up tasks in my project management software. 

So I hired an assistant to do all that stuff for me and now I have more time to do the work I enjoy and feel much less aggravated. 

When you’re starting out, you might feel it’s an unnecessary overhead. But once you start earning some money, outsourcing the stuff you don’t enjoy doing is well worth the investment. Again, Sarah puts it way better than I ever could:

as much time as possible doing the things that make you money + as little time as possible doing the things that don’t = the secret to freelance success

7. Embrace change

Your business will change and evolve over time, and this can be scary. But fear, while natural, won’t get you anywhere. It’ll only delay the inevitable.

I put off incorporating as an LLC for many months, even though it made perfect sense. 

I kept wondering: How will I pay myself? How will I do payroll? What if my business tanks and it’s no longer financially feasible to be an llc?

Hell, what if an asteroid falls on Companies House? 

Well, it’s been 3 years since I’ve incorporated. And, if I have one regret, it’s that I spent an unnecessary amount of time worrying for no reason. 

The same happened with VAT. 

For several months, I worried that if I registered for VAT, my clients would ditch me for being too expensive. 

But you know what? Not a single one did. 

So stop worrying and start doing. Move forward. Greet change with open arms.

8. Find your people

Maverick Words isn’t my first attempt at starting a business. It’s my fourth or fifth. 

It’s also the only successful one. 

There are many reasons for this — timing, attitude, the circumstances I found myself in when I started, experience… I could go on. 

But I’m convinced that the biggest factor of all is that, this time, I didn’t go it alone. I had help and support. 

When I started, I signed up to a course — Start Content Writing, now no longer available — that came with one-on-one mentoring and a Facebook group. 

Having someone to cheer me on and call me out when I did things wrong was invaluable during those early days. 

But what was even more invaluable was having the support of like-minded people who were going through the same journey and with whom I could share the highs and lows. 

This remains true to this day. I’ve met many people through Facebook groups and Twitter who I’m now proud to call my mates. We support each other when the chips are down, celebrate each other’s successes, and even send work each other’s way. In some cases, we’ve even partnered on client projects. 

Making friends with other freelancers has been one of the most fulfilling parts of my journey. It’s also created incredible opportunities for me that would’ve never been possible otherwise. 

So my parting shot to you is this. 

Don’t treat freelancers as your competition. Seek them out and do your best to make genuine connections. 

They’ll have your back if you have theirs. 

Got thoughts, tips, or lessons you’ve learned throughout your freelancing journey?

I’d love to hear from you. Tweet at me.

I’ve been freelancing full-time for 5 years. Here’s what I’ve learned
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10 thoughts on “I’ve been freelancing full-time for 5 years. Here’s what I’ve learned

  • Wooooo Untamed Writing crew represent! That’s another thing you get when you pay for the courses, folks reading the comments here/wondering if they should buy: fellow students that’ll help you out along the way. I don’t know how many times I’ve passed along a job to a fellow student because it wasn’t for me OR got a job passed along to me when I needed the work. We help each other out, y’all.

  • Great advice. Extra points for blue sky thinking 🙂
    I also have a similar routine hours wise, surprised to find someone else on similar hours, but it works for me too. Fab stuff.

    1. Hey Lou,

      Thanks for commenting. Glad you enjoyed this! Yep I don’t know too many people who enjoy working afternoons… takes all kinds I guess

  • LOVE every single thing about this blog. Sat here literally nodding away like Churchill in those insurance adverts. So pleased that everything has worked out for you, and chuffed to count you among my freelance mates! Here’s to the next 5 years!

  • Epic post, thanks.

    I echo all the points and as to the starting five businesses and only one succeeding thing- it’s spot on with the average. Most entrepreneurs have a hit rate of 1 in 5.

    I’ve been writing full-time for two years now after a lifetime as a contractor in fintech and I’ve learnt a whole lost just like you.

    My best piece of advice?

    Choose a niche, if it doesn’t work out then choose a different one. It’s your business so who cares what people think?

    1. Glad you enjoyed this Stuart. Yes, agreed. Ultimately you’re in control and you can change direction if you’re not happy.

  • This was a great write-up of your writing journey. I’ve also been freelance writing for about five years and I could relate to a lot of your points (like about having a niche and that making it easier to attract writing opportunities). I especially liked that insight from Cranston:

    “Talking about auditions, he said he became much more relaxed when he started viewing them as the start of a conversation, rather than something he’d either succeed or fail at.”

    This was my strategy when I used to have interviews for staff jobs. But it definitely applies to freelancing gigs as well. It just makes everything easier.

    I also like the point from Megan Rose: “working in short bursts takes a lot out of you. This went a long way towards assuaging my guilt over my inability to focus for long periods.”

    That just helped me unburden some guilt. Cheers! It’s true. I often find writing an article in 2-3 hours is tiring. And 6 hours of research/writing feels busy, even though that’s shorter than most people’s work day.

    Also, I saw you used to work at Hollywood Bowl in Finchley. Strange coincidence. I grew up in Finchley Central (now living in Whetstone), so I went there a lot!

    1. Hey Sam,

      thanks for your comment and glad you enjoyed this and got something out of it! It’s all a continuous learning experience isn’t it?

      Hah I spent loads of time at the Hollywood Bowl… for all of 6 weeks. It was a good experience though. I remember it fondly.

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