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10 lessons from five years of freelancing

10 lessons from five years of freelancing

This week sees an important landmark for me – it’s five years since I gave up my job and went freelance. Before that I’d been working in London for almost 10 years. I had a job and a company I liked, but couldn’t shake off the bored and restless feeling, so decided to see if I could make a go of it myself. And somehow I’ve made it through five years! So to mark the occasion I’m diverging from my usual travel talk to share 10 lessons that the last five years have taught me – whether that’s been the easy way or the hard way – about freelance life (illustrated with photos of some of the places I’ve worked along the way).

Read more: A Peek Behind the Scenes with the Blog Hop

Views of the Dents du Midi from La Grande Terche, French Alps

St Jean d’Aulps: six weeks in the snow after finishing work

1. Temperament is just as important as talent

Being great at what you do isn’t enough to make you a good freelancer – your personality type is just as important. You might be an copywriting genius or a world-class photographer, but if you’re the sort of person who needs to be managed and told what to do, likes to work regular hours or stresses out if they don’t get paid on time, then freelancing probably isn’t for you. You need a certain type of personality, with enough motivation not to waste the whole day watching TV but enough discipline to switch off so you don’t end up working 24/7. A laid-back temperament with a dose of ‘something will come up’ optimism is useful too when a project falls through at the last minute or another client ‘forgets’ to pay.

2. Prepare to be a jack of at least a few trades

It’s rare for a freelancer to do just one thing. I call myself as an editor, proofreader and designer, but even that mouthful doesn’t cover all the work I do. I write copy for a travel company’s blog, I create websites, I sell posters on Etsy. I’ve even painted a mural of life-sized people onto the wall of a doctor’s surgery. I definitely can’t say it’s boring! I said yes to pretty much every job I was offered when I started out. But over time you learn what you’re good at, and just as important you find out what people are looking for. It might well be that it’s not what you expect, or that your hobby or sideline ends up as part of your work – like blogging has for me. When I started this site it didn’t even cross my mind that I could actually make a business from writing about my travels, but five years on it’s become an important part of my work.

Eiffel Tower at dusk

Paris: an autumn housesitting in St Germain

3. You don’t need to spend a lot of money to get started

In my web design sideline I’ve met lots of people about to go freelance or setting up small businesses. Normally the first thing they want to do is set up a flashy website, but – at the risk of doing myself out of a job – they don’t necessarily need one. One guy came to us wanting an all-singing, all-dancing, super-pricey website with CRM system, forum and shop when he had no clients and hadn’t made a penny from his business. If you work in the digital world then it’s important to have a web presence, but generally a basic portfolio site is all you need to start, then you can add to it if you need to. Same goes for flashy logos, stationery and brochures – start with a big pile of business cards and see if you need the rest later.

4. It’ll be feast or famine

If you’ve spent years working for a monthly pay cheque, getting used to the unpredictability of freelance income can be a bit of a shock. Some months you’re splashing out on Champagne (ok prosecco at least) then the next month it’s back to student-style instant noodles. Freelance work often seems to come in waves, so you’re either rushed off your feed or twiddling your thumbs. And even if you manage to space your work out perfectly, then there will always be clients who pay straight away and clients who you have to remind five times before they’ll pay up. Although I have to fight the temptation to blow everything I earn on travel, saving in the good months so I have a financial buffer makes things far less stressful.

Rim Trail, Bryce Canyon National Park, Utah

Bryce Canyon: A road trip around the southwest USA

5. Flexibility makes up for almost everything else

As we’re talking money, I’ll admit I don’t make as much now as I did when I worked full-time in London. One year I nearly did, but then another was more like a third. But I don’t think many people go into freelancing to get rich, it’s the flexibility that makes it so attractive. Where and how I work is up to me – as long as I get my work done there’s no one to tell me how to do it. You can do four 12-hour days then head off for a long weekend, or work nine months of the year and travel for the rest. You can start early then have a long lunch with a friend, or spend your days working from a laptop in a beach hut in the tropics. However you choose to use it, having that flexibility is worth so much.

6. Work can take over

The flipside of flexibility is that if you can work anywhere and anytime, then it can be hard to switch off. I’m guilty of spending the evenings with my laptop – just finishing a bit of work off or just catching up on social media. Then before you know it you realise the day’s over and you haven’t moved from your computer screen. Freelance work can be unpredictable so the natural instinct is to say yes to every job you’re offered, just in case you never get asked again, and when you’re on your own there’s no one else to delegate to. But you need to make time to do other things – to see friends, to go for a walk, to read a book – or you’ll end up burnt out (I still struggle with this one though, so anyone who has tips please share!).

Blue and white in Fira, Santorini, Greece

Santorini: On board Celebrity Equinox on my first cruise

7. Networking doesn’t have to involve any actual ‘networking’

When I started out there was one thing everyone kept telling me I had to do that was guaranteed to bring me out in a cold sweat – networking. I had images of awkward small talk over warm glasses of white wine as people tried to ‘sell themselves’ whilst being very British and embarrassed about it. But I did go to a couple of events and gave it a go, and while it wasn’t as bad as I imagined, it wasn’t much use either. When it comes to advertising your services, the best network you have is your friends and family. The people who know you as well as knowing what you do. So much of my work has been through referrals – those ‘oh I know someone who does that’ recommendations count for much more than any networking event.

8. You are your best advert

Finding new clients is tough – for every new job there are a whole host of hungry freelancers out there competing for it. Which is why repeat business is so important. If you’ve already shown someone that you’re reliable and good at what you do, then they’ll remember you when the next project comes up. Most of my business comes from repeat clients now, and in some cases when people have moved jobs I’ve ended up working for the new company as well as the old one. It’s a win-win – you don’t have to keep searching for new clients and the company don’t have to spend the time and effort finding someone for each project. Meeting deadlines, being easy to work with and doing good work is your best advert.

Roof terrace at Riad Capaldi , Marrakech

Marrakech: Riad rooftop turned outdoor office

9. Know your worth (and not just in terms of money)

If your work is creative, at some point you will have a client say “my friend/child is a web designer/has a GCSE in art and can do it in a couple of hours”. And to them I say – off you go then! (if you ever think you have it bad just check out the brilliant Clients from Hell). Pricing your work is one of the hardest things about freelancing. There will always be someone cheaper – and more expensive. Check out industry websites and groups, do your research and pick a price you are comfortable with. Pricing is an ongoing process and if you get to the point where you have plenty of work or everyone says yes to the prices you’re quoting, then it’s time to put them up. And sometimes you’ll come across a job or client that saps your enthusiasm and energy so much that it’s just not worth it, however much they’re paying.

10. Prepare for the worst case scenario

When I was deciding whether to give up my job, I though about what the worst case scenario would be. If it all went wrong, if I was useless at running a business and no one would hire me – then I would have to get another job. So for the first couple of years I kept my CV updated and an eye on the job ads, until I got used to this being the new normal. But there were a few things that helped me when I started out. I had no mortgage, no debts and no dependents. I moved out of London so my living costs were lower. I had enough savings to keep me going for a few months. I stayed on good terms with my old company. Somehow this mix of luck and preparation came together – and fingers crossed it’ll stay like that for a long time to come.

Quadra Island, British Columbia, Canada

Vancouver Island: My first trip to Canada and biggest blog trip

So that’s my freelance wisdom! Are you a freelancer with any tips to share – or would you consider the freelance life?

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Ten lessons you need to know about being a freelancer – what the last five years has taught me about self-employment and being my own boss. #freelancing #blogging

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  • Reply
    January 14, 2016 at 4:02 pm

    I agree with nearly everything you say, Lucy. While I did not learn too much new from what you said, it is very sound advice – I am in a similar boat, having given up a well-paid job about 6 years ago to be a freelance writer.
    I am still at the ‘instant noodle’ stage (no champagne, nor even prosecco for me yet), but the flexibility is priceless.
    Repeat business is the best benchmark of success – treat your clients like royalty and hang on to them.
    All the best to you!

    • Reply
      January 14, 2016 at 5:43 pm

      Sadly my instant noodles months far outweigh my prosecco ones too – but I can always dream! But as you say the flexibility counts for so much, being able to spend my time how I want to has made such a difference.

  • Reply
    Katie MacLeod
    January 14, 2016 at 4:16 pm

    Loved this, Lucy! And it’s great timing for me, as I start to test out freelancing now that I have all my US paperwork sorted out. After working at a newspaper in Scotland for about eight years, I’m still keeping an eye on job postings here, but it seems that freelancing is the way things are moving in media on this side of the pond, so it’s exciting (and a little nerve wracking!). Will definitely be keeping your lessons in mind 🙂 x

    • Reply
      January 14, 2016 at 5:35 pm

      Thanks Katie – and best of luck with your freelancing! It’ll be interesting to see what the differences are between working for yourself in the UK and the US.

  • Reply
    January 14, 2016 at 4:56 pm

    Such an interesting post. As someone who is freelancing as well and currently mainly works for a single client, for whom I’ve been working for two years now, I can just stress pretty much all your points. Repeat clients are the ones, who really make you have reliable income. The flexibility issue is something I definitely have to comment on, too. I love having the pleasure to work whenever I want, but as you mentioned, it’s all about getting away from the screen from time to time. Sometimes, you just spend too much time working and forget about the amazing other things in life. There’s also something you can improve to enjoy freelancing even more 🙂

    • Reply
      January 14, 2016 at 5:40 pm

      Thanks Moritz, it’s interesting how different people’s freelancing careers can be – I spent one year working mostly for one client and other years doing all sorts of different things. The flexibility is great but work life balance is something I need to get a better handle on, at the moment I’m either travelling or home working all hours so need to bring a bit of the travel lifestyle into my home life!

  • Reply
    January 14, 2016 at 7:24 pm

    Congratulations on making this work for 5 years!! You have learned so much and it was good of you to share it with everyone else. You have the true entrepreneurial spirit!!

    • Reply
      January 18, 2016 at 9:11 pm

      Thanks Darlene, it’s been a bit of a learning curve along the way but no regrets!

  • Reply
    January 14, 2016 at 9:04 pm

    Great tips – I don’t think I could ever go back to an office job after freelancing. I’m definitely at the ‘must turn off computer occasionally’ end as I try to cram everything in to limited hours but the flexibility is perfect.

    • Reply
      January 18, 2016 at 9:17 pm

      Me either, I’ve got far too used to the flexibility now, though definitely need to be a bit better at stepping away from the computer!

  • Reply
    Britany Robinson
    January 14, 2016 at 9:15 pm

    Great advice and congrats on your fifth year! I’ve just completed my first year of full-time freelancing, and becoming a jack of all trades has been my biggest lesson so far. While it’s great to be passionate and focused on the work that you quit your job to pursue, you have to be willing to do the bill-paying, less-inspiring work, too. Once you figure out a balance of bill-paying and inspiring work though, it’s nice to have the variety.

    • Reply
      January 18, 2016 at 9:22 pm

      Thanks Britany – and congratulations on your first year of freelancing too. Definitely agree about mixing things up and that it’s always a balance between the jobs that you are excited about and the ones that pay. Hope it works out for you for many years to come!

  • Reply
    January 14, 2016 at 10:20 pm

    A very interesting read, thank you! And congratulations on five years of freelancing and following your heart!

    • Reply
      January 18, 2016 at 9:23 pm

      Thanks so much!

  • Reply
    January 14, 2016 at 10:33 pm

    Hey Lucy. Having embarked on the freelance life as a proofreader and writer post my very late university studies I think you’ve got it nailed with most of that.

    I don’t entirely agree with point 7 though. I’ve got lots from networking – above and beyond work – though there’s been that too. I’ve formed relationships and got all manner of support that I wouldn’t otherwise have come across.

    And yes – the flexibility of it is worth the rest for certain.

    Cheers from Angela – aka Born again Swindonian – aka AA Editorial Services 🙂

    • Reply
      January 18, 2016 at 9:26 pm

      Hi Angela, hope all’s well with you! It sounds like you’ve found some better networking events than me! I have met some great people but it’s tended to be more in a social context than at any business-y events. Some people do get a lot from them though so it’s always worth trying out.

  • Reply
    January 15, 2016 at 8:32 am

    Great article!

    I have only been freelancing for little over a year, but I’ve had the same lessons and experience as the ones you mention. If I can have such freedom and flexibility in the future, I’ll probably never give up freelancing, even if I don’t get rich. Money is definitely NOT everything!

    • Reply
      January 18, 2016 at 9:28 pm

      Totally agree – I won’t be getting rich from freelancing but the benefits in terms of freedom, flexibility and how varied my work is are worth so much. Congratulations on your first year and hope things keep going well!

  • Reply
    Bianca Malata (@ItsAllBee)
    January 15, 2016 at 11:13 am

    Lovely post. One of those things that scares me about freelancing and always very inspired but those that have take the plunge.

    • Reply
      January 18, 2016 at 9:32 pm

      Thanks Bianca, it’s definitely not for everyone but has been a great journey so far!

  • Reply
    January 15, 2016 at 12:54 pm

    Thanks for this post! It’s always so nice to hear about other freelancers’ experiences, as the profession can be a bit of an isolating one at times, and I’ve found myself wondering, “I wonder if others feel this way?” The flexibility is a massive benefit – everyone has different “peak hours” when it comes to being productive, and I work best very early in the morning and crash in the afternoon, which isn’t exactly ideal in an office environment!

    Happy travels!

    • Reply
      January 18, 2016 at 9:55 pm

      I totally agree, it’s so interesting to read about how others work when you’re on your own so much. I could never get on with normal working hours either, though I’m more of a start late, finish late type of worker!

  • Reply
    ladies what travel
    January 15, 2016 at 4:59 pm

    Congrats Lucy, some really good bits of advice there. I have to agree with them all – after almost 16 (eek!) years of freelance I still find they all ring true! Keri x

    • Reply
      January 18, 2016 at 9:58 pm

      Thanks, and wow, 16 years is amazing – something to aim for!

  • Reply
    January 15, 2016 at 9:12 pm

    Great post! Having given up the corporate PR world for freelancing in 2003, I’ve never looked back. Of all your tips above, #7 resonated with me the most. I learned very early on that networking didn’t have to be stressful or a chore. In fact, I made it a policy never to attend those boring, formal “networking” events . Instead, Instead, I networked casually at industry events, conferences, seminars, classes, social events, parties, lunches, etc. My rule was that it had to be an event that I was interested in and would have attended even if it didn’t present networking opportunities. I also went out of my way to be a great resource for other business people — introducing friends who I thought might benefit from knowing each other and working together. Real networking really is about being of service to others, and trusting that your efforts will be reciprocated. Wishing you many more years of happy freelancing!

    • Reply
      January 18, 2016 at 10:01 pm

      Thanks so much, and great tips about networking. The informal/social events are much more my thing too, where it’s about getting to know interesting new people and if they turn out to be useful business-wise then that’s a bonus but it’s more about making connections and new friends.

  • Reply
    January 15, 2016 at 10:25 pm

    Congrats, Lucy! 5 years is a substantial amount of time and sounds like you’ve weathered many different situations to get there. You hard work and courage paid off though as you’ve built a wonderful brand!

    • Reply
      January 18, 2016 at 10:03 pm

      Thanks, there have been some ups and downs but definitely no regrets – and so pleased that blogging has become a big part of my working life too (though is you add up all the time I spend on it it’s probably the worst paid bit!).

  • Reply
    January 18, 2016 at 3:58 am

    Lucy – I’ve been following your blog for a couple of years now, since I started my travel blog. I just took the freelance leap a few months ago to allow me to travel more and your article touched on some things I’ve already experienced as well as some other things I can prepare myself for – thank you so much for the wisdom!

    • Reply
      January 18, 2016 at 10:05 pm

      You’re very welcome – and big congratulations for taking the leap into freelance life, hope it all goes well for you!

  • Reply
    January 21, 2016 at 7:39 am

    Very cool post and the tips are great Lucy! Congratulations on your hard work. I’ve been enjoying reading your blog and following your adventures.
    Well done!

    When I first came to Germany, I freelanced for a year, but in those days employers didn’t like it and there was even a legal aspect to it that you had to have a minimum of three clients or you wouldn’t be considered to be freelance at all!
    I then accidentally found myself working for a British /Americcan corporate company in Berlin again and ended up being the boss for about 6 years before stepping down (when I had my son), and working as a corporate trainer instead, which offered more flexibilty and funnily enough, the same salary but far less hours lol!

    • Reply
      January 25, 2016 at 11:40 am

      Thanks so much! Funny how different countries have different rules about freelancing, I think here as long as you have more than one client you’re ok. Sounds like things have worked out well for you though!

  • Reply
    Lisa (Travel Loving Family)
    April 11, 2016 at 10:31 pm

    Congratulations on reaching your five year freelance anniversary Lucy! I am not surprised you have succeeded, you write beautifully and your images are truly stunning. I am also very guilty of allowing work to carry on into the evenings:( There is just always something to do online. I am very disappointed that we did not get to meet at Traverse and hope to meet you at some point soon, maybe at BritMums?

    • Reply
      April 12, 2016 at 6:26 pm

      Thanks so much – yes switching off (both myself and the laptop) is definitely my busiest challenge! Sorry not to meet you at Traverse too, don’t think I’ll be at BritMums but hopefully catch up at a blogging event soon.

  • Reply
    April 19, 2016 at 12:36 am

    Congrats on five years! As someone who is just starting my first year of full-time freelance writing, that is no small feat 🙂 It can be hard to see the payoff (especially in the beginning), but it’s definitely worth the flexibility in the end.

    • Reply
      April 19, 2016 at 2:15 pm

      Thanks Julia, and congratulations on making the leap to freelancing, I think that has to be the hardest bit! The flexibility really is worth the stress and it’s great to be able to build up something for yourself. Good luck with it all.

  • Reply
    Alastair Majury
    February 5, 2018 at 12:35 pm

    Coming up for 8 years contracting in my case but the general tips and advice still hold. I don’t think I could be permie now. Guess you are coming up for 7 years of freelancing now. Thanks for sharing, Alastair Majury

    • Reply
      February 8, 2018 at 10:50 am

      Yep just passed seven years – really has flown by! Don’t think I could ever go back now either.

  • Reply
    Emma Parker
    December 10, 2019 at 4:12 pm

    Thanks for this honest and hopeful post! I just finished my first year freelancing and can’t imagine any other way 🙂

    • Reply
      December 12, 2019 at 9:33 am

      Thank you – and here’s to lots more years for both of us!

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