Five Years of Freelancing: 20 Practical Tips

Dave Smyth
Sep 2, 2018 · 6 min read
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This calls for cake, right? (Audrey Fretz on Unsplash)

This week marks my five-year freelance anniversary. Technically I was already ‘freelance’ before I became freelance, but that was in an entirely different field. It’s been five years since I became a freelance web designer.

The time has flown, and I’ve learnt a great deal over the years. I made lots of mistakes in the beginning, but these have helped me to refine many aspects of my freelance life over the years.

To mark this milestone, here are 20 pieces of practical advice I wish I’d taken (more) heed of when I started out.

1) Don’t be afraid to talk about money
It’s easy to feel awkward about the topic of money and how much you want to be paid for your work, but you have to be upfront about it. If you put it off, you risk investing a lot of time discussing jobs that aren’t the right fit.

2) Use a contract
I put this off for way too long. I think I was nervous about using it for the first time or felt unsure about what to include. Both of those were excuses which left me vulnerable to all sorts of situations.

3) Take a deposit
If you work in project cycles, rather than a retainer, make sure you take a deposit at the beginning of a job. Without that, you risk doing a whole lot of work without being paid.

4) Reach out to other freelancers, use groups
I was so late to the game on this front. Speak to other freelancers, use social media groups (like Freelance Heroes or DIFTK), join Slack channels. As a freelancer, you may not have colleagues to discuss business things with, so it’s important to be part of some sort of community. It’s amazing how positive, supportive and useful these groups can be.

5) Charge enough
Every article that’s ever been written on “how to be a freelancer” talks about recognising your value and charging enough. Almost none of them state the benefit this provides to your clients: if you charge enough, you’re more likely to stay in business. If your clients enjoy and want to continue working with you, they’ll appreciate this.

6) Make use of the flexible schedule/time
It’s easy to sit in front of the computer all day, every day. Don’t do this. Make the most of your ability to work when it suits — it’s one of the biggest perks of working for yourself.

7) Learn when to say ‘no’
If you work for someone else, there could be lots of projects you’re not enthusiastic about or don’t believe in. There’s a strong likelihood you’ll also have to work with clients that aren’t a good fit, too. As a one-person business, you’re in the enviable position of being able to reject a project if it’s not right for whatever reason. Use this! Oh, and remember: a principle isn’t a principle until it costs you money.

8) Start a pension
Like everyone, I left this longer than I would have liked to. Do a bit of research and ask around. FreeAgent cover what you’ll likely need to survive in their excellent blog.

9) Don’t be afraid of the word ‘business’
Transitioning straight from the life of a jazz musician, ‘business’ was always a bit of dirty word. I now see that term in a completely new light. Business doesn’t have to be about sharp suits or drab meetings. The projects you take on will either be good business and bad business. If you want to stay in business, it’s important to know which is which.

10) Using accounting software (and pick carefully)
This was the first thing I bought when I went became freelance. The app I use now, FreeAgent (Spoiler Alert: use this link for a lifetime 10% off — I’ll receive the same), I avoided initially as I thought the setup was too complicated. I went with another Canada-based company and that turned out to be a mistake. They had an excellent app, but when I switched to FreeAgent earlier this year, I realised what I’d been missing out on by not using a UK-based company. Small things like tax forecasting and the ability to submit returns for you are really worthwhile.

11) Use apps to make your life easier
Aside from the accounting app, I didn’t explore other workflow tools until much later. Universally useful apps include Trello, TextExpander, Evernote and Grammarly.

12) Get insured
Oh boy, insurance will help you sleep well at night. Check out With Jack for a friendly and freelance-focused insurer. They also have a great series of videos talking about what they offer and how their insurance helps freelancers. How about that — enthusiasm for insurance!

13) Make time for self-development
When you’re stacked up with work, it can be hard to find time to develop new skills. Even if you’re doing this on the job, there may be times when you want to spend some time on an area you’re looking to develop that’s unrelated to your current work. I recently started taking half a day a week to do this. It doesn’t always happen, but it’s a great feeling when it does.

14) Don’t be too hard on yourself
Mistakes happen, projects don’t always run as smoothly as we might wish and other things might happen along the way. Learn from these experiences, but don’t lambaste yourself unnecessarily. If you need to reassure yourself, look back at your work and processes to see how everything has developed over the time you’ve been freelancing.

15) Save for tax time
I was quite lucky not to be stung here, but I know many freelancers that end up with a much bigger bill than they expect in the first year. Your accounting software or accountant might help. Otherwise, use the tax calculator to work out roughly what you might be paying. I try to put in my figures in May so that I know what I’ll be paying, and don’t forget those payments on account, especially in the first year.

16) Listen to podcasts
I’d heard of podcasts and didn’t really get what the fuss was about. I happened to listen to one and I was instantly hooked. I’ve learnt a lot from listening to these and picked up several pieces of handy advice. They may not be your thing, but give them a shot if you haven’t already.

17) There’s no shame in having availability
Busy-ness is not a badge of honour. It’s great to be busy, but there’s nothing wrong with sharing that you have time for some additional work. It’s not uncommon for potential clients to think that a freelancer may be too busy to take on their project, so don’t hide your availability if things are looking a little lean.

18) Get out
Some freelancers create a fake commute by walking around the block to bookend their day, others work in a coworking space or coffee shop. I work from home and have never enjoyed a commute (fake or otherwise), but I play a lot of tennis. Find what works for you.

19) Invest in your workspace
This isn’t always easy when starting out, but it’s essential to have a space that you can feel productive in and a setup that’s ergonomic. Laptops can be killer for your neck, and even a desktop or external monitor can be too low, so experiment. Also, make sure you get a decent chair — Hermann Miller’s are fantastic and can often be picked up second hand for a more reasonable price.

20) Enjoy it
I love my job. There are the occasional irritations here or there, but on balance I really enjoy what I do on a day-to-day basis. No job is paid well enough to put up with a lifetime of unsatisfying work, so make sure to allow yourself the time to enjoy what you do.

If you’re starting out on your freelance journey, I hope some of these tips are useful. I’d love to hear other suggestions and ideas from freelancers that have been at this for a while. Pop them in the comments below.

Dave Smyth is a freelance web designer based in London. You can follow him on Twitter, Facebook and Instagram. For more of his thoughts on design and freelance things, sign up for his newsletter.

This article originally appeared on his blog.

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