Pine Turns 4: The Highs and Lows of Being a Freelancer

It’s been 4 years since I stopped working for a design agency and started working for myself as a freelance designer. It was one of the biggest decisions that I’ve made in terms of my working life, but strangely at the time it didn’t seem too daunting.

After working as an employee in the design industry for 6 years I knew that I wanted out. I was sick of working really hard for someone else’s gain and the stresses of commuting up to 4 hours per day were something that I wouldn’t wish for anyone to experience.

Like many of us in the creative industries, I felt under-appreciated when working as an employee. We’re taught to work hard and churn out results even if we’re not feeling inspired to do so. We’re often overworked and made to stay at work after hours in order to meet deadlines that we have no control over for no extra remuneration. And when we create outstanding results, our bosses usually take a huge amount of the glory.  

I thought I could go it alone and do things better myself. So I packed in the 9-5 employee work day and started the unpredictable life as a freelancer.

So what’s it been like to work for yourself for the past 4 years?


Ok, but what’s it really been like?

It’s been incredibly rewarding at times. When you’re busy and you’re hustling and everything seems to be going in a positive direction then there’s no finer feeling than working for yourself.

But when things (or a series of things) go wrong, and you’ve got no colleagues to turn to for help, it can feel like a heavy weight is crushing you. I can't count the number of times I've almost given up! But don't let that deter you.

Let’s break it down into some Highs and Lows:


  • When you’re working hard and there are projects in the pipeline then there’s no greater feeling than working for yourself.
  • Winning my first pitch for a project gave me so much more confidence in myself as a freelancer.
  • Just doing things yourself, and not relying on a ‘boss’ to give you orders is liberating. If you trust yourself to do things off your own back then you’ll love freelancing.
  • The flexibility that freelancing brings is great. Want to take Thursday afternoon off to go for a hike in the sunshine. Sure, go for it.


  • Money is always a constant worry. Unless you have a string of retainer based clients, then money and cash-flow can be a real burden.
  • Finding your ideal hourly rate or fee is so hard! It’s taken me a long time to work out fees and rates for work.
  • Because you’re freelance, clients can assume that you work all hours of the day, or even weekends. Be strict about your working hours!
  • No project is guaranteed. I’ve found this too many times.

Illustration of the number 4
It's not always going to be sunshine and smiles.

Tips And Tricks

Find something outside of your work that allows you to fully switch off from “Work Mode”

For me, this is Rock Climbing. This sport requires so much focus that you have to be ‘present’, or you simply won’t succeed. Climbing resets my mind and allows me to completely forget about that design project that’s been stressing me out all day.

Find a mentor… or even a mentee

‘Talking shop’ to other freelancers or your friends is all good, but I found that it doesn’t seem to answer those important questions that you have day-to-day. Having a mentor to help you gain some useful perspective on the big issues is really important. A mentor could be someone who’s been in your shoes and made it through to the other side, someone who knows the industry, or even someone who knows business. An impartial ear is always helpful, no matter what stage you’re at in your career.
On the flipside to this, you might want to find and mentee. Someone who’s looking to get to where you are in their career. I’m always available as a sounding board for anyone who’s looking to become a freelancer… if you think my advice is relevant!    

You don’t have to live, sleep, eat, breath design to be good at it.

When I graduated as a graphic designer from University I was hungry and did everything I could to live and breath design. One thing that I’ve found from 10 years in the industry is that the hunger often dips. And I think that’s ok. There’s no written rule saying that you must be 100% focussed on your craft 24 hours a day. It’s not healthy to live like that. And it certainly doesn’t make you less of an expert if you don’t live, sleep, eat and breath your craft all of the time.

Be multi-disciplined

You don’t have to be a master at one design discipline to be a good freelance designer. You need to be flexible, as the clients you work with are never the same. In the freelance world you’ll get all sorts of requests for projects, so being able to use a range of tools from your design ‘toolbox’ is always important.

Nothing is guaranteed

I liken prospective client projects to buying your first house: Until those house keys are in your hand, anything can (and generally will) happen. Projects can be pulled from underneath you. Even when it feels like you’re about to bring in some big projects they can be cancelled without any notice.

If you’re not feeling ‘creative’ then don’t force it

Here’s something that you won’t ever get to say when you work for a boss: ‘fuck it, I’m not feeling creative today so I’ll do some none-creative tasks’. It’s something that I’ve learnt to embrace. We can’t be creative every day of our lives!... And there’s always those admin tasks that you’ve been putting off for weeks.

I could go on and on about the freelancing life. There’s so many tips and tricks that I’ve learnt over the years. But one thing is that being freelance is liberating. And it feeds in the punk rock and DIY way of doing things that I grew up on (yes I had a mohawk and played drums in a punk rock band in my teenage years. I still play drums in a punk rock band, sans mohawk).

These are just my honest views and experiences from 4 years of being a freelance designer. Don’t take my musings as gospel. But if you’d like to know more about my journey as a freelancer, or you have any questions or need some advice. Then get in touch:

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