Should I stay or should I go?

The Sea Garden by Celandine - midnight ocean colorway

The Sea Garden by Celandine – midnight ocean colorway












If we’re in the same approximate age bracket, I expect reading that title set you off humming ‘Darlin’ you gotta let me know…

Now that we’re back, the serious question. One that most freelance designers and illustrators – and probably all other freelancers too – have had to ask themselves at some point.

When do I quit my day job?

I’m a late comer to the illustration game. I started drawing quite randomly at the age of thirty, stopped again for a while to get through the first few years of motherhood, and started up again a couple of years ago. From that point on I’ve been pushing forward at full blast, but this is still a very short amount of time to grow into an illustrator’s shoes.

Throughout this journey I’ve held my day job. I work in administration and finance (super exciting), and I’m lucky – my salary is great, my boss is nice, and the work is not hard. But just like any full time job, it eats away the most productive ten hours of my day. After that I get a few hours of family time, and the entire campaign I’ve mounted to create a brand new career for myself at the tender age of 36 has to happen at night, after the kid has been wrestled into bed and all my strength for the day has already been ladled out to various activities that are not art.

I know lots of you will nod along with me when I tell you how weird this feels. 

Here I am, having discovered the one thing I want to do with my life, filled with boundless enthusiasm and energy to make it happen, practicing tirelessly, networking like a little ant, constantly brainstorming both art and business ideas, reaching out to clients, having clients reach out to me, and steadily making more and more money from art – and yet on the priority scale of my day, it sits on the furthest bench. This is the ONE thing I want to do, and yet it has to wait patiently in the corner for me to finish all my other daily tasks.

This kind of setup tugs at your heart. No matter how comfortable your day job – once you’ve found your passion, the Other Job will start to feel like a hindrance. The problem is that often this hindrance is providing you with food and rent money.

So how do you decide? When do you turn that fantasy job quitting speech you’ve been rehearsing for years into one perfect moment of reality? Different people make different choices. This is how I’d break down the options.


You’re just getting into the whole illustration and design thing and your energy is off the charts. You want to know where this feeling has been your whole life. You desperately want to give it your all. But building a freelance art career is tough – even if you studied art, and more so if you’re self-taught. It just takes time – developing a style, growing your confidence, finding your niche, working up a client base. So you hold on to your day job. Those who studied design-related subjects have a slight advantage here, because they can go for day jobs that are at least in the same ballpark as freelance design, and can grow the skills and contact lists they will need for later on. Those of us who received the memo a little later in life will have to make do with whatever field we’re in.

Quitting at this stage carries two types of risk – first, you might find out in a few months that while drawing for a living sounds like a constant party, it’s actually really tough when you have to come up with ideas to fit client briefs instead of just following your muse. Especially since there are so many artists out there, and so many of them are AMAZING. Second, art can pay well – eventually – but it’s unlikely to make you rich quick. It’s actually unlikely to make you rich, ever. So relying on it too soon to cover your living expenses can put you in a really uncomfortable position. You won’t be able to afford turning down any design job that comes your way, which means you’ll be doing a ton of stuff you don’t enjoy and slowly starting to resent the whole professional artist thing.

On the other hand, if you are free from the burdens of providing for your daily bread, this is AWESOME! By focusing on your art hard and fast, you’ll move forward like a comet.


As you get better, ideally you will be tipping the scales slowly – cutting down on the day job, passing on the uninspiring and poorly paid design gigs, and doing more and more of the stuff that feeds your creativity and fits your style. As you start finding steady streams of design-related income, you can take the day job down to four days a week, then half-time, then just occasional gigs to patch up your budget, if the type of work you do allows them.

On the other hand, you could be like me, still hanging on to the full-time job because – WHAT IF? What if you’re not as good as you thought you were. What if you run out of money. What if you just can’t make it work. If that’s where you are, you are not alone, believe me. And it’s ok. Just keep doing your thing. There will come a time when the choice will seem easy. It’s ok to wait for that moment. I’m waiting still, and I know many who are waiting with me.

You might also discover, as a friend of mine did, that you really like your day job. Especially if it gives you some flexibility – maybe you’re a freelancer in both fields, or you only work half-time, so there is still plenty of time for art. Being a half-time artist is just as cool as being a full-time artist, I promise.


As time passes, pressure starts to build. You’re getting new ideas, landing more and more design work, it takes increasing amounts of your time, and eventually it starts to head-butt into your other obligations. This is sort of where I’m at right now. Every so often I get a design job that takes more time than I can give. So the usual bag of tricks comes out – late nights, cancellation of all non-essential plans, even taking periods of unpaid leave to get the job done. I know that at one point there will come a design job offer I cannot refuse, and it will force me to finally take the leap. I’m curious to find out when this will happen. Honestly, I hope it’s soon.

Hanging on for too long is primarily a sign of insecurity and it can harm your progress. Growing a career in illustration and design is a bit like construction work – opportunities stack on top of each other like bricks, and satisfied clients will bring you more satisfied clients. If you’re missing design work opportunities because you simply can’t find the time to do the job, you are slowing yourself down. The ideal moment to quit the day job is the moment when you can see your design income stream is becoming steady, even if it’s not massive yet. If I had to eyeball it I’d say aim for the moment when you’re making about half of your day job salary through design-related work, more or less consistently from one month to the next. The time you free up by quitting will let you build on all your existing bases – your art style, your portfolio, social media presence, networking – and you should be able to sail smoothly into the wild waters of art freelance.

I’m about to put this theory to the test – my current plan is to be a full time illustrator by the end of this year. Yeah, scary stuff, I know. But also exhilarating.

Think I can pull it off? Did you make the leap yet? Have you got a D-Day set? Let me know in the comments! 

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2 thoughts on “Should I stay or should I go?

  1. Ooh, yes, the big question. I will be devoting one full day a week to design work from September (with the proviso that, if I haven’t made £XXX from design/art that month, I’ll have to give one of my Fridays to publishing work – nothing like a bit of pressure!), with the hope that I can, in time, increase that to two days a week. And then I can decide whether I want to go all the way, or just keep it half and half.

    I agree that there is a definite element of insecurity in doing it this way, but also financial necessity. When you already have a career which you do enjoy and are very good at, and where you are widely respected, it’s definitely a bit of a leap of faith to stop doing that entirely and move into something where you don’t have that reputation built over years and years! And then you have the problem that you’ll have been making decent money and taking a massive pay cut will, at the very least, be a major shock to the system, if not impossible without adding in things like downsizing and moving somewhere much cheaper (ooh, now there’s a thought).

    I’m very confident you can do it!

    • Tasha your approach seems perfectly balanced. It really helps when your original industry allows part-time positions and the rationing of work – the work I’m in mostly tends to want full time engagement but I’m hoping with my upcoming move I’ll have an easier time finding a part-time position.

      For the longest time I wondered if I was just dragging my feet and would never end up feeling ready, but I have to say that my experience is that at one point you just feel that you have amassed enough experience and have enough of a solid plan for future development that taking the leap feels natural and necessary. I’m glad I didn’t rush it, otherwise I’m sure it would have been quite a shock.

      As it is I feel pretty relaxed about it and am really looking forward to the change!! 🙂 Fingers crossed and all that 🙂

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