On having two freelance careers
In search of balance, financial security and a semblance of sanity
For those of you who are new here, welcome. In this Substack I write about freelance life, illustration business and sometimes travel (especially, but not always, travelling while working). I also write two other Substacks: The Illustrated Plant Kitchen where I write about following a mostly plant-based diet, with illustrated recipes and other food illustrations, and Authentic Maximalism, where I write about a fairly eclectic mix of things that don’t fit here or at TIPK.
It’s not unusual (in fact, I might go so far as to say it’s really quite common) to combine illustration, and other creative careers, with another job. Many illustrators have part-time, or full-time, jobs out in the world, some in other creative areas, but many doing something completely different. Others start full time, but add in part-time jobs to provide some stability or to provide inspiration or social contact. And others branch out into teaching or running creative retreats and so on.
I think there’s an idyllic vision of being able to sustain something like this a hundred percent full-time and not to have to look elsewhere for other income channels or fulfilment. And there are absolutely people who do so, and I wouldn’t ever suggest that it’s impossible.
I do still retain the vision of creativity providing me with a very comfortable living into and past my retirement age. The idea that I might stop drawing and writing purely because I hit an arbitrary age is frankly weird. However, 10 years ago I did think that I would be at that point by now. And I’m not. And I vacillate being sad and angry about that and being sanguine and accepting and acknowledging that I get a lot (and not just financial security) from my other, Career 1.0.
My Career 1.0 is also freelance (with approximately two years in total of educational publishing in-house work and another year and a quarter of in-house publishing work before university - which, incidentally, was a joint honours degree in Publishing, with French Language and Literature). I have spent over half of my life (just, I think, and my maths may not be exactly right) as a freelancer. And, despite following closely what in-house jobs are available and the occasional dream of going for something that sounds really quite interesting, I think the rest of my life will also be freelance (or self-employed in some way).
I love being in charge of my own schedule. I love working from home. I love the flexibility of being able to work on the weekend and take a day off in the week to do whatever I need or want to. I love that I can choose to work more or less and not have to ask anyone’s permission. I love that I can take on a variety of projects that can provide different types of work and cover different subject matter.
I don’t love the uncertainty, though. Which is perhaps part of why I am still doing plenty of Career 1.0 and haven’t fully transitioned to Career 2.0. Because, for the most part, we have a steady flow of projects coming in and tend more toward turning work away because we are at capacity than having to actively chase work. Maybe every six or seven years there will be a worrying lull, that is usually related to the politics of education and waiting for curriculum or exam changes (which did actually happen recently).
In Career 2.0 I haven’t reached the point where I have a steady stream of projects coming in. I don’t have a regular block of clients like we do in Career 1.0. And I do think that it’s harder to get to that point in illustration than educational publishing, unless you’re a versatile illustrator who can pivot styles, because it’s rare to have a client who is always going to need your style of work; they will need different styles for different projects, and so will go to a wide variety of illustrators. So you need a much much bigger rolodex of contacts to have that steady stream of project offers in illustration.
But the other thing that I think has and does hold me back from getting closer to that point with Career 2.0 is that Career 1.0 gets in the way. When I am fully booked (note to any art directors reading this, I do always keep some time capacity free for smaller illustration and pattern design projects - it is always worth reaching out, even if I am giving ‘very busy’ vibes) in Career 1.0 I tend to just get on with that work and use my creativity time to do mindful go-with-the-flow type sketchbook work. Because I use it as a way to relax and rejuvenate from the Career 1.0 work.
I will create new illustrations and new patterns, and share them. But they will usually be fairly random and follow a particular interest or inspiration or theme, o just be purely decorative, rather than following a plan that will fill portfolio gaps or build work that can be sold as prints and so on. Because the thinky, project managery, organised part of my brain is being filled up with the Career 1.0 work and it doesn’t feel the pull or need to do that kind of thing on Career 2.0.
The trouble there, though, is that Career 2.0 needs me to do some of that organised work. It needs my spreadsheets and trackers and schedules. It needs me to project manage what I am drawing and what I am sharing. So that, when I pick up the iPad or sketchbook in the evening, I will have a bank of sketches and prompts and colour palettes to go to that will tick off something in the list of useful things to do for Career 2.0. It needs me to proactively be reaching out and emailing art directors and other illustration commissioners, to show them my work and tell them what I can do for them, even when I am very busy with Career 1.0.
Because, it’s genuinely no good to wait for a nice free period and then reach out. The likelihood of reaching out at the exact moment that someone has the right project that they can contract to start immediately is really really low. It can take a month or two to get some illustration projects set up, especially big ones like books. So it’s important to reach out regularly. It’s important to set aside some time every day and every week and every month to maintain Career 2.0 and keep it rolling but also growing.
At the moment I have pretty much the perfect amount of work in Career 1.0. It’s all higher hourly rate work, the different projects are providing me with variety, so that I don’t get bored or fed up. It’s all interesting and enjoyable work that I am comfortable doing and I have almost no imposter syndrome at all (to be fair, I am not sure I would ever reach a point where I had none of that). I am hitting my weekly/monthly earnings targets fine without having to work loads of evenings and weekends and mostly haven’t dealt with too much project slippage, so there have only been occasional overlaps where I’ve needed to double up for a few days.
This is the perfect time, therefore, to be spending down time working on the organisational side of Career 2.0. Planning out what I want to add into my portfolio to get the type of work I would like to be getting. Making Trello boards and trackers and creating a bank of prompts and sketches to work on when I’m drawing. Writing and scheduling a tonne of Substacks. Making mockups using existing work. Scheduling LinkedIn and Instagram shares. Emailing art directors.
But I haven’t been doing any of that, really. I’ve been consistently doing my Morning Ink and sharing that. Here. On Notes. Notes that aren’t exactly full to the brim with people commissioning illustration. (I think, anyway.) Nowhere else - except the odd share here or there. And then I’ve been randomly drawing whatever comes to mind at other times. Mostly things that are sparked from the Morning Ink.
Not that they’re bad in any way. But they are not targeted and they are not hitting any particular need or gap that will draw in a particular project query. And that’s what I should be doing.
On Friday, I found myself doing something I’d meant to do for ages, which is to organise my work into sizes, so that I could update my portfolio and have it look neat. And adding in patterns. I haven’t actually uploaded them yet, because when I tried to upload them all Wordpress kept throwing json errors. I guess actually uploading them is the next task, then. But I found myself spending a couple of hours blasting through an organisational task that should help. I also collated a bunch of emails and contacts ready to send out emails next week. Today, I am collating all the random notes in my Career 2.0 notebook that I have scribbled down this year and turning them into a list of prompts, with a variety of 10-minute, 30-minute and 2+ hour tasks.
From next week, I will have a bank of things to draw, and a list of organisational tasks to do, so that I can plug away at Career 2.0, even when Career 1.0 is busy. So that, come July or August, which aren’t yet fully booked, some of the projects being added into the schedule will be Career 2.0 projects and not just Career 1.0 ones. So that, other than Morning Ink time, which is absolutely embedded and which I don’t want to let go of in any way, and some dedicated blocks of go-with-the-flow sketchbook or painting time, which are also really important, I will be drawing with a purpose again.
Are you splitting your time between different freelance careers? Did you used to and have transitioned fully to one? Or maybe you are one of the people who combines creative work with a part- or full-time ‘normal’ job? I am fascinated with how people navigate this sort of thing, so do tell me!
To provide me with the motivation to tick off something else on my 2025 bingo list (so far only completed two things), and because I constantly question what I can possibly offer for paid subscriptions, the new Paid Subscription benefit is getting a monthly zine in the post. Until I have more paying subs, it will start off in the more traditional way of being printed on our home printer and probably just being a single A4 folded page. It will also start as a shared zine between all three substacks and will combine bits from my Morning Ink, some thoughts from Authentic Maximalism and some recipes or food art from The Illustrated Plant Kitchen. That means you only have to be paid subscriber of one of them to get it.
If the paid subs grow enough then I will get it professionally printed and make it longer and may well separate them out to different zines for each substack.
Gift subscribers: Any of you with a gift subscription, you will just get a digital download that you can print at home. Because it would not be financially viable for me to print and post for free.
If this appeals, please do upgrade to paid!