How I Went From Unemployed Loner to Freelance Artist

This post is going to be a bit of a “Storytime with Chris”.  I want to share the time that I landed my very first freelance art jobs, which soon led me to travel around the world, painting for a living.

When I put it like that, it sounds like I must have made some sort of ground-breaking portfolio of art that immediately rocketed me to international fame, connecting me with all the big-bucks clients who personally flew me around the world!

Nah, unfortunately not.

The reality is a bit less impressive to be honest.  There was certainly no ground broken - I would say ground was trodden self-consciously and tentatively, and much less bravely than you might imagine.

In fact, I felt like a bit of a fuckup at the time.

The setup: Stuck in my hometown, in a typical 9 to 5

It's funny when I think back on it, but in 2015 I really was stuck working a boring 9 to 5 job in my hometown, like a cliche. I had moved back from the UK to Port Stanley in the Falkland Islands, the place of my birth, working as IT Support for the town’s hospital. I was doing alright; Port Stanley is a decent place, I liked most of the people I worked with, and the work was alright, but boy was this not what I wanted for myself.

I’d always been decent at art, but had been practising art seriously for about 6 years at that point - I’ll write something about those study years another time - and felt I could already be a working artist in some capacity.  If only I had the courage to actually complete some pieces and put myself out there.

Little did I realise that the relationship I was in was about to go south, and that would give me the kick-up-the-arse that I needed to make a change.

Quit the 9 to 5, moved back to the UK, but I still got no balls!

After my relationship ended, I had a strong need to change the way I lived.  I had always been at the mercy of circumstance, hanging out with people that just happened to be around me, working jobs that came my way, dating people that approached me first; you get it.

I quit my IT job near the end of 2015 and moved back to the UK, with a plan to paint a new portfolio of badass paintings and finally apply for freelance jobs. I was going to become the person I wanted to be, and take control of my life!

I fucked about for like, 9 months straight.  During this time I slowly blew away the money I’d saved up in my IT job, and then ended up on unemployment welfare. I guiltily rode that out for as long as I could, applying for jobs but never putting my all into it, practising art here and there, finishing a painting now and then, but I certainly was not on my game.

I couldn't get myself to call my portfolio ‘ready’ - it always felt like I could do better, like my portfolio didn’t represent my skill level.  I couldn’t get myself to apply for freelance art jobs, and I loathed the idea of getting a 9-to-5 job again as that would have been me taking a step backward, and having to admit I wasn’t capable of doing the art thing.  I was so frustrated with myself, and guilty, and I felt like an absolute dumb-dumb.

In mid-2016, during my monthly meeting with my welfare officer, she told me they were going to essentially force me to take a 9-to-5 next month.  I remember being sat opposite the woman and tears welling up in my eyes; I think I was frustrated at my own paralysis, knowing I was capable of something but being too scared to take the risk.  This is when I really felt like a fuckup.

But that ultimatum was the perfect, and second, kick-up-the-arse that I needed.

I put together my portfolio, and applied for freelance work

If I remember right, in the preceding months I had finished a few paintings that I liked, and a few more were in progress and had potential.  The week after my welfare meeting I blitzed the hell out of the work-in-progress pieces so I had 6 finished paintings, enough to be considered a small portfolio.  They were my best paintings to date, and basically the last chance I had to avoid going back into a worse 9-to-5 job than the one I quit less than a year earlier.

This was that 6 piece portfolio:

Now I needed to send it out there and get some bloody work.

I looked up artists who worked in my desired field and noted down the names of the companies and clients they were working for, and googled them looking for an art director email address, or whatever address I could get.  

When I found an artist posting a portfolio a bit like mine on a forum or a job board, I googled the hell out of that artist, trying to find where else they had posted their portfolio so I could post mine there too.

On every forum and job board I could find, I bookmarked every little job post or commission request from the last couple of weeks that might still be open.

I ended up sending about 80 emails and messages to independent authors, tabletop rpg companies and art directors at games companies, as well as posting my work on about 15 different forums and boards.

I crossed my fingers, and hoped my portfolio was good enough.

Spoilers: it was good enough

I got a bite!  My first client was the studio behind the digital card game/strategy rpg Pox Nora, which used to be owned by Sony but had since broken off into an independent studio.  I won't mention exactly what I was paid, but they hired me to do a few illustrations and I made just enough to cover 2 months of hyper-low-budget living expenses.

That money gave me enough time to find a second client, which I landed on Upwork.com, making concept art/illustrations for a worldbuilding project, and a third client whom I found on boardgamegeek.com, creating illustrations for his pen-and-paper rpg.  I was actually doing what I had wanted to do for years - supporting myself off my art.

Scraping by

I was undercharging and had to finish 3 or 4 illustrations a month just to cover my bills, but these two clients were giving me just enough work to get through each month.  Nothing spare for emergencies, nothing spare to buy more than the basic essential foods to subsist on, and definitely no money to go out with friends.  

In fact, I didn’t really have friends - it’s hard to maintain relationships when you have no free time and are embarrassed about your financial situation.  To top it off, any time that I didn’t spend working was just because I was feeling overwhelmed and procrastinating on doing the work!

I was trying to get better paid work but it was a hard road that was taking a long time - I needed to make a better portfolio, email art directors and apply for loads more job postings, wait for replies, talk with prospective clients about the jobs, finish the jobs and then wait for payment…. and it would be an iterative improvement, each job probably only slightly better than the last.

It would probably take me years to get to a more comfortable, sustainable place.

After a few months like this, I knew I hadn’t figured it out.  It wasn’t working, and sooner or later I was going to crumble under the grind.

While I loathed to consider it as I was already surviving on a pittance, I wondered: what if I could reduce my living costs even further?  Increasing my income might take a long time but decreasing my expenses would probably be immediate, right?

So I considered moving room, then considered moving house, then moving city, and then moving country.

And that’s when I discovered the digital nomad movement, and I came across Chiang Mai, the digital nomad capital of the world, and made the best decision of my life.

But we’ll go over that another time.

Conclusion: you can fucking do it

Looking at that 6-piece portfolio now, they’re not bad paintings.  They aren’t incredible either, but I definitely could have been working as an artist sooner; it wasn’t my skill level that was holding me back.

It was my lack of confidence, and fear of rejection, that was holding me back.

I only took the necessary steps when I was forced past what I was willing to take, when life was threatening to push me too far in the wrong direction.

But it didn’t have to be that way.

Nowadays I try to just make shit and put it out there more; I still want what I make to be received with awe and don’t want my work to be ignored and rejected, but those first jobs, those first small victories, are what got the ball rolling and gave me the tiny bit of confidence I needed to start taking small risks here and there - and it’s paid off hugely.

I love how I live now, and I owe it to the ‘fuckup’ version of myself who took a risk back in 2016.

I guess what I'm trying to say by writing this:

You can fucking do it.  If there's something you've been wanting for yourself but you've always held back, out of fear, or never feeling ready, or whatever else is stopping you, just know that I fumbled and fucked up a lot, I scraped by on unemployment and then earned a pittance trying to make this thing happen.  The journey was not impressive, it was embarrassing.

If you feel like a fuckup, I want you to know that I also felt like a fuckup, and cobbled together a cool life anyway. So take a step.

You can fucking do it.

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