All this portrait illustration stuff…
Subtitle: How Drawing People Helps Support My Illustration Career
or: The different reasons I draw people, and why it’s fantastic.
There are a ton of niches in illustration. And speaking on behalf of (almost) all of us: we want to try everything at first: children’s books, editorial, packaging, murals, greeting cards, pattern design... basically whatever anyone will pay us for (and quite a few things they won’t). Maybe it’s part Fear of Missing Out, part sheer longing to make a living doing what we love, but we illustrators want to do all the things.
Then, ideally, we find one or two areas that feel almost easy (because we love them) and that actually pay. Our niche. Our Happy Illustration Place.
Personally, I’ve always been set on picture books as my main illustration niche. I’d written a bunch just for fun before I ever got into illustration. So that part was decided early on. But once I did become an illustrator, I discovered the many other exciting possibilities and tried them all - even tumbling down the rabbit hole of graphic recording - which, in hindsight, felt like a frustrating waste of time. Still, it was useful. I figured out what didn’t fit me.
But there was one niche that fit like a comfy pair of socks: portrait illustration. And I didn’t even go down that path on purpose - I just stumbled down it by mistake. (But more on that journey in a bit.)
Eventually, I hope to be paid to write and illustrate picture books. That’s the future I’m building towards, and I love the experimental, intentional (and slow!) process of crafting stories, dummy books, and characters. And while that work doesn’t yet pay in money, it pays in experience, growth, and skill.
Right now, though, the thing that does pay actual money is portrait illustration. Not loads, but enough to keep me in pencils and sketchbooks, and to pay for the next market stall.
So this post is all about the Portrait Illustration part of my business. I refuse to call it a ‘side hustle’ - partly because I dislike the term, partly because it’s not on the side. It’s part of the main course of what I do: I’m an illustrator. This is one of the ways I illustrate.
How It Started
As I mentioned earlier, I didn’t plan to get into portraits. It started accidentally at a local fun day in 2022. At the time, I was still developing my style and, for some reason, decided to focus on drawing people. Inspired by that guy who did “Bad Portraits” in New York (I can’t remember his name now that I’m off Instagram… Do you know who I’m talking about?) I set up a free “30-second portraits” table at my church’s stall. Or maybe they were one-minute portraits. I can’t remember. What I do remember is that it was low-pressure, chaotic, and absolutely brilliant. And great practice.
What surprised me most was how much I enjoyed all of it — not just the drawing. The conversations, the intense eye contact (I have to really stare at faces, after all), the laughter and reactions when people saw their scribbly little likenesses. I loved it all. And I’m pretty sure they loved it too.
The next year, I ran my own stall at the same event - this time charging £5 per portrait, and again the response was brilliant. Plus, I was getting more confident in my style and my ability to see what made a person look like themselves. (Also helped by the fact that my dad lent me a book that I haven’t given back, called How to Draw Caricatures, by Lenn Redman, even though my portraits aren’t quite caricatures. But I’ll get into all that in another post…)
Those early events, and the experience I gained, led me to try more local markets in 2024. I raised my prices (obviously). Not only to make it viable, but because people saw the value and said so. (Which is very encouraging - and helpful when you’re still figuring out pricing.)
I also had a few people asking me if I do parties and weddings, and many people emailing me afterwards, asking for commissioned portraits. So I started branching out within portrait illustration itself: public fairs, private events and commissions.
Tip for Fellow Live portrait Illustrators:
In my experience, children under 15 are not willing to spend even £5 on a portrait when they could spend it on ice-cream or sticky sweets instead.
So why keep prices low? Adults are more likely to see the real value of portraits, and pay accordingly.
That year, through trial and error, I discovered that my portraits sell best at family-focused fairs - not necessarily art or craft markets - where families come to spend the day, not just pass through. Therefore, I planned to stick to fun days and family fairs, and only do two per month in 2025 so that I didn’t get exhausted… and instead I’ve been flat-out, drawing at all sorts of events almost every weekend. Oops. Turns out fellow marketeers are terrible influences - telling me about all the best events. And I’ve been enthusiastically signing myself up! But that’s another story too.
For now, let’s get into the details of the various kinds of portrait drawing I do:
The 3 Types of Portrait Work I Do
There are three main ways I draw portraits professionally. Each one offers something a little different - for me and for the person being drawn - in terms of how long it takes, how much it costs, how personal it is, and how much fun we have in the process.
Let me walk you through them:
These are custom illustrations, booked in advance. People send me photos and tell me who’s who (plus any extras like pets, meaningful objects, funny details, etc.).
Time: These take hours. But that’s spread out over several days. It includes a sketch stage, feedback, tweaks, and final artwork - which I often restart a few times - but hey, I can fuss with it as much as I like.
Effort: High effort, but in a good way. I can take my time, experiment a bit, and redo anything I don’t like.
Price: £20 - £100
People often buy these portraits as gifts, so they’re happy to invest. I’ve gradually increased my prices over time, but I’ll admit I still sometimes put in more hours than the rate really covers, especially when I get carried away making it just right. It’s a balance I’m still figuring out: charging fairly and not over-working.Perks: I work in my own time, in my own studio, with snacks. No travel, no tent, no gusts of wind blowing my drawings away.
2. Live Portraits at Private Events
This is when I’m hired to draw at a party, wedding, or other special event. The organiser hires me for a set time, and I draw as many people as I can during that window.
Time: Fast paced! The portraits are small (usually A6 to A5), and I sometimes have a queue of people all enjoying the atmosphere, chatting, and watching the fun of portrait creation.
Effort: High speed, high energy, but I don’t have to try convince people they want a portrait. I just show up, set up, draw, and be sociable.
Price: £200 - £1200
The client pays for a block of time, so I know in advance what I’ll earn. Travel costs (and accommodation if needed) are covered too.Atmosphere: These events are usually warm and fun. Everyone knows each other, there’s music, and people are in a party mood. I feel like part of the celebration.
Psst… A Little 2025 Wedding Offer
If you're getting married this year, here's a treat:
I'm offering 50% off all wedding bookings throughout 2025. All I ask in return is an honest review afterwards - and if you love what I do, please tell your friends and family.
3. Live Portraits at Fairs
This is when I set up a stall and draw people on the spot. It's fun, sociable, slightly manic, and always full of surprises. As hard as this one is, I get a lot of pleasure out of it, and often make good friends.
Time: For you, about 10–15 minutes per portrait. For me: usually a fair runs for 5 hours, but that doesn’t include the time it takes to travel, set-up, and pack away. In other words, it’s a full day!
Effort: Very physical! As well as setting up tables and gazebos, I’m drawing, chatting, taking payment, and trying to keep things dry (very important in England). Even on a quiet day, I can end up exhausted and needing a day or two to recover my energy!
Price: £10 - £30
This one’s a gamble. I pay for a stall, travel, and materials, but customer numbers vary. And, even when I’m flat-out drawing portraits, if everyone chooses the lowest-priced option, I can end up feeling underpaid.Audience: My best customers at fairs are young families, couples (of all ages), young adult besties… and dogs, of course.
Common obstacles at fairs:
One half of a couple is self-conscious and doesn’t want to be drawn.
Parents worry kids won’t sit still. (They don’t have to! It’s not a Victorian photograph.)
People say “we’ll come back later,” but by then they’ve spent their budget.
Mini Story: Once at a market, a lady asked me to draw her dog from photos. I said yes, so she sent me the pictures and went off to enjoy the stalls. I did the portrait while she wandered, and she collected it later. All lovely… except I had to guess what the dog’s tail looked like - none of the photos showed it! (Thankfully I got it right and she was happy with the portrait.) But she also missed out on seeing the process. So now, when people want a pet portrait at a fair, I invite them to sit with me and chat while I draw from their phone pictures. It makes the whole thing more personal - and I can ask important questions like, is this tail accurate?
(Of course, in the case of commissioned illustrations, I just send an email if anything is unclear in the photos.)
What I’ve Learned
Fast drawing is a skill. The more I draw people live, the better and quicker I get - even in my studio work. Speed is now no big deal to me. I laugh in the face of speed.
People care about value. When people see something fun and unique, they’re happy to pay. But I need to communicate that value clearly and confidently.
It’s OK to change. I didn’t plan to become “someone who draws portraits for money,” but here I am, and it’s grown into something I love.
A Note to Fellow Illustrators
If you’re considering offering portraits, do it! Start small at a local event. You’ll learn loads - about pricing, pace, people and your own style. Don’t worry about being perfect. Your personality is what’s important. People love seeing a real human behind the work.
A Note to Potential Customers
If you’ve ever been tempted to get a portrait done but were worried that your kids wouldn’t sit still, you’d feel awkward, or it’ll turn out looking weird, then please know: it’s meant to be fun. You don’t have to be still as a statue. I’m quite friendly. And you’re going to look quirky because that’s the point. I’ll do my best to capture the spirit of you, not a photographic likeness.
So come find me at a fair, or contact me for a commission.
Got questions? Well I’ve got answers:
How long does it take to draw me?
Usually 10–15 minutes for a live portrait, depending on the number of people and how chatty we are.
For a commissioned portrait, a few days, with a bit of back-and-forth so that I can make sure you’re going to love it.
And at a wedding? 5 minutes!
Do you draw children?
Of course! Wiggly children, sleepy children, children who want to draw with me. I bring extra crayons specially for them.
Do we have to sit totally still?
Nope! Just as long as you stay vaguely in the area. I promise I won’t draw anyone mid-sneeze. Plus, I’ve got colouring sheets and crayons for the kids, and dog treats for the hairier kids.
However, a commissioned portrait is a great option to get everyone and everything you want in the artwork - even if they never sit down.
Can you draw from a photo?
Yes, absolutely - especially for commissions.
At fairs, I also draw pets from phone photos if you sit with me and tell me all about them.
What if I hate the drawing?
Then we cannot be friends.
Hah! I joke! But really, I’ve never had a negative reaction to a live portrait - everyone has been pleasantly surprised to see themselves transformed into a sweet illustration.
For commissions, I work with you to get it just right. Feedback and tweaks are part of the process. I want you to be absolutely delighted with your portrait.
What should I wear?
Whatever you’re wearing! (Please, no nudes.)
For commissions and live portraits, you’re welcome to request certain colours and patterns.
Do you draw grumpy husbands/boyfriends/teens?
Of course. They secretly enjoy it, and you’ll love hearing them change their tune when they see the result.
’Tis My Own Wiggly Path
So I started out scribbling strangers for free at a local fun day and now spend a large chunk of my time - and get paid for - drawing portraits. It’s not the career path I imagined, but I’m glad it’s the one I’m walking.
Thanks for reading, and remember: portraits make great gifts, drawing in public makes great stories, and sometimes, your niche finds you. (I didn’t mean for that to sound ominous…)
