It usually starts with a glance. You’re setting up your stool or flipping open your sketchbook, and you notice someone nearby doing the same. A few quiet nods. A chuckle over a wobbly roofline. Then before you know it, you’re sketching side by side, trading stories, comparing splodges, and learning things you’d never have picked up on your own.
Sketching with others isn’t just good company – it’s good practice. It helps you notice more, try more, and worry less. And while solitude has its charm, there’s something deeply affirming about the way a group of sketchers can turn a park bench or a street corner into a buzzing little hub of creativity. Especially if you’re someone who still feels a bit unsure of your abilities (hint: that’s most of us).
As we get ready for our first sketching retreat of 2025 in just a few days, it’s the perfect time to reflect on why shared sketching experiences – whether in person or online – can quietly transform your art and your confidence.
Seeing More, Together: Observation Through Shared Perspectives
Sketching sharpens your powers of observation – but doing it alongside others gives those powers a boost. It’s like slipping on a new pair of glasses. You start noticing things you’d have missed on your own: a leaning drainpipe, a splash of colour, the way someone simplified a cluttered scene without losing its character.
One of the joys of sketching in a group is seeing how differently people interpret the exact same view. You might focus on the details in a shopfront, while someone else exaggerates the curve of the roof for a more playful effect. Neither is right or wrong – they’re just different ways of capturing a moment. And seeing those different choices in action can make you bolder in your own sketching.
Ian Fennelly often reminds us that urban sketching isn’t about copying the scene – it’s about telling the truth as you see it. When we sketch together, we get to learn how others see, which in turn expands how we observe. It’s enhanced learning through simple, shared attention.
Learning in Real Time: Feedback Without the Fuss
There’s something uniquely valuable about learning in the moment, sketchbook in hand, with someone nearby to ask, “How did you do that shadow?” or “What pen are you using for those lines?” These small conversations often lead to big breakthroughs.
In group sketching sessions – whether a local meet-up or a retreat – learning happens naturally. You get to watch techniques unfold in real time, absorb different styles, and pick up practical tips just by paying attention. And the feedback? It’s never about getting a gold star. It’s about moving forward. Supportive, specific, and honest, the kind that says, “That’s working – try pushing this part a bit further.”
When Ian leads workshops, he often uses the throwdown at the end – not to critique, but to showcase. He’ll highlight how one person handled composition, or how another played with tone, and those moments stick. They give us all a better understanding of what’s possible, and permission to try new things.
It’s learning by doing, yes – but also by watching, asking, and sharing. That kind of observation doesn’t just help – it accelerates your progress.
What I like most about sketching with others is getting tips and new ideas on techniques and checking out their sketching gear
Belonging and Bravery: How Community Builds Confidence
Let’s be honest – putting pen to paper in public can feel a bit exposing. It’s not just your sketch on the page, it’s you. And when things don’t go to plan (and they often don’t), it’s easy to feel like packing up and going home.
But here’s the thing: everyone else is feeling the same. Everyone has wonky bits, dodgy shadows, colours that turned out muddier than expected. And when you’re sketching with others, that shared imperfection becomes part of the fun.
Being part of a sketching group – whether for a single session or a whole retreat – lets you relax into your process. You stop worrying about whether you’re good enough. You start enjoying the act of drawing. And slowly, sketch by sketch, your confidence grows – not because everything looks perfect, but because you’re showing up and giving it a go.
The encouragement you get from others – “Love that shadow!” or “That colour choice is spot on” – sticks with you. It becomes part of your internal voice next time you’re sketching alone. That’s what real community does: it helps you hear the supportive stuff louder than the self-doubt.
Storytelling and Memory-Making: Sketching as Shared Experience
When you look back at a sketch from a group outing, you remember more than just the architecture. You remember the moment. The stories. The company.
That slightly smudged window? It was raining just a bit, and you were huddled under a café awning with three others, trading biscuits and griping about perspective. That extra pop of red in the corner? Someone else suggested it, and you gave it a go. These little interactions become stitched into the sketch, turning it from an isolated study into a shared memory.
Sketching in company adds layers to the story your drawing tells. It’s not just about what you saw – but who you were with, what you felt, and what you learned. That’s storytelling in its truest form. Not a tale written after the fact, but one built in real time, on location, with real people beside you.
And when you lay your sketchbook down for the throwdown – alongside ten or twenty others – you see not just different interpretations, but different lives, different eyes, different hands. That’s community made visible.
Mindfulness in Motion: Why Shared Sketching Helps You Focus
If you’ve ever zoned out completely while sketching – forgotten the time, blocked out the noise – you know the kind of mindfulness this practice invites. But doing it alongside others brings something extra: a sense of collective calm, of quiet focus, even among the chatter.
There’s something oddly relaxing about the soft scratch of pens, the occasional murmur of encouragement, and the shared silence of people lost in their lines. You’re in your own head, yes – but not alone. And that helps you stay present. Stay with the drawing. Stay in the moment.
Plus, let’s be honest – motivation can be hard to come by on your own. Even when the weather’s good and your sketchbook is calling, it’s easy to say, “Tomorrow.” But knowing someone’s expecting you, or that there’ll be others sketching in the square or at the café, gives you that gentle nudge. Not pressure – just presence. And sometimes that’s all it takes to show up.
Feeling Safe and Supported: Why Group Sketching Eases the Nerves
Not everyone feels comfortable sketching alone in a public space – especially in a busy town centre or unfamiliar spot. And that’s perfectly valid. But sketching with others offers a safety net, both practical and emotional.
In a group, you’re less likely to be interrupted or feel self-conscious. There’s a kind of unspoken protection in numbers. People pass by with a smile or a curious glance, but there’s rarely any judgement. You’re clearly “doing something” – and you’ve got company doing it.
More importantly, sketching in a group offers emotional safety. It’s a place where there’s no need to apologise for being a beginner. No need to pretend you know what you’re doing. Because chances are, someone else is figuring it out too – and happy to talk it through over a sandwich and a laugh about your toppling steeple.
In a world that often feels fast, filtered, and overly polished, these honest, unguarded moments with other sketchers offer something rare: connection that’s simple, creative, and real.
I love the idea of going out and doing urban sketching but i don't like the idea of being out there by myself and possibly having people come up and look at my so I really loved the opportunity to just go out and be in a group it made me feel really comfortable and really supported
Final Thoughts: Your Sketchbook is a Conversation - So Let’s Keep Talking
Sketching with others won’t solve every drawing dilemma. Your shadows might still feel awkward, and your colours might still occasionally turn to soup. But it will change how you feel about those things. It will give you perspective – not just on the buildings in front of you, but on your own progress.
It will remind you that art is less about perfection and more about presence. About being somewhere, seeing something, and choosing to take part. And when you do that in the company of others? That’s when the magic really happens.
So whether you’re joining us on the retreat, meeting up with friends locally, or hopping into a Facebook thread to share your latest page – do it. Show your work. Ask your questions. Be part of the story.
Ready to learn more?
If you can’t make it to one of our sketching retreats, this is honestly the next best thing.
Ian Fennelly’s 4-Week Live Landscape Sketching Experience starts in just a few days (July 15th), and it’s designed to feel as close to being there in person as possible – with live coaching, step-by-step guidance, and a community that actually feels like a creative circle of friends.
Even if you’re a complete beginner, you’ll be gently guided from a blank page to a finished, frame-worthy landscape sketch – one simple, confidence-building stage at a time. Each week, you’ll sketch alongside Ian (and hundreds of others), get supportive feedback, and build real momentum that actually sticks.
It’s calm. It’s kind. And it’s completely free for UrbanSketch+ members.
If you’ve been feeling a bit unsure or stuck with your sketching lately, this might be just what you need to get back into a rhythm – and remind yourself why you started sketching in the first place.
Join us for the 4-week experience. We’ll be sketching, sharing, learning – together.
