Adventure Sketching, Pickleball, & Bus Rides with Samantha Dion Baker

I spent an hour yesterday drawing with

Samantha Dion Baker

—artist, author, and one the best Substackers on drawing—and came away feeling like I'd just had the best kind of therapy session. Which, as it turns out, is exactly what Sam's work is all about.

Sam joined me from her studio in Dumbo, and what started as a casual chat about pickleball evolved into a masterclass on using art as a tool for presence, sense memory, and genuine human connection. It’s crazy I get to speak to people like this every week (it’s even crazier that they speak back.)

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The Accidental Artist

Sam's artistic journey is one of those creative pivots that make you believe in second acts. She spent years as a graphic designer (same!), creating pristine designs—all clean typography and careful spacing. Then life happened: kids arrived, screens became suffocating, and she found herself reaching for a sketchbook just to remember things.

"I was drawing things so well or comfortable drawing things," she told me, flipping through pages of her early work. "I was just doodling like letters and arranging things. It was very designy."

But here's the thing about doodling when you're not trying to be an artist: it becomes honest. Sam started documenting daily moments—not because she planned to publish them, but because drawing made her more present. The practice was meditative, almost inadvertent therapy.

When she published her first collection, Draw Your Day, Amazon classified it in the art therapy section. "I didn't really think about it when I was writing it," she said, "but I was like, oh, yeah. That makes sense."

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The Art of Paying Attention

What I love about Sam's approach is how unforced it feels. She's not precious about her sketchbooks—they're repositories for whatever catches her attention, regardless of artistic merit. We talked about the tyranny of the "perfect sketchbook," those Instagram accounts full of museum-quality watercolours masquerading as casual sketches.

"I'm not happy with 90% of my pages”, she admitted. But that's the point. The sketchbook isn't a performance; it's a practice.

Her upcoming book, Draw Your Adventures (out July 15th—pre-order it now!), explores this idea of documentation versus decoration. It's not about capturing the Sistine Chapel; it's about noticing the "Call Your Mum" mural near your son's new apartment, or the woman across from you on the bus.

"Sometimes it's completely unrelated," Sam explained, "but it will still bring you back if you're present and you're taking it in."

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The Technical Bits (For the Process Junkies)

Mid-conversation, we naturally gravitated toward tools—because what are two artists without strong opinions about pencils? Sam's a devotee of Blackwing pencils and has worked with them for years (she even illustrated their iconic poster of all the limited editions). But her real secret weapon is Derwent Inktense paints.

"I always describe them as like a cross between acrylic wash because they dry flat and watercolour," she said, layering colours on a portrait of her friend's dog, Wayne. "They're more forgiving than watercolour." (Watch the video above to see her drawing Wayne!)

My new obsession: The Wren.

I confessed my own tool obsession whilst wielding a Wren fountain pen I'd discovered the night before at a comedy show (thanks

Lauren Layne

and

Anthony LeDonne

). We compared notes on everything from mechanical pencils (neither of us likes them) to date stamps (both obsessed) to that magical Faber-Castell 14B pencil that somehow exists despite breaking all the rules of graphite grading.

(This is probably where I should mention that Sam's giving away 50 copies of her book at her launch party on July 15th in Dumbo. RSVP required—don't just show up like you're crashing a wedding.)

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The Interrupted Artist

One of the most honest parts of our conversation was when Sam talked about working around constant interruptions. Her artistic practice developed not in some pristine studio, but in the margins of motherhood—quick sketches between playground emergencies, continuous line drawings because she might have to stop mid-pencil stroke.

"I was constantly being interrupted," she said. "So my process, I've learned to work in stages."

This resonated deeply. How I often wait for the "perfect" time to create—the uninterrupted afternoon, the ideal lighting, the moment when inspiration strikes like lightning? Sam's work is proof that creativity thrives on constraint, that the most meaningful art often happens in the spaces between other obligations.

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Adventure as a State of Mind

As we wrapped up (Wayne the Cairn Terrier now immortalised in both our sketchbooks), Sam explained the philosophy behind her new book. Adventure isn't necessarily about passport stamps or mountain peaks—it's about approaching the world with the curiosity of someone who might want to draw it.

When you're carrying a sketchbook, you notice differently. You see the baroque curve of a fire escape, the precise way someone holds their coffee, the particular quality of light filtering through a bodega window. The tool changes the observation, which changes the experience, which changes the memory.

"It's choosing the choices of what to draw when you're on an adventure," she said. Whether that adventure is crossing Brooklyn on a bus or crossing continents on a plane.

Sam's book launches in two weeks, and honestly, it arrives at exactly the right moment. Summer in New York means everyone's moving, travelling, or at least pretending they have plans more interesting than sitting in air conditioning. But as Sam's work reminds us, the most profound adventures often happen within walking distance of home.

Just bring a pencil.

‘til next time

Your pal

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Pre-order Draw Your Adventures here. Pre-orders genuinely matter for authors—they determine everything from print runs to bookstore placement. If you're planning to get a copy anyway, ordering now is the best way to support Sam and ensure the book finds its way to the people who need it.

Subscribe to Sam's Substack for a regular dose of artistic wisdom. If you're in New York, join us at her book launch on July 15th in Dumbo!

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Coming soon… I'm doing something very special with Blackwing pencils and Amy Kurzweil. Can't say more yet, but it's going to be pretty epic! Stay tuned.