The Confidence Gap in Plein Air Painting, and How Workshops Help

There’s a moment plein air painters know well, when you arrive at a location, look around, and suddenly feel like you’ve forgotten how to paint. The light is shifting, the wind is doing its thing, and every brushstroke feels like a potential mistake.

This is the confidence gap.
And it’s completely normal.

Plein air painting asks a lot of us: quick decisions, bold simplification, and the courage to make marks without the comforts of a quiet studio. Most of us don’t struggle with lack of ability, we struggle with belief. In ourselves, in the process, in the idea that the first 20 minutes of chaos are worth pushing through.

Over the years, I’ve noticed something: when painters step into a workshop  environment, that confidence gap suddenly becomes smaller, softer… easier to cross.

Here’s why:

1. You stop painting alone

There’s something stabilising about being surrounded by other people also wrestling with shadows that won’t stay put and trees that keep looking wrong. Shared struggle makes everything a bit funnier and far less intimidating.

2. You paint more decisively

With gentle guidance and a limited window of painting time, most people start making quicker choices. Those choices build momentum, and momentum builds confidence.

3. You learn to trust your eye

Workshops give you a safe space to make mistakes and try again. Almost every student has a moment where the scene suddenly makes sense to them, that click, and once that happens, they walk into the next session with a new level of certainty.

4. You realise it’s not about perfection

It’s about being present with the light, the shapes, the colours, and the place you’re in. Some days the painting works beautifully; other days the experience is the win.

5. You carry the confidence home

That’s the quiet magic of workshops: the confidence stays with you long after the easel is packed away.

If you’ve been wanting to build your plein air courage, or simply give yourself a few days to paint without rushing, I have two opportunities coming up in 2026:

May 2026: Plein air painting workshop (details on my Workshops page)

If you’d like to grow your plein air skills with support, structure and beautiful locations, you’ll be very welcome.