Last year I made this carved & painted drawer front the other way ’round. Carved first, painted after. I tried the reverse this time.
Most 17th-century carvings I’m familiar with that include paint have it as the background. So it’s like a 3-D coloring book. Carve out the recesses, then paint them. Like this English box:
But the cupboard I’m making has only one carving on it and its foreground is painted black. Here’s a detail from the original.
Prepped the oak board a few months ago. Trimmed it to size, then painted it black with dry pigment mixed in linseed oil/thinner/fast-drying medium. Then laid out the pattern with a compass, marking gauge, awl & square.
When that step was just a concept, I was concerned that the layout would be difficult to see. But the tools scratched right through the paint so the lines were bright. BUT – if you do this, make sure you have worked out the geometry first. I made a layout error and had to re-paint and wait til the new coat of paint dried. Just a day or two with that drier added, but a stupid mistake that could have been easily avoided.
This carving uses no V-tool for the outlines. I struck the shapes with a few different gouges and chisels.
Then using a very shallow, narrow gouge, began removing the background. This particular carving is pretty shallow.
Here’s a detail showing that background. Eventually it will get a coat of linseed oil so the oak behind will not be so stark. That’s much later though.
Whether you carve first or paint first, you must be careful at various points. There’s touch-up regardless of the method. This approach certainly makes the painting easier – and the carving is not any more difficult. So maybe it’s the way to go…
Here’s a post, including a video, from last year when I carved the same drawer front. Pre-painting. https://pfollansbee.wordpress.com/2021/08/18/the-cupboard-project-carved-drawer-front/
PETER FOLLANSBEE: JOINER’S NOTES 
I would think the benefit of painting in the background would be that you can paint sloppily and then just plane off the top surface and have crisp clean edges. Have you not seen any evidence of that?
recently i did some chip carving on a tool tote i made a couple years ago. i painted it when i made it and had no plans to carve it at the time. low and behold i love the contrast between the carved pine and paint. same here. really makes everything pop. i can’t imagine trying to paint some and not all for chip carving.
very cool