What did Kaladin draw in Shallan's sketchbook in Oathbringer when in Shadesmar?

Question

Kaladin drew something in Shallan's sketchbook in Oathbringer around chapter 95-105 I think.

While at the reverse Thaylen city in Shadesmar, I think.

What was he drawing? There is an illustration at the end of chapter 107 I think is his.

Answer 1

The drawing was made by Veil, who unlike Shallan has no talent for it. It's mentioned several times in the books that Shallan is the only one of her personalities that can draw well, there's plenty of more examples of that in the next book.

Remember, Alethi men can't write so this can't have been drawn by Kaladin, because he wouldn't be able to write the comment "drawing is easy". The comment "clearly it isn't" was written by Shallan. Also, nobody but Veil would get the idea to draw on top of one of Shallan's existing sketches. As noted by another answer, Kaladin also comments on the bad drawings: "Did Adolin get hold of your sketchbook?"

As for what the picture represents, it's not a fearspren, but possibly one of the sentient ones from either boat they take. The most likely possibility is Ico, described as (from Stormlight wiki):

He resembles a Shin man, with large, childlike eyes made of metal. He is shorter than the Alethi, but sturdy. He wears tan clothing, sporting a multitude of buttoned pockets.

This description seems to match the picture fairly well. Ico is a Reacher and they look like this, again illustrated with bare feet.

A more far-fetched theory, to speculate wildly, is that it could be Veil's drawing of Kaladin, given the glare. Possibly the clutter to the top left is either a shash brand or hair pulled down to cover it. He'd have a beard since they can't shave in Shadesmar, given how rare water is, plus Kaladin wears a beard now and then through the books. The bare feet would be the running "no boots" internal joke between Shallan and Kaladin.

Answer 2

I can't find any reference to Kaladin actually drawing a picture in Shallan's sketchbook. Plus, he certainly couldn't have written the "drawing is easy" message. I believe it's Veil doing the bad drawings. That kind of sarcastic message sounds more like her anyway.

From chapter 97

Shallan lowered her pencil, looking with dissatisfaction at the attempt she'd made at drawing a fearspren. It looked like a child's scribble.

Veil was seeping out

He does look at the sketchbook in chapter 99, but only comments on the bad drawings

She trailed off as Kaladin flipped to the next page in her notebook. It seemed like an attempt at drawing Captain Ico, but was incredibly juvenile. Basically just a stick figure.

"Did Adolin get hold of your sketchbook?" he asked.

She snatched the book from him and closed it. "I was just trying out a different style."

I'm fairly sure the drawing of the captain mentioned here is the one in the picture of her sketchbook at the end of 107.

Kaladin does borrow some paper from her in chapter 97, but only to draw the city he saw in his vision at the lighthouse

Kaladin put his fish down, then gestured at Shallan. "Can I have some paper?"

She let him have a sheet from her sketchpad. With an unpracticed hand, he drew out the buildings he'd seen in his momentary...whatever it had been. I've seen this pattern before. From above.

"That's Thaylen City," Shallan said. "Isn't it?"