Well it's difficult to respond in the abstract. Maybe
@Manbearcat has thoughts on this dynamic. The first thing I would say is that for every roll, the GM sets the position the character is in and the possible effect. So a failure could mean the PC has a worse position or a more limited effect. At a more fluffy level, I present flashbacks cinematically. So we think about, ok, if this was a movie, and it had a flashback where a character tried to do a thing and failed, what would the consequences be? I think the author is very comfortable with metagaming and backing out of being "in character" to have a conversation at the table as to how this would play out.
Here is John Harper, author of the game, on position and difficulty:
FWIW, for my 5e players, the flashbacks weren't the thing that was most difficult to grok. More difficult is that Blades is a very mechancis/procedures-heavy game. So whereas in 5e there's a very loose way the GM says "make a this check, make a that check," in Blades you have to think a lot more about what's going on and how a roll will affect the fiction going forward. The other thing they found difficult is to not be super cautious and to conserve stress. In fact, flashbacks didn't initially come up that often because the players didn't want to spend any stress.