When I used to play basketball as a kid, I had a coach that would always say "keep practicing, keep shooting, and eventually the shots will start falling". I bring that up because I've been on a pretty frustrating rating plateau for about the past 6 months, despite the fact that I've been studying hard, know a ton more, and am playing better chess than before. In the last 3-4 weeks I've had a half dozen winning positions against 2200+ players, but have only been able to win one of the games, drawing one, and losing the rest in time trouble. It's frustrating to lose or draw those positions, but I suppose it's better than not getting them at all.

Have any of y'all experienced something similar? I'm just hoping something clicks in my brain soon and I can start putting those games away.

Were these blitz or slow? Online or OTB?

About half were G/90'+30" inc and half were G/30'+5" delay. All were OTB.

So earlier, you just lost to this guys, now you get great positions and blow them? You must be quite a pessimistic guy to not see the progress here.
Just keep playing good chess and beat them next time. If possible, try to play at longer time controls. G90+30s/move is already pretty fast for a tournament time control, especially to convert good positions. I consider 120m/40moves + 30m/rest or alternatively 90m/40 moves + 30m/rest + 30s increment the fastest time controls where you can actually play decent chess.

Agreed, I was always encouraged when I started to get winning positions against these players in slow OTB games, even if I failed to convert them.

In blitz, OTB or online, it's a little different since speed is such a large part of the skill.

Y'all are right, appreciate the feedback. I think I'm overly pessimistic and see things too much as black and white. The way I look at it, I'm still getting a 0 instead of a 1, but there is certainly some middle ground there. I shouldn't expect to go from losing easily to beating them without some sort of something in the middle.

FYP, he actually has won some of those games.

6 winning positions against higher rated opposition and you've scored 1.5, obviously that's frustrating but I imagine you could have had draws offers accepted in all 6 games, would you have felt better to score 3/6 in that case?

I would hope not.

The 2 important factors are firstly, of course, that you're playing well enough to get in these positions in the first place and secondly you've got the balls to try and close these games out.

Keep on going as you are imo, the more you get into these favourable positions the better you'll learn how to convert them under pressure and the better player you'll become. It seems to me that you're becoming better already but your rating is telling you otherwise. It's just a number, the same as your opponent's rating is just a number, keep striving to play your best and the results will come.

If, in the process of getting a better position on the board, you get yourself into time trouble that you can't handle, was it really a "winning" position?

If a lower-rated player did the reverse to you, and had a good position on the board but you were confident he couldn't convert it with the time he was taking, would you feel like you'd lucked out?

Time management is a huge part of practical chess, but to answer your first question, yes, I think the position can be classified as winning regardless of time on the clock. Now spending too much time to arrive at that position or the practical chances of being able to convert affect the outcome of the game, but I think the position itself can and should be classified as winning.

Time management is an interesting topic worth discussing. On one hand, a valid argument is what's the use of spending all of your time to arrive at a superior position if you're not able to finish it off due to lack of remaining time? On the other hand, what's the point of moving quickly early on, only to be in a worse position that you potentially can't come back from, even if your opponent is low on time? Personally, I prefer to at least get a good position even at the cost of minutes on the clock. My hope is to get a superior position and through experience be able to convert while low on time. Plus, since I'm still trying to improve, time spent really trying to understand the position OTB is time well spent in my opinion, even if it costs some points early on.