I won based on time and while I believe I still would have won were the game to be played out there were plenty of spots I feel I could have played better. The upper right I looked up afterward, I had figured out the joseki on my own up until he deviated. I think I made an alright continuation but how could I have answered?

He was playing against handicap stones so I understand his/her over extension and goal of causing chaos so that potential superior reading ability could win the match. I think I did alright in some places but more poorly in others.

Hi leonprimrose,

Did you read Q14 ?

Did you consider P15 connect (and give up R14 if W wants it) ?

Did you consider o13 ?

Did you consider P9 ?

Instead of reducing your own libs like this, if you simply drop to P18, then can W cut at o16 ?
( In general -- often, but not always, as there are infinite exceptions --
this kind of self-reducing-liberties move is a bad habit; unless there's a very good follow-up. )

Did you read P18 ?

Did you think this is the biggest move on the board ? Do you still think so ?
( Even if it's the biggest move on the board, did you consider fixing your shape with L16 ? )

You outplayed W all the way in this game, so there is not a lot to learn from it. But it looks like you have a tendency to overplay, neglecting defects (cutting points) in your own position when attacking. Against a stronger opponent, this will backfire. I will try to point out a few places where I think this happened. (And I see that Ed Lee has pointed out many of the same places.)

and seem determined to cut. You chose to block at Q14, leaving a severe cut at O14, which would split B into two somewhat weak groups. You should be able to handle this fight, but it is dangerous. Consider the alternative of blocking at P15, with the intention of sacrificing the R14 stone. Try playing out some sequences. If W cuts at P13, just extend to Q12. B is much stronger in the center in this fight. If W later captures the R14 stone, you get a nice squeeze. This way would preserve your advantage without complicated fighting.

is an overplay. This move leaves three serious cutting points in your shape, which should set off warning alarms. Can you really handle all those cuts? Simply play R12, strengthening the center and leaving one less cutting point. This keeps W pressed low and gives a very good result. You do not need to kill W here. You do not need to punish W more severely than R12. (Quiz: if B plays R12 and W extends to S13, how should B answer?)

is another overplay. After a few moves, you had to give up this stone, giving W a pretty big territory. If you want to continue in this area, pressing W low with P11 looks best -- note that W cannot cut.

is big, but the hanging connection at L16 leaves much less aji. I am not sure which move is objectively better in this position. But since you still have a good lead, I would lean toward strength and safety, rather than trying to maximize territory. I have the impression that you did not even consider the safer move.

W made use of the M16 cut aji to invade. At , W could get a good result by playing J13, making miai of L14 and G14. W would have a much harder time invading here if the B moyo had no weakness at M16.

Thank you both for the considerations in moves There may have been less to learn from the game specifically but I'm glad I asked. I have a bad tendency at overplay and I'm trying to curb it. I try to not play complacently but it causes me to not be able to tell what's giving too much and what's overplay I feel like I could be several stones stronger once I work through that particular bad habit because it alone costs me more games than anything else.

Do you have any tips on how I might work on breaking the habit?

My quiz question in the comment to move 16 was meant to see if you could break your habit

Oh! I would think R11 and follow him on the second line would be proper

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(a) is dangerous because it leaves another cut in a B position which is already thin. I was afraid this would be your "habit" move.
(b) are all safer and stronger, leaving no additional cuts. If W cuts at x, B can fight.
(x) is definitely worth considering, defending the most serious existing cut. If W cuts below, B can fight. If W pushes along the second line, B can happily follow on the third line.

lol you know I considered the bamboo joint. in the game I considered r12. im always worried that im playing a move thats too slow and end up second guessing the sturdier moves