One of the common themes of games I play is that I get into a superior position out of the opening, but I miss a whole heap of ways to convert them into a win. I've no idea why, and thought forumites may be able to help.

Here is a game I played last night.

[Event "Birmingham League Division Five"]

[Site "Halesowen"]

[Date "2012.03.29"]

[Round "?"]

[White "Alex Holowczak"]

[Black "xxxx"]

[Result "1/2-1/2"]

[PlyCount "100"]

1. e4 e5 2. Nf3 Nf6 3. Nxe5 Nc6 4. Nxc6 dxc6 5. d3 Bc5 6. Be2 Be6 7. O-O Qd7 8.

Nd2 O-O-O 9. c3 Ng4 10. d4 Be7 11. Nf3 f5 12. e5 h5 13. Ng5 h4 14. h3 Nh6 15.

b4 Nf7 16. Nxe6 Qxe6 17. a4 Nxe5 18. b5 g5 19. Qc2 Nd7 20. Re1 Qf6 21. Bd3 Rhf8

22. Bxf5 Qxf5 23. Qxf5 Rxf5 24. Rxe7 cxb5 25. axb5 Rxb5 26. Rxa7 Rb1 27. Re1

Nb6 28. Bd2 Rxe1+ 29. Bxe1 Nc4 30. Ra8+ Kd7 31. Rxd8+ Kxd8 32. Kf1 Ke7 33. Ke2

Kf6 34. Kd3 b5 35. Ke4 c6 36. Kd3 Kf5 37. Bd2 Nb2+ 38. Ke2 Na4 39. Kf3 c5 40.

dxc5 Nxc5 41. Be3 Na6 42. Bd2 Nc5 43. g4+ hxg3 44. fxg3 Ne4 45. Be1 Nf6 46. Ke3

Ke5 47. Kf3 Kd5 48. g4 Kc4 49. h4 gxh4 50. Bxh4 Nxg4 1/2-1/2

Clearly, I'm just a pawn up for free by move 6. I overlooked the e5 thing. But I missed many opportunities that Fritz throws up. I then got to the endgame knowing I was clearly better, but being unable to work out how to win. I even knew I had to play f4 at some point to avoid a blockade on the kingside, but I couldn't drum up the courage to play it, because I couldn't see that it'd be winning once I'd done all that.

My efforts the previous evening were in a similar vein.

[Event "Cannock League Division One"]

[Site "West Bromwich"]

[Date "2012.03.28"]

[Round "?"]

[White "Alex Holowczak"]

[Black "xxxx"]

[Result "1-0"]

[PlyCount "88"]

1. e4 d5 2. exd5 Nf6 3. Nf3 Nxd5 4. d4 c6 5. c4 Nf6 6. Nc3 e6 7. Bf4 Be7 8. Bd3

h6 9. Qc2 Nbd7 10. Rd1 Nb6 11. O-O O-O 12. Rfe1 Nh5 13. Qd2 Nxf4 14. Qxf4 Nd7

15. Ne5 Nxe5 16. dxe5 Qc7 17. Ne4 Kh8 18. Re3 f5 19. Rh3 fxe4 20. Qxe4 Rf5 21.

g4 Bg5 22. gxf5 exf5 23. Qd4 Be6 24. Qd6 Qf7 25. b3 Rd8 26. Qc5 a6 27. Qb6 Rd7

28. Be2 Rxd1+ 29. Bxd1 f4 30. Rd3 Kh7 31. Bc2 Bf5 32. Qd4 Qg6 33. Kf1 Qe6 34.

Rd2 Bxc2 35. Rxc2 Qh3+ 36. Ke2 f3+ 37. Kd3 Kg8 38. Qe4 Qd7+ 39. Kc3 c5 40. Qd5+

Qf7 41. Qxf7+ Kxf7 42. Kd3 Bf4 43. Ke4 Bxh2 44. Kd5 Bg1 1-0

I knew 18. Nf6 was the right move, but I couldn't work out a clear win, and saw phantom counterplay opportunities for my opponent. So I settled for 18. Re3, completely missing 18...f5. I even saw that 22. f4 was the right move, but again thought it risky so shied away. I then made things much worse for myself in my opponent's time trouble (at move 30). It was 1-1 in a 4-board match by the time move 32 racked up, with the guy sat next to me clearly winning. So 32. Qd4 was an attempt to grovel a draw. For some reason, he declined the draw offer and gave up the chance to take the rook, after which I was completely winning. After that I was comfortable, and knew I'd win. (I won on time because he hadn't bothered to check - or indeed, press - his clock for many of the preceding 10 moves.)

So my questions are:

1. How can I improve such that I convert the good positions I seem to get?

2. Why do I always chicken out when there are risky moves that are good, when there are so-so alternatives available? How do I get out of the mindset where I play the conservative moves, when riskier moves are more accurate?