All who have seen the Simpsons know of the Kübler-Ross model for coping with grief and tragedies (denial, anger, bargaining, depression, acceptance). I go through a similar process (albeit a bit more positive) each time I record my playing:
1) Expectation – during the actual recording session spirits are usually high, and it always sounds good when I’m playing. A little bit of stage fright usually appears by just pressing the record button, but that usually disappears after a few takes.
2) Exhiliration – when you put your recordings into a mix (I usually have a backtrack or at least som VST-drums) it sounds awesome! You fiddle around a bit with EQ and maybe add a few effects and it sounds even better.
3) Depression – after a few listens I start to hear every little mistake, and they rapidly increase in number every time I play back the track. At this stage I’m usually considering deleting the whole project.
4) Maturation – after a few days and even more listens (and perhaps a pause withouth listening) I can hear the recording a bit more objectively. I can still hear the errors, but they don’t bother me so much. I’m usually quite proud of my recordings in hindsight. It’s also a lot of fun realizing the new ones are much better than the old ones.
Even though it can be hard, recording yourself is one of the best way to develop your playing. I have quite a good music ear in my own opinion, but it’s not working as well when I’m sitting with my guitar in hands. It’s much easier evaluating your playing from a recording.
My tips: record yourself as often as you can find time and energy, and be nice to yourself when evaluating those recordings.