Cringing at the old you is a good sign. It means the new you has better taste.

Wincing at an earlier version of yourself requires standards that version did not have. The embarrassment is uncomfortable and it is also evidence: you can only see the flaw because your judgement improved in the meantime. Someone who feels no discomfort looking back has usually not moved much.

Let the cringe be brief and take the information out of it. Ask what specifically you can see now that you could not see then. Then extend the same courtesy forward, since the you of five years from now will have the same reaction to today, and that is the arrangement working as intended.