I am probably the biggest re-starter in all of Elder Scrolls history. I have probably started hundreds of characters since Oblivion was released.
To me, it's not a problem to be overcome (I know, that's the disease talking
). It's possible to restart many times and enjoy the process. My favorite part of most games is the beginning. I sometimes do the tutorial dungeon just for the fun of it. It's relaxing to me. I love levels 1-10 in Oblivion. There's something optimistic about it for me. I feel like I have a chance to erase past mistakes, wipe the slate clean (something I wish I could do in real life).
Restarting is a problem only if we do not enjoy it. And here, I think some people do not enjoy it because they are told they are not
supposed to enjoy it. They are told that the "proper way" to play a video game is to start at the beginning and proceed in an efficient manner to the end. If a person hears that enough times they might begin to think that maybe they're doing something wrong if they start a new character.
If you still want help here are some older threads on the topic that may give you some ideas about changing patterns:
http://www.gamesas.com/index.php?/topic/1153682-restartitis/
http://www.gamesas.com/index.php?/topic/1116923-re-starters-anonymous/page__p__16406202__fromsearch__1#entry16406202
http://www.gamesas.com/index.php?/topic/1115805-completely-random-character/page__view__findpost__p__16384187__fromsearch__1
http://www.gamesas.com/index.php?/topic/1123563-anybody-ever-play-as-a-character-which-is-counter-intuitive/page__view__findpost__p__16519583__fromsearch__1
http://www.gamesas.com/index.php?/topic/1121584-what-personal-rules-do-you-apply-to-your-characters/page__view__findpost__p__16501462__fromsearch__1
http://www.gamesas.com/index.php?/topic/1115709-self-imposed-rules-for-a-new-game/page__view__findpost__p__16390151__fromsearch__1
http://www.gamesas.com/index.php?/topic/1113643-an-interesting-new-way-to-play/page__view__findpost__p__16341241__fromsearch__1
http://www.gamesas.com/index.php?/topic/1117184-has-anyone-ever-just-played-as-the-unchanged-character/page__view__findpost__p__16411708__fromsearch__1
http://www.gamesas.com/index.php?/topic/1114533-how-do-you-limit-yourself-in-morrowind/page__view__findpost__p__16579862__fromsearch__1
http://www.gamesas.com/index.php?/topic/1121067-does-your-character-have-a-personal-mission/page__view__findpost__p__16494963__fromsearch__1