Bemakom SheBa'al Teshuva Omed
The Talmud teaches that one who has sinned but then asks for forgiveness comes closer to G-d than someone who never sinned. This means that a person who was wicked but left their evil ways reaches higher than a person who has always done the right thing.
If so, the Talmud asks, should a righteous person intentionally sin, in order to have the opportunity to change his ways? After all, he can't reach the level of a reformed sinner if he never sins.
The answer is no, he shouldn't sin. One reason is, he might enjoy it and never repent. But more than that, if he sins just to repent, his repentance will not be sincere because his sin was not sincere. If you sin just to get closer to G-d, you never rebelled properly. And if you didn't rebel, you can't truly regret. If you didn't actually go off the path you can't get back on.