Refers to actions that hinder your progress, often unintentionally and habitually. He's always procrastinating, like he's his own worst enemy.
Pro Tip 2/3
Irony and regret
Used when someone realizes their actions led to a negative outcome they wanted to avoid. She became her own worst enemy by missing deadlines she set herself.
Pro Tip 3/3
Avoidable problems
Implies problems could be prevented if one didn't act against their own interests. By spreading himself too thin, he was his own worst enemy.