I think it depends on what they do with the rest of their lives. If they spend a ton of money to go to college and become a teacher then 5-10 years into their teaching career their past is found out, they are fired and can't get another teaching job, then I would guess they do regret it.
If they made enough money to live a decent life on the interest and returns of their investments, or they go into a field that doesn't care about their past then they may not.
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