Who said he'd have to blow up his 401K at age 39 or 49? Why would that be the assumption?
All he would have had to do is put himself on an aggressive plan to pay everything off in 3-5 years, with the funds he has coming in, and he'd be well ahead of the game. Instead he chose to immediately forfeit roughly 38 percent of his retirement savings -- the 10 percent penalty for early withdrawal and the probably 28 percent he pays in income tax.
So if he withdrew $50,000, he just flushed $19,000 down the toilet. And this is to say nothing of the thousands of dollars in free money the company was willing to give him that he refused to take, in addition to reducing his own tax burden by putting his own money away.
Extraordinarily stupid.