The best thing you can do is have an honest talk about the mistakes you have made and how it has hurt you more ways than just financially. Help him make a budget based on his real goals that he wants to follow. Should the budget include $5 each day for coffee or save $5/day for Tahiti? Understanding that you should buy what you need so you can later afford what you truly want is a hard concept for many. Each purchase should trigger - do I need or want this? If the answer is want, it can wait and should be planned. For some, the coffee each day is a mental health issue and more important than other things. It just needs to be clear what the priorities are. You can't reach your destination without guidance.
Goals should include not only the big stuff but smaller things as rewards. Once I have my emergency savings met, I can buy a new tv.
Of course, failure to plan is planning to fail.
Saving as much as you can while young is great advice!
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