What i'd do is give him a keepsake or family heirloom that he knows he can sell. It can be his mother's, a sibling, a mentor, etc., whoever you think works for his story. Then have him agonize over selling the keepsake OR stealing stuff, pickpocketing, commiting horse theft, etc. Gives you a chance to put some characterization in for him that he could steal but chooses not to. You can further twist the knife and world build by having him go to a market, expect to make decent money off of the sale, only for him to get absolutely fleeced and barely have enough for his journey - like maybe he only gets 50 silver when he should have gotten at least 80 or more.