@Ethan Schneider First off, he's lucky to have a friend such as yourself who's concerned about his well-being and wants him to be in a better position than he is right now. There's been a ton of great feedback in this forum thus far, and I applaud all of the great suggestions from everyone.
A couple of things that I'd recommend to you are:
1) Be His Friend, First and Foremost
Your job has always been to be his friend and not his business partner. When someone is "down on their luck", it is often meaningful relationships that will help them the most. If he does in fact have depression (whether situational or genetic), it can be a nasty spiral. And true friendship can be one of the things that helps him to persevere and give him a reason to start digging himself out of his current situation.
2) Focus on Things That Awaken Those Passions and Desires He Once Had
Your friend has a Master's Degree. Your friend works in Pizza Delivery. He obviously has some sort of work ethic. And this type of work ethic is what's going to serve him in the future, if he can continue to persevere. Too often, we're focused on external aspects of "accomplishment" and "wealth", and assume that if we're not externally succeeding, then we're failing miserably at life.
I like what Jordan Peterson has to say about wealth: he states, "Wealth constitutes what you have when someone takes all your money away." This includes things like integrity, leadership, skillset, and demonstrating competency in multiple directions. That's real wealth. And these are skills that can be built up all the time and aren't dependent upon external circumstances.
Given your friend's level achievement, he was certainly someone that likely had tremendous passion and desire at one point in his life. And unfortunately, it seems that life circumstances have extinguished the flames of passion and desire that he once had. Take it from me, I have failed miserably in my life, many times. And as someone who has two Master's Degrees (which I don't think were super helpful for where I actually want to go in my life) and accumulated a lot of student loan debt in the meantime, it's never too late. Mental, physical, vocational, financial, familial, spiritual, and emotional limitations do not define who we are, nor do they dictate where we are headed. John Maxwell put it best when he said:
3) Try To Adjust His Focus On Serving Others First
Just as John Maxwell said above, "Be more concerned with what you can give rather than what you can get because giving truly is the highest level of living." This is so true. Many times, simply focusing on serving others can help to get the magnifying glass off yourself and your imperfections/failures. When we are outward focused, instead of inward focused, we can engage in more meaningful activities, situations, and environments and hopefully re-ignite those things that we were once passionate about.
Sorry for the long response, but I come across so many people that are in the same situation as your friend, and I truly believe that we are not confined to the limitations that society or our family tries to put on us. Best of luck to you and your friend!
