So, the thing to do when you're procrastinating is to skip the whole "What's wrong with me?" shame spiral, and simply ask yourself, "Why?" In the cartoon, Goatee Guy helpfully does this for Hoodie Man. Then, Goatee helpfully affirms the validity of Hoodie's concern ("a big expensive hassle"), while reminding him that procrastination isn't the best response.
Listening is respectful, yields useful information, and also helps the other person be more accepting of your information and viewpoint. (My go-to book on this topic is How to Talk So Kids Will Listen and Listen so Kids Will Talk by Adele Faber and Elaine Mazlish, a classic parenting book I strenuously recommend for nonparents, as well.)
Notice, also, that, as much as Goatee wants Hoodie to get insurance, he doesn't blow smoke. He admits that health insurance is a lousy gamble, but reminds Hoodie that, even when you don't like your choices, it's still important not to procrastinate.
Much of the time when we procrastinate it is because we don't like our choices. When that happens:
(1) Make sure you're seeing the situation as clearly and objectively as possible. Sometimes we respond defensively or reflexively or simply out of habit.
(2) Make sure you're aware of all your options: we often miss a few. (Talking with a trusted friend or advisor can help.) And,
(3) Accept the situation for what it is, instead of comparing it with the fantasy of how you wish it were, or someone else's "better" situation.
And you'll have an easier time taking action.
Since the bankruptcy wouldn't be his most serious problem, he's framing it as a trivial problem: that's either/or thinking. Dichotomization is a perfectionist characteristic.
Goatee's response is interesting. I think he's trying to convey to Hoodie the difference between being merely clever and truly wise. Perfectionism, being reductive, can usually come up with snappy answers, but those answers will almost certainly be wrong. Perfectionism is inherently delusional, and you should never make important decisions--or any decisions--out of a perfectionist mindset.
This helps restore Hoodie's perspective, and helps him make the right decision.
I would have liked the cartoon a wee bit better had Goatee offered to help Hoodie through the first step of the difficult process of buying health insurance, or maybe even the whole thing. (A process that, just this week, got a whole lot easier - thank you President Obama and Democrats!)