So much of the content of your work -- blog mostly, but even the radio show and now this video -- is ironic, self-deprecating, light and somewhat dismissive in tone. I like that, and I assume that's your natural voice, but if I were working with you I'd want to know whether you're hiding from failure by adopting a posture of dismissive, self-deprecating humor.
The problem with irony as an artistic strategy -- like sarcasm as a conversational strategy -- is that it's a one-trick pony. It can make one point well, but it can't go deeper, it can't explore an idea metastatic-ally, if you will (I just made that up, but you get the idea I hope).
Ben Casnocha, who has mined a veritable cottage industry out of irony, thinks that: 1) irony can be "an act of self-protection, and can be a sign of insecurity" (here), 2) the "shift to earnestness [over irony] in communications represents a milestone in a romantic relationship" (here), and 3) " too much non-seriousness [read: irony] is hard to take. But in small doses, I find it endearing and funny. It's a balance." (here). Elsewhere, Kelly Stout argues that "sincerity is the post-irony irony" in her lucid exposition of what I have previously called the conformity theory.
Here are my two models for thinking about irony:
1) Irony and earnestness are the two opposite ends of a spectrum that exists in an equilibrium. If you imagine a world full of irony, earnestness would be highly valued (when recognized). In a world full of earnestness, irony would be especially funny and also highly valued. These two factors inevitably push the world to someplace in the middle of the extremes, with people employing various personality styles at various times. Sometimes people get locked into a specific personality type due to inertia, so personalities types can exist even when they are no longer optimal. The more lock-in, the more people will expect to be able to take advantage of the "market failure."
2) Individuals use irony when they are afraid of the prospects of being earnest. This decision could be more rational, such as wanting to defend one's ego by not publicly pre-committing to a goal which might fail. Or the choice of irony over earnestness could be less rational, such as unconsciously avoiding a anxiety-conditioned fear. Either way, the use of irony by any one person will be less tied to other people's use of irony and more based on their own personality and mixture of conscientiousness / neuroticism.
