He's a loser. 27 years old and still an intern that relies on his families allowance to live.
We see in the game that he's supposed to have this potential to be a writer, but what kind of writer is he going to be? He has no real life experience, nothing that he's lived himself that he can base his writing on. I've read writers like this, and it's just junk. Based upon what they can derive from other writers or Wikipedia articles.
Ian is presented to us as the male protagonist, the other side of the coin to the female protagonist Lena. And yet Ian isn't even a patch on Lena, she's out of his league.
The publishing industry is filled with a
lot of qualified people fighting for the few positions available — and I suspect that is at least as true for USA as for Europe. Internships are probably more or less the only route available to get the attractive jobs. That a lot of creative industries are based on poorly paid internships in several countries, hardly makes Ian a loser, that’s just a thing employers can get away with when there’s enough people willing to do whatever it takes to be hired.
The guy’s also almost finished writing a book, which is bound to become a success if you’ve made the right choices, and a big literary magazine wants him to write for them. If anything he’s ahead of schedule to succeed in his professional life. It’s true that things are looking slightly bleaker for him at the start of the game, but that’s the whole premise of the story: Both Ian and Lena are at a low in their lives, and they’re not sure where to go from there. That’s what we’re choosing for them in the game.
Writing Ian as a guy with everything working out for him from the start would’ve made the story significantly less interesting. Therefore you can also make the choices that ends in him losing his job and becoming a delivery guy who sits at home in the evenings, jerking off to videos of his best friend fucking girls he’s attracted to himself. That’s his loser route, but that only happens if you choose it for him.
And the idea that books from writers with limited life experience always are junk, is just plain stupid. As a writer you need to know your topic, but your topic doesn’t have to be derived from years of years of dramatical life experiences, at least not if you’re writing historical fiction or sci-fi, like Ian can do.