Is going 1099 prestigious?
I have friends that work at brand name companies (Facebook, McKinsey, etc.) and you can tell they are proud to have that name on their resume, even if they don't actually care about the work.
I've never worked for a brand name company so I don't have any resume prestige. It has never been important to me so I never pursued it.
But, I do find working for myself is "prestigious" in the sense that a) not many people do it and b) I get an above average income with above average perks.
This prestige is all internal to me though. No one else would go "woah you're a 1099 sub-contractor! How did you get that job!" Well, maybe you guys, but it's a small group ;).
If external prestige in the form of a widely recognized brand named company is what you're looking for, the 1099 life is not a good choice.
If you get a kick out of doing something a bit off the beaten path to get paid more and have more free time, then the 1099 life is a good option.
"Prestige is like a powerful magnet that warps even your beliefs about what you enjoy. It causes you to work not on what you like, but what you'd like to like."
- Paul Graham, How to Do What You Love
Want the full playbook? Check out Going 1099.