Súper close group? Me. I am very far in my career, generally super happy and easy going, very few concerns in life right now. Married, own house, very confortable income on my own (6 digits), and DINKs. Well traveled, bunch of projects and lots of nice experiences under my belt. Owned several business, great success in investments, etc.
Expanded group? As in coworkers who've become friend or others? I am friends with two CEOs, but one of them is a financial institution with several hundreds of millions in assets so it'd be him career and money wise, but he's not the happiest guy ever.
I don't compare myself though, it's a waste of time and everyone's definition of success is different. To me it's money, fulfillment and happiness. I have a close friend who's always broke but he's super chill, enjoys his job and doesn't have concerns. "Basic" life but that's what he measures success against. So, good for him!