Self actualization vs. Being in a pretty solid living condition are very different things. Marten's got a good gig. A lot of people settle. It's a normal part of the human condition in much of the world. Shit job for survivable pay, doing something you enjoy on your own time when you have energy. Rinse, wash, repeat.
Let's go to Maslow's shall we?
When we're talking about living conditions we're talking about tiers one and two. Marten friend's pretty solid there. Tier 3 as well, not one but TWO dads, a mom who is very loving... in her own special way, lots of friends. No current romantic partner, but Marten's done okay when he's actually been in the saddle even if he is a bit shy about getting on the horse. Or ends up facing the wrong end on occasion. Marten's issues are solidly spread across four and five. His confidence is no where to be found, and while he has friends we've noted in this very forum on many occasions that Marten gets maligned by said friends fairly often. Now I personally think those friends respect him, but it might not feel that way to Marten.
What Marten is reaching for in his life is meaning. Purpose. He has his passions and desires, but just can't seem to run with them. Understandably so. Risks are fucking scary. It's even harder to take risks when you don't even have the semblance of a game plan. I'm not going to bother and dig it up, but during the unemployment ark Dora asked him what he wanted to do his answer was "Something with music I guess". Hardly something to aspire to. Rock god? Okay there's a way to plan for that. Music professor at SMIF? Very plannable (step 1: gather more black mail on the faculty... uh... get music graduate degree *cough*). Music blogger/journalist? Well maybe not, we saw how long that blog project lasted.
So I'd say Marten's issue isn't so much his ability to take chances. As we've noticed he can be brave when he needs to be. However where Marten runs into trouble is the same place many of us do. Setting a course so we know what chances to take. How many people do you know who are doing there jobs because that's their dream job? How many people do you know who, as childhood fades can even tell you what their dream job is?
All the wind in all the sails in the world won't help you if you don't know where your destination is. "All I ask for is a tall ship, and a star to steer her by" we all have the metaphorical ship. Some in better condition then others fair, but the star. Ah the star. Without that a ship may as well be beached.
So when I say I wish I had Marten's problems, it's sensible to feel that way when you're struggling or having issues with work, food and shelter, rebuilding a social circle and being lonely, the more base of the needs on Maslow's... it can be appealing to have those base needs taken care of and struggle instead with the more ethereal.