Well sometimes it's believed that being overly comfortable is a way to appreciate one's efforts and value, but I do believe that while this is true, it might signal complacency at the end of the day. Being or ending up being complacent is something we shouldn't even consider and this is because sometimes we might be wrong in the positive accessment of ourselves. So we need to maintain a balance. I'm glad this feels relatable. 
As for contenting, I think it might be difficult but one needs to grow individually even if we want to reference others, their contents and their style as our inspiration, but growth is what we instinctively decide to do on our own and this greatly correlates with you too. 

> I like your mindset when you had a low-paying job. How you chose growth- to focus your energy on learning to do the job better and to rather work on yourself than have a pity party.

When one grows up in a difficult and challenging environment, you'd have to be wise to survive because survival itself is a skill. So yeah, I chose to be tethered and kept learning.