I'm probably an outlier. But I never made career progression a consideration. Instead I focused on different application domains and then applied my ever expand

I'm probably an outlier. But I never made career progression a consideration. Instead I focused on different application domains and then applied my ever expanding IT skills to those domains. I accomplished lots of completed projects as a contractor. Over the years I became very knowledgeable about insurance, superannuation, industrial control, fault-tolerant transaction processing, databases (DB2, Oralce), telecoms and network engineering. I don't recommend grad school for career advancement purposes (I got a PhD in SE after 20+ years in industry). IMO grad school is only valuable if you have an interest that you want to deep dive into and don't mind the cost. Academic jobs are hard to come by and you run the risk of being seen as over-qualified after you complete, assuming you do complete - many drop out. I believe that purpose is outside of work. i.e. work to live, not live to work.