Dean (still) uses this phrase to refer dismissively to Sam’s activities while Dean was in Purgatory. It expresses Dean’s hurt at what he sees as Sam’s willingness to 'give up’ on Dean and settle down in the 'normal’ life Sam has always wanted. In fact I’d argue that the first half of season 8 tells a different story about what actually went down. Episodes 8x05 and 8x09 in particular show Sam driving dangerously, almost frantic with fear, when he believes the life of somebody important to him (first Dean, then Amelia) to be under threat. Episode 8x04 offers an uncomfortable suggestion about what the possibility of total isolation might plausibly drive someone to do. Given this subtext, Crowley’s dig at Sam in 10x01 acquires a different weight.