I've always worked, pretty much, by myself on my music. I've only co-written one song, I've never really been in a band and I pretty much always perform with just me and my guitar. I always got overwhelmed thinking about making any sort of recording 'cause I'd think about programming the drums and playing multiple guitar parts and harmonies and what about the horn section... I realized that I don't have to be Paul McCartney and play all the instruments. I don't have to be Brian Wilson and arrange everything perfectly.
What I have to do is focus on my strengths (singing & songwriting) and build a team of other people who do the other things really well.
This is what has made working with Aaron Young so much fun. He is such a great musician that I played him Born To The World and he was taking notes while I sang. When I finished he said "There, I've done the chart." He asked for the guitar and played the song through for the first time and I sang along.
I've been playing the song for 15 years and I still make mistakes. Building a team is definitely a good idea.