Don’t wanna sound to harsh on him but if we don’t know what was Alan’s peak we sure know his valley is now…
Lols. As jbaent says, he's doing OK for a 70-odd year old musician. As Alan himself says, he's never worked a day in his life in a "real job" - that's the way you do it!
The strange thing for me is that he kind of went under the radar in the 90s, you would think with a CV that read Clapton's musical director/arranger for Dire Straits he would have had some big gigs at that time.
I guess, not every musician is suitable for everything. If Mark Knopfler is great at playing the guitar, it doesn't automatically mean he would be a great studio musician, which he told a million times in interviews himself. It's a completely different skill set, mindset, and everything else set. A studio musician is somebody who works ALL THE TIME, like Hal Blaine.
As for never working a day on a real job — that's utter bullshit, sorry. Only people with psychological traumas and complexes could say that. Same as in Russia, it's considered bad to "work for a dude", as opposed to working on your own business, and you can often find businessmen in Russia who say they never even think about working for somebody.
If you never worked on a real job, then you don't know what life is, as simple as that. Go work on a farm, work as a paperboy, dig graves, go to the office from 8 to 6, and move furniture and audio equipment. I've had a fair share of bad and "real" jobs in my life, and I wouldn't trade this experience for anything.