[4] Interviewed by Vulture Magazine, Stapleton said:[5] "There’s a lot on this record that I’m finding out, as I’m starting to talk about it a bit, was very reactionary and in the moment.

[6] Jonathan Bernstein of Rolling Stone reports that "Starting Over feels comfortable experimenting with whatever its author throws at it" as Stapleton "digs deep into familiar territory, spinning a fiery tale of liberation", finding it a "sincere tale".

[11] Chris Willman of Variety finds that "Starting Over is not intended to live up to its title; if anyone is so solid in his musical convictions that he could never try to reinvent himself, it's Stapleton.

But it would be hard to consider an album that contains not just one but two Guy Clark covers that pay homage to one of Stapleton's songwriting heroes as banal".

[13] Jeremy Winograd of Slant Magazine finds the arrangements of the songs "sparse and uncluttered" leaving the singer-songwriter's voice "raw".