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In 2012 Greg's first child was born, followed by his second in 2015. His father died in 2017. Meanwhile, he started his private psychology practice in 2013 and moved into it full-time in 2016. As a result of these major life events, Greg stepped back from producing solo music between the years of 2012-2020. During that time he and Sigmund Blue released their third and most ambitious album, he and Brandi Parker of Sigmund Blue founded the band Dipod and released their debut album, and Greg reunited musically with the talented John Daly to record Spit'n Lyon: An Unsung Soldier's Song.

On the heels of this last project, as the COVID-19 pandemic was beginning, Greg began working on a new solo album, Hindsight (titled as a cheeky reference to its 2020 recording and release). He started with six older songs, written between 1995 and 2007, and finished the 12-song lineup with 6 new compositions. For this album, Greg also switched from Cubase, the digital audio workstation he had been using since the early 2000's, to Reaper, which promised more compatibility with a wider variety of instruments and effects, as well as smoother performance overall. He had also adopted a new drum sound thanks to the MIDI program Addictive Drums during the sessions for Sigmund Blue's last album. Between these two significant changes to his setup, Hindsight took on a more polished, more commercially viable sound. He also focused his songwriting and song selections in such a way as to reduce extended instrumental sections and focus more on tight, radio-friendly song structures (with some deviations, of course). The result has been well-received and lauded as an exciting new direction in Greg's music.

For the cover art, Greg enlisted the help of his uncle, Tim Corner. Tim has a special place in Greg's musical development, as he taught Greg some of his first songs on guitar, and also taught Greg his first multitrack recording technique (this approach, which involves two cassette tape decks with one's output fed into the other's input, made Greg's earliest studio experimentation possible). The only direction Greg gave Tim was that the album was comprised of half older songs and half new songs, so the theme was "looking backwards and forwards at the same time." Tim had Greg take photographs of himself walking down a St. Louis street, and using these photos a reference, Tim painted the cover that you see above in his home studio at Martha's Vineyard. This is the first album cover of Greg's that is an oil painting, as previous covers were all based on photographs: For My Part (Greg's photography with Brandi Parker providing lettering), Cathexis (photography by Jenny Sarrat), and Greg Goldman (photography by Brandi Parker, manipulated manually after the photo was printed).