This comic strip came about by chance and coincidence, in a way that was very social-media-contemporary, yet very Boomer-ish in nature.

Steve Greenberg had tried many times and for many years, way back, to create and sell a conventional comic strip to syndicates, but eventually gave up on the idea as newspapers and syndicated strips went into decline.
His wife, Roberta, stumbled onto a "Facebook" thread involving lyrics to Led Zeppelin's "Stairway to Heaven" and the various posters were making smart-ass remarks using the song lyrics. She eventually used Google to try to learn who the person was who'd initiated the thread.
By cosmic coincidence, this person, David Laurell, was a magazine editor for "Life After 50," a publication in a small chain Steve already freelanced to (as the regular contributing editorial cartoonist for the alt-weekly Ventura County Reporter).
Roberta emailed David and urged him to use Steve (who happened to be in his 50s) for "some kind of artwork" and, after some back-and-forth, they settled on the comic strip concept. Steve's original name for the strip turned out to already be taken, and Roberta came up with the name "Boomerish," which Steve liked and which suited Life After 50's mission of aiming at the Baby Boomer demographic.

Here is the Facebook conversation between Roberta and David:

David Laurell: I'm not alarmed (feeling it may simply be a spring clean for the may queen) Ð but I think there may be a bustle in my hedgerow. — January 5, 2011 at 8:23pm

A Facebook friend of Roberta clicked "Like" on this, and Roberta found herself in the middle of the thread and chimed in:

Roberta Greenberg: There's still time to change the road you're on. — January 7 at 11:08am

David Laurell: Thanks for all your input...every word of it makes me wonder! — January 7 at 6:28pm

Roberta Greenberg: oooooo and it makes me wonder. — January 7 at 10:49pm

David Laurell: By the way, does anyone know what the going price is for a heavenly stairway? I mean, I may like to buy one, but don't know If I could afford it. — January 8 at 4:46pm

Roberta Greenberg: I saw one at the 99 Cent store. — January 9 at 10:09am

David Laurell: Wow...what a deal! I'll take two! — January 9 at 5:46pm

Roberta Greenberg: Your stairway lies on the whispering wind. Aisle 6. — January 9 at 8:47pm

(Keep in mind that David and Roberta had never met and had no idea with whom they were conversing)