After going through a breakup in 2014, Sheffield worked together with illustrator Dami Lee to create the webcomic No Girlfriend Comics, which chronicles his experiences of suddenly being single after a two-year relationship.

He hosts the Insert Credit Show podcast with his co-hosts, Frank Cifaldi and Alex Jaffe.

Though he felt his emotions were unique to himself, he realized that his reactions and resulting routines were very similar to those of other people that have gone through a break-up.

According to Lee, "it felt right to end it at 20 comics instead of continuing the series; it represented a passing phase that everyone goes through at some point.

"[1] Sheffield and Lee worked together again to create the webcomic Hot Comics for Cool People, which was syndicated in SF Weekly in 2016.