Trying to Fit the Ocean in a Cup

Commercial

The album was the No. 37 most sold Christian album in the United States.

Critical

Trying to Fit the Ocean in a Cup has received mostly favorable reviews from the critics to judge the album. Of the positive reviews, The Phantom Tollbooth gave the highest rating of a four and a half stars out of five, and the four star ratings came from Allmusic, Christianity Today and Jesus Freak Hideout, which it got one eight-star review from Indie Vision Music. Furthermore, Cross Rhythms' rated the album a seven-star release. The two mixed reviews came from Melodic.net, who rated the album a three star album, and The Christian Manifesto's two and a half star rating.

The Phantom Tollbooth's Shawn Dickinson proclaimed it as "a memorable disc which showcases Josh's witty songwriting and capacity for highly infectious hooks," and noted "how the entire project fits together and is an enjoyable experience from beginning to end." Jared Johnson of Allmusic found that it is an album that was "done right in every way." At Christianity Today, Christa Banister affirmed that "the final product is a taut, highly listenable collection that should hold even the most fickle listener's attention today, and for years to come." Jesus Freak Hideout's Adam Dawson called the release "enjoyable, catchy, and full of relevant Christian themes", which it "may not perfect, occasionally suffering from a bit of overproduction and lack of acoustics", yet vowed that it was a "promising debut." At Indie Vision Music, Eric Pattersson noted that "musically, there's nothing groundbreaking, but the quality of composition and performance is refreshing in a world of three minute songs with three chords or maybe four." Cross Rhythms' Niall Dunne said that "as with any good album, 'Trying To Fit The Ocean In A Cup' goes much deeper than the surface level radio hits that inevitably do well." At Melodic.net, Kaj Roth called it "a rather comfy affair". Calvin E'Jon Moore of The Christian Manifesto wrote that the release "doesn't break any new ground" and alluded to how that "sometimes there are way to many Christian songs that over-contemplate the pain we all experience, only serving to further depress."