U2 has something in common with its corporate partner Apple: they both make a lot of money. And they both struggle to be cool.

U2 earns gigantic paydays with high-profile concert tours that appeal to its Baby Boomer fan base. According to Forbes, U2 was one of the highest paid musical acts of 2016 based on the success of its latest tour, Innocence + Experience, which earned $55 million.

But the band’s songs have barely put a dent in the Billboard charts throughout the 2000s (how many U2 songs from the 2000s do you listen to regularly?) and U2 has become joined at the hip with Apple, a brand that has been about as exciting as vanilla ice cream since Steve Jobs passed away.

U2 wants to change that perception. In 2017, U2 will hit the road for a tour that will celebrate the 30th anniversary of The Joshua Tree, thus introducing one of the group’s coolest works to the digital generation. Reportedly the tour will include an appearance at Bonnaroo, one of the key music festivals for establishing credibility and coolness with digital natives and millennials. And for entertainers, especially musicians, being relevant to the present-day generation of tastemakers (digital natives and millennials today) is important to being cool. Led Zeppelin is cool. Chance the Rapper is cool. Coldplay is not cool.

Artists can lose and regain their coolness for many reasons. In the late 1960s, Frank Sinatra lost his coolness when he tried too hard to connect with a younger audience by recording horrible cover versions of songs like Petula Clark’s “Downtown.” He regained his coolness when he stopped trying to be cool and focused on being Frank Sinatra. In the 1980s, Johnny Cash lost his coolness when he rejected his inner rebel and slipped into a comfort zone of touring as a feel-good gospel act. He regained his coolness when he partnered with producer Rick Rubin to make the American Recordings series of albums, which re-established his contemporary relevance through covers of rock songs such as “Hurt.”

U2 defined cool in the 1980s and 1990s by making music with bite, emotional depth, and boldness. Throughout the 1980s, U2 was the defiantly soulful and socially conscious alternative to the synth-heavy sound of the second British invasion, and The Joshua Tree demonstrated that you could be spiritual and cool at the same time. In the late 1980s, U2 suffered a temporary lapse of coolness during the Rattle and Hum tour, when the group’s pious tendencies turned into messianic self-indulgence. But U2 regained its equilibrium by recording experimental, edgy works such as Achtung Baby, Zooropa, and Pop. Even if those albums were not always critically successful, U2 was challenging and pushing its audience in new directions.

But in the 2000s, starting with the release of All That You Can’t Leave Behind in 2000, U2 committed the Johnny Cash mistake of settling into a comfort zone — in U2’s case, by churning out straightforward pop songs, all of which have pretty much sounded the same. According to U2: The Definitive Biography, by John Jobling, the commercial success of All That You Can’t Leave Behind helped U2 emerge from a financially troubled time — which might help explain why U2 has tried to repeat that album’s formula ever since, resulting in music that no longer resonates.

U2 also hurt its own coolness by falling out of touch with the listening habits of digital-era consumers. In the post-Napster era, U2 relied on the record album to tell its story and in doing so clung stubbornly to a dying format. When U2 realized that people no longer buy record albums, the band infamously tried to force an album on unsuspecting listeners by collaborating with Apple in 2014 to distribute U2’s Songs of Innocence as a “gift” download through iTunes. The unwanted distribution of Songs of Innocence caused U2’s social media sentiment to plunge by 41 percent in one week and exposed how irrelevant the band had become to the digital age, with Twitter users asking questions such as, “Who is U2? And why do their songs keep popping up in my iPhone?”

Since The Songs of Innocence debacle, U2 has continued to struggle with a perception of no longer mattering. In 2016, U2 offered to play a private concert as part of a promotion for (RED), which Bono cofounded to eradicate AIDS in Africa. The private concert promotion on Facebook has inspired plenty of laudatory comments from fans, but you don’t have to search very hard to notice the snarky pronouncements proliferating among the fan reactions, such as “I wouldn’t open the curtains if you were playing in my back yard. And don’t foist your mawkish MOR noise on my iPod ever again either while we’re at it!” (via Facebooker Cathy Smith).

So how can U2 reestablish its relevance and coolness? Here is what I’d do if I were managing the U2 brand:

• Maximize the value of The Joshua Tree. Digging into the past is a wise move, as Guns N’ Roses proved through its successful Not in This Lifetime tour, which reestablished GNR’s relevance in the digital age. Playing at Bonnaroo would be a start. U2 should also hit the millennial music circuit with stops at venues such as Coachella and Lollapalooza. Surprise shows at smaller millennial-friendly gigs would help U2 connect on a more personal level with younger generations of fans.

• Unleash The Edge. As a standalone figure, The Edge is way cool. (Check him out as he slays the guitar in It Might Get Loud.) I’d create a stronger narrative about his status as one of the great guitar gods, through advertising, social media posts, and music trailers promoting the upcoming shows. Putting a bigger spotlight on The Edge as the great guitar innovator that he is would demonstrate that even if U2 has not always progressed musically, he’s always been on the vanguard of guitar, similar to the way Slash has symbolized all that is good and cool about GNR.

• Be visible in the right places. The band’s takeover of The Tonight Show Starring Jimmy Fallon in 2015 reminded the world of how funny and cool U2 could be. Jimmy Fallon is the kind of personality whom Baby Boomer musicians cozy up to in order to be relevant. U2 has plenty more opportunities to shine in the right shows, especially via digital — how about Bono appearing on Carpool Karaoke, for example?

• Release great music. The most important step U2 can take is to create music that is relevant and interesting, which Songs of Innocence was not. In 2017, U2 will release its follow-up, Songs of Experience. Certainly the time is right for U2 to recapture its fire and grit if U2 wants to do so. We live in very uncertain and troubled times, which could make that socially conscious side of U2 more relevant again, as has been the case with Roger Waters and The Wall

For rock and roll acts, growing older does not mean losing your coolness quotient, as AC/DC, Guns N’ Roses, and Neil Young have demonstrated. But you do have to state a case for your relevance when you continue to play music for decades, as I’ve discussed on my blog. By announcing a series of shows celebrating The Joshua Tree in 2017, U2 has taken a step in the right direction, as The Joshua Tree will never grow uncool. But will U2 create new music that resonates in 2017?