Key Moments

“We Won 3 Grammys and Still Felt Like Failures” - Dan + Shay (Live Performance)

Modern WisdomModern Wisdom
People & Blogs6 min read95 min video
Nov 14, 2026|20,605 views|141|7
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TL;DR

Dan + Shay, despite winning 3 Grammys, grappled with feelings of failure, highlighting the disconnect between external validation and internal fulfillment, and the constant pressure to outdo past successes.

Key Insights

1

Dan + Shay experienced an 'existential crisis' regarding the relevance of their music in the age of AI, prompting them to shift towards writing more personal and present-moment songs.

2

The song 'Say Something' was written in the wake of their friend Ben's suicide, and its release proved more impactful than any award, with fans reporting it saved lives.

3

Following up their first major hit, like 'Tequila,' was more challenging than achieving it, as the duo felt pressure to match or exceed previous success.

4

Performing the national anthem at the World Cup was one of the most nerve-wracking experiences for the duo, surpassing even the Grammys in its intensity.

5

The duo believes that people connect more deeply with pain in music because sad songs offer healing and a sense of shared experience, fostering empathy rather than just happiness.

6

Dan + Shay's relationship faced a critical juncture in 2021, where they had an honest conversation that either led to their breakup or a stronger recommitment to their partnership.

The paradox of success and the pressure to top previous hits

Dan + Shay, despite achieving significant commercial success including three Grammy awards, reveal that they often felt like failures. This internal struggle stems from the immense pressure to consistently outdo their previous hits, a challenge they found more difficult than achieving their first major success. The duo shared that after a major hit like 'Tequila,' every subsequent song felt like it had to be at least as good, creating a self-imposed high bar. This competitive drive, while fueling their success, also led to a focus on results rather than the process, and a constant feeling of never quite arriving. They acknowledge that external validation from awards or chart positions doesn't necessarily equate to internal fulfillment, especially when chasing the next big thing overshadows appreciating current achievements. This internal conflict highlights the often-unseen emotional toll of sustained success in the music industry.

Shifting to authenticity and personal narrative

In the current landscape, influenced by AI and the rapid pace of music consumption, Dan + Shay experienced an 'existential crisis' about the relevance of their art. This prompted a deliberate shift in their songwriting process towards more personal, autobiographical content that reflects their present lives. This move was a departure from their earlier work, which often involved storytelling or songs written from past experiences, like 'Tequila.' The duo felt a strong conviction that for this particular season of their careers, they needed to create music that was 'inevitable'—songs that felt essential and deeply connected to their current emotional state and life experiences. This focus on authenticity is crucial in an era where audiences are increasingly discerning and seeking genuine connection.

The profound impact of 'Say Something' and healing through music

The deeply personal song 'Say Something,' written in response to the suicide of their friend Ben, became a pivotal moment for Dan + Shay. This song, born from shared grief and vulnerability, resonated powerfully with listeners, proving more impactful than any award. The duo received numerous DMs and personal testimonies from individuals who found solace and even salvation in the song's message, with some reporting that it talked them off a ledge. This experience solidified their understanding of music's capacity for healing and connection, especially through pain. They theorize that people connect more deeply with sad songs because they offer a form of catharsis and validation, allowing listeners to feel less alone in their struggles. This contrasts with happy songs, which tend to foster shared joy but not necessarily empathy or deep connection.

Navigating high-pressure performances and public scrutiny

Performing the national anthem at the World Cup was an exceptionally nerve-wracking experience for Dan + Shay, even surpassing the intensity of performing at the Grammys. They describe feeling the weight of the moment intensely, to the point of experiencing a near panic attack. This event underscored the high stakes of national anthems, where any misstep can lead to significant public criticism, while success is often met with a muted acknowledgment of simply fulfilling an expectation. The duo also discussed their past tendency to decline anthem performances due to the high risk and low reward, a decision they ultimately reconsidered for the World Cup. The experience of being mobbed at the airport afterward, being thanked for their service, highlighted the profound emotional impact of such a significant public moment.

The dichotomy of success: awards versus impact

Despite winning multiple awards, including three Grammys, Dan + Shay frequently grappled with feelings of being failures. This paradox highlights the disconnect between external accolades and internal self-worth. The constant pursuit of the 'next big thing' meant they often didn't fully appreciate their achievements in the moment. They recall winning Grammys but being so focused on the next goal that they didn't pause to celebrate. This perspective is reinforced by the profound impact of songs like 'Say Something,' which offered a different kind of validation—saving lives—that arguably outweighs traditional awards. This reflects a broader theme of seeking a deeper 'why' beyond commercial success and industry recognition, finding purpose in positively impacting listeners' lives.

The evolution of songwriting and navigating life stages

As Dan + Shay have aged and their lives have become more settled with marriages and children, they acknowledge that it becomes harder to draw from the same wellspring of youthful heartbreak or turmoil for songwriting. The 'tumultuous' experiences of their early twenties, which often fueled popular music, have been replaced by different kinds of challenges and reflections in their mid-to-late thirties. These new themes include anxieties about aging, the potential loss of loved ones, and the complexities of family life, as explored in songs like 'Young.' While they still aim for hits, their current focus is on drawing from genuine, present-day experiences, even if those experiences are heavier or less conventionally 'romantic.' This shift allows them to sing with conviction, connecting with audiences on a more profound level through shared human experiences.

The 'Domino's' inside joke and early days of struggle

The conversation touched upon humorous anecdotes from their early days, including an inside joke about the pizzeria Domino's, which Shay initially misheard and misunderstood for years. Their early days were marked by significant financial struggles, living in a dilapidated house with no heat or AC, and even breaking into a party for a free keg. These stories paint a vivid picture of their 'come-up' from obscurity to global fame, highlighting the stark contrast between their past and present circumstances and the resilience required to navigate such beginnings.

Conflict resolution and fostering a duo's longevity

The duo recounted a critical period in 2021 where their partnership was strained, leading to an honest and emotional conversation that could have ended their careers. They emphasized the importance of active effort in maintaining their relationship, likening it to a marriage that requires continuous nurturing. Key to their resolution was mutual respect, empathy, and the willingness to apologize and offer grace. They realized that while they might not always agree, their shared goal for Dan + Shay's success, combined with a commitment to fostering their bond, allowed them to overcome significant challenges. This experience highlighted the necessity of communication and intentional relationship-building for the sustained success of any creative partnership, especially duos.

Common Questions

Dan + Shay met at a house party in Nashville when they were both broke. Shay actually broke into the house at 507 Morton Avenue because the door wouldn't work, finding Dan inside with sheets draped to keep heat in.

Topics

Mentioned in this video

People
Megan Moroney

A fellow country artist mentioned in an inside joke about 'Domino's' pizza, highlighting her badass personality.

Kenny Chesney

An amazing songwriter and storyteller, whom Dan + Shay opened for on a stadium tour after their period of internal conflict.

Donald Trump

Mentioned as an example of a public figure who is immune to being hurt by criticism, allowing him to accumulate significant attention regardless of sentiment.

Luke Combs

A successful country artist whose writing arc is discussed in relation to creating honest love songs while happily married versus earlier, more tumultuous periods.

Justin Bieber

Featured in Dan + Shay's song '10,000 Hours,' which was part of their rising success before the COVID-19 pandemic.

David Beckham

A famous footballer (soccer player) whose appearance on the LED screen during Dan + Shay's national anthem performance almost made them lose composure.

Conor McGregor

An MMA fighter mentioned as an example of how aging affects athletes, making the host realize his own age.

Florida Georgia Line

A country music duo and friends of Dan + Shay, whose breakup and eventual reunion are noted as an example of the challenges and humanity in duo relationships.

Darius Rucker

A good friend of Dan + Shay, known for his work with Hootie & the Blowfish and his solo country career, who initially downplayed his desire for the Rock & Roll Hall of Fame but was encouraged to campaign.

Andrew Huberman

A neuroscientist and podcast host who uses LMNT electrolytes, cited as a testament to the product's quality.

Logan Paul

Described as one of the best media personalities in the world, known for his tolerance of distaste and ability to strategize multiple steps ahead in media.

JD Vance

A political figure who was a guest on the Joe Rogan Experience, noted for the street shutdown with Secret Service, implying the growing influence of independent media.

Luke Bryan

A country artist mentioned for discussing the challenge of writing new music after achieving success and having fewer 'life experiences' to draw from.

Brooks & Dunn

A successful country music duo mentioned as both an admired act and an example of a duo that experienced internal struggles.

Tom Cruise

A famous actor whose appearance on the LED screen during Dan + Shay's national anthem performance almost made them lose composure.

Jason Aldean

An artist mentioned as an example of a great storyteller, even if he doesn't write all his own songs.

Hall & Oates

A famous musical duo whose strained relationship is mentioned as an example of common challenges faced by duos.

George Clooney

Mentioned as a celebrity who owns a tequila company, implying that Dan + Shay should have received an endorsement for their song 'Tequila'.

Ben Von

A friend of Dan + Shay, a pillar of the Nashville community and early believer in their songwriting, whose suicide inspired their personal song 'Say So'.

Matthew McConaughey

A famous actor mentioned jokingly by Shay as his true identity after a long, vulnerable conversation.

Taylor Swift

A highly successful and polarizing artist, mentioned as someone who generates drama, which can be a way to capture attention.

Shania Twain

A legendary country artist whose success is mentioned when discussing the ever-moving bar of achievement in the music industry.

Chris Stapleton

A country artist known for his embellished national anthem performance, which is acknowledged as exceptional but not the style Dan + Shay chose.

Morgan Wallen

A contemporary country artist whose recent success is highlighted as an example of how the bar for achievement constantly rises in the music industry.

Garth Brooks

A legendary country artist whose success is mentioned when discussing the ever-moving bar of achievement in the music industry.

Jared Allen

A good family friend of Shay and NFL Hall of Famer, who initially downplayed his career achievements but was encouraged to campaign for himself.

Sam Hunt

A country artist whose success is mentioned as a benchmark in the music industry.

Jimmy Carr

A comedian who was a guest on the host's podcast, quoted for his poignant insight on suicide and the transfer of pain.

Whitney Houston

A legendary singer whose national anthem performance is cited as an example of a rare, career-changing moment of excellence.

Jake Paul

A media personality whose ability to handle criticism and strategically manage attention is discussed.

Locations
Gatlinburg

A city in Tennessee visited by the host during his road trip across America before deciding to move.

Broadway

A famous street in Nashville, known for its bars and live music, where the host experienced the impact of 'Tequila' live.

Charlotte

A city in North Carolina visited by the host during his road trip across America before deciding to move.

Nashville

The city where Dan + Shay met and where their early struggles, like low rent and dilapidated housing, occurred. It's also a hub for country music.

New Orleans

A city in Louisiana visited by the host during his road trip across America before deciding to move.

Austin

The city where the interview is taking place, and where the host moved to from England, partly inspired by Dan + Shay's song 'Tequila'.

England

The host's home country, and also the country whose football team played against Croatia in a game attended by the host in Dallas.

Houston

A city in Texas visited by the host during his road trip across America before deciding to move.

Dallas

A city in Texas visited by the host during his road trip across America before deciding to move.

Norfolk, Virginia

A city in Virginia visited by the host during his road trip across America before deciding to move.

Lake Norman

A lake in North Carolina visited by the host during his road trip across America before deciding to move.

Croatia

The country whose football team played against England in a game attended by the host in Dallas.

Sofi Stadium

The stadium where Dan + Shay performed the national anthem for the World Cup opening, featuring a large LED wall.

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