Welcome to Fail Files 👋

Failure. We all hate it. It’s a messy, uncomfortable truth… That can ultimately lead to progress. You can learn so much from failing—sometimes more than from winning. So let’s reframe it together.

Failure isn’t always pretty, and sometimes it’s harmful. But it’s often in those very moments that we learn the most. Even when the failure feels off-track or unjust, there’s usually something we can take away from it.

Failure is essential for growth, even foundational to success.

Each week, Fail Files breaks down a failure that matters. Whether it’s a personal mistake, a systemic collapse, or a business flop, we’ll dig into the lessons that can help us rethink what’s next.

Ready to explore failure and where it can take us? Let’s go!

This week I wanna talk about two “failures”, and what we can learn from them.

1) Selena Gomez cries on social media because of recent deportations. #epicfail?
2) Doechii goes from being unemployed in 2020 to Grammy award-winner in 2025.

1. Selena Gomez

🤷🏽‍♀️ W T F H A P P E N E D ?

Selena Gomez posted a video on Instagram where she was visibly emotional and crying, expressing her distress over immigration raids ordered by the Trump administration. These raids targeted undocumented immigrants in several major U.S. cities. While they were supposed to focus on those with serious criminal records, many of those arrested were simply undocumented, which is a civil offence, not a crime. Some of those detained were even U.S. citizens or members of Native American nations. Gomez's video was criticized for appearing performative and lacking substantive action.

🧠 L E T ’ S A N A L Y Z E

Why is this kind of a fail?:

• Symbolic vs. Substantive Action: Emotional displays, such as crying on social media, can raise awareness but often lack the tangible impact that actions can achieve. People with significant influence and resources can drive real change, and relying solely on emotional expression can seem performative.

• Expectation of Leadership: Celebrities and influential figures are often considered leaders in social movements. When their response is primarily emotional, it can be perceived as a lack of leadership or commitment to the cause, especially when they have the means to contribute more effectively.

• Potential for Influence: With a vast platform and financial resources, individuals like Gomez have the potential to mobilize support, fund initiatives, and advocate for policy changes. Failing to leverage these resources can be seen as a failure to utilize their position for the greater good fully.

✅ A C T I O N I T E M S

What she should/could have done instead (or in addition to) her first reaction:

• Direct Financial Support: Gomez could have donated to organizations that provide legal aid and support to immigrants, such as the National Immigrant Justice Center or the Immigrant Justice Campaign.

• Amplify Resources: Use her platform to share resources and information about immigrant rights and legal assistance, directing her followers to credible organizations and content creators.

• Advocacy and Awareness: Craft and share statements, give interviews and use her influence to advocate for immigration justice.

• Leverage Her Influence: Collaborate with other public figures to create a more significant impact and mobilize her fanbase towards actionable support for immigration issues.

Should we get to the more uplifting story now?

2. Doechii

🤷🏽‍♀️ W T F H A P P E N E D ?

In 2020, Doechii, a young Black woman and aspiring artist, faced a significant setback when she was fired. This was a critical blow, as she had no financial safety net or family wealth to rely on. Often challenging for those without connections or resources, the music industry seemed an insurmountable barrier. Homeless and without income, Doechii found herself at a crossroads, captured poignantly in a viral video where she expressed her heartbreak and determination to keep pushing forward.

🧠 L E T ’ S A N A L Y Z E

Before being discovered, Doechii was relentless in pursuing a music career despite the odds stacked against her. She spent countless hours honing her craft, writing music, and performing at local venues whenever possible. She utilized social media platforms to share her music and connect with a broader audience, building a grassroots following.

Her dedication to her art was evident in her willingness to take on any opportunity that came her way, no matter how small. She networked tirelessly, contacting industry professionals and other artists and seeking advice and collaboration opportunities. Her breakthrough came when she decided to visit various music studios, offering to work as an intern to learn more about the industry and showcase her talent. This proactive approach eventually led her to Anthony “Moosa” Tiffith Jr., the president of Top Dawg Entertainment (TDE), who recognized her potential and encouraged her to move to Los Angeles.

By 2022, she was signed to TDE, and her debut mixtape, "Alligator Bites Never Heal," was released. This work, deeply personal and reflective of her struggles, resonated widely and led to her historic win of the Best Rap Album at the 67th Grammy Awards. Her journey to sobriety and faith played crucial roles in her success, as highlighted in her heartfelt Grammy acceptance speech.

✅ A C T I O N I T E M S

Doechii's journey offers some real, hard-earned lessons:

• Use Adversity as Fuel: When you're at rock bottom, like Doechii was, use that desperation as a driving force. It's not about waiting for the right moment but creating it when everything seems against you.

• Hustle Relentlessly: Opportunities rarely come knocking. Doechii didn't sit back; she actively sought every chance to get her foot in the door, even if it meant working for free. This kind of hustle is crucial when you're starting with nothing.

• Own Your Story: Your struggles and experiences are powerful. Doechii's music connected because it was raw and honest. Don't shy away from your truth; let it be the foundation of your work.

• Break the Mold: The system isn't always set up for people like you. Doechii didn't let that stop her. She pushed through barriers and redefined success on her terms. Challenge norms and create your path.

• Be a Beacon for Others: Remember those still struggling as you climb. Doechii's story is a reminder that success isn't just personal; it's about paving the way for others who face similar challenges. Use your platform to make a difference.

Thanks for reading our 38th issue. 🚀

Remember: failure isn’t the end; it’s a moment to pause, reflect, and evolve. Every breakdown carries the potential for breakthrough, and every failure is an opportunity for growth.

So, what did you learn from today’s failure? How will you use it to move forward, shift your perspective, or take action?

Let us know—your insights are part of the bigger picture. Until next time, keep exploring, keep learning, and keep evolving.

And most importantly, DON’T be afraid of failure, babe; welcome it.

Have a great week,

Shiv 💁🏽‍♀️