Fail Until You Don't

1. Embrace Failure as Information, Not an Endpoint

Fail. Learn. Repeat. Fail. Learn. Repeat. Keep failing, until you don’t.

Failure is information. The author argues that failure isn't bad; it's a necessary part of the process. Instead of fearing failure and avoiding trying, view setbacks as data points that teach you what doesn't work. This perspective allows you to learn and adjust your approach.

Winning by losing. The biggest winners are often the biggest losers because they try more things and learn from their numerous failures. The author's own journey is filled with rejections and missteps, from radio jobs to TV shows, but each one provided valuable lessons that eventually led to success.

Shift your mindset. Psychology research supports this view, highlighting the power of a "growth mindset" where you believe abilities can be developed through dedication and hard work, rather than a "fixed mindset" where talent is seen as the sole predictor of success. Embrace the struggle as a path to improvement.

2. Define Your Fight: Know What You Truly Want

If people keep saying no and you keep wanting it, that’s the definition of Fight-worthy.

Identify true desires. It's crucial to distinguish between goals you genuinely want and those you pursue due to external pressures or romanticized notions. The author uses examples like learning piano or a friend wanting to paint – if you don't put in the work despite having resources, you likely don't want it enough.

Actions reveal priorities. Your actions, or lack thereof, are the clearest indicators of what is truly important to you. If you consistently fail to prioritize something, it's probably not your real "Fight."

The Masochism Meter. A simple test for identifying your true Fight is whether repeated rejection makes you want it less or more. If being told "no" doesn't diminish your desire, you've found something worth fighting for.

3. Face Your Fears Head-On to Feel Alive

Being nervous is how I feel alive.

Fear is a signal. The author views nervousness not as a negative, but as a sign that something matters. Embracing this feeling is a "rush," a "mental bungee jump" that makes him feel alive.

Confronting biggest fears. The author shares his personal story of finally meeting his biological father after 30 years of avoidance. This act, driven partly by the desire not to be a hypocrite while writing this book, was his biggest fear and proved that facing it, while terrifying, was ultimately liberating.

Turn anxiety into adrenaline. Learn to manage nerves by acknowledging them and spreading the physical sensation throughout your body, rather than letting it concentrate and overwhelm you. This technique helps maintain composure and focus during high-pressure moments.

4. Accept That Not Everyone Will Like You

Repeat: sometimes people aren’t going to like you, and you can’t do anything about it.

Popularity isn't the goal. While being in entertainment might seem like it's all about being liked, the author learned that trying to please everyone is futile. From hecklers at comedy shows to online haters, negativity is inevitable when you put yourself out there.

Focus on authenticity. The author's experience of never quite fitting in (too country for pop, too pop for country) taught him the value of trusting his own instincts rather than chasing acceptance. This authenticity, ironically, can make you more relatable and likable to the right people.

Hate is noisy, love is silent. Negative feedback often feels louder than positive support. Don't fall into the trap of searching for the "negative needle" in a haystack of compliments. Focus on the positive and the work itself, not the opinions of those who don't matter.

5. The Grind: Discipline in the Mundane Daily Tasks

This is the Grind. It’s the dirty work.

Consistency over glamour. The Grind is the relentless, unexciting, everyday effort required to achieve your goals. It's waking up at 3 AM for a radio show you hate the timing of, or consistently doing small tasks that aren't glamorous but are essential.

Building blocks of success. Success isn't built on big breaks alone, but on the countless small, disciplined decisions made daily. These seemingly insignificant actions create the structure for your dreams, like bricks building a home.

Relentless repetition. The Grind is about taking the Fight and doing it again and again. It's the repetition that's hard, but it's also what separates those who succeed from those who give up.

6. Master the Art of Baby Steps for Big Goals

Ten miles is impossible, but putting one foot in front of another? That’s not so hard.

Avoid overwhelming yourself. Big goals can feel daunting and lead to inaction or anxiety. Break down your objectives into the smallest possible steps, making them manageable and less scary.

Focus on the next step. Like running "tree by tree" instead of focusing on the entire ten miles, concentrate only on the immediate task at hand. This approach alleviates anxiety and makes the process feel achievable.

Small wins build momentum. Achieving small, incremental goals provides quick successes that are encouraging and build momentum. This is crucial for maintaining motivation during the long Grind.

7. Sweat the Small Stuff: Details Build the Foundation

The details don’t just matter in professional settings. In fact, they probably mean even more in personal ones.

Details reveal character. The author looks at small details, like whether trash cans are overflowing or if someone is chronically late, as indicators of a person's attention to detail and discipline. These small factors add up and are better predictors of future success than impressive titles.

Consistency in the little things. Developing a disciplined approach to small, everyday tasks is crucial because if you can't get the little things right, you won't get the big things right. Examples include:

• Being on time for everything
• Preparing meals or clothes the night before
• Returning shopping carts

Impact of small acts. Small acts of kindness or discipline, like picking up litter or not getting angry at a waiter, reveal character and have a cumulative positive effect, both personally and on the world around you.

8. Build Resilience by Sucking It Up and Playing Hurt

Winners win because they play.

Hurt vs. Injured. The author distinguishes between being "hurt" (can push through) and "injured" (must stop). When you're only hurt, metaphorically or physically, pushing through builds mental toughness and a reputation for reliability.

The Ryman Auditorium story. The author recounts hosting a major charity show while severely ill and vomiting. Despite feeling terrible, he pushed through, performed, and even convinced Garth Brooks to sing, demonstrating the power of showing up even when you're hurting.

Consistency builds trust. Being dependable and showing up consistently, even when it's difficult, builds a reputation that benefits you in the long run. People know they can rely on you, and this opens up opportunities.

9. Learn from Mistakes, Especially Past Ones

Emotion is the worst when it comes to trying to figure out why something did or didn’t work.

Reflection requires distance. It's hard to objectively analyze failures when emotions are high. The author suggests stepping back and gaining perspective before trying to understand what went wrong.

Learn while doing. Knowing that failure is likely, try to learn as much as possible during the process. Pay attention to the steps you take so you can trace back and identify where things went wrong.

Look back strategically. Keep a list of past failures and revisit them when you're not emotionally invested. Analyzing older mistakes can provide clarity and lessons applicable to current challenges, helping you avoid repeating the same errors.

10. Repeat the Process, Even After Winning

Success doesn’t make doing the same thing over and over any less boring.

Winning isn't the end. Achieving a goal doesn't mean you switch to autopilot. To maintain success and stay motivated, you must continue to Repeat the Fight and the Grind, seeking new challenges and ways to improve.

Avoid complacency. Even in areas where you are successful, constantly seek to evolve and change things up to keep the process fresh and engaging. The author does this with his radio show, avoiding formulas and striving for something different each day.

Appreciate the wins. While the instinct might be to immediately move on to the next goal, consciously set aside time to appreciate your accomplishments. This helps prevent burnout and allows you to enjoy the fruits of your labor.

11. Leverage Your Network: Surround Yourself Wisely

Ultimately, being nice for no ulterior motive is the most self-serving thing you can do.

No one succeeds alone. Despite being a self-proclaimed loner, the author recognizes the critical role of others in the Fight, Grind, Repeat process. Cultivating relationships, both personal and professional, provides support and opportunities.

Invest in relationships. Treat relationships as long-term investments, putting in effort consistently rather than only reaching out when you need something. Genuine connection is more valuable than opportunistic networking.

Choose your circle wisely. Surround yourself with people who not only help you but also push you to be better. This might mean finding cheerleaders in areas where you lack confidence or honest critics in areas where you are strong.

12. Pay Your Debts: Be Reliable and Follow Through

A Lannister always pays his debts.

Promises matter. The author emphasizes the importance of following through on commitments, whether to others or to a higher power. Being reliable builds trust and character.

Snowball your obligations. Like paying off small financial debts first to build momentum, tackle small promises or obligations to build a reputation for dependability.

Learn from others' mistakes. Observing others who fail to follow through and the negative consequences they face can reinforce the importance of paying your debts, both literal and figurative.

Last updated: May 31, 2025