Fail Fast, Fail Often

Success isn’t about avoiding failure—it’s about embracing it and learning along the way.

1. Fear of failure keeps us trapped in unfulfilling lives

Most people feel stuck in their lives because they are afraid to try something new and fail. This "not-yet" mindset makes us postpone action indefinitely while waiting for the perfect plan or the right moment. Meanwhile, life passes us by.

Instead, we should find happiness in the present by taking small steps toward change. This can start with simple activities like pursuing hobbies or moments of joy. Even small pick-me-ups, like a brief walk in nature or a soothing ritual, can improve how we feel and behave.

Success often follows seizing opportunities instead of waiting for perfect plans. Gary Erickson started the Clif Bar company after feeling dissatisfied with the energy bars he ate during his cycling trips. His spontaneous decision to create tastier, natural bars led to an internationally successful brand.

Examples

• Doctors who cheered themselves with candy made better decisions at work.
• Erickson launched Clif Bars based on a cycling experience instead of a detailed business plan.
• Waiting endlessly for "not-yet" moments turns into passive living.

2. Fun fuels happiness and unexpected achievements

Living a fun life doesn’t just make us happy—it can also lead to surprising achievements. When people pursue enjoyable activities, they often find fresh energy and open new doors.

Consider Madison, a legal assistant unhappy with her work. By starting a drama club—a fun outlet for her love of acting—she found fulfillment and a second career as an acting coach. Adding fun to daily life increases optimism, creativity, and even professional opportunities.

Research suggests maintaining a 3:1 ratio of positive to negative experiences benefits emotional health. Small but intentional joys, such as savoring morning coffee or calling a friend, are steps toward building this ratio. Knowing where you have the most fun, using a "fun map," helps focus energy on rewarding places and activities.

Examples

• Madison created a drama club while stuck in a corporate rut, eventually leading to her dream profession.
• A 3:1 ratio of pleasant to unpleasant moments supports emotional resilience.
• Regularly revisiting places of joy helps anchor a life full of enjoyable experiences.

3. Failure is a practical tool for improvement

While fear of failure is widespread, it’s often the most direct route to mastery. Trial and error allow people to make swift corrections and develop new skills with hands-on learning.

A pottery teacher once split students into two groups: one focused on creating flawless pots, the other on making as many as possible. Surprisingly, the quantity group produced higher-quality pots, as they improved with every attempt. Mistakes, far from being setbacks, were essential steps toward excellence.

Major successes often involve initial failures. Comedian Chris Rock tests his jokes with small audiences, allowing some to flop, before presenting tight, refined routines on bigger stages. Similarly, Howard Schultz learned from early issues to build a better Starbucks.

Examples

• A pottery group making more mistakes learned faster and created better work.
• Chris Rock uses small audiences to weed out underwhelming material.
• Howard Schultz adjusted early Starbucks menus after initial failures.

4. Embracing beginner status leads to growth

Trying something new often feels awkward or intimidating. People worry about looking bad compared to their experienced peers. Yet the only real failure is not trying at all.

Fear of looking foolish guarantees missed chances. Whether it’s applying for a promotion or speaking to someone new, letting fear dictate decisions removes any chance of success. Beginners, by contrast, learn unique lessons that enrich their understanding of themselves and their interests.

Discovering what doesn’t work offers clarity. For example, someone starting martial arts might realize they dislike high-contact classes but enjoy related disciplines like tai chi. Each attempt provides insights, connections, and pathways to unexpected opportunities.

Examples

• Avoiding a career move out of fear of failure blocks personal progress.
• Taking up martial arts introduces new interests and friendships.
• Stepping out of the comfort zone fosters discovery and confidence.

5. Reignite curiosity to enhance daily experiences

Children are naturally curious, asking endless questions to explore the world. Adults, however, often stifle their curiosity through fear of irrelevance or failure. This limits their ability to discover new joys and insights.

Staying curious opens doors to personal and professional growth. For instance, Steve Jobs combined interests in spirituality, art, and technology. Instead of sticking to narrow expertise, his wide-ranging curiosity drove Apple’s revolutionary designs.

People often avoid exploring hobbies out of insecurity. One example from the book involved a woman who wanted to learn guitar but doubted it was worth the effort. If she had allowed her curiosity to lead, even trying briefly could have enriched her life.

Examples

• Steve Jobs pursued a broad range of interests to develop innovative products.
• Children instinctively unlock discoveries by being curious.
• Picking up a new skill, like learning guitar, satisfies untapped potential.

6. Break large goals into small, manageable steps

Setting ambitious objectives is important, but achieving them requires breaking them into smaller, doable tasks. Tackling everything at once often feels overwhelming and leads to failure.

Allan, a man struggling with obesity, aimed to lose 30 pounds and run a marathon within a year. By taking on too much, he burned out and gave up quickly. Instead, starting with lighter exercises and gradually building intensity might have allowed him to succeed over time.

A series of smaller wins builds momentum. People who focus on hitting tiny milestones, like walking 30 minutes a day, find it easier to stay motivated and committed.

Examples

• Allan’s overly ambitious health goals caused his quick burnout.
• Breaking down goals fosters pride and momentum.
• Approachable steps maintain motivation better than drastic changes.

7. Test-drive careers before committing to them

Commencing a career without experiencing it firsthand is comparable to agreeing to lifelong commitments without knowing compatibility. Many people regret staying in jobs that make them unhappy because they feel chained by prior decisions or years of education.

The author met a chemist who had studied for over ten years but loathed his work. He felt trapped by his time investment, ignoring that he could still try new fields. People should proactively sample roles before deciding whether they’re a good fit.

Take internships, volunteer spots, or shadowing opportunities to experience jobs without long-term risk. These exploratory steps foster clarity about what kind of work feels right.

Examples

• A chemist stuck in an unfulfilling job felt unable to change due to sunk costs.
• Test-driving careers prevents people from feeling locked into bad choices.
• Internships reveal career paths you might not have anticipated.

8. Build meaningful communities, not just networks

The people you surround yourself with profoundly influence your life. Being part of a community creates mutual encouragement, unlike conventional networks that involve impersonal exchanges.

Communities revolve around shared goals or natural connections. Steve Jobs thrived because he recruited people who shared his vision and work ethic. They supported his creative risks and growth.

By joining communities aligned with your interests, whether human rights groups or entrepreneurial forums, you gain inspiration and practical help along your journey—and provide it in return.

Examples

• Steve Jobs thrived within a community of like-minded innovators.
• Friends or groups you admire amplify your behaviors and values.
• Helping others within a shared community strengthens mutual bonds.

9. Take risks to live a richer life

Ultimately, life is richer when you step outside your comfort zone. Risks and failures teach lessons that cautious living cannot. Without them, new experiences and successes remain out of reach.

Avoiding risk can lead to regret over what was never attempted. Embracing failure allows you to constantly grow. Whether starting a project, fostering relationships, or simply taking that first leap, trying is always better than holding back.

The author’s message is simple: rather than fearing failure, see it as an essential part of a rewarding existence.

Examples

• Taking calculated risks leads to personal and professional breakthroughs.
• Regret over avoided risks often outlasts fear of failure.
• Failing forward creates momentum for future successes.

Takeaways

1. Create a "fun map" of places or activities that energize and inspire you, then focus on incorporating more of them into your routine.
2. Test out hobbies, skills, or career paths through small experiments to eliminate fear of commitment and discover new interests.
3. Build a supportive community by finding like-minded people who encourage and enrich your pursuits.