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The Uncomfortable Simplicity of Success: STOP BEING A PEOPLE PLEASER

Gary Vaynerchuk, commonly known as Gary Vee, is an American businessman, author, speaker, and internet personality. He is a co-founder of the restaurant reservation software company Resy and Empathy Wines. First known as a wine critic who expanded his family's wine business, Vaynerchuk is now more known for his work in digital marketing and social media as the chairman of New York–based communications company VaynerX, and as CEO of VaynerX subsidiary VaynerMedia.

In a world obsessed with complexity, Gary Vaynerchuk, a serial entrepreneur and internet personality, presents a counter-narrative: the path to success is uncomfortably simple. The video underscores the importance of self-awareness, the courage to face judgment, and the need to redefine success. This article aims to dissect Vaynerchuk’s philosophy, offering actionable insights for those willing to challenge traditional notions of success.

Key Takeaways

  1. The Simplicity of Success: Success, whether in life or business, boils down to basic principles that people often overlook in favor of quick fixes.
  2. Judgment as a Barrier: The fear of judgment, whether from anonymous online users or close family, often holds people back from pursuing what they genuinely want.
  3. Redefining Success: Society’s current definition of success is skewed towards financial gain, leading to a cycle of unhappiness and unfulfillment.
  4. The Power of Storytelling: Narratives and analogies can serve as powerful tools to shift perspectives and inspire action.
  5. The Importance of Self-Awareness: Understanding one’s strengths and weaknesses is crucial for both personal and professional growth.

The Uncomfortable Simplicity

Gary Vaynerchuk starts his talk by highlighting the uncomfortable simplicity that underlies most challenges, whether in business or personal life. He likens it to a health conference where the solution to better health is simply to eat better and exercise. Yet, people look for quick fixes, from fad diets to performance-enhancing drugs, avoiding the basic, effective solutions. This avoidance often stems from an unwillingness to face the uncomfortable truths about what it takes to succeed.

The Fear of Judgment

One of the most significant barriers to success, according to Vaynerchuk, is the fear of judgment. This fear spans a spectrum, from anonymous online trolls to close family members. People are often paralyzed by what others might think or say, leading them to make choices that are safe but unfulfilling. Vaynerchuk argues that the key to overcoming this fear is to start the process of genuinely being able to handle judgment. The goal is not to win the approval of others but to live authentically, regardless of external opinions.

The Edges of Life

Vaynerchuk emphasizes that life is a “game of the edges.” People often focus on the middle 90-99% of their lives, ignoring the edges that actually matter. These edges are the extreme ends of our social and emotional spectrums, the people and things we care about the most and the least. Once you understand and manage these edges, you can live more freely, unburdened by the judgments and expectations of others.

Redefining Success

The current societal definition of success is heavily skewed towards financial gain. This perspective is not only unrealistic but also damaging, leading to a cycle of unhappiness, depression, and unfulfillment. Vaynerchuk argues for a redefinition of success centered around happiness and self-fulfillment. He points out that even a $440,000 annual income puts you in the top 1% of American earners, challenging the notion that “making it” means earning millions.

The Power of Storytelling

Vaynerchuk believes in the transformative power of storytelling. He uses narratives and analogies to present his ideas, aiming to catch people at the right moment with the right message. Storytelling serves as a tool to shift perspectives, challenge existing norms, and inspire action. It’s not about convincing others to adopt his viewpoint but to offer a different lens through which they can view their own lives.

Self-Awareness: The Ultimate Asset

Understanding one’s strengths and weaknesses is crucial for both personal and professional growth. Vaynerchuk stresses that while skills can be taught and improved upon, natural talent sets the upper limit of what one can achieve in a particular field. Self-awareness allows individuals to focus on what they are genuinely good at, rather than pursuing paths that society deems valuable but are not personally fulfilling.

The Thrill of the Hunt

Vaynerchuk concludes by sharing his personal love for “the hunt,” the process of striving for success. Whether it’s garage sailing for hidden treasures or building multi-million dollar businesses, the journey itself is the reward. This perspective liberates one from the fear of failure and judgment, allowing for a more authentic, fulfilling life.


Gary Vaynerchuk’s philosophy offers a refreshing perspective on success, challenging societal norms and encouraging individual authenticity. By addressing the uncomfortable simplicities, facing our fears of judgment, and redefining what success means to us, we can pave the way for a more fulfilling, happier life. It’s not about the destination but the journey, and understanding this can be the first step towards true success.

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