The Jockey Over the Horse Strategy

In the exhilarating world of horse racing, the common advice is “Don’t bet on the horse, bet on the jockey.” This intriguing slogan, as depicted in the vivid image for JMR Racing, transcends the racetracks to offer profound advice for careers, wealth management, and networking.

Don’t bet on the horse, bet on the jockey Strategy

Why Bet on the Jockey?

The jockey in horse racing is akin to the pilot of a ship or the CEO of a company. While the horse’s quality is undeniable, it is the jockey who understands the course, makes strategic decisions in real-time, and adapts to changing conditions during the race. Similarly, in your career and investment decisions, it’s crucial to focus not just on the opportunities themselves (the “horses”) but also on the people involved (the “jockeys”) who drive these opportunities toward success.

Choosing the Right Mentors and Leaders

In your career, consider the leaders and mentors you follow as your jockeys. Their guidance and wisdom can steer you through the complexities of the professional world. A skilled mentor reads the situation, anticipates challenges, and navigates through them, effectively guiding their protégés. Choosing a mentor is less about their position and more about their capability to guide you towards your career objectives, just as a bettor would choose a jockey who understands how to maximize their horse’s strengths.

Investing in People, Not Just Portfolios

When it comes to wealth management, the principle of betting on the jockey applies to choosing fund managers, entrepreneurs, or financial advisors. Their track record, decision-making process, and adaptability in various economic conditions are crucial. An adept financial “jockey” knows when to be aggressive, when to pull back, and how to manage the resources at their disposal to secure the best outcome for their stakeholders.

Building High-Value Connections

Networking, much like horse racing, is dynamic and requires a keen understanding of the environment. In this analogy, the “jockey” could represent either you or the people you connect with. Networking effectively means knowing your strengths and how to leverage them, but also recognizing and aligning with those who can change the course of your career or business. High-status networks, like experienced jockeys, bring nuanced skills and deep understanding, turning ordinary opportunities into wins.

A Story of Strategic Partnership

Consider the story of Alex and Jordan, two aspiring entrepreneurs. Alex, much like a thoroughbred with potential, had a revolutionary business idea. However, it was Jordan, skilled in navigating the start-up ecosystem, who brought in the strategic know-how. Jordan’s understanding of when to seek funding, pivot the business model, or introduce the product to market was critical. Together, they raced towards success, with Alex’s idea being the horse and Jordan’s strategies acting as the decisive jockeying skills.

Just as in horse racing, where the choice of jockey can make all the difference, in life and career, the people you align with—whether mentors, financial advisors, or network contacts—can dramatically influence your success trajectory. “Don’t bet on the horse, bet on the jockey” is a reminder of the power of human insight, expertise, and decision-making in navigating the racecourses of careers, wealth, and networks. Choose your jockeys wisely, for they are often the true drivers of outcomes in the game of life.

How will you measure your life?

Balancing Achievement and Fulfillment:
Christensen’s work emphasizes the delicate balance between career achievement and personal fulfillment. He suggests that while professional accomplishments are measurable and visible, personal satisfaction is often less tangible but equally important. The key lies in defining what success truly means on a personal level and aligning it with one’s professional goals.

How will you measure your life?

Investing in Relationships:
One of the central tenets of Christensen’s book is the significance of investing in relationships. He argues that strong personal relationships are the most substantial source of long-term happiness. For executives, this might mean reevaluating priorities to ensure that relationships with family, friends, and community are nurtured alongside career aspirations.

The Danger of Marginal Thinking:
Christensen cautions against marginal thinking – making decisions based on short-term gains rather than long-term values. This approach can lead to compromises in both personal integrity and life goals. For leaders, maintaining a steadfast focus on core values and long-term objectives is crucial for true success.

The Motivation Factor:
Understanding what motivates us is another critical aspect. Christensen points out that motivation often comes from intrinsic rewards – the sense of satisfaction from the work itself – rather than extrinsic rewards like money or status. Leaders need to identify what intrinsically motivates them and their teams to foster a fulfilling work environment.

Creating a Personal Strategy:
The concept of developing a personal strategy is pivotal in Christensen’s philosophy. Just as businesses require strategic planning to thrive, individuals need personal strategies to achieve their life goals. This involves setting clear objectives, understanding the resources available, and regularly reviewing and adjusting these plans.


“How Will You Measure Your Life?” offers a reflective and strategic approach to life’s biggest decisions. For executives and leaders, Christensen’s insights provide a framework for aligning professional achievements with personal fulfillment. By focusing on what truly matters, leaders can navigate their lives with purpose and satisfaction, creating a legacy that transcends professional success. This book is not just a guide to living but a reminder of the values that define a truly successful life.

Six Thinking Hats Framework

Always approach problem-solving using the Six Thinking Hats framework, which is a valuable tool for examining issues from various perspectives:

  1. White Hat (Facts and Information): Start by gathering all the available data and facts related to the problem. What do we know?
  2. Red Hat (Emotions and Feelings): Consider the emotional aspects of the problem. How do you and your team feel about it? What are your initial gut reactions?
  3. Black Hat (Critical Thinking): Analyze the potential drawbacks, risks, and challenges associated with the problem. What are the potential pitfalls and obstacles?
  4. Yellow Hat (Optimism and Positivity): Focus on the positive aspects and opportunities that may arise from solving the problem. What are the potential benefits and solutions?
  5. Green Hat (Creativity and Innovation): Encourage creative thinking and brainstorming for new ideas and solutions. What innovative approaches can you explore?
  6. Blue Hat (Process Control): Finally, take control of the thinking process. Summarize the insights gained from the other hats, prioritize actions, and outline a plan to address the problem. What’s the next step?

By systematically examining the problem from these different angles, you can arrive at a well-rounded and thoughtful solution.

Six Hats framework