When Someone Brings You a Problem, Ask this

It sounds easy. It looks gentle. But it changes the entire dynamic of how people approach you, how they think, and how they grow.

So what do you think you should do?

It Builds Confidence

Many people come to you with a problem because they believe your answer is better than theirs. As soon as you ask this question, you hand the thinking back to them. You let them see that their judgment matters. Confidence does not grow from outsourcing decisions. It grows from making them.

It Trains the Mind

Most problems are not solved by knowing every fact. They are solved by understanding the options, the tradeoffs, and the impact. When you ask this question, you force the person to walk through these steps. They learn to think through consequences. They learn to compare paths. They learn to slow down and choose.

It Reduces Dependence

If you answer every question, people stop thinking for themselves. If you ask them what they would do, they begin to trust their own reasoning. Over time, you spend less time firefighting and more time guiding. The person becomes someone who brings you solutions, not crises.

It Reveals Their True Concern

Sometimes the problem they share is not the real issue. When you ask what they think they should do, you uncover what they are afraid of, what they are unsure about, or where they are stuck. You hear their reasoning. You see the gap. You know exactly where to help.

It Creates Ownership

The moment someone says what they think the next step should be, they take responsibility for it. They are no longer waiting for your instruction. They are taking action. Leadership is not given. It is practiced. This question helps people practice.


One sentence that captures the idea:
When someone brings you a problem, the smartest thing you can do is ask the question that sends the thinking back to them.

Not to avoid solving, but to help them grow, to help them reason, and to help them become the kind of person who knows what to do next time.

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.

The 95:5 Rule

The 95:5 rule

Have you heard of the 95:5 Rule? Based on research by Professor John Dawes, this rule states that at any given time, only about 5% of buyers are actively in-market for a particular product category. The remaining 95% represent future buyers who will enter the market when the need arises.

But what does this have to do with your career? Turns out, quite a bit.

Think of your career journey like a long hike. At any given point, you’re actively exploring a small number of opportunities – maybe 5% of what’s out there. These could be new roles within your company, a promotion you’re chasing, or skills you’re actively developing. This is your “in-market” 5%.

However, the vast majority of potential paths are not yet on your immediate radar. They represent the 95% of future possibilities that will become relevant as your circumstances and goals evolve over time. Just like a hiker can’t see the entire trail at once, you can’t pursue every career option simultaneously.

To make the most of the 95:5 Rule in your career:

  1. Actively invest in the 5% – Give your full energy to the opportunities you’re currently pursuing. Whether it’s crushing your current role, learning a new skill, or interviewing for a dream job, be “in-market” with gusto.
  2. Keep an open mind to the 95% – Don’t get tunnel vision. Keep scanning the horizon for new possibilities, even if you’re not ready to pursue them yet. This could mean attending industry events, growing your network, or simply staying curious.
  3. Trust in the journey – Just like a hiker has faith that the trail will open up new vistas, trust that your 95% of future possibilities will become clearer with each career step. Each role, project, and connection is shaping your path.
  4. Regularly reassess – As the “in-market” 5% shifts, periodically reevaluate your career priorities. Are you still energized by your current focus? Is it time to bring some of that 95% forward into active exploration? Pausing for self-reflection keeps you agile.

By embracing the 95:5 Rule in your career, you can balance active pursuit with open-minded exploration. Focus on the most impactful 5% while trusting that the 95% will continue to reveal new opportunities as you grow. Your career hike may be long and winding, but it’s all part of the adventure.