5 Questions Successful People Ask

Rich dad said, “The most successful people in life are the ones who ask questions. They’re always learning. They’re always growing. They’re always pushing.”

Conversely, rich dad said, “The losers in life think they have all the answers. They can’t learn because they’re too busy telling everyone what they know. They can’t grow because they’re too busy telling everyone else where they need to grow. They can’t push because they think they’ve already arrived.”

Over the years, I’ve taken rich dad’s lesson to heart and tried my best to always ask questions so that I can learn, grow, and push myself to become more successful. I do not take where I am in life for granted and I do not think I have all the answers.

This is why even though I hold financial education seminars, write books and articles, and speak with the media, I still go to many seminars, read many books, and pay attention to the news. I always have something to learn, and the world is full of teachers.

Over the years, I’ve learned that there are five questions in particular that the most successful people ask themselves. These are foundational questions that lead to all the other important questions we ask. You may recognize them, but I’m guessing you may not have asked them for a while — at least not deliberately.

The five questions are: Who, What, Where, When, and Why?

Who am I?

The ancient Greeks were a wise bunch. They produced the likes of Socrates and Plato, who’ve shaped philosophy for thousands of years. One of their maxims was simply, “Know thyself.”

Before you can be successful in life, you have to know who you are. Because as you become successful, many people will want you to become something you’re not. As the demands of life grow, if you’re not careful, your freedom declines.

Always be asking, “Who am I?” and stay true to yourself, not others’ expectations.

What do I love?

There’s an old maxim that says, “Write what you know.” My problem with this has been what if I don’t love what I know? Things will get boring pretty fast.

Rather than stick with what you know, discover what you love in life and pursue it with passion. By pursuing the things you love, all the other things in life will fall into order.

What you love will also define success for you. For some, family is success. For others, it’s a thriving business. By understanding what you love, you can adjust your priorities accordingly and achieve your definition of success.

Where can I grow?

Successful people are never content to stick with the status quo. Rather, they push themselves to grow. What areas of financial education can you grow in? How can you become a better partner in business and in life? How’s your health? Are you exercising and dieting? What are your financial goals for the next year? How can you achieve them?

Questions like these lead to establishing goals that push you past your comfort zone, allow you to grow, and help you become successful.

When should I act?

We should always be moving forward with our goals and financial education, but prudent people also plan, and they do so with the help of advisors. As the old proverb goes, “Without counsel plans fail, but with many advisors they succeed.”

Each year, Kim and I sit down and plan out our financial goals for the upcoming year. We then plan out the steps and timelines for those goals to break them down into measurable steps for success, and finally, we meet with our advisors to get their feedback and wisdom.

One story I’ve shared before is my Bentley fund. I wanted a new Bentley, and though I had the money to buy one outright, I instead developed a plan to buy assets that would provide cash flow to cover the cost of the new car. I worked closely with my advisors to establish this plan, and knew it would take about a year. Patiently, I executed each part of the plan, and in about a year, I had both a new cash flowing asset and a new Bentley. It took patience and knowing when to act, but the delayed gratification was worth the effort.

Why am I doing this?

Of all the questions listed here, “why” might be the most important. When I was in school, teachers hated the “why” question. Often this is because they didn’t have an answer. They were so busy telling us what to do that they rarely understood why. Such is the power of entrenched systems of thought.

The most successful people are mavericks who aren’t afraid to ask why, especially when everyone thinks it’s obvious.

I love this story of Steve Jobs told by Bill Lee:

Jobs is supposedly obsessed with every detail that goes into Apple devices. Not so. He focuses on the details relevant to the customer's experience. When one of Apple's design teams was tasked with developing a DVD-burning software program for high-end Macs, developers spent weeks putting together a plan. On the appointed day to present it to Jobs, they brought pages filled with prototype information, pictures of the new program's various windows and menu options, along with documentation showing how the application would work. When Jobs walked into the meeting, he didn't so much as look at any of the plans. He picked up a marker, went to a whiteboard and drew a rectangle, representing the application. He then told them what he wanted the new application to do. The user would drag the video into the window, a button would appear that said "burn," and the user would click it. "That's it, that's what we're going to make," he said.

While Apple’s developers were consumed with what they were doing (building DVD-burning software), Jobs was concerned with why they were doing it (to make life easy for the customer). One way of though leads to a product, the other leads to a fortune.

Successful people cut through the clutter and details of life to see clearly why they are doing something or why something should be done.

How long has it been since you’ve asked yourself these five questions? What ones have you particularly neglected?

This week, spend some time writing down your thoughtful answers to these five questions and start making the necessary adjustments in your life to live in harmony with your answers. Only then will you be on the path to success.

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