9 Important Questions Successful People Ask Themselves (Because They Work)

The quality of our questions determines the quality of our lives.

A few years ago, before I started my company, I was in a dreary situation that I didn’t know how to get out of. I wasn’t passionate about the work that I was doing, I wasn’t surrounding myself with the right people, and I felt like a hamster running in circles.

I didn’t realize it back then, but this was largely because I wasn’t asking myself the right questions. Instead of asking, “How can I improve this situation?”—I was asking “Why is this happening to me?” You can probably see that this only left me with more issues to deal with, rather than solutions.

I finally got around to understanding that the common trait of successful people in all walks of life is that they master the skill of asking really good questions.

The following nine have dramatically changed my life (and a few are even asked by some of the most successful leaders today).

1. What Would This Look Like if it Were Easy?

This is a question I got from Tim Ferriss, who’s the bestselling author of The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich. As humans, we have this natural tendency to over-complicate situations or problems when they don’t need to be.

The question I’ve been training myself to always ask is, “How can we simplify this?” This question alone has saved me hundreds of wasted hours hiring new staff.

2. If This Was My Last Day on Earth, Would I Be Proud of This?

This question isn’t meant to bring me down, but to be used as a reality check. I leverage it as a motivator to push myself to do my best work every day, and to treat people with the respect they deserve.

3. What’s On the Other Side of Fear?

This question poses two different outlooks for me. The first is that we usually exaggerate our fears to be bigger than they actually are. When we fear going on stage to speak in front of a crowd, or tell someone how we really feel, the likelihood of something going terribly wrong is nearly 0%.

The second way I use this question is to remind myself that whenever I feel stressed or fearful of doing something, it’s usually the most important thing I need to do. Whenever I feel uncomfortable taking on a task, conversation, or decision, it’s a trigger that I should actually get it done right away.

4. Is This a “Hell Yeah?”

One of Derek Sivers’ most popular articles to date is about what he calls, “hell yeah or no.”

The idea of this phrase is that when you’re feeling overstretched or spread too thin, it’s because you’re saying “yes” to too many things. The result is that we overcommit to a lot of “good” opportunities without leaving room to focus on the “great” ones. Asking yourself this question will force you to say “no” to nearly everything, and will open up new opportunities that really excite you.

5. What’s the One Thing I Could Do That, If Completed, Everything Else Becomes Easier or Unnecessary?

This idea comes from the book, The ONE Thing: The Surprisingly Simple Truth Behind Extraordinary Results by Gary Keller, which has drastically changed the way I manage my time. In simple terms, the one thing refers to identifying your lead domino in whatever you’re trying to accomplish.

As Sivers’ question points out, it’s often more important to choose what not to do, so we can focus on what’s truly important.

6. If Not Now, When?

This question has been used by several thought leaders, but it was popularized by Eckhart Tolle, author of The Power of Now: A Guide to Spiritual Enlightenment.

I ask myself this question whenever I find myself putting off an important decision or task. By asking “when” at the end, it forces me to come up with a specific time that I will complete something instead of telling myself “someday” (which may never come).

7. How Do I Protect the Downside?

When you observe many of the most successful entrepreneurs, they’re not big risk-takers that believe in “going big or going home.” They’re quite risk-averse in fact, and are always trying to protect the downside whenever they can. In your career and in life, the best way I’ve found to mitigate your risk is to prepare for them before they arise. Creating a habit of asking this question has helped us plan for worst-case scenarios and frankly, it helps our team sleep better at night.

8. Is This What Actually Happened, or Is This My Own Story?

Much of what we think is not actually what happened, but it’s a story we’ve crafted in our own minds.

It’s not our fault necessarily, because all we have is our previous experiences to refer to. I would find myself stuck in my limiting beliefs when things didn’t go my way, and it became a self-fulfilling prophecy.

It’s important in our careers to do our best to remove emotional decision-making as much as possible, and rely on the data and information at hand instead.

9. What if I Did the Opposite?

This is one of my favorite questions ever. It’s a constant reminder that in order to truly do anything that’s impactful, it needs to be different than what anyone else is doing or has done.

It’s always worth questioning whether the traditional approach is actually the best way, or if it appears that way because everyone else is doing it. I’ve found that more times than not, it’s the latter.

This article was originally published on Rype App. It has been republished here with permission.

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Daily Muse
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