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Ryan Holiday Quote on Questions and How The Best Questions Lead To The Best Answers

“Tim Ferriss always seems to ask the best questions: What would this look like if it were easy? How will you know if you don’t experiment? What would less be like? The one that hit me the hardest, when I was maybe 25, was, ‘What do you do with your money?’ My answer at the time was ‘Nothing, really.’ Okay, so why try so hard to earn lots more of it?”

Ryan Holiday, Medium

Beyond the Quote (269/365)

The first and last questions listed above were the ones that hit me the hardest: “What would this look like if it were easy?” and “What do you do with your money?” The thing about asking better questions is that they lead to better answers. When you can become the person who asks “the best questions” then you’ll inevitably start getting the best answers—answers that never occur to most people because their minds aren’t even looking in the right places. And the people with the best answers are the ones who almost always get the best results.

Tony Robbins often refers to the following question that most people ask themselves during hardship to illustrate this point: “Why do bad things always happen to me?” That type of question is only ever going to pull a very specific type of answer. Can you see it? Answers that, no matter how hard you try or how deeply you think, will always lead you to suboptimal thinking and a poor state of mind. How could they not? Your answers are going to have to justify why you were selected for bad things to happen or will only justify shitty occurrences.

What’s a better question to ask during hardship? Tony suggests asking yourself, “What good can come from this?” And THAT’S a question that can bring about completely different results. Even suboptimal answers to a question like that are going to far supersede even amazing answers to, “Why me?” So, when Ryan Holiday points out that Tim Ferriss seems to be asking the best questions, it should be noted that that is no easy feat and that Tim Ferriss might be a character that you should look deeper into. How else to discover great questions? I digress.

Now that we understand the importance of asking better questions, onward to the first question that hit me the hardest: “What would this look like if it were easy?” The most recent example I have that illustrates the power in this question can be illustrated with my daily writing practice. This time last year I was hyper focused on creating video content. I knew that good video content performed much better on social media than straight text content. So I doubled down on it. After several months, however, it turned out to be WAY more effort that it was worth for a one man show.

I had to not only come up with the original content for the videos, but I had to then record (which required proper cameras, lights, microphones, backdrops, outfits), edit (which required video editing software, editing skills, time for editing), optimize (which required typing out captions, changing the video dimensions for each social platform, create an eye-catching thumbnail), and share (which required hash-tagging, seo-optimizing, description editing). Eventually, I asked myself the Tim Ferriss question: “What would this look like if it were easy?” and I decided to shift directions.

The options I came up with were either a) It would be easier if I hired help to manage the different above mentioned tasks; b) I could do less and take a hit on quality; or c) I should shift my focus. I decided against hiring help and against a sacrifice on quality and thought it would make the most sense for me to cut out all of that fluff that happened AFTER the original content was made and use that time to just make more original content. And that’s what I did. All of that time that I would usually be spending recording, editing, optimizing, and sharing, I now was spending writing, writing, writing, and writing. And I couldn’t be happier with how things have played out since then. What used to be one post a week and hours and hours of video editing is now seven posts a week in text form. It’s easier and more true to what I really want to be doing anyway.

As for the second question: What do you do with your money? My experience while answering this questions was much the same as it was for Hoiday—“not much.” I pay my bills, buy food, and sometimes purchase items for myself. I’m not interested in the superfluous. I’m interested in paying off what I have, investing in experiences, and saving for a rainy day. So, like Holiday, I decided I’m not going to kill myself to make a whole lot more money. I’m going to keep my focus on what I love doing and I’m going to get really damn good at it. So good that, in theory, the rest will take care of itself. How about you? What do you do with your money? What would less be like? What would it look like if it were easy? How soon can you start? What good can come from this? …Good luck.


Read Next: Questions. The Ultimate Mind Hack?


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Matt Hogan — Founder of MoveMe Quotes

Written by Matt Hogan

Founder of MoveMe Quotes. On a mission to help busy people do inner work—for better mental health; for healing; for personal growth. Find me on Twitter / IG / Medium. I also share daily insights here. 🌱

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