How to Ask Better Questions from Tim Ferriss



To think means to ask questions. The form of questions that we ask matter because well-formulated questions can lead us to the answers we are searching for. The practice of asking questions, especially better questions, is becoming rare these days as people are more favoring answers than questions. We all want answers but we seem to forget that the only way to get better answers is by asking better questions. To understand what makes good questions, Tim Ferriss, the best-selling author, the host of podcast Tim Ferriss show, a modern day of Stoic philosopher, offers some practical tools on guiding us to be better at asking better questions.

These are some of the main points of the video:

    1. Ask questions that can be answered quickly and concretely

“Can it be answered relatively quickly? For instance, if you found someone you idolize in an elevator, Jimmy Fallon, if you asked Jimmy a question, could he come up with a really concrete answer in 5 second or less. If the answer is no, find a different question, for you or for other people. What is your favorite book for instance, not a good question, because people have read hundreds or thousands of books in many cases. But what book or books have you gifted the most to other people? It’s gonna be a short list. The search query is really refined. It’s fast click.

Much like asking yourself: what makes me happy? It’s not really a great question, too broad and takes too long to search. But let’s just say: what makes me feel most relieved after work when I get home?” […] Now it’s more refined and you can answer it much more quickly and is more actionable.

    2. Don’t ask questions that can be answered on Google

“A few things you should not do, if you meet someone who is, say, above your weight class in terms of professional development and you want to connect with them, don’t ask them questions that you can answer on google.”

   3. Avoid broad questions

“Don’t ask them really broad questions. They couldn’t conceivably answer quickly. What should I do? What advice would you give me for succeeding? These are not good terms. If you can’t define success, in say, 10 words or less, get rid of it, lose it from the question.”

At the end of the video, Ferriss, who has been asking hundreds of excellent questions on his podcast, says:

“And I would encourage you to strive to be interested in the form of good questions, if you seek to be perceived as interesting. Stop talking. Start thinking about questions. And then stop and listen.”

Ryan Holiday Reflects on How to Handle Rejections


Ryan Holiday. Via: (


Any inception of a creative project is physically and mentally laborious. There is often a gap between the initial idea and the final product. This sometimes makes us vulnerable, but there is nothing that makes us more vulnerable than being criticized, rejected, and misunderstood for the projects that we have created, despite our best efforts. When our projects have reached the audience, they are no longer ours. Instead, they now belong to the public. They will be judged and acted on by other people.

We cannot control what people think about our projects, but we can control how we want to perceive their criticisms. This is exactly the hard-earned wisdom that Ryan Holidays offers in his, heavily-researched, self-help book titled “Ego is The Enemy,” (Public Library) especially in one of the essays, The Effort is Enough.

In our world, which is addicted to glorifying the concept of success, Holiday lends us his sobering perspectives on seeing success as merely a reward and criticisms as something that falls beyond our control. What he preaches in this book is his argument on how to detach ourselves from the notion of success and move towards the work that we are called to do with an immense sense of vitality. Simply, this means to work hard. Once the work that we do is “leaving” our hands, it is up to the public to praise or reject.

This essay started off with a story of Belisarius, a man which Holiday considers as “one of the greatest yet unknown military generals in all of history.” Belisarius was an extraordinary man because of his ability to save Rome after the barbarians had taken it. Some of his major accomplishments were winning the wars at Dara, Carthage, Naples, Sicily, and Constantinople. He usually did not have a lot of men behind him and he often had to go to war against a riotous crowd of tens of thousands. His persistence and military strategy were impeccable.

However, that’s not the most significant characteristic in Belisarius that impresses Holiday. What makes him stand apart from any other historical figure is the way he gracefully handled extreme criticisms and mistreatment from his public after all the victories that he brought. Not only was he not rewarded for the good that he did, but he was often punished for it. Belisarius realized that public criticisms did not matter much, as long as he did his job well. He focused on what he could control, his energy, and ignored what he could not control, public criticisms.

Holiday writes:

“He was not given public triumphs. Instead, he was repeatedly placed under suspicion by the paranoid emperor he served, Justinian. His victories and sacrifices were undone with foolish treaties and bad faith. His personal historian, Procopius, was corrupted by Justinian to tarnish the man’s image and legacy. Later, he was relieved of command. His only remaining title was the deliberately humiliating “Commander of the Royal Stable.” Oh, and at the end of his illustrious career, Belisarius was stripped of his wealth, and according to the legend, blinded, and forced to beg in the streets to survive.


The person we don’t hear complaining about any of this? Not at the time, not at the end of his life, not even in private letters: Belisarius himself.


In his eyes, he was just doing his job–one he believed was his sacred duty. He knew that he did it well. He knew he had done what was right. That was enough.”


Belisarius Begging For Alms, 1781 – Jacques-Louis David. © Web Gallery of Art. Via: (


For Belisarius, doing his job was more than enough. This attitude is something that we need to cultivate. We need to focus on what matters, our effort and forget the public acclamation and criticisms.

Holiday goes on to write that our lives will be much enjoyable if we are not attached to outcomes. He writes:

“It’s far better when doing good work is sufficient. In other words, the less attached we are to outcomes the better. When fulfilling our own standards is what fills with pride and self-respect. When the effort–not the results, good or bad–is enough.

For some people, this art of practicing material non-attachment is not easy, especially for people whose ego always dictates their lives. The substance of this book is about how ego can ruin our paths of becoming who we want to be. Holiday sees the danger of ego:

“With ego, this is not nearly sufficient. No, we need to be recognized. We need to be compensated. Especially problematic is the fact that, often, we get that. We are praised, we are paid, and we start to assume that the two things always go together. The ‘expectation hangover’ inevitably ensues.”

Holiday, once again, admonishes us to not use external reinforcement to motivate us.

“Maybe your parents will never be impressed. Maybe your girlfriend won’t care. Maybe the investor won’t see the numbers. Maybe the audience won’t clap. But we have to be able to push through. We can’t let that be what motivates us.”

Drawing inspiration from the legendary basketball coach John Wooden and one of the greatest Roman Stoics Marcus Aurelius on this topic, Holiday writes:

“How do you carry on then? How do you take pride in yourself and your work? John Wooden’s advice to his players says it: Change the definition of success. ‘Success is peace of mind, which is a direct result of self-satisfaction in knowing you made the effort to do your best to become the best that you are capable of becoming.’ ‘Ambition,’ Marcus Aurelius reminded himself, ‘means trying your well-being to what other people say or do. . . Sanity means trying it to your own actions.'”

At the end of this essay, Holidays offers us one of the hardest reality truths that we need to embrace:

“The world is, after all, indifferent to what we humans ‘want.’ If we persist in wanting, in needing, we are simply setting ourselves up for resentment or worse.”

After everything that we have invested into our work–the countless nights of sleeplessness, vitality, love, thoughts–all we need to remind ourselves and each other is essentially coming back to this sentence, “Doing the work is enough.”