Tim Ferriss Illustration by Lizabeth

5 Admirable Questions You Can Get From Tim Ferriss

Want a quicker way to think creatively today?

Ask yourself better questions.

I’ve recently read Tim Ferriss’s eBook 17 Questions That Changed My Life which you can download for free at his website (recommended).

Known as an investor and self-described human guinea pig, Tim’s written one or two popular books about taking four hours to do anything and how to become a world-class performer using smart habits, savvy routines, and wise tactics.

After reading this short eBook and implementing one of the questions he suggested, I stopped procrastinating about getting my work done and enjoyed the process more (hint, it was the fifth bullet point below).

Tim is great with What If questions, a habit of divergent thinking that will naturally get you more creative, imaginative, and productive.

So, I’ve distilled my top five favourite questions inspired by Mister Ferriss as a quick reference guide for you to take advantage of throughout your working day, plus give you some food for thought.


Five Questions from Tim Ferriss

# 1: What if I did the opposite for 24 hours?

Begin by considering some habits that may no longer be serving you, for example:


  • What if I drank fruit cocktails instead of beer and wine?
  • What if I listened instead of talking all the time?

Then move on to consider the “What if I did the opposite?” question for your working and creative life.


  • What if I wrote only short-form articles for a week?
  • What if I painted only outdoors for a month?
  • What if I worked from 5 pm until 10 pm instead of in the daytime?

You get the idea. I believe this question needs to be inside everyone’s better thinking toolkit.

Just don’t do anything stupid with it.


# 2: What tasks would I focus on and prioritise if I could only work two hours each week on my side hustle or creative project?

Bring in the laser for this one.

It takes some intense concentration to brutally look at where you might be wasting time and which activities give you the most negligible results.


# 3: What should I put on my “Not-To-Do” list?

Many people are addicted to their “To Do” lists while pursuing better productivity and endless goal setting. Therefore, it’s a cracker of an idea to turn it around.

So, try creating a “Not to Do” list for yourself instead.


# 4: What would this look like if it were easy?

I love this question, being someone who unashamedly acknowledges their talent for “complicating what is uncomplicated” in my quest for perfection.

Asking this question of a boring situation can also help you shift your perception around any negative attitudes and decide to enjoy what you are doing.

Or else, it can help you acknowledge your abilities, that you can do stuff without it being perfect, and that’s okay.


“If I feel stressed, stretched thin, or overwhelmed, it can be because I’m overcomplicating something or failing to take the simple and easy path. Instead, feeling I should be trying “harder.”

~ Tim Ferriss

#5: Am I hunting antelope or field mice?

Many people are excellent at being efficient, so good in fact that they are often exhausted, overwhelmed and confused through overwork.

What if you slowed down and focused more on the big picture, what’s most important, and put your energy into the twenty per cent of the work that will give you eighty per cent of the results instead.


“Try shifting your current perception to focus on the big things and let the little stuff slide.”

– James Carville.

Completing The Process

“What If” questions are ideally part of a three-step thinking cycle that goes like this:


  1. First, I complain about something: Why can’t I do this? Why does it have to be this way?
  2. Second, I notice the issue is not serving me: I move forward with a “What if?” question.
  3. Third, I take action by creating a possible solution. I further inquire: “How might I do this?” or “How might this work?”

The action takes us from mere dreaming to doing something creative about the situation.


“It is easier to get people to act their way into a new way of thinking than to get people to think their way into a new way of acting.”

– Millard Fuller, co-founder of Habitat for Humanity.

Asking better questions will give you more options and make you much sort after in your professional career.

And it’s also fun.

So why be stressed when you can learn to view everything as an opportunity for growth and utilise your better-thinking skills to create a meta-world of possibilities instead.


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