Smart Questions For Self-Growth

In his newest book Tools of Titans which I’m currently obsessing over, Tim Ferriss talks a lot about the importance of continuously asking yourself smart questions.

“Questions determine your focus”, says Tim.

And I know that he got that from his role model and mine:

The quality of your life is the quality of your questions. ~ Tony Robbins

I decided to do something about those questions. Too many times I stumble upon a really good one, and think to myself:

“Gee, wouldn’t it be great if I started collecting those all in one place, so that I could journal about them when I have more time, or as an alternative to wasting time on Facebook?"

Also, another quote definitely kicked my ass and made writing this article so much more appealing than Facebooking:

The amateur tweets. The pro works. ~ Steven Pressfield, Turning Pro

This article is that collection of the questions that intrigue me.

Journaling About Questions? What Is That?

I think by writing.

I open my laptop, start a new blank document, and give it a title such as this one:

“If there was no way to fail, what would I do?"

And then I start answering that question in writing.

Below I’m giving you a peek into how I do it: I answered some of the questions right here, in this article (in far fewer words).

The results of journaling are sometimes mind-blowing. How come? Because I entertained an important question for more than 5 seconds. I contemplated it. Some people take their questions with them into their meditations, others into their showers. What do you usually obsess over in the shower? Try a smart question instead.

How I Collect the Questions

  1. I find them in the books I read, or in online articles.
  2. I have an Evernote note titled “Useful Questions for Self-Growth”.
  3. I copy and paste or write down the question (and usually the source, as you’ll see) in that note.
  4. I update this article with newer questions I will copy and paste from that Evernote note.
  5. Because I use Evernote on my phone too, it’s ridiculously easy to capture any thought and put it where it belongs, fast.

My List of Useful Questions (So Far)

Older questions are at the top, newer ones at the end.

Where am I playing the victim in my life, and how can I shift to taking charge as an owner?

When do I feel the most stress, and what do I do to relieve myself from it?

How do I prevent further stress?

That’s out of your control; what can you control?

What might I do to accomplish my 10-year goals in the next 6 months, if I had a gun against your head?

This one is by Peter Thiel, with the last part added by Tim Ferriss.

Instead of labeling a lot of things good/ bad, ask: can I evolve from this?

If there was no way to fail, what would I do?

What does it look like when I’m holding myself back?

What is my biggest weakness?


  • Perfectionism
  • Bad time management
  • Holding myself back
  • Censoring myself
  • Being afraid that people will attack me for criticizing something of theirs
  • Having double standards: drill sergeant toward myself, while cutting everyone else slack

What am I continuing to do myself that I’m not good at?

This is one of Tim Ferriss’ quarterly review questions. Apparently, a couple of times a year, he calls a meeting with himself for a performance review. I wonder if he gets anxious before that interview.

Do I, like Arnold Schwarzenegger, have a clear vision where I want to go?

Prove it! Paint the picture of what will it look like when I have succeeded in my goal (of creating a successful publishing empire).

If I had a clearer vision, would that make me work harder for it?

Questions for Facing a Tough Decision

Source: this Steve Pavlina article.

  • Will this help me grow?
  • Would my best self do this?
    • Pavlina: “My best self is brave, generous, and creative.”
    • Me: My best self:
      • is generous
      • does not hold grudges
      • has an abundance mindset
      • is brave
      • believes people are naturally good
      • is trusting
  • Do I want the memory? Which memories do I want (when I’m on my deathbed)?
  • How will this sculpt my character as a human being?
    • Pavlina: “If you accept a misalignment in your life, you’ll attract more of the same."
  • Could I reverse or undo this decision?
  • Can I test this decision?

How do I operate at no risk and receive huge rewards?

This one is by Tony Robbins again, who says: “Because you ask a question continuously and you believe [there’s an] answer, you get it.”

How I can make my bucket-list dreams pay for themselves by sharing them?

Tim Ferriss created a career from doing crazy experiments and writing about them publicly.

This very article is my attempt at starting to do the same: sharing my preoccupations and my personal experiments with others, without fear. The worst that can happen is that you get to know a little bit more of who I really am on the inside.

I also create lots of byproducts when I write, or when I work on client projects. All kinds of frameworks, lists of protocols, rules, processes… I have an entire Google Drive (two, actually) full of stuff like that. I will liberate all those things and let people use it. Most for free, some for money.

How could I create and publish my best ideas within 1 minute?

It now takes me anywhere between 15 and 30 minutes to publish anything longer than a Linkedin post. If I created some sort of template… But in which app? Will see.

My Best Self: what kind of a person is she?

Which 20% of my activities bring 80% of my results?

First define results, what you want to measure.

Make “easy” your next criterion. Which of these highest-value activities is the easiest for me to do? I can build an entire career on 80/20 analysis and by asking this question.

What is the smallest possible project that is worth my time?

This one is by Seth Godin.

What is the unique mojo that I bring, and how can I try and amplify that?

  • Amplify your strengths rather than fix your weaknesses.

What would this look like if it were easy?

Am I doing what I’m uniquely capable of, what I feel placed here on Earth to do?

  • Or: Am I replaceable? (the way venture capitalists are - you can always find another one)

How much of my life is Making versus Managing?

Am I fooling myself with …?

“The first principle is that you must not fool yourself, and you are the easiest person to fool.”—Richard P. Feynman

What bullshit excuses do I have for not going after what I want?

Want to Contribute Your Questions?

Contact me and I’ll open another section in this article with contributed questions.

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