A list of reflective questions to ask yourself

Many of the questions I’ve gotten from books, podcasts, or somewhere online. Often, I thought to remember it, but it only surfaced after a week or so—long after I’d forgotten the source.

I’ve tried hunting down the source for the questions, but some are unfortunately pretty hard to find. Some of these questions have been posed by others—people I know I didn’t get it from.

I’ve found that most of these questions can be grouped into these categories, or a mix.

💡 How am I complicit in creating the conditions I say I don’t want?

Question from Tim Ferriss Show with guest Jerry Colonna (podcast ep. 373).

It’s a powerful question to ask because we contribute and feed conditions, even if we say that we don’t want them. And likewise, we might say we want something, but don’t take the steps needed to get it. We fool ourselves.

This places the power in your own hands. It focuses on what you can control (What is in my control).

💡 Where am I making things more complex than they need to be?

I’m not sure where I got this question from. I think it was Tim Ferriss. I’ve seen others with the same question.

💡 Where am I standing in my own way?

This question is similar in nature to the ones above. From Ryan Holiday, Stillness is the Key.

💡 How will today’s difficulties reveal my character?

From Ryan Holiday, Stillness is the Key.

I love this question. It promotes growth and really gets the best out of everything. I ask myself a variation of this every day (currently, 2022-05-05 - Thu May 5).

💡 What is the harder choice I’m avoiding?

From Ryan Holiday, Stillness is the Key.

Sometimes we need to get kicked into gear. This question helps with that.
Often, I know exactly which choice is holding me back.

💡 Why am I so worked up about this?

From Ryan Holiday, Stillness is the Key.

This question helps you reflect a bit about your irritation, anger, and other nagging feelings. Why does this matter so much to me?

Stoicism helps us answer the question. But if we don’t bother asking, it might take a long time before the feeling passes.

🎯 What’s the smallest step I can take toward a big thing today?

From Ryan Holiday, Stillness is the Key.

This is a very important question. It is basically the premise of much of habit building. Like the starter step from Tiny Habits—and it’s in the name, like with Atomic Habits.

💡 What would this look like if it were easy?

From Tim Ferriss. Testing The “Impossible”: 17 Questions That Changed My Life (#206) – The Blog of Author Tim Ferriss

For me, this question is similar to the #💡 Where am I making things more complex than they need to be question. But it starts with the solution and allows you to work backwards.

🎯 Am I hunting antelope or field mice?

From Tim Ferriss, Testing The “Impossible”: 17 Questions That Changed My Life (#206) – The Blog of Author Tim Ferriss. Khe Hy has also told this story in Khe Hy How to Leverage Your Second Brain to Do $10k Work. It’s about prioritization. Why go for the low hanging fruit? Don’t do it just because it is easy.

Very similar to The Focusing Question asked by Gary Keller in The One Thing.

🎯 If I could only work for four hours this week, what would I work on?

From Tim Ferriss, at least, inspired by him. Kind of unsure where I got this from. I’m pretty sure I adapted it from here.

It’s an interesting question to ask. Implicitly, it leverages the same principles as The Pareto Principle. You need to focus on the absolute essential.

💡 What if I did the opposite?

From Tim Ferriss.

Following the Inversion mental model. Sometimes finding what the opposite of something is can be hard. So you can also ask yourself, what if you tried to really sabotage yourself? What would you have to do then? If you wanted failure?

Like in Charlie Munger‘s prescriptions for misery given during his { Poor Charlie’s Almanack#1 Harvard School Commencement Speech.

🎯 How could I achieve my 10-year goals in six months?

Adapted from elsewhere. Probably from Tim Ferriss.

The question really forces you to think about

  • what is the real objective, what aspects really matter
  • how could I achieve it/them in record time

For example, getting a SWE masters takes 5 years (if you do it traditionally). MIT has a CS course that takes 4 years. Scott Young did it in 1 year.

If you do what everyone else does, you get what everyone else gets.

🎯 What can I execute on right now that will prove that my outcome and vision are not only possible, but coming true?

From The 1% Rule.

💡 What stories are you telling yourself that prevent you from growth?

Made this one after lots of reflection on the type of stories we all tell ourselves. We have so many limiting beliefs, many of which we simply take to be axioms—things that are true, never to be questioned. Examine from first principles whether the claim actually holds up. Experiment, test.

💡 What am I putting off?

Perfect question to ask. Got it from How Notion Keeps Me Sane . I already say: If you procrastinate: eliminate, delegate, or improve. Asking this question helps identify which path to take.

👉 A good followup: what if I just did it now?

💡Did I let other people dictate how I spent my time?

This is an important question to ask for me. Lead or be led. Got the question from How Notion Keeps Me Sane .

Prioritize so others don’t do it for you. Essentialism talks about this. Indistractable does too.

💡 What does it look like to move from mindless consumption to mindful creation?

From Building a Second Brain. This one is big for me, because I think I’m fooling myself into thinking I’m just an ultra-slow mindful creator, but more probably just consuming to consume.

Performance Assessment by Chris Sparks

🗺 Vision

Are you designing a life in alignment with your top values?

  1. Do you have a life mission you want to achieve?
  2. Do you have a vision for your career?
  3. Do you have a consistent long-term review process?
  4. Do you have a consistent long-term planning process?
  5. Do you keep track of your projects?

🚦 Prioritization

Are you working on the most important things?
6. Do you plan and review your top priorities for the week?

  1. Do you plan and review your top priorities for the day?
  2. Do you work on your Top Priority first each day?
  3. Do you have control over your own schedule?
  4. Are you decisive?

🏭 Systems

_Are you making what you want to do easier to do?
11. Do you leverage your time well?

  1. Do you manage and delegate well?
  2. Does your physical workspace inspire you?
  3. Do you track important metrics?
  4. Do you have systems for learning?

🧘‍♂️ Presence

Are you showing up as your best self every day?
16. Do you start your day intentionally?

  1. Are you focused?
  2. Do you prioritize your physical health?
  3. Do you prioritize mental health and recovery?
  4. Do you finish your days effectively?
Outgoing links: #💡 How am I complicit in creating the conditions I say I don’t want, #💡 Where am I making things more complex than they need to be, #💡 Where am I standing in my own way, #💡 How will today’s difficulties reveal my character, #💡 What is the harder choice I’m avoiding, #💡 Why am I so worked up about this, #💡 What would this look like if it were easy, #💡 What if I did the opposite, #💡 What stories are you telling yourself that prevent you from growth, #💡 Where am I making things more complex than they need to be, #💡 What am I putting off, #💡Did I let other people dictate how I spent my time, #💡 What does it look like to move from mindless consumption to mindful creation, #🎯 Am I hunting antelope or field mice, #🎯 If I could only work for four hours this week what would I work on, #🎯 How could I achieve my 10-year goals in six months, #🎯 What’s the smallest step I can take toward a big thing today, #🎯 What can I execute on right now that will prove that my outcome and vision are not only possible but coming true, Tim Ferriss, What is in my control, Tim Ferriss, Stillness is the Key, Stillness is the Key, 2022-05-05 - Thu May 5, Stillness is the Key, Stillness is the Key, Stoicism, Stillness is the Key, Atomic Habits, Tim Ferriss, #💡 Where am I making things more complex than they need to be, Tim Ferriss, Don’t do it just because it is easy, Tim Ferriss, The Pareto Principle, Tim Ferriss, Inversion, { Poor Charlie’s Almanack#1 Harvard School Commencement Speech, Tim Ferriss, Scott Young, The 1% Rule, first principles, If you procrastinate: eliminate, delegate, or improve, How Notion Keeps Me Sane , Indistractable, Building a Second Brain, Chris Sparks