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On Mood Booster Questions

5 min

I have been quite intrigued by the power of good thoughtful questions. So much that I started curating questions.

Luckily, I had chanced upon some of the threads on Twitter who had already done the work for me.

Along these directions, I happened to have found interesting minds on Twitter that have already compiled and curated good questions that inspire you to reflect and refresh.

This was when I was reminded of journalling when a friend of mine mentioned how this act helped her endure the tough phases. Helping her cope with grief and sadness. Journalling to her was a form of catharsis - therapeutic emotional purging.

But this was not the only case. I have seen others use neat decorative bullet journals and finding joy in doing so. This was how I started thinking about how I could classify these journalling questions based on the related mood/emotion.

What is one repeating problem you can automate or eliminate today?

What would your closest friend tell you to do?

What is a mistake you seem to repeat each year? What can you do to prevent it this time?

Have I stepped back and forgiven myself recently?

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

Where am I feeling the Resistance?

What am I most proud of in my life?

Where do I have healthy momentum right now? Where do I have unhealthy momentum?

If you met someone exactly like yourself ... - same experience - same resources - same problems ... what advice would you give them?

What do I actually want?

Where am I taking myself too seriously?

How could I change my environment to make bad habits harder and good habits easier?

Where is momentum working for me? Where is it working against me?

What's currently energizing me?

How will being anxious about this serve me?

Am I doing/not doing this out of fear?

Some questions to consider before you speak: Does this need to be said? Does this need to be said by me? Does this need to be said by me right now?

Does this activity fill me with energy or drain me of energy?

How are you complicit in creating the conditions you say you don’t want?

What area of my life am I most neglecting?

What's currently draining me?

How can I learn from this experience?

What are the big things/little things I'm grateful for today?

Is this making me a better person?

What is best in the short-term? What is best in the long-term?

Has the most important thing changed? Am I chasing an outdated target?

What would happen if I shut my laptop and spent the entire day outside without technology?

Am I treating myself as someone I'm responsible for helping?

What's the biggest bottleneck to achieving the goals I've set? Why aren't I working to solve it?

Am I seeking comforting lies or inconvenient truths?

Is my calendar aligned with my priorities?

Am I hunting antelope or field mice?

How would the type of person I want to be handle what is currently stressing me?

What's something on today's to-do list that I shouldn't waste my time with?

Where am I adding more complexity than necessary?

What would I do to make today horrible?

What's the first thing you think of when you wake up most days?

What is 1 thing I will do differently tomorrow?

How will my life be different in a year?

What is the highest leverage action I can execute on right now?

If you do not work on important problems, how can you expect to do important work?

What's the worst thing that could happen if I took the leap I'm scared to take?

Am I seeking leverage with my time, energy, and attention?

What would it take to snap me out of my bad mood immediately?

Sometimes you have to pass through the fire. What fire or pain should you seek out in your life over the next year so you can learn its lessons?

Imagine the most important goal or project you are working on right now. Fast forward six months. Imagine the project has failed. Why did you fail?

If I died today would I be happy?

Am I confronting the brutal facts of my situation?

What difficult conversations am I avoiding?

What would I do if there was no risk attached?

If I had 30M in the bank, how would my day-to-day change?

What is the little bit of extra work that has huge upside?

What are you working on when time fades away?

What are my actions moving me closer to?

What's nagging me that I could automate or pay someone to take care of for me?

Where could I invest $500 today to improve my quality of life?

What would this look like if it was fun?

What is it that I can think of, read, watch, listen and talk about for hours on end without realizing it?

What is your idea of happiness?

What is one small thing I could do today that would make a meaningful impact on my future?

What would my absolutely ideal day look like today?

What would the ideal rest of the week look like?

What am I most grateful for today?


It is also to be taken into consideration that being repeated the same question all over again every other day makes it boring. Also adding to the fact that such a listicle might be quite difficult to complete. You want journalling to seem less like a chore. To avoid it, I have created a script for random generation of these questions. In this way, everyday there is a fresh journalling prompt based on the specific mental state I am in while I journal.

Dickie Bush, James Clear, Greg Isenberg have some examples of journalling prompts from which I had categorised them into respective moods.


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