Following the powerful 28 questions, here are 42 more you can use to crank up the self-awareness dial. Enjoy.
questions about your inner world
1. Is my social media use intelligent?
Thought I’d hit you where it hurts right away.
I know what you’re thinking: social media curtailment = buzz kill. But it’s your own buzz you’re killing with social media use and abuse.
Author of Deep Work, Cal Newport argues convincingly that social media overuse erodes our ability to focus and build anything of value. Disaster.
Become discerning about what droll you allow your mind to feast on.
If good old fashioned willpower isn’t working for you, then there are loads of apps you can use to help you to curb your enthusiasm.
2. Do I let unexamined thoughts run amok in my day?
Feed the fertile soil space between events and your interpretations of them (by practicing mindfulness). You’ll be much happier for it.
3. What in my life needs my attention? And what kind of attention does it need?
(See also questions 19 and 31.) To answer this question, you need to know your values.
As well as figuring out what life areas need attending to, identify the quality of the attention needed. Is it a drive/willpower kind of attention, or a softer, more loving, nurturing form of attention?
Know your yin from your yang, and work it.
4. Am I making good decisions?
A decision is a narrowing of possibilities. That is all. Are you making good ones?
You’ll know if generally your decisions move you to self alignment, and the accompanying feelings of rightness, joy, balance, appreciation and gratitude.
5. Does my routine serve my highest values?
Routines aren’t exactly sexy…but their results are.
Creative people rely on routines. Entrepreneurs rely on routines. Everyone who has a desire to stay sane and enjoy wellbeing uses some sort of a routine!
Morning routines seem to be ultra significant. Carefully craft yours.
6. Am I being open?
If life is too structured, then we can expect to have the same experiences day in day out.
Make allowances for opportunities and synchronicity, and both will grace you.
The best way to court possibility? I wrote about that here.
Meditate. Clear your mind daily of your past and present based concerns.
7. Am I too invested in my thoughts, feelings and judgments?
This is kind of like question 2, but different.
Life involves a delicate balancing act of paying enough attention to our feelings, whilst simultaneously ignoring them. And by ignoring them, I mean not letting them dictate your decisions or your ability to meet your intentions.
Our litany of judgments is largely determined by something outside of our control – our subconscious mind.
Asking yourself this question helps you to stay aware of that.
8. Is the gratitude I do feel mostly based on comparison?
Comparison gratitude is perfectly natural. However, if it is the only form of gratitude you practice, then what happens when you compare yourself and you come up short?
Feeling grateful for things that do not involve a judgment about others is sustainable gratitude. Stuff like new friends, old friends, family time, your dog, yoga practice, writing habit, or whatever.
9. Am I owning (taking responsibility for) my emotions?
Own – or be owned!
10. What am I making excuses not to do?
Do you need to reduce the number of buts in your repertoire?
11. Is my nervous system relaxed?
Signs of a relaxed nervous system: a calm and consistent sort of happiness and wellbeing, feeling content, adaptability/flexibility, and ability to focus and concentrate. Signs of a frayed nervous system? Anxiety, nervousness, depression, anger, irritation, intolerance, moodiness and tiredness.
The health of your nervous system is super important. I wrote about how to balance the nervous system here.
12. Do my actions and decisions contain a good balance of my heart and my head?
Most of us are too much the one way. This takes us out of balance.
When we are too heart-oriented, it’s all about how we feel. Being too head centered ignores how we feel for the sake of getting the job done.
Don’t use your gender as an excuse. We all have a head and a heart, and we all need to draw on both to make our decisions.
13. Am I taking responsibility for the state of my life?
Until you are, you aren’t being as powerful as you could be being.
14. What do I feel deserving of/entitled to?
This is a tricky one. We do deserve happiness, but we need to see ourselves at source of that. Feeling entitled ultimately stops us from taking action.
15. Am I caught up in the disease of more?
The disease of more is always feeling like you are chasing something in order to reach this elusive pinnacle of happiness and success. Unfortunately, it doesn’t work. We stay wanting.
The solution is to stop seeking betterment for the sake of it, and instead seeking to align ourselves with what we value the most. Trade offs are inevitable.
16. Have I ever felt flow?
Flow states – those states of timelessness – arise naturally from activities that feel the most essential to our nature. And no, I don’t just mean orgasms and eating cake. There will be other things that get you into a flow state.
Swimming. Writing. Playing with your kids. Whatever allows your attention easily to rest on the crest of the unfolding wave of the present moment.
Notice whether you are getting any. If you’re not, set an intention to discover your flow experiences.
17. Does being alone still scare me?
Unless and until you get okay with it (and I wrote about how here), you’ll make compromises with who you spend the time with. And when you do that, that is a slippery slope.
18. Where am I getting my sense of security from?
Until security is internally sourced, life is going to be a scary turbulent place.
Internal security is the knowing that whatever happens, whatever your circumstances, you have the fortitude to withstand it.
19. What do I want (really)?
What do you value?
I value family and friendship. Love and relationships. I value learning and creative outlets. And clean and healthy living.
If you can’t easily name five things you value right now, then you need to ask yourself this question until you know.
20. What do I spend the most time and energy worrying about? Does worrying help? What actually would?
For most of us, it’s the same things. Money. Relationships. Existential dilemmas.
Worrying is counter productive to all of them.
What works is identifying limiting beliefs and reframing. This enables effective action, instead of the paralysis worrying causes.
21. What questions are unresolved in my heart? Can I change the way I carry them?
Here is a poem (it’s by Rainer Maria Rilke) that recently shifted my perspective on hanging questions.
22. Am I clear on where this I am/this is going? How can I get clear?
It is okay to not have a crystal clear vision for the kind of future you want to enjoy. But knowing our rough direction of growth/progress at any one time is how we know what to say yes or no to.
23. What can I do to improve my experience of this situation?
If you are having a tough time, there will be actions you can take to improve your experience. There nearly always is. Do them.
24. Am I overthinking this?
Here’s a clue as to whether you are pointlessly overthinking something:
It has already happened and/or it is outside of your control.
For anything that falls into that category, say goodbye to overthinking. I wrote about that more here.
25. What do I want out of this specific experience?
This just gives any experience a sense of purpose. It also helps you to know your values.
26. Am I living ‘if/when’?
‘I’ll go to yoga if/when I’m feeling better’ = you’ll never go.
Go, and then you’ll feel better.
27. What’s stopping me from enjoying this moment/my life right now?
It’s very possibly you.
28. How do I take myself off balance and out of harmony?
Our traits make us out of balance, a well as our lifestyles. Don’t adopt other people’s notions of balance; go on your own.
29. How good can this get?
How great – how obscenely awesome – can your life get? Contemplating (or visualizing) this actually helps to make it happen.
30. Are the things I value the most broadly the same as my friends’?
If you aren’t around those with the same values as you, you risk holding yourself back from progress and more importantly, happiness.
We all want and need to have good (inspiring/motivating/honest) people around us.
31. Are my good life buckets leaking?
I love Jonathan Fields’ simple tool for helping you to know what life areas need attention. It is also a good way of assessing balance.
32. How would progress/development look for me in the next three months?
I’m not a huge fan of five year plans – but I love a three month plan!
33. How is my underlying fear affecting my life right now?
Your underlying fear, unique to your Enneagram style, will help you to see your strategy for dealing with childhood trauma (which we all have). Your strategy will be influencing a lot of what you do.
Learning to observe it is the best way I can think of for not letting fears rule you.
questions about how you’re being in the world
34. Will the thing I am upset/angry/annoyed about still upset me a month from now?
This is a really useful question to have on hand whenever you feel angry or irritated by anything. I find it immediately contextualizes the thing.
35. Have we been here before?
We tend to zoom in on the same faults and flaws about others, and in life. Why? Because our reactions to other people’s flaws is a clue to hidden or repressed parts of ourselves.
I have a familiar complaint (who knows when it started) of feeling encroached upon by other people. When I experience this familiar complaint, reminding myself that it is ‘my thing’ helps me to see how I might be distorting a situation.
36. What is my effect on those around me?
Pay attention to your effect on those around you. This will tell you who you are being, in case you are being self-deluded about that.
It’s not about pleasing others, or trying to win approval. The point is to notice whether you are currently contributing to others in an overly positive way, even if that is just by giving them your full attention, or if you might be an energy vampire. Being honest with yourself about that is the starting place for changing it.
37. Am I being aware of and responsive to the needs of those around me?
Personally, I believe that self care and self-love comes first. But it doesn’t take all day every day to look after and prioritise yourself. You can probably afford to extend the energy and generosity occasionally without depriving yourself of what you need.
Also, it’s a feedback loop. Contributing to those around us feeds us as it feeds them.
38. Am I unhealthily preoccupied with myself?
This is kind of like the last question but a bit more direct, isn’t it?
Narcissism is a modern day malady we all need to be wary of. If you spend most of your time and energy on all things you, consider how well that it working out. My experience is: not very well.
I do think a period of self focus is necessary for any spiritual/growth journey. But that shouldn’t go uninterrupted, nor continue on indefinitely.
39. Who and what am I using to reaffirm deeply held beliefs about myself?
We use what’s around us to reaffirm our beliefs.
If you believe that fundamentally, people aren’t to be trusted, then you will draw in the untrustworthy. Use what you notice about your reality (especially reoccurring frustrations) as the clues they are.
40. What of my stuff am I projecting onto the people around me?
Those annoying things you notice are clues to your Hidden Self. Accept them, embrace them, stop pretending.
41. Am I showing up as fully as I can?
Are you being your most authentic you, in your personal life and at work? When we do that, life takes on a sort of effortless quality.
42. What expectations am I placing on others?
Within our close relationships, our interdependents, it is healthy to have reasonable expectations. At practically any other time however, having expectations on other people is a fool’s errand.
Much better is to know your own boundaries, know when people cross them, and make a decision not to spend any more time with them.
That’s it! Until the next list, that is. Have you got any good questions I can add to my list? Send me an email: firstname.lastname@example.org