10 Questions for Better Self-Awareness

I don’t think it’s a stretch to say that most of us are less self-aware than we like to think.

And this lack of self-awareness is one of the more underappreciated reasons why we struggle emotionally:

  • How many relationship struggles and insecurities stem from a lack of awareness about what you and your partner’s core values are and how well aligned (or not) they are?
  • How many struggles with productivity and procrastination and low self-confidence come down to not being aware of your authentic preferences and goals?
  • How many struggles with stress and anxiety and overwhelm originate in a lack of clarity about your own limits and boundaries?

Put another way…

If you don’t understand what it is you really want, or what kinds of inner obstacles might get in the way, how likely are you to succeed (and be happy) long-term?

Unfortunately, becoming more self-aware is one of those things we all nod our heads in approval at theoretically… But when it comes to actually taking action on becoming more self-aware, well, that’s a bit harder.

As a simple way to start being a little more self-aware, I thought back on some of my favorite questions I used to ask my clients in therapy as a way to expand their self-awareness.

If you’re interested in becoming more self-aware but aren’t quite sure where to start, give these questions a ponder.

I’ll list them on their own first so that you can read them and come up with some answers on your own. Then I’ll list them again with some brief thoughts about why I think they’re interesting and helpful for improving self-awareness.

10 Questions for Better Self-Awareness (just the questions)

Read the questions here first on your own and reflecting on them a bit before moving on to the expanded versions with my commentary.

  • When was the last time you publicly acknowledged being wrong about something important?
  • If you had perfect confidence for 5 minutes what would you do?
  • What’s your proudest achievement?
  • In what types of situations are you most likely to lie?
  • What does your ideal day look like?
  • When was the last time you stood up for yourself?
  • What are your biggest regrets in life?
  • What’s something you believe strongly but rarely talk about?
  • What do you love most about yourself?
  • What do you hope to gain by becoming more self-aware?

10 Questions for Better Self-Awareness (expanded)

Here are the same 10 questions but with a little bit of commentary from me about why I like them and how they might be useful in trying to become more self-aware.

1. When was the last time you publicly acknowledged being wrong about something important?

It’s hard to be self-aware without humility. And it’s hard to be humble if you don’t acknowledge mistakes or errors. So, if you want to be more self-aware, looking for patterns in your overall tendency to admit mistakes (or not), can be really helpful.

Now, a key thing to keep in mind here is that your willingness to admit mistakes might be very domain-specific. For example, you might have no problem admitting mistakes at work around technical issues. But when it comes to admitting mistakes with your kids, you might struggle greatly.

So, pay attention to your patterns of acknowledging mistakes with others. And most importantly, look for gaps. Because those gaps may well be the most fruitful opportunities for greater self-awareness.

2. If you had perfect confidence for 5 minutes what would you do?

The idea here is to confront big fears that you typically ignore or stay deliberately ignorant of.

When you imagine having perfect confidence for a few minutes it gets you to reflect on two things:

  1. Where in my life could I really benefit from being more confident—which is a backward way of asking where in my life am I really afraid?
  2. Having only five minutes forces you to prioritize the biggest, most impactful fears.

3. What’s your proudest achievement?

I like this question because it forces people to confront the issue of pride.

For a lot of people, pride is seen as an intrinsically bad thing (think, Pride cometh before the fall.) Which is unfortunate because healthy levels of pride in yourself are incredibly good for us emotionally. And in fact, not having healthy pride can make you more vulnerable to a lot of emotional struggles.

So, the thing to watch out for with this question is the process itself:

  • Is it a struggle to think of things?
  • And if you do think of some, how much feeling is attached to those memories?
  • Can you recall some of the positive feelings or is it just very factual and devoid of much emotion?

4. In what types of situations are you most likely to lie?

This question is a good backdoor into subtle insecurities because lying is often a way of masking an insecurity—both for ourselves and others.

For example:

  • You had a rough day, and as soon as you get home, your spouse asks how you’re doing.
  • You smile and say Oh, fine—a white lie motivated by the desire to not appear weak in front of your spouse, but maybe also, to help you feel a little less weak or afraid yourself.

Note: for the purposes of this exercise, try not to view your lying behavior in moral terms, and instead, think of it mechanically. In other words, instead of Why am I such a liar? try What emotional function is my lying serving?

The goal isn’t to beat yourself up. It’s to understand more about yourself.

5. What does your ideal day look like?

This question is useful for exploring preferences. Specifically, it’s a good question to help you examine inherited preferences (wanting things because it’s what other people want or you feel like you should want) vs authentic preferences (wanting things because it aligns with your personal values and temperment).

For example:

  • Initially, you said that your ideal day starts off with you waking up at 5:00 am, meditating for an hour, taking a cold shower, and then going for 5-mile-run.
  • But is that really how you want your ideal day to start or is that what you think your ideal day should be like?
  • And while those two things aren’t necessarily mutually exclusive (what you really want vs what you think you should want), it’s worth being aware of if they are.

6. When was the last time you stood up for yourself?

This question is all about assertiveness and boundaries. A lot of people struggle to be assertive and ask for what they really want confidently. Similarly, they tend to struggle with saying no to what they don’t want and setting healthy boundaries.

But it’s easy to avoid looking at these two areas because once you do, you start to realize:

  1. How much their absence is negatively affecting your life, and
  2. How difficult it will be to start being more assertive and setting better boundaries.

7. What are your biggest regrets in life?

This question works on a couple levels:

  1. Looking carefully at your regrets can tell you something about your values. Specifically, if there is a pattern or set of commonalities in your regrets, it might indicate a particular value or ideal that you hold instinctively but haven’t fully clarified or pursued. For example, if most of your regrets involve not taking advantage of interesting but intimidating opportunities, that might suggest that being adventurous or bold is something you value but haven’t clarified well enough.
  2. How your mind reacts to thinking about regrets can be an indicator of how balanced your relationship with your emotions is. For example: If you really struggle to think of anything you regret, it might be a sign that you’re a little too closed off to difficult emotions—that you tend to ignore the negative and focus on the positive to an unhealthy degree. On the other hand, if you immediately get overwhelmed by and lost in thoughts about things you regret, that could be an indicator that you’re too open or sensitive to certain emotions. Remember: there are plenty of perfectly good reasons to ignore your emotions.

8. What’s something you believe strongly  but rarely talk about?

This one is interesting because it gets you to think about uncomfortable values.

If you were in a room and someone asked everyone there to raise their hand if they valued love or honesty, of course, just about everyone is going to raise their hand because love and honesty are comfortable values to acknowledge and express publicly.

But imagine if the question instead was to raise your hand if you valued obedience or free love?

It’s worth exploring the values you keep hidden in the shadows.

9. What do you love most about yourself?

Similar to the question about proudest achievement, this one is all about exploring your capacity for self-love.

And again, like pride, the idea of self-love sometimes gets a bad rap because people conflate it with narcissism or self-indulgence or vanity. But in reality, the capacity to love yourself is essential for healthy psychological functioning.

So, pay attention to your experience as you ask yourself this question and reflect on it:

  • Is it a struggle?
  • Does it feel awkward or even wrong?
  • What might those experiences be signalling?

10. What do you hope to gain by becoming more self-aware?

This question is obviously a bit meta, but being self-aware about our motivations for more self-awareness is important.

A lot of people’s desire to be more self-aware is very instrumentally motivated. For example: If I boost my self-awareness, then I’ll be less anxious.

And while there’s nothing wrong with this attitude per se, when the desire for self-awareness becomes overly instrumental, it can itself become an obstacle to self-awareness.

Because ultimately, self-awareness is not so much a tool as an attitude or stance. But treating it like an object to use can have the ironic effect of narrowing your view onto the external rather (goals, oucomes, results) than expanding on the internal (your own patterns of thought, emotion, and behavior).

But what do you think?

Got any good questions from your own experience that have helped you become more self-aware? Drop them in the comments!


Add Yours

Self awareness is often for me like an epiphany…a sudden burst of a-hah! clarity and feels very comforting and exciting even if my/others behavior in reflection wasn’t as well mannered, comprehensible or quick as I have preferred.


So often we avoid envy/jealous because it feels so… gross! But really it can be pretty instructive to explore it.

Thanks, Robyn!

As always, your approach to teaching us how to deal is once again enlightening and practical. Each of your posts helps me understand a little bit more and I will be forever grateful for all the excellent content you create and share with us. For me personally it has been a very important complimentary element in my personal journey with therapy and getting to know myself better. Thank you!

I do regret some things the way they turned out, but my input had very little to do with the result. Having married a nice person who grew up into her mom is just what it is. There is no do over. So why regret? It’s more about not doing something today I will regret later, isn’t it? Or doing it in a way I can be proud of, even if it fails. No regrets, but there IS a learning curve.

Robyn’s comment, “What makes you sick with envy?” is a topic I’d like to have Nick Wignall write about more in depth. I agree, Robyn, if someone is very envious/jealous, it points to their own desires that they have not achieved. I’ve had some success in my area and find some people almost shunning me. Not everyone, but people from whom I expected some support or a “Great.” This is a topic that is major in our lives as a society as well. Thanks.

Leave a Reply