How to Be More Self-Aware: 3 Simple Exercises

Most of us realize that it’s important to be self-aware, but how do you actually improve your self-awareness?

A reader asks:

Everyone talks about how important self-awareness is but you never hear them explain how to actually do it—how to become more self-aware. Anything practical you recommend?

Here are three of my favorite practical exercises you can use to improve your self-awareness.

NOTE: You can watch or listen to the video version here →

1. Draw a Timeline of Your Life

Here’s what you do:

Get out a piece of paper, turn it horizontal, and draw a line from the left side to the right.
On the far left, write “Birth,” and on the far right, write your current age.
Now, add the most important or impactful events from your life onto the timeline. They could be “major” milestones like graduating from college or getting married, but they could also be smaller but still meaningful events like that conversation with my boyfriend when I realized how much I”m motivated by avoiding regret.
Spend about 30 minutes filling the timeline in as fully as possible.

Once you’ve drawn your timeline and filled it in, here are a few reflection questions to ask yourself:

How did it feel doing this exercise? Which specific emotions did you notice? What types of thoughts went through your mind?
What’s something that surprised you as you did the exercises?
Do you notice any patterns or themes?
If you had to pick one event as the single most important, which would you pick and why?
What’s missing from the timeline? NOTE: This question is intentionally ambiguous and there are many ways to interpret it.

There are a lot of ways this exercise can improve self-awareness. But here’s my favorite:

Putting your entire life on a single piece of paper forces a radically different perspective on yourself.

For most of life, we’re in the weeds—focusing on everyday things like dropping the kids off at school, scheduling meetings, and paying bills. But periodically, it’s very helpful to pop our heads up and take a wider perspective—to take a look at the whole forest, not just the trees right in front of us.

This radical perspective shift, if you take it seriously, will nearly always open up new insights and observations about yourself and the way your life is going.

And if you want to take this exercise to the next level, try this:

Find a trusted friend or partner and do it together.
Each of you draw your timelines individually.
Then swap and draw the other person’s timeline as best you can.
Now compare notes and discuss!

2. Track What Annoys You

Often we learn the most about ourselves by looking at the things that bothers us most in others.

Try this:

Open up the notes app on your phone and create a new note called “Annoyance Tracker”
Now, each time you notice yourself feeling annoyed, irritated, or bothered throughout the day, quickly jot down what was bothering you in your notes file.
Do this for a couple weeks.
Then, find 30 minutes, make yourself a cup of coffee or tea, and spend some time reviewing your inventory.

If you want a little structure, here are some good questions to ask yourself:

What patterns do you notice among your annoyances?
How do you feel right now reviewing these annoyances?
If you showed up on other people’s annoyances lists, what would it be for?
Often annoyances represent expectation violations… For each annoyance, ask yourself: What expectation or assumption of mine was violated in this situation?
Another way to think about annoyances is that they are micro-resentments: Annoyance at others is often a reflection of resentment at ourselves for not being more assertive about what we want or don’t want. So, for each annoyance, ask yourself: What assertiveness opportunity does this annoyance suggest?

On a very practical level, this annoyances tracker exercise is helpful because you’ll be better able to anticipate and handle difficult situations well if you’ve tracked them for a couple weeks.

But on a deeper level, making annoying situations explicit will gently force you to confront your role in the annoyance.

Specifically, you’ll start to notice that many—though certainly not all—of the things that bother you about others are actually things that bother you about yourself but you are hesitant to acknowledge or do something about.

What annoys us about other people often points to what we dislike about ourselves.

And as uncomfortable as it is, understanding what we dislike about ourselves is just as important for self-awareness as understanding what we like about ourselves.

3. Ask for Targeted Feedback

We all have blindspots—things about ourselves that we can’t see because of our own biases or limitations. But often, these blindspots are perfectly visible to other people. Which means, asking other people for feedback is a fairly obvious way to become more self-aware.

And yet, we almost never do this. Why?

I think it’s because most people are not very good at doing feedback well—either asking for it, giving it, or receiving it.

Doing feedback well is a topic I could spend hours on, but here’s the simple version:

The secret to good feedback is specificity.

Here’s what I’d recommend:

Think of an aspect of your personality or behavior you’d like to be more self-aware about. E.g.: How you come across in high-stress group scenarios.
Now think about someone in your life who both A) Knows you well, especially in regard to the aspect you identified above, and B) You trust to have your best intentions at heart.
Now, ask them for specific feedback about you and your behavior in that situation. For example: Instead of asking your manager How am I doing at work? try I’m working on getting better at presenting in group situations. Do you have any feedback for me specifically on how I deliver presentations with our leadership team? Note that keeping the feedback domain-specific and behavioral in nature makes it much less threatening for the other person to give you honest feedback.
Finally—and perhaps most challenging—it’s essential that you take the feedback well. Because if you get defensive when someone gives you feedback, they will be much less likely to give you honest feedback in the future.

Finally, once you’ve received your feedback, here are a few questions to reflect on:

What was most scary about this process?
What was feedback like in your family of origin? How do you think that impacts your relationship with feedback (asking for it, giving it, receiving it, etc)?
If you had no fear or anxiety, where else in your life would you ask for feedback? What do you suppose that means?
Who’s an important person in your life who could benefit from your feedback? Why haven’t you given them that feedback?
In what aspect of your life do you most need feedback?

Before we wrap up, I have one final point I want to make on the connection between self-awareness and feedback:

Self-awareness should not be a solitary project.

Most people think about self-awareness as something you do by yourself while meditating or journaling. But in reality, the biggest insights and breakthroughs in self-awareness are almost always the result of the willingness to be vulnerable and honest with other people.

That might be your shrink or coach, but it might be your spouse, your manager, or your best friend.

Next Steps

Another important aspect of self-awareness I didn’t talk about is personal values—what are the principles or ideals that matter most to you and that you use to guide your decision making?

If that question feels a little intimidating, you’re in good company because most of us have not seriously reflected on what our values are.

But if that is something you want to explore, I put together a collection of my favorite exercises for discovering your values called The Values Discovery Toolkit.