Getting to know yourself: eleven questions for deepening self-awareness

2008, my first (and last) date with K*: I didn’t know that it was possible to shock someone into self-awareness, but that’s exactly what K* just did. She asked a simple question, “What are your three biggest passions in life?”

I knew that I was passionate about building my speaking company, Ignited Leadership, but then I drew a hard blank. For the life of me, I couldn’t recall what my two other passions were.

In that moment, I had become so intensely disconnected from myself, that I couldn’t even name the three things in life I loved the most. That’s an intense level of disconnection…


Everything you experience in life flows from how well you know yourself.

Your self-awareness directly informs your day-to-day life. It also dictates whether or not you choose to chase your dreams, if you’re open to love and connection, and how you respond to everything from tragedy to joy.

In fact, when people struggle with being happy, being confident, or knowing what they want to do with their lives, the struggle is often the result of not knowing themselves well enough.

But knowing yourself is deceptively difficult…

The struggle for self-awareness

Most people have built busy lives defined by alarm clocks, stress, work, other people, bold aspirations, and busyness.

Downtime tends to be used for entertainment. The fleeting moments you do get to yourself are often punctuated by the background noise of text messages, social media, podcasts, Netflix, and music.

On it’s own, none of this is bad. In fact, a lot of it is fun. But it all blurs together to hold you back from dedicating time to focus on yourself. Without time to focus on you, you can’t know yourself, at least not at a deep level.

I know that sounds like a bold assertion, but pause for a moment: what are your three biggest passions in life?

If you’re like most people, the answer to that question is not immediately obvious. In fact, passions are one of those things that everyone talks about, but few have truly considered.

Or even more simply: are you happy?

Chances are you just had a conversation with yourself that went something along the lines of, “Hmm, am I happy? Yeah, I guess I’m happy. I mean, a lot of people have it way worse than me. I’m seeing my friends this weekend. I’ve got enough food. So yeah, I’m happy!”

If it took you a few beats to connect to your base level emotion, you have room to grow in your self-awareness. But don’t worry, almost all of us do.

In search of a better solution

Many people get hung up on a quest to “find themselves,” “get to know themselves,” or “figure out what they want to do with their lives.” The search often goes on for years on end, leaving many in a state of perpetual confusion. Most end up settling for mediocre answers about who they truly are.

I get it. I’ve been there.

To further complicate things, the common ideas about how to find yourself are clunky. They require considerable amounts of time and often require such significant effort that they become prohibitive. These include:

  • Traveling for months on end
  • Reading literature in hopes of finding yourself reflected in the characters
  • Reading tons of self-help/philosophy so that you can finally figure out what’s wrong with you and how to fix it (hint: there’s nothing wrong with you and you don’t need fixing)
  • Giving away your possessions so that nothing distracts you from yourself
  • Meditating or praying for hours a day
  • Engaging in years of Freudian style talk therapy

I’ve dabbled in most of the ideas above. Some, like travelling, can work well, but all of them are disruptive. What if there was a way to get to know yourself at a deep, penetrating level that didn’t require such an intense commitment?

Good news: there is…

How to get to know yourself

If you wanted to get to know someone else, you would spend time with them. You’d observe their habits. You’d ask them questions and listen to their answers.

You get to know your true self the same way you get to know someone else. You ask yourself bold, open-ended questions, and answer them as honestly as possible.

More on that in a moment…

On vulnerability and white lies

“Live by the foma* that make you brave and kind and healthy and happy. *Harmless untruths” – Kurt Vonnegut

Being vulnerable sucks.

It’s also the only way to grow.

When you’re vulnerable with yourself, you’ll form a stronger connection to you. The stronger the connection, the better your life becomes.

Many people have learned to ease the moment-to-moment pain of life by telling themselves (and others) white lies, or what Kurt Vonnegut refers to as “foma.” You know those times when you’ve tried to convince the world that you’re doing, “Great. JUST GREAT!!!” when in reality you’re in a rut? Yeah. That’s what I’m talking about.

While the deception may feel good in the moment, it causes damage in the long run. The lies prevent you from knowing your true self.

If you want to form a stronger connection to you, it’s your job to cast away the white lies. The more vulnerable you feel during this process, the more effective it will be.

Your secret weapon: honesty.

How to interview yourself

Increasing self-awareness is as simple as holding space and using it to interview yourself. Though the exact process can be modified, here’s what I recommend:

  • Schedule four, two-hour blocks of time to interview yourself over the next month. Put these appointments into your calendar.
  • When you interview yourself, do it someplace you find inspiring. This could be a quiet lake, a coffee shop with a great vibe, the atrium of a gorgeous museum, etc.
  • Before you start, turn your phone and computer off. This is time for you to focus exclusively on you. If you’re struggling to create silence in your life, that’s a clear sign that you’ve become addicted to distraction.
  • Don’t just think of answers; write them down. Use pen and paper. Doing this will slow you down, draw you into the moment, and force you to crystalize your answers.
  • Make it special. Buy yourself a nice pen and journal for this project. Get a lavender latte and a chocolate croissant at the start of each session. Wear your favorite shirt. The trick is to signal that this is sacred time dedicated to focusing on you.

Even if you ignore all of the other tips above, be sure that you are unreachable during your time reflecting. At minimum, put your phone in airplane mode, turn off the wireless card on your computer, and resist the urge to jump online.

11 questions to spike your self-awareness

A good interviewer spends time preparing questions for her subject, while remaining open to spontaneity. She asks questions no one else has the audacity to ask.  She follows her subject down rabbit holes even when it’s unclear where they’re going. She accepts that some questions will have short answers.

The questions below are designed to aid in your preparation. I have found them to be important in my life. Feel free to answer all of them or only a few. The more time you invest in yourself, the greater your results.

Pay particular attention to the questions that excite you and the ones that make you nervous. The answers to those questions will provide important insight. Revisit the answers that feel incomplete at later sessions.

As you go through this process new questions will arise. Perfect! Add them to your list for future sessions. With each honestly answered question, you’re getting closer and closer to you. Here are eleven to get you started:

  • Your doctor calls. She informs you that you’ll be dead in six months. How does that change your life? How would you spend your remaining time on earth?
  • You’ve just inherited $100,000,000. Now that money is no longer an issue, what do you do with your life? Bonus: how can you start doing that – even just a bit – today?
  • Are you happy? If not, what do you think you need to be happy?
  • What lies have you been telling other people? What lies have you been telling yourself? Why?
  • What would your perfect day look like?
  • What do you hope people say about you at your funeral?
  • What’s missing from your life? What can you do to get it?
  • Have you ever felt fully loved by yourself or someone else? If the answer is no, what would it take for you to feel loved? Is something inside of you blocking that?
  • In what areas of your life are you underestimating yourself?
  • What gifts, talents, or passions have you been hiding from yourself and the world? What can you do to start engaging them more often?
  • In what areas of your life are you out of integrity? How can you fix that?

Where do you go from here?

By taking the time to interview yourself, you are forming a stronger sense of self-awareness. The next step is to translate awareness into reality. You do this by making the life you live a reflection of who you truly are.

Attempting to change everything all at once is seductive but unrealistic. A better approach is to consistently make small changes. Over time, the small changes will compound and become significant changes. You will become more you.  


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16 thoughts on “Getting to know yourself: eleven questions for deepening self-awareness

  1. Something that has worked for me as well is thinking about your safe place. Whether it’s your bed or a bench in a park nearby, etc and write it down and think about why it’s your safe space and how in this place you can tell your honest truth. Then think about the things in that space and how they can work as metaphors for these white lies we hide behind. Mostly the silver lining is we all just want to be loved and for fear we don’t believe we deserve it. Thank you for your questions.

    1. Hey, Pearl! This is a really sharp technique you’re suggesting. I like that. Grounding yourself in a physical place (even if it’s just the memory of that place) to facilitate opening to truth. Good stuff. 100% agree with you. As far as I can tell, the base human desire (and my base desire too) is to be fully seen, and loved.

  2. Dear Jason, this article comes at the very right moment for me, you know I am begining my business after 5 wonderful years at the university. Actually today I spent almost the whole morning reflecting about my life, trying to make sense of this transition I am going through. Thanks a lot my friend, absolutely everyword you say is brilliant and amazingly true. Awesome job!!!

    1. Richar, great to hear from you (and my apologies for the delayed response). Congratulations on starting your business. That’s huge! That one of the first steps on your path was spending a day reflecting and trying to make sense out of your transition leads me to believe you’ll be very successful. And I’m so glad to hear my writing resonates with you. Thanks for reading. 🙂

  3. Being a Gemini (the twins – split personality) I get to observe myself all the time.

    “Roses are red, violets are blue. I’m a schizophrenic. And so am I too!”

    Just kidding! But only a little. I don’t hold with horoscopes, but I do respect some of what’s said about the star signs as I observe the truth of it in my own life experience.

    I stumbled across my own interview process, and it’s more passive than active. Almost like meditation (which you’ve now got me into).

    I observe what I do, all day, every day.

    I record it, along with how it makes me *feel*

    When I feel good, and time disappears, I’m in the flow of what I should be doing. What *I* am all about.

    When I don’t feel good, I’m doing something I should not be doing. What somebody else (who is good at it) should be doing for me or with me.

    Self-awareness is absolutely the key – “Know Thyself”.

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