100 questions to inspire rapid self-discovery . . . . . . (and spark your next talk, date, blog post or book.)


Evolutionarily-speaking, we are designed to understand + be understood.

We’ve got five distinct senses.

We’ve got a whole brain region devoted to connecting abstract ideas to words + symbols.

We’ve got 45 miles of nerves running through our bodies, with impulses that travel at 325 miles an hour.

And — depending on your belief system, or how many glasses of Gewurztraminer you’ve imbibed — we’ve got a soul. An essence. A source of intuition.

As human beings, we’re uniquely gifted with the ability to dive deep, to probe + connect, to soften the barricades that divide us, and to really get each other.

We don’t always succeed, of course.

But maybe we’re not asking the right questions …

Here’s a collection of 100 questions to inspire self-discovery + understanding … and maybe your next blog post, journal entry, book outline, first date or dinner party conversation. ❤

Enjoy the Q’s. Go learn something new. Revel in the miracle of your capacity to understand + be understood. (Enough preamble: c’mon, just play!)

ϟ What’s the best compliment you’ve ever received?

ϟ What’s one thing you’re deeply proud of — but would never put on your résumé?

ϟ What’s the most out-of-character choice you’ve ever made?

ϟ If a mysterious benefactor wrote you a check for $5,000 and said, “Help me solve a problem — any problem!” … what would you do with him or her?

ϟ What’s going to be carved on your (hypothetical) tombstone?

ϟ What are you FREAKISHLY good at?

ϟ What’s one dream that you’ve tucked away, for the moment? How come?

ϟ What are you STARVING for?

ϟ If you could have tea with one fictional character, who would it be?

ϟ Do you have a morning ritual?

ϟ Do you believe in magic? When have you felt it?

ϟ Is there something that people consistently ask for your advice on? What is it?

ϟ Have you ever fantasized about changing your first name? To what?

ϟ When was the last time you astonished yourself?

ϟ What’s your personal anthem or theme song?

ϟ Do you ever yearn for your life, before Facebook?

ϟ What’s your definition of an ideal houseguest?

ϟ If you had an extra $100 to spend on yourself every week, what would you do?

ϟ If you could sit down with your 15-year old self, what would you tell him or her?

ϟ What are you BORED of?

ϟ What’s the best birthday cake you ever ate?

ϟ How do you engage with panhandlers on the street?

ϟ Do you think LOVE is chemical, intellectual, spiritual — or completely undefinable?

ϟ Have you ever dreamed about starting a business? (Or if you’ve already got one — a new business?)

ϟ Are you afraid of flying in airplanes? (How come?)

ϟ What’s your most urgent priority for the rest of the year?

ϟ If you could master any instrument on earth, what would it be?

ϟ Have you ever been genuinely afraid for your physical safety?

ϟ What are you an expert on? Is it because of training, lived experience, or both?

ϟ Has a teacher ever changed your life? How so?

ϟ Are there any household chores you secretly enjoy? Which ones — and why?

ϟ How do you reign in self-critical voices?

ϟ If you could custom blend a perfume or cologne, what would it include?

ϟ What does FEAR feel like, in your body?

ϟ Do you think you’re currently operating at 100% capacity?

ϟ What do you value most: free time, recognition, or money?

ϟ If you could save one endangered species from extinction, which would you choose?

ϟ Are there any laws or social rules that completely baffle you?

ϟ Would you like to write a book? (About what?)

ϟ If you could choose your own life obstacles, would you keep the ones you have?

ϟ Have you ever SCREAMED at someone? (What did they do?)

ϟ Do you think there’s going to be an anti-technology whiplash, in our lifetime?

ϟ Where + when do you get your BEST IDEAS?

ϟ Have you ever met one of your HEROES?

ϟ What’s in your fridge, right this moment?

ϟ Can you tell when someone is LYING?

ϟ Can you tell when someone is telling the TRUTH?

ϟ Have you ever pushed your body further than you dreamed possible?

ϟ Are you living your LIFE PURPOSE — or still searching?

ϟ Have you ever had to make a public apology? (How come?)

ϟ What’s the WORST piece of advice you’ve ever been given?

ϟ Do you think we’re designed for monogamy? (Why or why not?)

ϟ How do you CELEBRATE your victories?

ϟ Would you consider yourself an introvert, extrovert, or ambivert?

ϟ Do you ever hunt for answers or omens in dreams?

ϟ Do you think everyone has the capacity to be a LEADER?

ϟ Is WAR a necessary EVIL?

ϟ Are YOU a starter, a finisher, or an implementer?

ϟ Have you ever unplugged from the Internet for more than a week?

ϟ Do you think we should live like we’re dying?

ϟ Do you have any habits or quirks you wish you could ERASE?

ϟ What was the most AGONIZING hour of your life?

ϟ Have you ever dramatically changed a habit, or gotten yourself out of a rut? How’d you do it?

ϟ Would you rather be a lonely genius, or a sociable idiot?

ϟ How would YOU fix the economy?

ϟ What was your very first JOB?

ϟ What brings you SHEER DELIGHT?

ϟ Are you highly useful in a CRISIS?

ϟ Do you like to be SAVED — or do the saving?

ϟ What’s one mistake you keep repeating (and repeating)?

ϟ If you were heading out on a ROAD TRIP right this minute, what would you pack?

ϟ Do you have any irrational fears?

ϟ When you see peers + competitors getting things you want, how do you react?

ϟ If you were to die three hours from now, what would you regret most?

ϟ What’s something you’ve tried, that you’ll never, ever try again?

ϟ If you could enroll in a PhD program, with your tuition paid in full by a mysterious benefactor, what would you study — and why?

ϟ Have you ever had a complete + total nervous breakdown? (How did you recuperate?)

ϟ Have you ever set two friends up on a date? (How did it go?)

ϟ Have you ever questioned your FAITH — or lack thereof?

ϟ What’s your recipe for recuperating from extreme heartbreak?

ϟ Have you ever had a psychic reading? Did you believe it? Was it accurate?

ϟ Have you ever (actually) kept a New Year’s Resolution?

ϟ Have you ever met someone who was genuinely EVIL?

ϟ Do you believe that everyone deserves redemption + forgiveness?

ϟ What was the BEST KISS of your entire life?

ϟ Do you secretly miss Polaroid cameras?

ϟ Do you have any physical features that you try to cloak or hide? How come?

ϟ What makes YOU so special, anyway? (No, really.)

ϟ What’s in your pocket (or purse, or man-purse) right now?

ϟ Ever fantasize about being in a rock band? What would your group be called?

ϟ What’s your guiltiest of guilty pleasures?

ϟ Who’s on your panel of imaginary mentors?

ϟ Have you ever stolen anything? (Money, candy, hearts, time?)

ϟ When was the last time you saw an animal in the wild?

ϟ What’s the hardest thing you ever had to write — and why?

ϟ Who’s the last person that deeply disappointed you? (What happened?)

ϟ Have you ever won an award? What was it for?

ϟ How long can you (comfortably) go without checking your emails or texts? How do you feel about that?

ϟ What do you deserve + get to receive, no matter what?

ϟ What are you ready to set into motion, today?


P.S. Choose your favorite question and answer it, below.
Let the games begin!



I think I want to make these into Moo cards. :)

Loved it! Thank you Alex. If someone handed me a check for $5,000 to solve a problem, I would take this person (and myself) to Tony Robin’s fire walk event. The problem would be solved in 2 days or less:-) Where are you mysterious benefactor ?

What’s in my purse (actually, a backpack) right now….

my wallet with all the basics but also with “files” of little bank envelopes assigned different “accounts” that I put money into each pay period… or try to, at least… There’s one for rent, for my daughter’s wedding, for Christmas 2013, for my son’s tuition, one for band stuff, and a blank one that I REALLY want to write “vacation” on!

an envelope for receipts

a bottle of acetaminophen

my “lil fat notebook” for random thoughts, lists, etc.

extra pair of glasses


a bouncy ball that my nephew gave me …one of his treasures:)

my camera

a pill box with all the days of the week with my supplements/vitamins in it

my fem hygiene products


lip balm

2 recipes

the registration confirmation for a conference that I am attending next week


a tape measure

my keys

my cell phone

a sparkly plastic star that I found on the ground and took it to mean good luck

Michelle C. Coyle on Apr 18, 2013 Reply

If you could only say one more thing to the world (and the entire world would actually listen) and you had to frame it in a Tweet (140 characters or less), what is the last message you want to leave in this world?

I love this game!

Betsy McDowell on Apr 18, 2013 Reply

Really good question / excellent thing to ponder – thanks!

ϟ Have you ever questioned your FAITH — or lack thereof?

After my mom passed away Christmas before last, I entered a period of confusion and didn’t know who I was anymore or what to do with myself. I lost a few friends who didn’t know how to deal with my loss and found out that a few others were much more dependable than previously realized. Around that time I started talking to one of them about her religious beliefs (I’ve never been into organized religion though I was exposed to it at a young age through both positive and negative experiences) and after almost a year of uncertainty I almost got baptized. Then I woke up one morning and knew I was just looking for community and direction in life, and if I joined the church I’d be miserable because it wasn’t where I’m supposed to be. However, the experience got me asking myself questions I hadn’t before and exploring my spiritual self. I found a sense of “faith” in the Universe, about everything having a place and knowing that I am always where I *need* to be to learn whatever lesson I need at the time.

Dorothy Joy on Apr 18, 2013 Reply

This has been a wonderfully inciting exercise! All of them made me think, but this one also made me laugh out loud.
“Ever fantasize about being in a rock band? What would your group be called?
Bitchin Kittens.”


My cologne would smell of cut alfalfa warming in the sun with a bit of crushed sage and rosemary and a drop or two of lavender, vanilla and honey.

I want that cologne…just sayin!

Christine on Oct 8, 2013 Reply

Thank you very much. I’m a photographer and trying to communicate my message and you are helping my so much. I am not naturally very good with written words and this is fabulous! I’m going to ask my clients ten questions before a shoot and let them answer at least five to get to know them better and to write about them on my blog in a meaningful way.

I am in love with this list! What fun inspiration!! Best kiss ever, and I am totally going to blog about this when spring finally arrives. Rolling around in a mud puddle in the rain.

These questions are fantastic!

“Have you ever SCREAMED at someone? (What did they do?)”

We were in our third year of marriage. In the five years we had been together, he had never heard me raise my voice until this night. I had had enough. My dialogue began in the usual cool calm manner, but the driving point came out at SCREAM volume. Just one sentence. He took a step backwards, his face absolutely stunned, and at a loss for words for the very first time. He stopped doing that thing that was driving me crazy.

Um, you just wrote an entire book I’d buy in a blog post. Generosity, unleashed! thank you.

Oh, I LOVE these! They are also incredibly great questions to ask on social media to stoke the fire of interaction. What a HUGE gift! Thank you. So many of these are my favorite. But I picked the one whose answer I’ve told next to no one:
ϟ Have you ever fantasized about changing your first name? To what?

Yes. I’ve always wanted to change my name to Noah. Maybe someday, I will.

Alex, I answered every single Q. Revelatory, as always. Thank you. C

SARAH LEWIS :: Dooooo it. The mini ones!

EDITA :: Ha! Simple as that. :)

MICHELLE :: I want to know what your “2 recipes” are …

BETSY :: I love this game, too!

DOROTHY :: Beautiful story, Ms. Joy. xo.

JENNA :: I want the EP, right MEOW!

HELEEN :: Awesome idea! You could even do a photography series where you create a series of 10 portraits, thematically related to each question & answer!

LAURA :: Roll away!

VAL :: Whhhooooa. Stunning, indeed.

JEN :: YOU are welcome.

NANCY :: You’re totally a Noah. (I’m a Hazel.)

CLARE :: Such an over-achiever. ;)

Alexandra Franzen on Apr 20, 2013 Reply

Fave Read of The Day: 100 questions to inspire rapid self-discovery http://t.co/t8MnM7IZeW via @alex_franzen #yandy

LOVE this! Printed it out for the next road trip my boyfriend and I go on. :)

What brings you SHEER DELIGHT?

ICE CREAMS and GELATO!!! never fails to make my day :)

Vida on Aug 6, 2013 Reply

Hi Alex, such a great post here, those are really awesome.. But I’m not sure about one of your above question: Do you ever yearn for your life, before Facebook?


Are you living your LIFE PURPOSE — or still searching?

This one is my favorite because I Googled “self discovery” and the results led me here, but to answer the Q, I think it’s pretty obvious that I’m still searching. Sometimes I feel like I’m wandering aimlessly. I mean, I’m a productive tax paying citizen, but I’m not “happy” there, but its a great paying job. Truthfully, I want to know what its like to actually LIVE the phrase, “You’ll never work a day in your life if you’re doing what you love.” There ARE things I love, the problem is I bore easily.

8ESBABY on Aug 26, 2013 Reply

What brings you SHEER DELIGHT?

making salad. dancing to a really awesome choon. holding my son’s hand.

Great Q line up, figured I’d respond to the least likely one:
Have you ever met someone who was genuinely EVIL? Yes
I was on the hiring committee for new entry level employees, we were making some final decisions about a middle age man who had been interviewed by another manager – I was asked to briefly meet him and then based on my meeting we might consider a 2nd interview.
I shook I man’s hands and immediately felt incredibly sick (similar things have happened to me before), so ill infact that I felt a definite sense of violence by him towards young children. I excused myself and deferred to my manager later. I asked for a second background check, (my boss luckily saw my concern and backed me up). Something had happened with his first background check and we were on hold with HR, they expedited another – I was called in person within 24hr, HR said the following: ” we don’t know why you requested an expedited background check, but what this man has done is so horrific we cannot devuldge it over the phone for breach of confidentiality – we will not ever be hiring him, and thank you”. Follow your intuition- ALWAYS!

Sarah on Sep 23, 2013 Reply

I am using your questions right now. Texting with a guy from online dating.. :) I think they tell a lot about a person. Thanks for the awesome questions!

Katie on Oct 2, 2013 Reply

Wow Alexandra, really like the questions. I have seen how questions can change people in various workshops that we performed with our company (check our site http://www.musekick.com). The answers of people can really inspire others as well!

What’s one dream that you’ve tucked away, for the moment? How come?

Having a career in singing….Because when I was younger, I never had the self confidence to register that I could make it anything other than a hobby. Now that I’m older, I see…and I’m trying to figure out how to make it happen.

Monica on Nov 1, 2013 Reply

May I use these questions on my blog? I will attribute them to you because of the marvelous work you have done. All I will do is answer them.

Certainly, Devin! :)

Alexandra Franzen on Nov 4, 2013 Reply

Wonderful and creative list. Thanks for sharing this in a blog. I will definitely use these questions when I’m teaching English to my students and to other people I meet at work or on holiday besides in my relationships.

Esther on Nov 29, 2013 Reply

If I were to die in 3 hours what would I regret the most?
That I left the house with so much clutter and didn’t keep the house with more Feng Shui appeal and be more of a minimalist. Yep, really, that I didn’t so more housework!!!
ϟ What was the most AGONIZING hour of your life?
When my son, age 12, was lost in Wash D.C. for 3 hrs. Since he didn’t know the address or phone number of where we were staying he couldn’t connect with me to tell me where he was or if he was okay.
When the police found him, they thought he was a runaway and didn’t believe his story. I didn’t know how to find him or how he would find me again. It was my MOST agonizing 3 hrs.
We both learned a lot from that experience. It brought us closerat and made him realize how important it was to really know where you are at all times, esp when traveling.

Esther on Nov 29, 2013 Reply

If I could choose my own life obstacles, I would choose the ones I’ve had. I have not always followed the traditional path and so I have started over several times. I’ve had love and lost love, had businesses and lost a business, moved from one place to another and started over. My friends have always remained, beyond every curve in the road I have found something wonderful waiting for me.

Margie on Dec 1, 2013 Reply

If you could sit down with your 15-year old self, what would you tell him or her?

Believe in yourself and always do what your heart tells you to do.

Roanna on Dec 1, 2013 Reply

Have you ever stolen anything? I stoled an eraser when I was younger.

I’m using your post in my blog over a period of timehttp://pobrandy.wordpress.com/2014/02/15/inspiration/ I’m actually so excited about the list – I’ve already started answering the first 10 in my next blog post in progress. FUN!!! Thank you!

Brandy on Feb 16, 2014 Reply

“What was the best kiss of your entire life?”

The kiss my boyfriend and I shared that first time. It set off a wonderful year long relationship that I’ve been too careless to take care of. I only hope it isn’t too late to fix what’s been broken.

If you were to die three hours from now, what would you regret most?

Not loving my family enough, always putting other things first, not being there when they needed me, always finding other things to do that were not important.

Paul on Feb 27, 2014 Reply

It would have taken this Libran hours to decide my favorite question Alex. So I closed my eyes, scrolled through all the questions and trusted I would intuitively click on the question that I most needed to answer right now. Which was:

‘What’s your recipe for recuperating from extreme heartbreak?’

Grounding: Contact the Earth with your bare feet and she will heal you, physically, emotionally, mentally and spiritually. She will let you see that her world is SO much bigger than your personal pain. Gradually the focus of your ‘heartbreak’ will start to shift ~ To being the ‘heartbreak’ of our Mother Earth and increasingly you will feel her wish to also be healed and the responsibility you now have to reciprocate this love.

my first job was as a teacher


This is one of the coolest websites I have EVER seen! Wow!

Thank you for the time you invested in this.


I second that. Also, the audience here super cool as well.

Milan on May 27, 2014 Reply

Do you have any physical features that you try to cloak or hide? How come?

My left nostril is oddly shaped and I always try to make sure my nose is down in photos so it isn’t shown.

Awesome questions…so much great stuff here I’ll be sure to have fantastic questions and conversations at many parties to come…

Some of these are not actually serious answers, they’re just for fun but most of them are true :-)

1) That I look beautiful

2) Being loud

5) Loudest girl on the planet R.I.P

6) Talking

Lol I can’t be bothered anynore because they aren’t numbered…

Brilliant set of questions. I have used some of them for a rapid fire interview my VP will be having with a business partner.
Thank you for this brilliance.

Great list. Makes my mind bubble and twitch…in a good way.
Fav question?
> Do you believe in magic? When have you felt it?
> I believe in most of anything. Unless it’s non-existence is proven. Reincarnation? Sure God(s)? Possibly. Aliens? Why not?
Magic? Most definitely! I believe in the magic of the own mind. It manifests itself on odd moments, when you expect it least. And it is strong! It can change your life, if you let it.

Maurice Klabbers on Jul 30, 2014 Reply

Just followed this link (possibly from another link, or a link within a link?) from your most recent email. I’ve decided to start answering these on my Tumblr! http://keyboardsanddarkness.tumblr.com/post/94248298889/5-questions

Such fun!

I am starving for time.

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