143 Questions To Ask Yourself Before You Die

This is a piece I wrote for a personal development podcast which isn’t online any more called “Go Legendary”. I thought it might fit here — thanks for reading.

Sometimes, We All Need A Kick In The Butt.

This list was designed to do just that.

Grab a sheet of paper, read through the list, and write down the first answer that comes to mind. You’ll need to think about some more than others, but if you can get through all 143 of them, you’ll have packed more introspection into one session than most people do in a year–or maybe their entire lives.

Ready… set… go!

What I Know About Me and The World

  1. who am I?
  2. what do I know to be true?
  3. what are three of my best qualities according to me?
  4. what are three of my best qualities according to my best friend?
  5. what are three of my best qualities according to my significant other (or ex)?
  6. what are my three worst qualities?
  7. who is my best friend?
  8. what excuses have I been telling myself to keep me from action?
  9. what does my name mean?
  10. was I named after anyone?
  11. when was the last time I did something for the first time?
  12. who was my childhood hero?
  13. what three words describe my current first impression?
  14. what three words describe my ideal first impression?
  15. when i’m wasting time, what do I like doing?
  16. i need to calm myself down. what do I do?
  17. i need to pump myself up. what do I do?
  18. i just woke up. what’s the first thing to cross my mind?
  19. what’s my favorite thing to do when i’m by myself?
  20. what makes me want to work out/exercise? if I don’t, why not?
  21. what, if anything, would I like to be responsible for?
  22. do I have any traditions? what are they?
  23. what limitations do I think I have?
  24. what would be different if I didn’t have them?
  25. when I meet a new person, what do I notice about them?

The Story So Far

  1. what’s the motto for this era of my life
  2. who are the primary characters in my story right now (besides me?)
  3. how are they influencing me?
  4. how am I influencing them?
  5. what do I want more of in my life to make me happy?
  6. what do I want less of in my life?
  7. when was the last time I lost track of time?
  8. what’s the most important thing to focus on right now?
  9. what’s my quest in life?
  10. what are three things that make me happy?
  11. what are three things that i’m grateful for?
  12. when was the last time I sang karaoke?
  13. when was the last time I helped someone?
  14. who has helped me get where I am?
  15. what choice do I regret in my life?

What’s Next for Me?

  1. where do I want to visit next?
  2. what one habit would I like to make?
  3. what one habit would I like to break?
  4. who would I meet, if I could meet anyone?
  5. what sport (extreme or otherwise) would I like to try?
  6. what natural wonders do I want to see before I die?
  7. what celebrations/festivals/parties do I want to attend?
  8. what parties do I want to throw?
  9. what will my funeral be like?
  10. what’s an adventure that I can have in the next 30 days?
  11. what needs to be in my will?
  12. do I want to get married? if married, do I want to get divorced?

Your Creative Side

  1. if/when I get interviewed on TV, who will do the interview?
  2. if/when I get interviewed on TV, what will we talk about?
  3. if I were going to build ONE of something, what would it be?
  4. if I could invent something to change the world, what would it be?
  5. would I rather write a book, tv show, or screenplay?
  6. what would this written work be about?
  7. what skill/hobby would I like to master in my life?
  8. what’s something that I collect, or would like to collect?

The Best In The World

  1. what is the best book I’ve ever read?
  2. what book should everyone else read?
  3. what book have I been wanting to read (but haven’t yet)?
  4. what is my favorite photograph?
  5. what’s my favorite piece of artwork?
  6. what is the best movie ever?
  7. what’s a classic movie I haven’t seen but have wanted to?
  8. if I could have ONE superpower, what would I choose?
  9. if I could become an animal, what would I choose?
  10. if I won the lottery, what would I do with my winnings?
  11. who is one of my current heroes?
  12. if a genie gave I three wishes, what would I ask for?
  13. what is the best food ever?
  14. what’s one food i’d like to try?
  15. what is my favorite color and what does it symbolize?
  16. if I were in a musical group, what type of music would I play?
  17. what is the best smell in the world?
  18. what time of day are I most productive?
  19. what time of day are I most useless?
  20. what’s my dream job?
  21. what do I do better than anyone I know?
  22. what are my biggest strengths/assets?
  23. what are my hidden talents?

The Darker Side of You

  1. have I ever committed a crime?
  2. if I were going to plan a heist, what would I steal?
  3. what’s the worst thing i’ve ever done for myself?
  4. what’s the best thing i’ve ever done for myself?
  5. What’s a secret that I’ve never told anyone (about yourself or about someone else)?
  6. what has been the saddest moment of my life?
  7. what am I afraid of?
  8. If I wasn’t afraid of these things, how would my life be different?
  9. Am I afraid to die? why?

What If…

  1. what is the thing i’re most proud of accomplishing so far?
  2. what will I regret doing or not doing if I continue living as I are?
  3. what do I want my legacy to be?
  4. if I retired today, what would I do?
  5. at what age do I plan to retire?
  6. given $ : 100, 1000, 10,000, 1mil – what do I do with it?
  7. i have to get a tattoo. what and where?
  8. what was the best part of being a kid?
  9. i have to change my name. what’ll it be?
  10. You have to write a letter to someone (that’s right, a real letter.) Who’s it going to? What’ll it say?
  11. what would I change about my appearance?
  12. if I could tell my past self anything, what would it be?

Deep Questions

  1. what parts of my life have become stagnant?
  2. what are my most appealing characteristics?
  3. am I doing something that matters?
  4. what am I doing to help others?
  5. what am I afraid of?
  6. who do I love, and what am I doing about it?
  7. am I taking enough risks?
  8. what’s a calculated risk I could take this week?
  9. what makes me angry?
  10. what was my most fulfilling/content moment?
  11. when am I proud of what i’ve done?
  12. what grudges am I holding?
  13. when do I stand up for myself?
  14. what path does my heart say I should follow?
  15. do I smile more, or frown more?
  16. what did I used to love doing, when I was young?
  17. what excites me about the future?
  18. where do I want to be tomorrow?
  19. what do I look forward to every day?
  20. when I daydream, what do I see?

Unlocking Your Passions

  1. what subject can I talk about for hours?
  2. what do I most enjoy doing for others?
  3. what are five experiences that gave me a sense of growth and fulfillment?
  4. what makes me smile?
  5. what’s easy for me?
  6. what sparks my creativity and gets I imagining?
  7. what would I do for free?
  8. what would I regret not having tried?
  9. if I could subscribe to only 5 magazines, what would they be?
  10. if I were stranded on a desert island with food, water, and shelter, what would I miss most?
  11. what external barriers are holding me back from pursuing my passion?
  12. what do people frequently ask I for help with?
  13. if I had to teach something, what would I teach?
  14. if I were giving a TED talk (18-minute presentation to a young, intelligent and influential audience), what would it be about?
  15. what are my values (http://thinksimplenow.com/resources/ThinkSimpleNow-Values.pdf)
  16. what challenges have I already overcome?
  17. what challenges are I now facing?
  18. if I could live in one place for the rest of my life, where and why?
  19. what’s on my bucket list (to do before I die)?

Daily Reminders

I read a blog post recently that inspired me to take some action — specifically setting up reminders to take action. I wish I could remember exactly which blog it was, but I’ve tried to dig and been unsuccessful. If I find it, I’ll certainly update the post with the source.

Anyway, the author had several steps to ‘get off your ass and make changes, be awesomer’ (I’m paraphrasing, of course) and one that I did in the moment was set up some reminders. That was about a month ago, and it did have some effect on me. As of today, I’ve modified and updated the alerts I set for myself.

Here’s the reminders I currently have:

  • 12AM: What are you grateful for? (I usually go to sleep around then)
  • 12PM: What is the most effective use of your time and energy? (I’m awake and generally have started my workday by now, so this helps to refocus me on what’s most important)
  • 4PM Sunday: Review Asana, Evernote, and journal. (Trying to insert a GTD-style weekly review into my routine)
  • 6:30PM M-F, Sun: Meditate (simple breathing/gratitude meditation)
  • 7:30PM MWF: Work out get huge! (3 days a week. Usually between meals at this point which was an excuse of mine for not doing this before)

Previously, I used the Reminders app for iOS. It doesn’t work quite the way I wanted for a daily reminder, since it wants to “check off” the reminder, and makes a note of how many days ago the reminder was set. I don’t care when I set the reminder, and I don’t want to go to the Reminders app when the alarm is triggered, so now I’m using the Clock app with simple alarms. I just changed the “label” text to be the reminder.

Feel free to steal these alerts, add your own, and all that good stuff.

About Girls

There’s something I have to tell you. It’s not a very popular viewpoint, and I hope you won’t think less of me after I say it. They’re weird, and sometimes difficult to decode. This might sound weird, but… I like cats.

Wait–I mean, I like girls!

It’s so easy to get them confused sometimes.

You see, growing up, my mom and I were always a cat family. Cats, of course, are well known for their ability to turn normally sensible and intelligent people into what are essentially two-year-olds with a better vocabulary. I myself have been known to tell my feline friends, “you’re so adorable,” or indeed to have discussions (mostly one-sided) about the finer points of how they like to have their ears scratched… Except for the occasional paw-swat.

With some practice, I now consider myself to be pretty darn good at understanding our fuzzy friends. Given the average kitty and perhaps an hour of time, we will become fast friends–that is,until she is distracted, spooked, or food becomes part of the equation. As cool as I am, I could never compete with cat food.

It’s pretty much the same with women. I still can’t compete with food, but with some study and a lot of practice, I now consider myself decently proficient with people in general, including women. It wasn’t always easy, though… I have often found myself very confused by a girl’s actions. I don’t mind this anymore–in fact I think It’s part of what makes girls so magical (we never quite understand them!)

For instance, a girlfriend of mine used to remark, “Don’t be jealous of my (thing)!”
Here’s what it looks like in context: Continue reading “About Girls”

New York’s The Greatest! (If You Get Someone To Pay The Rent)

The title of this post is taken from LCD Soundsystem’s song “North American Scum”. You should click below to listen while you continue reading…

I’m fortunate to have my job with The Art of Charm for many reasons, but one of my favorite is that it allows me to travel sometimes. Like now, for instance. We are back in NYC for the month of June, tearing it up, and wondering, “Why did we ever leave?”

And then, we remembered–after having spent our whole month’s budget in the first week of living here. “Oh yeah, it’s really expensive!” This isn’t all bad, though, because it will allow us to partake in something we’ve clearly been lacking since eating healthily in Los Angeles: Subway Five Dollar Footlongs! Continue reading “New York’s The Greatest! (If You Get Someone To Pay The Rent)”

What Time Is It? Adventure Time!

This is only the most awesome show in the world right now. Really, how can any video that has candy-zombies and thinly-veiled sexual innuendo directed at baked goods not be good?

If you don’t already know about Adventure Time, think about this for a second: are we really that good of friends? How long have you known me?

Just kidding. I just think this show is so goddamn awesome that everyone should know about it. Also, thanks to the good people of internet fan-piracy, it’s online! Cartoon Network doesn’t let me embed the episodes on my blog, so you get this legal-grey-area version below. Mmmm, grey area.

Update: If you haven’t seen the pilot episode, you should start with that (it is equally-if-not-more awesome).

Say it with me now… What time is it? Adventure Time!


My favorite Adventure Time quotations:

  • Mathematical! Rhombus! That was totally math!
  • Ugh. The Ice King is an oxy-moron.
  • Finn: Why are you always stealing princesses?
    Ice King: I’m going to make one marry me!
    Finn: That’s … stupid! (kicks the Ice King in the face)
    Ice King: Your hat is stupid!
    Finn: My hat… IS AWESOME!!
  • Look! Those ninjas are stealing that old man’s diamonds!

Hungry for more? You’re my kind of person! I used to have a link here to a shady-ish site with an episode of Adventure Time. It’s since been removed, so unfortunately, you’ll have to search the torrent of internet files yourself. If you REALLY want to find these episodes, shoot me a message from the contact form.

In related news, Finn is my new role model. Mathematical!