Have you come across David Foster Wallace’s 2005 commencement speech at Kenyon College? It’s a beautiful thing. It spells out the daily and mundane frustrations that a 21st century college-educated American will encounter in life. And it reminds all of us who are fortunate enough to be in that position that we always have a choice about how we experience the world and how we relate to the people around us. It’s powerful stuff. And perhaps along with Steve Jobs’ commencement speech at Stanford (also in 2005 – dang, ’05 was a high-water mark for commencement speeches!), DFW’s speech is one of the few that anyone seems to remember.
What was I talking about again? Oh yeah…this question. It reminded me of DFW because it’s essentially a question about daily obligations. Cooking, cleaning, etc. It’s a fun one to ask your friends! (But ask it because you want to have fun with friends, not because you want to fantasize about a life that’s not your life. Your life is precious. Look, both David Foster Wallace and Steve Jobs, who were giving speeches in 2005, are now on the other side. Life is precious! (Dang. Re-reading these speeches put me in a weird head space…)) Continue reading If you could have unlimited free service for 5 years from a chef, housekeeper, masseuse, personal assistant, or chauffeur, which one would you choose?→
I’m a bit of a junkie when it comes to reading about productivity, personal development, forming habits, etc. To wildly varying degrees of success, I’m always trying to further develop my strengths or shore up weaknesses or start new good habits. But after a point, the most helpful thing to do is just to know yourself enough to understand that some “bad” habits are probably going to stick because…they just are. As long as it’s nothing insane, I say maybe don’t worry so much about it. I’m going to stay up too late. On weekends, I’m going to wake up too late as well. Every third roadtrip or so, I’m going to cave and eat twenty chicken mcnuggets. Nuggets!!!! Mmmm bbq sauce, sweet chili. (Sorry, not sorry.) My friends need to know that about me. Continue reading What is one guilty pleasure you enjoy too much to give up?→
A deep conversation with your best friend might change your outlook on something forever. That’s great. It makes sense that a significant change would come from a relationship that big and that meaningful. But sometimes, incongruously, a very brief interaction with someone you don’t know well (or at all) can leave a lasting impression on how you see things or how you move through the world. I shared a late lunch with an elderly woman in Toulouse, France for 30 minutes and then never saw her again. I’ve thought about her regularly for the past decade. Who has impacted your life quickly but forever? Continue reading What person would you say has had the biggest impact on your life in the shortest amount of time?→
Republican. Democrat. Christian. Muslim. Entrepreneur. Parent. Crossfitter. Apple devotee. Hipster. The groups we join (and stick with) do indeed signal to the outside world something about us. But you can’t ever truly know people by the boxes they check. You only really see a person when you start to understand how her unique personality does NOT line up 100% with the group identities that characterize her broadly. A Democrat who believes that life starts at conception. An entrepreneur who’s terrified of risk. A hipster who sincerely loves the new Justin Bieber album. Outside the lines is where friendships get interesting. It’s where real people live. Continue reading What’s one major way that you differ from the group(s) you most closely identify with?→
So this is a double-barreled question and both parts are equally important. What do your friends dream of accomplishing, or trying, or having? You need to know these things. But also, we all have roadblocks (real or perceived) that prevent us from living out our dreams. You need to know these things as well (about your friends AND about yourself). Continue reading Is there something you’ve dreamed of doing for a long time? Why haven’t you done it?→
In the Stony Brook study from which this question comes, this is classified as one of the deeper level questions. Nobody’s family is perfect but this prompt asks you to reflect very intentionally about what could have (or sometimes SHOULD have) been different. This is a good conversation to have with a close friend because it can remind us that ALL families have their shortcomings. There’s no need to feel ashamed about parts of your own family. You can look back on your experience with a bit more perspective and a bit more compassion. Continue reading If you could change anything about the way you were raised, what would it be?→
In good years and in bad, there are always things to be grateful for. Talking about them makes the year seem better, no matter what kind of year it’s been. And reflecting on this question provides us with a much needed pause – a bit of space to take in what’s happened in the recent past and to feel thankful. It’s what meditation advocate and teacher Tara Brach would call a “sacred pause.” Go ahead. Ask this question and hit pause for yourself and a friend. Continue reading In the past year, what have you felt most grateful for in life?→
This question gives you such a cool angle on someone’s day-to-day life. Learning about what small-ish purchase has changed someone’s life can tell you a lot about hobbies, routines, frustrations, splurges, all kinds of things! Plus, you might get some really good ideas for your own next life-improving purchase. Continue reading What $100 (or less) purchase has most positively impacted your life in the last year?→
This question doesn’t feel intimidating but it actually tells you a TON about a person’s values. Does she think of Sheryl Sandberg? Does she think of a beloved college professor? Does she think of her grandmother? In a very direct sense, someone’s definition of success dictates their whole life. Continue reading When you think of the word “successful” who comes first to your mind? Why?→
Not only does this question tell you what your friend reads, it tells you what she thinks is worth sharing with the people she’s close to. This question could also add a title to your “to-read” list. Bonus! Continue reading What book have you gifted the most to other people?→
I’m always looking to steal ideas for how people stay motivated, positive, and moving forward. And when you ask this question of your people, not only do you get some good ideas to try out but you also get to know how your friends cope with stress and setbacks. Continue reading What helps you stay positive?→
What if we cared about new questions like we care about new phones?
