Who is your most unlikely friend?

 

Of all your friendships, which one probably makes the least sense to outside observers? Maybe you and that particular friend have very different personalities or interests or backgrounds. I’m curious about how these unlikeliest friendships start and why they work. I also wonder about the corresponding question: Who is your most LIKELY friend? (This would be the friend that makes you think, “Well of course _____ and I are friends!”) There’s a lot to unpack in these questions about what we value in our friendships, what parts of our whole selves we make visible to the world at large, and even how we choose to let people into our inner lives. Continue reading Who is your most unlikely friend?

How can I treat this person like a child?

 

So I’ve categorized this question as “Ask your Significant Other” but really it’s a question to ask yourself ABOUT your significant other. How can I treat my partner like a child? Stay with me because this needs some contextualization. This question came from author Alain de Botton who wrote the most popular NY Times article of all of 2016 titled “Why You Will Marry the Wrong Person.” Let’s go straight to Alain as he explained on the On Being podcast:

“I think that one of the kindest things that we can do with our lover is to see them as children. Not to infantilize them, but when we’re dealing with children as parents, as adults, we’re incredibly generous in the way we interpret their behavior. If you walk home, and a child says, ‘I hate you,’ you immediately go, OK, that’s not quite true. Probably they’re tired, they’re hungry, something’s gone wrong, their tooth hurts, something. We’re looking around for a benevolent interpretation that can just shave off some of the more depressing, dispiriting aspects of their behavior. And we do this naturally with children, and yet we do it so seldom with adults. When an adult meets an adult, and they say, ‘I’ve not had a good day. Leave me alone,’ rather than saying, ‘OK. I’m just going to go behind the facade of this slightly depressing comment…’ We don’t do that. We take it all completely personally. And so I think the work of love is to try, when we can manage it — we can’t always — to go behind the front of this rather depressing challenging behavior and try and ask where it might’ve come from. Love is doing that work to ask oneself, ‘Where’s this rather aggressive, pained, noncommunicative, unpleasant behavior coming from?’ If we can do that, we’re on the road to knowing a little bit about what love really is, I think.” Continue reading How can I treat this person like a child?

What is the best investment you’ve ever made? (of energy, time, money, any resource…)

 

Here’s another gem from Tim Ferriss’s podcast. (It’s tax time so I’ve been binging on podcasts while catching up on business bookkeeping. Tim has added a lot of great questions to his repertoire since I last tuned in!) I have two answers to this question. 1) My business and social venture, HaitiHub, has demanded a very significant amount of time, energy, and money over the past six years that it’s been my full time work. But HaitiHub has taught me so much about entrepreneurship, about design, about business models, and about creating a thing for real people. And it’s been such an honor to build up and serve our community of language learners. And in the strict sense of the word “investment,” I feel good that HaitiHub can conceivably continue creating impact and income over the long haul. 2) Investing in my (sometimes torturous) long-distance relationship with Emily from 2006 to 2011 meant hundreds upon hundreds of emails, many mismatched time zone phone calls, many used up vacation days and sick days, and honestly, a considerable amount of heartache at different points. But our marriage now is a wonderful and humbling thing. It pays dividends out in joy. Best investment I’ll probably ever make. Continue reading What is the best investment you’ve ever made? (of energy, time, money, any resource…)

What’s one thing you’ve changed your mind about in the last few years?

 

I’ve put this question in the category of things to ask someone you disagree with. But when you ask it, you don’t need to make the question about politics or religion or whatever topic on which you don’t see eye to eye. (In fact, it’s probably better to leave it open-ended.) The usefulness of this question comes in 1) remembering that changes of heart and changes of mind ARE actually possible, 2) seeing HOW your counterpart was persuaded and better understanding what kinds of new information he finds persuasive, and 3) acknowledging, even in an indirect way, that YOU yourself have not always been right about every issue. And it doesn’t even matter what the issue is. It could be the most “trivial” thing. If I used to think that Diet Coke was good but now I think it’s unhealthy and that regular Coke is better, talking about that process of change will still help the tone of our dialog when conversations swing back to weightier issues. Continue reading What’s one thing you’ve changed your mind about in the last few years?

What’s a clear sign that you’ve moved to the next level of friendship with someone?

 

Part of what makes good friends more than just acquaintances is that you can let your guard down around them and be more fully yourself. For some people, they’ve reached the next level of friendship when they can just stop by unannounced and with no particular plans. For others, they’ve reached the next level of friendship when they can talk openly about the things in life that aren’t going perfectly. For me, it’s about food. I’m not a big guy but I’m very often hungry and I can definitely eat a lot. There have been times that Emily and I have come to dinner at another couple’s house for the first time and I’ve thought to myself at the start of the meal, “Yup I’d feel full if I ate everyone’s food tonight.” Hahaha! Then when we’re leaving, Em says to me as soon as we’re back in the car, “You’re still hungry, aren’t you?” and we drive to Chick-Fil-A (or start brainstorming about leftovers at home). But with close friends, I’ve come clean about this and now they poke fun at me and admit things like “We knew you were coming so we picked this recipe that makes a TON of servings.” And you know, I feel really taken care of in those moments. Truly surrounded by friends. Continue reading What’s a clear sign that you’ve moved to the next level of friendship with someone?

Who is one person in your life with whom things are not complete?

 

This idea of “complete” and “getting complete” comes from the thought exercises in the Landmark Forum. The basic idea is this: A relationship in your life is “complete” only if you’ve said everything that needs to be said to that person. This could be an apology, a thank you, a confession, a “I’m so pissed at you for what you did”, an “I miss you”, or any number of things. Everyone can come up with a shortlist of at least 2 or 3 things that you KNOW you should say to the people in your life because leaving them unsaid gives you a nagging feeling, or makes you feel more distant, or makes you feel disempowered in your day-to-day. Identify just one of those people with whom things are not complete. What would you need to say in order to “get complete”? At different points in my life I’ve felt not complete with members of my immediate family, with friends, with people I’d dated… Getting complete with them has been hugely rewarding and freeing and restorative. Try it! I swear! Continue reading Who is one person in your life with whom things are not complete?

What’s one song that nearly everyone of your generation would be able to sing along to?

 

My friend Patricia is an art therapist who works in a medical clinic. She mentioned that her patients (many of them in their senior years) will sing the same song together as a send-off when another patient is discharged. The song “Happy Trails,” by Roy Rogers and Dale Evans, was the theme song to a popular radio and then TV show in the 1940’s and 50’s. Most of the elderly patients know it and enjoy singing it as their “roommates” leave the clinic. That got us thinking: when we’re all senior citizens, what song will we all be able to sing to each other? There’s more music now and wider tastes than in the 1940’s and 50’s, that’s for sure. So it’s an interesting question to ponder. You wanna know my best guess? When I’m 85 years old, getting wheeled out of the rehab clinic, I’ll say my farewells to a chorus of… “In West Philadelphia born and raised, on the playground is where I spent most of my days…” Continue reading What’s one song that nearly everyone of your generation would be able to sing along to?

In what two places of your everyday life are you the most different?

 

I came across a really interesting quote in a Vox article that said, “…America contains multitudes, and we are different, and act differently, depending on what is being asked of us.”

This got me thinking about how and when my actions vary widely during the span of one day. When I lived in LA and had 2 hours of commute time every day to work, boy… stuck in traffic on the 405 freeway I acted aggressively and was uncompromising. But once I was at work (which was a religiously-affiliated non-profit), I was calm and level-headed. Maybe this makes me hypocritical. Or maybe it just makes me human. What about you? What two normal life situations make you act the most different?

Calling Time Warner customer “support” vs. Tucking in your daughter.

Hip hop dance class vs. Scheduling a doctor’s appointment.

Writing an ambitious to-do list at 3am vs. Waking up at the crack of noon…

What’s your range? I think it’s important to remember that we each contain multitudes. Continue reading In what two places of your everyday life are you the most different?

If your mother wrote a book about you, what would it be called?

 

Love this! It’s a funny question. My sister told me about this one after she heard it on the new “Exactly” Podcast. I’m really not that sure what my mom’s book about me would be called. One possibility, though, would be: “Carlo, if you die I’m going to kill you.” Haha! She told me that after I’d decided to live and work in Haiti. That title sums up a lot about our relationship. 1) There’s a tremendous amount of love there. 2) My mom hasn’t always approved of the risks I’ve taken in life. 3) She’s always respected me and never prevented me from living life or growing up. 4) We joke with each other. There’s a lot in there! This is a great question. Continue reading If your mother wrote a book about you, what would it be called?

What did you do to prepare for this interview?

 

For author and consultant Suzy Welch, this question reveals a lot about a candidate’s likelihood of success on the job. If a potential new hire has “stalked” the company and its key members online and has learned enough to speak confidently about the business, this isn’t creepy – it’s thorough. On the other hand, if the candidate printed out his resume and stopped there, that might be an early sign of an underwhelming hire. Continue reading What did you do to prepare for this interview?

Can we talk about people we know personally?

 

I’m thinking of Thanksgiving dinner conversations as I write this one. And I’m thinking of the terribly contentious presidential election we’re all just emerging from. I know there are a lot of folks out there who are dreading the prospect of a political food fight erupting at the dinner table. If things start to get heated, you could always just change the subject. (“How about those Cubs finally winning it all?! Am I right, Uncle Breitbart?”) But I’ve never seen that work really well, myself. And it’s probably not productive. We DO NEED to be talking with each other. We DO NEED to listen across the party lines that exist even within our own families (ESPECIALLY within our own families!). But it’s difficult to hear each other when blood pressures rise and people start unholstering their talking points. Talking points… Pshh. Talk about a guaranteed waste of time. Instead, if you can’t (or don’t want to) avoid the political conversation, try this one: “Can we talk about people we know personally?” And follow it up with, “Because I’m thinking of my fishing buddy, Michael, who hasn’t had full-time hours at the plant in over a year.” Or, “Because I’m thinking of my dear friend Janice who is scared that her marriage will be invalidated…again.” Return over and over to ACTUAL PEOPLE YOU KNOW PERSONALLY. It’s disarming. Actual people are Kryptonite to talking points. If you keep the conversation about the people in your lives, both sides can end up with something productive even if you don’t ever agree. You’ll at least start to understand each other’s worldviews. Continue reading Can we talk about people we know personally?

A deranged serial killer points a gun at you and says “Make 1 phone call right now. If the person answers, I will shoot you.” Who do you call?

 

Haha! This question is too damn funny. Apparently it was making the rounds on Facebook recently. I’d call my mom’s cell. She often doesn’t remember to keep it on her so I’d have maybe a 60-40 chance of not getting shot. I struggle to come up with someone in my life who is just guaranteed straight to voicemail. Maybe that’s a blessing! Continue reading A deranged serial killer points a gun at you and says “Make 1 phone call right now. If the person answers, I will shoot you.” Who do you call?

If you could invent a brand new holiday, what would it celebrate?

 

What would it be all about? And how would people observe the day? My sister immediately answered this question by exclaiming, “National Nocturnal Day!!” She said on that day, everyone would sleep all day and work all night. As a natural night owl who often feels guilty waking up late after burning the midnight oil, she would love a day that was all for the nocturnally inclined. People would leave their lights on as they worked on passion projects, side hustles, and caught up on work. Coffee shops would be bumping at 3am. Haha! That’s her holiday. What’s yours? Continue reading If you could invent a brand new holiday, what would it celebrate?

Who is the most reasonable person you know who is voting for the other candidate?

 

Just a few more days until the 2016 presidential election season comes to a close. Thank God. Trump or Clinton. Boy oh boy. All indications point to a very close race. But no matter what happens, at the end of this, we will see (as we’ve seen for the past 4 elections), that the country is nearly split down the middle. Us vs. Them, with less and less common decency and civil interaction every time a new president is chosen. This is a trend that we need to reverse for the sake of our country’s future. So let’s all ask this question: Who is the most reasonable person I know who is voting for the other candidate? When you come up with a name, go grab coffee together. Talk about politics. Or don’t. But interact, listen, and continue to be reasonable with each other. It’s a low bar, but an important one. Continue reading Who is the most reasonable person you know who is voting for the other candidate?

Are there any “slang” words or phrases in your family?

 

So apparently my friend’s dad made up an expression that he would say any time he was about to go poop. And for some reason he’d say it to one of the family pets. For example: “Mr. Whiskers, I’m going to the super bowl! I’m gonna take you to the super bowl!” As a saying, it only kind of makes sense. (Presumably “bowl” comes from “toilet bowl” but why the super bowl? And why would the pets be brought along?) The point is that it’s funny, and random, and would only make sense within my friend’s family. It’s slang that’s localized to her single household. What do they speak at your house? Continue reading Are there any “slang” words or phrases in your family?

Do you have a favorite book that was read to you?

 

Any book that YOU yourself read is off limits for this question. What book do you really remember because it was read TO you by a real live person? (Audio books don’t count here.) When my sister and I were discussing this question, we both remembered the book “Bunnicula” that my mom read to us when we were in early grade school. Every night for a few weeks, we’d climb up onto my mom’s bed and she’d read a chapter or two before we had to go to sleep. I don’t remember a single detail about that book. But I remember the title and I remember loving that time together and being so eager for the next night when we could hear another chapter. My sister obviously remembers it too. I don’t think we’d talked about that book in 20 years but just today we both instantly were saying “Bunnicula!” Continue reading Do you have a favorite book that was read to you?

When was the last time that you had to build up your courage to do something?

 

#11 on this really great list points out that courage is not something we need to have at all times. To have a really fantastic life, in fact, we only need to be courageous every now and then for like 20 seconds at a time, max. That’s usually the amount of time it takes to make that uncomfortable phone call, or finish speaking the actual sentence where you ask your boss for a raise, or walk over to that person you’ve been wanting to meet. You don’t have to walk through life as a constantly courageous person. You just have to be able to build up enough courage for that 20 second sprint. So when was the last time you had to build up your courage to do something? Continue reading When was the last time that you had to build up your courage to do something?

If you had to give a toast tonight, what story would you tell about [Name] or [Name]?

 

Dang! I just made up a brand new category for this single question. I don’t normally make new categories until I have at least 5 questions but I couldn’t resist. This one is too good. (And I’ve been going to too many weddings in the last several years not to share it.) So you know how at some weddings you and your +1 are seated at a table for dinner with people you only kind of know? And you know how conversation that involves everyone at that table is sometimes hard to get going? Well next time, just wait for that lingering silence and then throw out, “Hey, if you had to give a toast tonight, what story would you tell about [Name] or [Name]?” You’ll have the tightest table at the whole reception faster than you can say, “Cupid Shuffle.” You’re welcome! Continue reading If you had to give a toast tonight, what story would you tell about [Name] or [Name]?

What’s one thing you’ve learned from an animal?

 

The animal could be your own pet. Or it could be a deer you saw on a hike. It could even be a killer whale from that crazy Blackfish documentary that blindsided Sea World and forced them to start phasing out their orca shows. The biological diversity on our little planet is truly staggering. Humans plus, oh you know, just a couple million other species. So what’s one lesson that you’ve learned from interacting with or observing an animal? Continue reading What’s one thing you’ve learned from an animal?

What’s something you own because you just like the idea of having it (more than you actually use it)?

 

I grew up in Southern California (310 represent, baby!) and I’ve always loved the beach and the ocean. I learned to surf as a Junior Lifeguard when I was 10 years old. I’m not great, but I do love it. When I moved to North Carolina it meant living as far from the ocean as I’d ever lived. That was really unsettling for me. So when I got to NC, one of the first things that I started looking for on Craigslist was a surfboard. As soon as I found a good deal on a decent board, I snatched it up and IMMEDIATELY felt a sense of relief wash over me. Security blanket effect, for sure. In the five years that I’ve owned it, I’ve surfed it three times total. In fact, I’ve surfed way more often on my old boards at home when visiting my family back in SoCal, haha. But I’m always going to own a surfboard out here in NC, regardless of how little use it sees. I realize that, logically, this makes no sense. But I don’t care. And I have a feeling I’m not alone. But you tell me… Am I? Continue reading What’s something you own because you just like the idea of having it (more than you actually use it)?