Category Archives: …Ask Yourself

In your life and in your city, where would you realistically go to meet people unlike yourself?

As communities (both online and in real life) continue to polarize and become more insular, I think it’s important to be aware of HOW to access people and groups that don’t share your particular background. Forget about getting to know a diversity of people if you don’t even know WHERE you can realistically connect. And I say “realistically” because everyone knows where “the other side of the tracks” are in their cities. Everyone knows which schools/churches/neighborhoods are unlike their own. But very few people will ever go to those other spaces and get to know them and the people in them. It doesn’t really work that way. In my city, the downtown YMCA is diversity central. The cars in the parking lot range from beat up to brand new. The bumper stickers on those cars promote Dems and the GOP alike. The people inside are black, white, brown… Some people are ripped as they walk out of the weight room. Some people are out of shape as they walk onto the pool deck. And routines are such that you end up crossing paths and conversing with the same handful of people every week. This provides real opportunity to encounter someone vastly unlike yourself and strike up a friendship. Not everywhere is like this. What comes to mind for your life and your city? And how could you spend more time there? Continue reading In your life and in your city, where would you realistically go to meet people unlike yourself?


What new thing have I looked like an idiot doing recently?

Everyone wants to look good. We all hate looking silly, inexperienced, and unskilled at things. The only problem is that “needing” to look good is directly opposed to lifelong learning and healthy risk-taking. I hate looking like a newbie at things but if I’m serious about self-improvement, then there’s also just no way around it. To help myself out, I’ve made it a “goal” to regularly look like an idiot while doing something I’m not good at. (Currently it’s basketball. I joined our local church league for the second season in a row. I scored 2 points the entire season last year. This year is going better but it would be hard for it not to!) When I’m achieving this “goal” consistently, I can be sure that I’m continuing to step outside my comfort zone. Continue reading What new thing have I looked like an idiot doing recently?


What one thing do I say to myself most often?

“Self-talk” refers to the things we regularly say to ourselves that affect our everyday lives. “You got this!” An athlete might say that to himself before competing. Or someone heading into a job interview might say the same. When self-talk takes a turn for the negative, a person could consistently say to herself, “You’re such a screw up,” and this would impact her day-to-day. What one thing do you say to yourself most often? When I think about this honestly, what I echo most often to myself is either the statement, “You’re not doing enough,” or the question, “Are you doing enough?” I worry that I’m wasting time or wasting my youth or not maximizing the advantages I’ve been given and not doing enough in the service of society… This self-talk motivates me but it also probably takes a toll in a way that “Wow – you’re great!” would not (if that were my most regularly occurring self-talk instead). For now, I’m not necessarily going to try to change my self-talk but I think it’s important to understand what it is. Continue reading What one thing do I say to myself most often?


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?


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?


What circumstances tend to repeat themselves in your life?

Every few years do you become restless with your work and wonder if you should switch to something that makes more of a difference in the world? Do you exercise religiously for 3 months straight and then hardly at all for the next 15 until you sternly recommit to the importance of working out again (for 3 months)? Are you drawn, continually, to writing? (Guilty on 3 counts over here in my corner.) These are patterns that I see in my life. What are yours? They could be any range of things. Maybe you’re repeatedly asked to take leadership roles. Maybe you’ve had a string of bad bosses. Maybe you feel a strong urge to travel abroad every few years. These cycles are not necessarily positive or negative; they’re just patterns. And when it comes to self-awareness, I think patterns are worth finding. Continue reading What circumstances tend to repeat themselves in your life?


What do you already know you won’t accomplish in your life?

I’ve never run a marathon, or piloted an airplane, or learned to speak Mandarin. But I might! One day, I might do those things. They are within the range of things that are still possible for me to do with my life. It’s unsettling, though, to think of the things that I already know — for sure — I won’t ever accomplish. For example, I already know that I won’t be a pro surfer. At 2 years old, that option for my life was still open. At 32, it no longer is. I just won’t be able to make that happen now – no matter how badly I might want it. Even if I started training today, that ship has sailed. That’s what happens as we grow older. The list of things you know you won’t do gets longer. My maternal grandmother is in her nineties. She’s mostly in very good health but she can no longer travel by airplane. Anywhere overseas that she’s never been, she will never be. That wasn’t always the case for her but it is now. Day by day, things become impossible. For all of us. We should remember that. A random Tuesday of some random week might be your very last chance to…[fill in the blank]. Isn’t it crazy to think that, as a FACT, everything imaginable that can be done with a human life will eventually pass through those brackets? Some things have passed through them already. This year and every year, more will. They’ll pass through on a Tuesday. Or a Thursday. Or a Monday. Do you know what that makes today? Sacred. Continue reading What do you already know you won’t accomplish in your life?


How am I part of the problem?

Tonight I heard Rev. Alan Storey speak. He’s a Methodist minister from South Africa who has done some amazing work in the post-apartheid communities of his home country. He’s also a white man. I was struck when he said, “It can actually be very empowering to learn that you are part of the problem. Because when you’re part of the problem, if you change just yourself, you are contributing directly to the solution.” That’s a heck of a thought. It reminded me of a sobering thing I heard when I was still living (and commuting) in Los Angeles and hating my rush-hour slog: “You’re not IN traffic. You ARE traffic.” So when it comes to any number of things – a broken political system, a rapidly gentrifying neighborhood, bumper to bumper traffic – how are you part of the problem? That’s where you’ll find your power. Continue reading How am I part of the problem?


If you had to fast from something other than food for 24 hours, what would you choose?

This inspired list of 50 ways to live a happier, healthier life recommends (at #9) to fast from internet usage for 24 hours every week as a way of reconnecting with yourself and giving your loved ones the attention they deserve. I’m drawn to the idea of fasting as a practice. Are you? If not food or internet, what thing that you normally consume eagerly would you choose to abstain from for 24 hours? What do you think that kind of fast would do for you in your life? Continue reading If you had to fast from something other than food for 24 hours, what would you choose?


How long before an “interest” becomes merely an aspiration?

In the early days of Facebook, there was a section of your profile that had two adjoining boxes: interests and then activities. One of my college friends (can’t remember exactly whom) had filled the “interests” section with lots of things – reading, running, listening to live music, learning some form of martial arts… And then in the “activities” section, he wrote simply: “Trying to make this box match the one above.” Clever. And poignant. It’s stuck with me all these years and reminded me to think deliberately about making my daily actions match my deeper interests. But I don’t always manage it as well as I’d like. Or well at all. How long before an “interest” gets demoted to the “to do list”? To merely an aspiration? I don’t know. But if I haven’t spoken ANY French at length in 9 years, how “interested” can I actually be in it? There’s no judgement around any of this. It’s just a question to ask yourself so that you can either 1) renew your commitment or 2) make room for newer, more relevant interests. Continue reading How long before an “interest” becomes merely an aspiration?


When was the last time the world made you stop, awestruck, and say, “Wow.”?

I was at home in Los Angeles (where I grew up) over this past 4th of July holiday. I surfed a lot as a kid and still love it. My wife Emily is learning. During the long weekend, we took a mini surf trip to Doheny State Beach – a 1 hour drive south to some of the most beginner-friendly, fun waves in Southern California. We were in the water already by 7am. It was still overcast but the water was glassy and there weren’t a lot of other surfers out yet. Perfect little 2-foot waves rolled in all morning. From the lineup I watched Em catch waves, ride them 100 yards to shore, and turn back in my direction, smiling. The sun broke through the clouds and I thought, “Wow.”

Noticing these moments when they happen is, I think, one of the keys to happiness. Continue reading When was the last time the world made you stop, awestruck, and say, “Wow.”?


What does your toothbrush tell about you?

TEDx speaker Anna Rosling-Ronnlund curates photos of everyday objects from households, rich and poor, around the world. She hopes “visitors will browse through galleries of toothbrushes, tables, shoes and toys and see how each object is transformed by the pressures of poverty.” This gallery of toothbrushes, in particular, struck me. I worry about money in daily, middle class life – I do. I also have the nicest toothbrush imaginable. Sonicare. (Costco did a great sale on it that I jumped on a year ago.) When the anxious thoughts start flying that I should make more money because I’m a new husband, because I should provide, because starting a family is probably in my future, because money is a measure of a man, because we need more stuff… I want to remember the question: What does your toothbrush say about all this? Continue reading What does your toothbrush tell about you?


Am I needlessly making this a “whether or not” question?

Here’s another one from Chip and Dan Heath’s genius book, “Decisive: How to make better choices in life and work.” The book lays out the 4 biggest stumbling blocks when it comes to making good decisions. The very first one is “Narrow framing (unduly limiting the options we consider).” According to the brothers Heath, any time you catch yourself pondering a “Should I ________ or not?” question or a “I’m deciding whether or not to _________,” statement, a loud warning alarm should go off in your head and you should realize 3 things: 1) You’re not even considering two options – you’re just giving an up or down vote to ONE option; 2) Other alternatives are out there (“Should I quit my job or not?” hides alternatives that become visible when you widen your scope (“Should I quit my job outright to become a sculptor or should I try to negotiate for part-time hours first and free up more time for sculpting?”); 3) The research overwhelmingly shows that considering more than one option leads to better decisions. The trick is realizing you’re stuck in a narrow frame. Continue reading Am I needlessly making this a “whether or not” question?


What are the last 10 expenses/purchases you made that were over $50? What does this say about your values?

This is a slight modification from something I heard in a sermon. The original phrasing was: “Your checkbook tells you what your values are.” This might be a touch reductive, but there is a TON of truth to it. If you say you value something but none of your resources go towards supporting it, then what does that really mean? What do your resources actually support and promote in the world? Take a look at your checkbook (but also your credit card statements, automatic payments, Mint or other apps) and find your last 10 expenses over $50. (For the sake of the exercise, you can ignore things like regular groceries and utilities.) What do your expenses tell you about your values? Did a church get a part of your hard earned cash? Did a charity? Did restaurants get most of it? Did a used surfboard from Craigslist? Did you spend on a close friend for his birthday? Did you travel? (Feel free to tweak the parameters – look at the last 15 expenses or look at only the ones over $100.) Sometimes self-awareness involves no reflection at all – just a bit of time with your personal finances. Continue reading What are the last 10 expenses/purchases you made that were over $50? What does this say about your values?


What’s the name of the lady who cleans this building?

The CEO of Charles Schwab, Walt Bettinger, tells a story of the only test he ever failed in college. He was trying to maintain a perfect 4.0 GPA but his business strategy professor gave a 1-question final that caught him off guard. In Walt’s words:

“…the professor said: ‘I’ve taught you everything I can teach you about business in the last 10 weeks, but the most important message, the most important question, is this: What’s the name of the lady who cleans this building?’

That had a powerful impact. It was the only test I ever failed, and I got the ‘B’ I deserved.

Her name was Dottie, and I didn’t know Dottie. I’d seen her, but I’d never taken the time to ask her name. I’ve tried to know every Dottie I’ve worked with ever since. You should never lose sight of people who do the real work.”

This is a great story. I wish the sentiment were actually visible in the financial industry broadly. But even if we don’t see it there, we can still put this into practice in our own lives. Scooping ice cream, waiting tables, going door-to-door for a non-profit… I’ve done those things and to this day I remember the people who were authentic and kind. If it was you, thank you! Continue reading What’s the name of the lady who cleans this building?


What’s your favorite flavor of shit sandwich?

I can’t explain this question better than Mark Manson who wrote it in his great blog post titled “7 Strange Questions That Help You Find Your Life Purpose.” So I won’t even try. Here’s Mark:

“What unpleasant experiences are you able to handle? Are you able to stay up all night coding? Are you able to put off starting a family for 10 years? Are you able to have people laugh you off the stage over and over again until you get it right? What shit sandwich do you want to eat? Because we all get served one eventually. Might as well pick one with an olive.”

The whole blog post is worth reading. I’d encourage you to check it out. So how about it? What flavor for you, then? Continue reading What’s your favorite flavor of shit sandwich?


In the past 5 years, what has become more important to you? And what has become less?

I value balance in life. And I seek it out when I’m praying, or exercising, or breathing deeply. But I also try to remember something I read about imbalance (I think in David Whyte’s excellent book called The Three Marriages). We often forget that we need imbalance as well. Walking, after all, is a controlled form of imbalance. Swinging one leg out in front of the other is not as stable as standing with your feet firmly planted. But without that motion, we go nowhere. It’s with this in mind that I’m drawn to the question. How have priorities shifted in the last 5 years? Does the shift feel right to you? Do you imagine it will shift back? Continue reading In the past 5 years, what has become more important to you? And what has become less?


You say you care about the poor… Then tell me, what are their names?

And then he dropped the mic. This question is directly from Father Gustavo Gutierrez. He’s one of the founders of liberation theology – a social justice movement and philosophy that started in the Catholic church. I love this question because it reminds me that for any issue it’s essential to bring everything back to ACTUAL relationships with REAL people. Without barbecues and phone calls, birthday greetings and actually knowing people’s names, how can I say that I care about the poor? What I also love about this question, “What are their names?” is that it applies so broadly. How can I say that I care about the political process and healthy democracy if I can’t remember the last time I had a meal and a laugh with someone not in my party of choice? Or how can I say that I care about peace in the world if I’ve never had a conversation longer than a few sentences with someone of a different faith? Tell me, what are their names? This is crucial. Continue reading You say you care about the poor… Then tell me, what are their names?


What 5 people do you spend the most time with?

Blogger / entrepreneur / crazy-person Tim Ferriss famously said in his first book that you are the average of the 5 people you interact with most. (It’s not a perfect thought experiment but I still find it compelling.) If this is true, who am I? Do I like that person? Do I respect that person? Should I be surrounding myself with different colleagues? Different social circles? Sometimes the changes you struggle to make individually in your own life will just happen more naturally when you alter your environment. Anyone who has ever found a morning workout buddy and noticed “Woah! 7am runs are actually happening now!” knows this. Ask this question about the 5 people you interact with most and you’ll be closer to finding your “workout buddy” for eating healthier, or your workout buddy for goal-setting, or your workout buddy for feeling grateful in life. Continue reading What 5 people do you spend the most time with?


In what period since you were a teenager did you have the most personal growth and change?

“If you wanted to have another such period, what could you do to bring it about or otherwise shake up your life?” Two fantastic questions once again from Gregory Stock. There’s an implicit progression here: Step 1. Identify when in your life you’ve MOST developed and grown. Step 2. Figure out what it was about this time that made it so growth-inducing. (Was it the physical setting? The people around you? The responsibilities you signed up for? The daily practices you put in your life?) Step 3. Have the self-knowledge necessary to put yourself back into that place whenever you want it or need it. Continue reading In what period since you were a teenager did you have the most personal growth and change?