“You tweet the news so you can say you knew first, not because you really care.” The problem is, we don’t really care. We only care about looking like we care. That’s not sympathy, that’s narcissism. And if we don’t work to reverse this brand of digital heartlessness, we’re in serious trouble. But values aren’t taught, they’re caught. We need to find people who care, find proof that doing so leads to more money and more happiness, and find a way to tell everyone about it. Last year I wrote a book called Try Caring. It was a combination of cool things I learned from my clients and angry rants about stupid companies that don’t get it. Maybe that’ll help. Inspired by The Lefsetz Letter.

“I need to be analog and have a pulse in the city.” I traveled almost every week for a decade. It was a huge pain in my ass, but it was part of the job. If I wasn’t on the road, I wasn’t making money. And then all of the sudden, it wasn’t my job anymore. My life became the mathematical inverse of itself, both personally and professionally. Now, I rarely leave town. With the exception of major holidays and occasional getaways, I stay put. And it’s goddamn glorious. I feel like a whole person. I feel like a member of my community. I feel like I’m not missing my life. Here’s a toast to having a homebase. Inspired by the world’s greatest traveler.

“The more mysterious your own creative process is for you, the greater the fear the well is going to run dry.” I rarely get blocked because I have a clear understanding of how I build. For example, I know that if I don’t write it down, it never happened. I know that I sing better when I’m standing up. I know who my muses are. I know that I can’t go more than two days without creating something. I know that I’m more creative when listening to music. And I know that my inhale to exhale ratio is about four to one. These are the realities of my creative process. It took me many years to figure them out, but now that I know, the likelihood of hitting a wall is drastically lower. Sundance knew that he shot better when he moved. Each of us should have that same level of understanding about our own work. Sparked from avideoabout writer’s block.

“We came late to the banquet and were served up crumbs.” This cartoon about thrashing Millennials got me thinking. Instead of wasting time pontificating about what young people may or may not want, why don’t we just ask them? That’s what I never understood about generational studies. It’s always some professor who’s completely out of touch with people half is age trying to tell them who they are. Sorry doc. It doesn’t work that way. What works is when you treat people like adults. What works is when you see people as people, not preferences. And for the record, they’ve never used the term millennial. Ever. 

“There was a euphoric amount of optimism.” From a physical standpoint, I’m not interested in risk. I have zero need for speed. I don’t play extreme sports. I’ve never been in a fight. And I walk away from even the slightest hint of violence. People have called me a pussy more times than I care to remember, and I’m totally okay with that. Here’s why. When it comes to emotional, psychological risk, I’m quite the daredevil. Relocating to a city with no job and no friends? Starting a business with no money and experience? Delivering a speech in front of four thousand foreigners? Sign me up. That’s the kind of risk I can get behind. If gambling on yourself is wrong, I don’t want to be right. Inspired by Alex Winter’s killer documentary.

“Without an audience, you’re the tree that falls in the forest.” It’s one thing to sing songs in the comfort of your own bedroom, it’s another to stand on a corner and perform for complete strangers. Big lesson for me this year. Turns out, having an audience changes the way you experience your art. You learn to see it through other people’s eyes. Take kids, for example. They’re too young to bullshit you. If they like your song, they vote with their feet. If they don’t, they start crying. You can’t get that kind of feedback from singing into a hairbrush. If it’s true that nothing happens until a sale is made, maybe it’s also true that nothing happens until a seat is filled. Thanks for the heads up, Henry.

“A relationship is like taking a four credit class.” Yet another article about the death of courtship. Really pisses me off. Not that I’m against hooking up. That’s what college is for. But the process of dating, pursuing, courting, chasing––even breaking up––is a invaluable experience that every young person should have. It teaches us how the heart works. It allows us to practice commitment and communication  It gives us a holistic view of our most human tendencies. And it offers us an opportunity to develop our relational and romantic muscles, two strengths that are infinitely useful later in life. What good is being a great sprinter when most of life is a marathon?

“If there’s schlepping involved, it’s more likely to be real work.” Possibly the most brilliant blog post I’ve read in years. Venkat breaks down conspicuous production. Proving that our most important work involves grit, delayed gratification and the willingness to burn some serious calories when nobody’s watching. Growing up, that was always hard for me. Impatience was a furious itch that needed scratching at any cost. You couldn’t slow me down with the back of an axe. But, life has a funny way of teaching you exactly what you need to learn. Somehow I discovered the value of the schlep. Somehow I learned to prioritize sweaty work over sexy work.

“We carry our love of competition right through to the hospital and into the cemetery.” I’ve never been a competitive person. It’s simply not in my blood. I don’t play to win, I play to keep the game going. Despite dirty looks from people who hate to lose. But I’m not against competition as a whole. I think it’s human and healthy and necessary for the advancement of our society. Hell, without competition, we’d still be using car phones. The problem is when our appetite to achieve victory diminishes our ability to enjoy playing. There has to be a balance. Inspired by anarticledebunking the value of life expectancy.

“Every occurrence, including the affairs of human beings, is due to the laws of nature.” I made the decision to retire almost exactly ten years after I started my company.  Literally, the same week in May, a decade later. That’s interesting, I thought. I wonder if there’s any significance to such fortuitous timing? So I went for a long walk in the park. That usually uproots a few good solutions. It forces me to think about how nature would solve this problem. And after a few hours, something occurred to me. The number ten is by far the most significant labeling system nature has. It’s the mathematical base for everything. The major organizing principle of the universe. That’s why decades are such important life markers. There truly is something special about what transpires during a ten year period. No wonder the lifecycle of my business ended on that very week. Anyway, that’s how I choose to interpret my experience. And I find that figuring out life through the filter of nature is a hell of a way to go. Inspired by the smartest man alive.

“Thank you for matching my crazy.” I appreciated this acknowledgment in Attempting Normal. Isn’t that what we all want in a partner? Someone who understands that we all have our own shades of crazy, and the best gift we can give each other is the willingness to match colors? That’s love. I’m reminded of my second date with my fiance. The whole time, I kept saying to myself, “Wow. This girl can actually keep up with me.” That never happened before. I wasn’t used to being with someone who matched me. What a relief. What a pleasure. What an exhale.

“Apple’s mission is to teach their customers to have better
taste.” The best stores are temples to belief systems. They’re places where we practice our religion. Since I was a kid, I’ve wanted to open my own used book store. Not because I would make a ton of money, but because it would memorialize things that matter to me. Reading. Learning. Language. Curiosity. Contribution. Community. Hospitality. Humanity. Work. Forget about selling books. The real reason behind the store is to create a primary container of meaning. An excuse to hang with people who share the same worldview. Inspired by thisinterviewwith Seth Godin.

“Great ideas originate in the muscles.” I saw this Edison quotation on the chalkboard at my yoga studio. Appropriate, considering how many of my best ideas show up during class. Or any workout, for that matter. Solvitas perambulatorum. Once you figure out how powerful that process is, your entire relationship with exercise changes forever. You can’t wait to get on the bike. Because you know that by the time your shirt is soaking wet, something brilliant will float to the surface. Other than farts.

“I like it when nature likes me.” Last year I officially fell in love with nature. But not in the typical, granola, save the whales kind of way. I still hate bugs. And you couldn’t get me to go camping if Jesus was building the fire. But as a human being, I have an inherent need to connect with something bigger than myself. I’ve tried to satisfy that need in a variety of ways, but nature seems to be my favorite option. Nature, I can count on. Nature, I can prove. Nature, I can physically see and know that I’m a part of. Inspired by an interview with David Sedaris.

“Solitary confinement is the infliction of a permanent disfigurement.” The initial prospect of working alone is highly attractive. Nobody to answer to. Nobody to deal with. Nobody to distract your work. Nobody, nobody, nobody. But after a few years of working out of the living room in your underpants, the novelty of solitude starts to fade like porkfat dissolving in handsoap and water. You feel disconnected from the world. I remember getting to the point where I had to make myself leave the house to go get coffee, just to interact with other human beings. And I don’t even like coffee. Yikes. The other thing is, prolonged solitude has aftershocks. After working alone for ten years, I recently shifted my worklife to a collaborative team environment. Which has been amazing, but my prolonged solitude has decimated my capacity to relate socially. It’s like learning how to ride a bike again. Double yikes. Inspired by an article about our prison system.

“How can you make real sex more attractive than internet porn?” Douglas Rushkoff dreams of a world where people are just as seduced by reality than technology. Sounds like paradise to me. I’m not a luddite by any means, but I’d rather have analog beguile me into submission than have digital sneak up on me from behind. There’s just something about the physicality, the tactile nature of things we can touch and smell and taste that can’t be beat. Kindle is an amazing tool, but I miss underlining sentences. I miss the sound of the pen scratching paper. Hell, I even miss the paper cuts between my fingers. 

“Is your business treasured or do people just give you money?” This is my favorite passage in Hugh Macleod’s new book. Reminds me of my neighborhood market. Out of seventeen thousand bodegas in the city, this is the one I treasure. Every day, I walk through the door hoping they will give some
joy to me, and they always deliver. I don’t have to work hard to do business with them. Their sandwiches are super tasty. And the cashiers often play jokes on their customers. That’s how it’s done, son.

“Pay attention to the vital few and ignore the trivial many.” Wise words from John Paul Digoria. Couldn’t agree more. The tricky part about his philosophy is, you have to know the difference between the two. If you’re cursed with a broken sense of priorities, unable to discern what’s worth doing in the first place, even the best advice in the world won’t do you any good. The key is creating a filter. A question to ask yourself before moving forward like, “Is this activity guaranteed
to provide me with the experience of meaning?” or “Does this make me money or make me happy?” Sounds like a a lot of work––and it is––but after a few months, you start to internalize the process and the filter becomes second nature.

“The world cannot be deprived of this talent.” That was Dr. Drew’s reasoning for wanting to treat Tom Sizemore’s addiction. This guy was so good at what he did, that it would be a crime to rob the world of his gifts. What a beautiful response to natural talent. We should all be so lucky to have someone like that in our corner. A cheerleader who believes in us, maybe more than we believe in our ourselves, and sees something that we’re too close to ourselves to see. I’ve had my share of those people in life. I call them shovers.

“It was a little something, but my anxiety turned it into a big something.” Anxiety is the great amplifier. It either makes us see things that aren’t really there, or makes things that are there, seem much worse than they really are. Over the years, I’ve experienced my share of anxiety, usually around feelings of loneliness. And what I learned from my therapist was, the moment those waves come crashing in, you grab a surfboard and ride the anxiety back to shore. The surfboard being the mechanical tool, i.e., deep breathing, exercise and meaning making activities. And the shore being an ideal state of being, i.e., relaxation, happiness and human connectedness. Sound hokey? It is. And that’s why it works.  Inspired by Josh Groban’sbackstage freakout.

“I don’t write jokes, I write moments.” Interesting approach to the creative process fromMarc Maron. I think every artist has their version of this. I’ve always told people that I don’t write books, I write modules. Uncategorized chunks of creative material. Objective, portable content that accumulates and categorizes into its own structure. Which eventually, probably, turns into a book. By thinking in this way, you lower the threat level of the creative process, train yourself to be an incrementalist and prevent premature cognitive commitment. 

“In the harsh light of hindsight.” When something is happening, I’m totally confident. I believe I’m doing the right thing. Acting the right way. Making the right choices. Then, after everything blows to hell and I’ve tiptoed my way out of the wreckage, I always look back and say to myself, “What the hell was I thinking? How could I have been so blind?” At which point, I vow never to say never again. And that lasts about six months. Inspired bySleep No More.

“There’s a very early arc, so you have to be  proactive when
the game is done.” Venus Williams started training when she was four years old. Four years old. So now that she’s starting to wind down her first career, the question becomes, how will she exist beyond the tennis universe? What will three decades of professional sports prepare her to do next? That’s what interests me. The evolving human identity. The struggle to live larger than our labels. The redefinition of work as the primary expression of who we are. Tennis is fun to watch, but it’s not as compelling as the narrative thrust of people who play it.

“A series of notes beyond the range of human hearing.” Daniel Crawford turned a hundred years of climate change data into a stunning musical composition. Amazing level of creative ingenuity. Also, from a messaging standpoint, I like that he’s using music as a side door approach to proving an important point. Fundamentalist wackjobs may be able to argue their way out of believing in climate change, but nobody can debate the reality of classical music. Almost like using a kids book to teach children valuable life lessons, but for adults. Hmm. Maybe that’s how we reach people whose beliefs are too convenient to be killed. 

“You have petite sensation, the little feelings you get from
being alive in the world.” When I first started practicing yoga, my intention was mainly respiratory. Having just recovered from a collapsed lung, I needed a healthier relationship with my breath. Six years into it, my practice has evolved into more of an emotional experience. Now, doing yoga is also a daily routine of confronting and working through my emotions. Maybe it’s because the room is a hundred degrees. Maybe it’s because I’m half naked. Maybe it’s because I’m staring at myself in the mirror for ninety minutes. But after a few postures, any feelings that are present, have nowhere to go but out. Inspired by Rafael Black.

“It wasn’t anything radical, but it was
just what the world was looking for.” Great insight from an adorable documentary called The History of Typography. Got me thinking about innovation: Maybe every idea doesn’t have to be some game changing, paradigm shifting, competition befuddling, insanely great innovation that blows the world’s hair back. Maybe all the idea needs is the right combination of utility and timeliness. We spend so much time and money and energy trying to make history, when all people really need is stuff that makes life easier.

“Success by proximity, isn’t.” Achievement through association pisses me off. Just because you’ve interviewed a bunch of successful people, doesn’t mean you’ve achieved success. That’s like trying to get in shape by reading a book about weight lifting. Success isn’t a function of osmosis or proximity. It’s not a communicable disease. Success is what happens when you’re busy creating value. The end.

“I felt like I got through a door just as it was closing.” When I started my company right out of college, all of my friends were entering into the corporate world. A decade later, when retired and went into the corporate world, all of my friends began starting their own companies. Funny how that works. What’s interesting is, the old rules of entrepreneurship are crumbling. Today, starting your own company is a thousand times easier than it used to be. Which means the marketplace is more crowded and more competitive than it used to be. Looks like I made it out just in time. Inspired by an old interview with Hunter S. Thompson.

“Something trivial that purged their minds of fear.” Interestingtheoryfrom Dan Brown. Says that we spend a lot of our time glued to the screen because it’s a quick, easy and efective way of not thinking about death. Jeez. Hate to be so black and white about it. But I wonder if it’s true. I wonder if it’s all just one big distraction. I wonder if were subconsciously aware of our own demise, but consciously create ways to avoid confronting it. 

“If we don’t capitalize on ourselves, someone
else will.” Such a frightening prospect. But in the age of data mining, I guess anything is possible. Also, I wonder what it’s like to be someone who makes other people rich. It’s one thing to earn a fortune for yourself, but to know that every success you have puts dollars in the pockets of others, and often people you don’t even know or like? Weird. Inspired by a conversation between Seth Godin and Mitch Joel.

“Advertising
is something people tolerate at best and loathe at worst.” If you ever wanted proof of the power of overcompensation, look no further than advertising. The shittier your product, the better your ads have to be. Why else would a company create an entire brand about the most interesting man in the world? Because their product is the most horrible beer in the world. And magically, their campaign has become the coveted case study for effective maketing. But if they were truly effective, they would have spent fifty million dollars making their product better instead of creating a racist meme. Thanks for the inspiration, Doc.

“You will continually pour rain on your own parade.” Eric Maisel’s philosophy on clinical depression is fascinating. Reminds me of a few people I used to know. Serious issues with depression. But I guess I never really understood their experience. I’ve certainly been disappointed, unhappy and sad before. Even had a few anxiety attacks over the years. But I never classified it as depression. My perspective was always mindset based. How is meaning supposed to arrise if I’ve already decided that life is always out there, waiting to hand me an ass
whipping? With a persistent negative evaluation of everything, how am I to find personal fulfillment and joy? Then, my solution was always action based. What physical action can I take, right now, that will flood me with meaning and joy and overwhelm this crappy mood? So far, it seems to be working.

“Poised in a great ballet of expectation.” The smartest choice I made in my yoga practice was to stop counting. No more looking at the clock. No more head games trying to figure out how much time is left in class. And no more counting how many days in a row I’ve practiced. All that quantifying did was create an unnecessary expectation, which started to affect the outcome. This is my tenth class in a row, surely my calf muscles should start cramping up soon, I’d think. And then they would. And it would hurt like hell. All because numbers affected my expectations. Inspired by a novel aboutsexual soul transmigration. 

“You can’t do comedy without an audience.” Famous last words from George Carlin. And yet, I never realized how right he was until I started busking in the park. Turns out, the physical act of performing music for people changes the biology of the songs. Notes, riffs, rhythms and lyrics––that didn’t work when it was just me in my bedroom––magically made sense in front of a crowd. It’s the strangest thing. No wonder I can’t wait to get back to the tunnel every week. 

“The name of the game is creativity, not
technology.” Killer insights from the original mad men. Got me thinking about insanely creative people, and how they got that way. It’s simple. First, heredity. Their genetic package had a predisposition to critical and artistic thinking. Second, environment. Their family, friends, teachers, mentors and early childhood support system encouraged, practiced and rewarded creative activity. Third, reps. Their formative years were spent honing a craft, practicing a skill and training the brain. But they never stopped. Practice didn’t end after the ten thousandth hour. Fourth, lifelong learning. They dedicated themselves to studying, respecting and improving the creative process. Fifth, commitment. Not just discipline. Not just hard work. But actual devotion to being a creative person. And sixth, drugs. Lots of drugs.

“No one who is good at building houses has an emotional problem with hammers.” Looking back to my entrepreneur days, I could have saved myself a ton of time and a mountain of anxiety if I just dealt with my money issues early on. I should have treated money as a tool to build with instead of a wall to blast through. But having come from wealth, the story I told myself was that money wasn’t important. That it was better to be heard than paid. Noble, perhaps, but not the smartest way to run a business. Thanks for the nudge, Seth.

“You get what you don’t pay for.” My theory is, if you’re going to use an online dating service, fork over the money. Pay a hundred bucks and make it official. Otherwise you’ll never fully commit to finding someone special. That’s how commitment works. We need something that’s bigger than any excuse. Halfway will be the end of us. Otherwise we’ll just keep complaining about how there’s nobody out there, how hard it is to be single, and that it’s impossible to find the right person, meanwhile, organizing ourselves as living proof of our own argument, creating a self-feeding cycle of loneliness and ice cream.

“Ensured that one day I’d be well
equipped to live my dream.” At the end of Questlove’s new book, he thanks his parents. I teared up when I read this passage. Probably because I feel the same about my folks. They knew that when I graduated college, moved across the country and started my own business, all they could do was trust that their twenty years of parental labor laid a strong enough foundation to turn my dream into a reality. They were right. This is all their fault.

“I didn’t break her, I can’t fix her.” Years ago, I made a small career out of trying to fix the person I was dating. Turns out, I can’t make you just like me, no matter how many books I read. Painful realization, but possibly the best thing I learned from that relationship. The other realization was, we are strongest in our broken places. And once we learn to accept, understand, love and leverage those cracks, amazing things are possible. Inspired by Dennis Prager’slecture.

“I trust my behavior more when everyone
else is sleeping.” Fascinating line of thinking from Tim Ferris. It’s amazing how our behavior changes when there’s no audience, no peer pressure and no immediately feedback. I used to get up very early in the morning to write for very the same reason. It was cold, dark and quiet. No voices weighing down on the work. Even my own brain wasn’t really awake yet. Just the heart doing its thing. Good times.

“After swimming in purgatory for fifteen years, we were making a steady living.” Love this passage from Questlove’s new book. The sad part is, few artists make it past that point professionally. Most never fully break out of the ghetto. Some make enough money to get the opportunity to do the work again. And a select few actually become rock stars. That’s why it’s often wiser to keep art as your passion, not your profession. Otherwise it’s one hell of a slog.

“Everybody says they want shorter, but what they really want is something that rivets them, they’ve got endless time for great.” Couldn’t agree more, Bob. All this rhetoric about declining attention span and hyperspeed technology means nothing when you’re really, really good. Awesomeness is the trump card of time. Instead of whittling down your work to bite-sized, digestible chunks, focus on being really good for a really long time. Set yourself on fire and people will stick around just to watch you burn. Even if it takes more than ten seconds.

“They have never done anything else for a living, because they haven’t needed to.” Man, that’s so cool. Imagine having one career, your whole life. That’s what Carol King did. Her genius was the ability to put all her talent into the service of a single idea. And she’s been one of the best for a long time. What’s interesting is, that trend may not continue. Future generations are likely to have five careers and twenty employers across their working lifetimes. The days of working a single occupation will soon be long behind us. Which could be good or bad.

“I like going to places where fame has no value.” There’s something existentially relaxing about living in a culture where reality television doesn’t exist. I could easily move to a country like that. A place where community is more important than celebrity. Where family is more important than fame. Where belonging is more important than beauty. Sounds like paradise to me. I wonder how the food is? Inspired by an interview with Ellen Page.

“When you start liking somebody, you have a silly voice.” I remember when my brother first met his wife, Anna. After three months of dating, there was a noticeable change in his voice. It sounded softer. Gentler. More loving. And it’s stayed that way ever since. I guess that’s what love does to us. It changes our biology. Inspired by Billy Crystal’s podcast interview.