The difficulty with complexity.

As a society, we are facing a crisis of understanding.

Fake news is just the latest expression of a deeper problem: We have more and more difficulty thinking about (and talking about) complex topics.

In short, it’s hard to convey nuance and multiplicity with the media we have today.

Social networks are built to facilitate transmission of ideas that can be embodied in a catchy meme or 140 characters and a Twitter card. Anything that requires a few paragraphs or more to explain sufficiently runs the risk of being ignored or (at best) misrepresented under a catchy headline.

Online news sites live and die based on how many monthly visitors they get, which means their headlines and story choices are all geared towards generating clicks and shares, not understanding.

Television “news” focuses, as it always has, on the sensational and the provocative, and it has even started catering to the need for short-attention-span entertainment by adding background music and jokes.

Radio, for the most part, is dominated by those who can shout their opinions the loudest and provoke the strongest listener reactions. The exceptions, like NPR and PRI, are somewhat better, but even public radio has a hard time conveying complexity or nuance in a 4 minute segment (or even an hourlong weekly science show), given the imperative of entertaining and engaging the audience.

And even an ostensibly #longread-friendly environment like Medium suffers from human nature’s tendency to focus on the pithy highlight, the tweetable excerpt, the clickable headline.

Yes, in part this is human nature. We are programmed to notice the new, and to respond quickly and viscerally to stimuli that promise food or sex, or that seem to present a threat.

But as Daniel Kahneman has written in Thinking Fast and Slow, that is not the only mode of human thinking. It is also possible to engage a more logical, deliberative mode of thought. This mode of thinking is not as fast at coming to decisions but it is better suited to problem-solving, especially when the problems have many contributing factors, competing stakeholders, and unpredictable outcomes.

We need this kind of slow thinking, especially now. Because while our media leads us to ever-simpler, ever-more-catchy reflexive ways of intuitive thinking, the world itself is incredibly complex. Some examples:

  • What happens when the Arctic warms to 50 degrees above its normal December temperature is the result of an incredibly complicated system of interactions. What will happen next is hard to predict. What to do about it is even harder to figure out. And yet discussion online devolves into simplistic binaries: “the climate crisis is real and we’re fucked,” versus “global warming is a Chinese hoax.”
  • The companies that are working on autonomous vehicles, such as Google and Uber, seem to be getting closer and closer to truly “self-driving cars.” What will this mean for the tens of thousands of people for whom driving a car — or a truck — is their livelihood? How soon will self-driving cars actually be on the road? How autonomous will they be? How should governments respond to ensure the safety of all on the roads? How will insurance companies respond? How do we build a safety net, or alternate employment, for those who may be put out of work? None of these are easy questions to answer, particularly since the technologies themselves are still in development and their future arc is not entirely clear.
  • Health care in the U.S. seems in some ways incredibly advanced and in other ways the system seems complex and opaque and on the verge of collapse. Efforts to improve its functioning, such as Obamacare, are themselves incredibly complex, and that leads to further misunderstandings, errors, unpredictable outcomes, and, yes, political mischaracterizations. A slogan like “repealing Obamacare” might play well politically but practically speaking it’s far from clear how that might work, and how to proceed in a way that doesn’t lay waste to vast numbers of stakeholders, from those in poverty to those who own stock in insurance companies.

As a writer, a former journalist, and person who currently makes a living helping companies communicate better, I think about this constantly. Those of us in the “content business,” broadly speaking, have a responsibility to find ways of matching what we produce with the complexity of the world around us.

It is not just a matter of raging against the publication platforms and the social media available to us. Likewise I think it is useless to rant about the stupidity of the public (though that is often a satisfying outlet for the frustration of attempting to communicate). And we certainly can’t accomplish this by lecturing to people about how they need to pay closer attention and read that 10,000-word essay by Elizabeth Kolbert more closely.

No, I think we need to use our skills as communicators to engage readers and draw them in to stories that convey complexity and nuance. There is some hope here: As Nicholas Thompson has written, long-form storytelling is a thriving niche. There is demand for longer, more complicated stories, especially those that are well-told.

But length alone is not enough. I’ve read too many #longreads that seemed to be long for the sake of length, as if writing more words conveyed an impression of seriousness and depth. Actually, it does, but that’s just another example of how our intuitive brains can be easily fooled by superficial things. If you take the time to read these long stories closely, you’ll quickly realize which ones are long because they need to be long, and which ones really just need more editing.

So that brings me to the question I’m asking myself — and anyone who cares to join me — in 2017:

How can writers, journalists, designers, filmmakers, and artists work to convey complex, important ideas more accurately, completely, and engagingly?

That’s the question that motivates me this year. What about you? If you have good answers to this question, or — even better — some questions of your own, I’d love to hear from you.

Also published on Medium.

Illustration by Daniel Friedman on Flickr.

Santa is real.

This year I took the kids shopping with me on Christmas Eve. I gave them $60 each: A twenty to buy a present for their mom, a twenty to buy a present for their sibling, and a twenty to buy some stocking stuffers for the other three members of the family. “You’re going to help play Santa this year,” I told them.

The fifteen year old went off and got a single stocking stuffer for each of us, a nice pair of pie pans for her mom, and two big bags of taffy for her brother. Done! And everyone was happy.

The ten year old spent an hour combing Cost Plus for a huge pile of stocking stuffers, and went slightly over his limit. (I bailed him out.) He got some nice mittens for his sister and a Downton Abbey calendar for mom. Also good.

On Christmas, after we’d opened all our presents, the 10 year old started talking about how he learned the truth about Santa. “C told me that Santa isn’t real two years ago. I like to pretend that he is real, but I know he’s not.”

“Whoa, whoa,” I said. “Santa’s not real? What about your mom over there? Do you think she’s not your real mom?”

“No,” he said. He knows that he has a birth mother and an adoptive mother, just like he has a birth father and an adoptive father. But we’re not “unreal” … we actually do the work of taking care of him, feeding him, buying him clothes, driving him to soccer practice. We’re pretty real, I reminded him.

“And guess what,” I added. “Santa is real, too. Who do you think Santa really is?”

“You guys?” he said, pointing at me and KJ.

“And you,” I said, pointing right at him. “You helped buy all those stocking stuffers, and you put them in the stockings. So you were Santa, too.”

His eyes lit up. “Yeah!” he said. Then, in a very deep, Santa voice, while posing like a bodybuilder: “I’m Santa Claus! I’m Santa Claus!”

Photo: One of the not entirely appropriate stocking stuffers the little dude got me.

Signing off Facebook for awhile.

I’m done with Facebook for now, so I am signing off for awhile.

Partly I am annoyed with the company for not taking a stand against the Trump administration and its elected leader’s comments about making lists of Muslims and immigrants. For the company’s COO to attend a meeting with Trump yesterday and say absolutely nothing about that is not what I would hope for.

But mostly I’m fed up with the addictive design of the service. I don’t like myself when I use Facebook too much. It feeds me too much crap that just reinforces whatever cynical political mood that I’m in. I have had some useful conversations and event debates, but it takes an effort to get past the depressing crap. And it keeps encouraging me to click, and scroll, and click, and scroll, in a way that I dislike.

So for now I’m signing off, and will try to stay off through the end of the year. I may even deactivate my account. For now you can find me on Twitter @dylan20, and of course I’ll always be here on this site.

Photo source: Jolie O’Dell/VentureBeat


How Google and Facebook are transferring content revenues to themselves

Jonathan Taplin:

Since 2000, recorded music revenues in the United States have fallen to $7.2 billion per year from $19.8 billion. Home entertainment video revenue fell to $18 billion in 2014 from $24.2 billion in 2006. United States newspaper ad revenue fell to $23.6 billion in 2013 from $65.8 billion in 2000. And yet, by every available metric, people are consuming more music, video, news and books. During that same period, Google’s revenue grew to $74.5 billion from $400 million.

The former editor of The Guardian, Alan Rusbridger, estimated that Facebook had “sucked up $27 million” of the paper’s projected digital advertising revenue in the last year by essentially keeping Guardian readers on Facebook, rather than linking them to the Guardian site.

“They are taking all the money,” he noted. “They have algorithms we don’t understand, which are a filter between what we do and how people receive it.”

Source: Forget AT&T. The Real Monopolies Are Google and Facebook. – The New York Times

Nonviolence and Standing Rock

A really insightful essay on why nonviolence plays such an important role at Standing Rock — and how it might work going forward.

“The way we see and treat someone is a powerful invitation for them to be as we see them. See someone as deplorable, and even their peace overtures will look like cynical ploys. Distrust generates untrustworthiness. On the other hand, when we are able to see beyond conventional roles and categories, we become able to invite others into previously unmanifest potentials. This cannot be done in ignorance of the subjective reality of another’s situation; to the contrary, it depends on an empathic understanding of their situation. It starts with the question that defines compassion: What is it like to be you?”

Standing Rock: A Change of Heart, by Charles Eisenstein

If language is not correct

“If language is not correct, then what is said is not what is meant; if what is said is not what is meant, then what must be done remains undone; if this remains undone, morals and art will deteriorate; if justice goes astray, the people will stand about in helpless confusion. Hence there must be no arbitrariness in what is said. This matters above everything.”


Specific gratitude

Keeping a gratitude diary, or less pretentiously, taking some time out of every day to write down the things you’re thankful for, is an effective way to increase happiness.

And I’d like to suggest one small addition.

In addition to writing down things you’re thankful for (rainbows, puppies, burritos) take some time each day to express your gratitude to a specific person.

Send a thank-you note or a postcard. Send an email or text to that person. Pick up the phone. Or simply say “thank you” face to face.

It could be a good friend or family member who you love and who loves you. It could be someone at work you think is overdue for some appreciation. Or it could be the barista serving you a coffee or the bus driver taking you home. Take a minute to let that person know you recognize them as another human, and that you’re grateful for what they’re bringing to you.

I think this will not only spread happiness, but also an understanding of the ways in which we’re all interconnected and interdependent.

As the Buddhist grace goes, “Seventy-two labors brought us this food. We should know how it comes to us.” This prayer is meant as a reminder of codependent origination, or what Thich Nhat Hanh calls the inter-being of all things: sunshine, air, water. In fact seventy-two is an understatement; I always remember this prayer as “10,000 things.” Whatever the number, some of those things are specific people: Those who grew the food, who harvested it, who sold it, who shopped for it, who cooked it, and who washed the dishes afterward.

We should know how things come to us.


Further reading:

Behind Our Anxiety, the Fear of Being Unneeded (the Dalai Lama and Arthur C. Brooks)

A 23-Minute Morning Ritual That Will Transform Your Whole Day (Marcel Schwantes)


The radio tells me that calls to suicide hotlines are up 30 percent since the election. The news tells me that racists will be in the white house. Friends share stories with me about how bad things are about to get. A writer I respect says we have less than two months at best. People are saying farewell to American democracy. My daughter asks if she will be deported or enslaved.

Enough, I say. To all who have a stake in making you feel awful: Enough. It is time to huddle. It is time to take care of each other, and ourselves. It is time to plan and ready ourselves for resistance. But we know how to do this. We have been countercultural. We have been oppositional and defiant. We have gone to protests and put signs on lamp posts and worn slogans on our shirts and pinned statements to our jackets. We’ve talked to people, and sometimes shouted at them, and we’ve listened to them shout at us. We have grown our hair long as a signal to others, and we have cut it short as a signal to others. We have thrown parties. We have played our music. We have told our jokes, our many, many jokes, and those jokes have brought the bright air back into the rooms we were in, if even for a moment.

And we have sat quietly, breathing, watching how our world is created anew with each breath.

Perhaps it has been a long time–perhaps some of you are young enough that you don’t remember these times. But some of us do, and we’ll show you how it’s done.

We got this.

Something to lose

graffiti on a wall spelling out the word Resist

In the past few days I’ve been thinking about how much I have to lose.

I enjoy the evenings at my son’s soccer practice, overhearing snippets of English, Spanish, and Arabic. I love the Spanish-speaking soccer moms who bring way too much food to weekend soccer tournaments, plying us with sandwiches, endless fruit salad, macaroni salad, ceviche tostadas. And coffee, god bless the coffee they brought this morning.

I value the bilingual school where my kids are learning to be fluent in Spanish just as their classmates are learning English.

I love that the ladies in the hair braiding salon, where my daughter was getting her hair done, raised my spirits yesterday with their jokes about Mitch McConnell and the incoming “coochie snatching president.” They even teased me about my lack of braiding knowledge, joking that I could give a lecture on the topic after spending an hour or two there. (As if.)

I love my neighborhood and my town, a medium sized suburb where you can walk down the street and hear six different languages in five minutes. Where you can eat a dozen different kinds of food from all over the world. Where you can work in a coffee shop side by side with entrepreneurs who came here from god knows where for a chance to make their dreams come true. Where you can drink your coffee right alongside moms pushing strollers, retired folks out with their friends and their little fluffy dogs, and high school students of all kinds working their homework and their budding caffeine addictions.

I love the swims in the clean water of the SF Bay — water that has been cleaned up thanks to the hellraising efforts of several generations of activists, mostly women. I love that some of my swim buddies are gay, and that they can feel safe and welcome wherever we go together, for swims and for lunches afterward.

I treasure my children, who are a different color than my wife and I, and who could not be more part of our family if they had come from our bodies. I’m grateful to the many people who believed enough in us, and in the potential of our love and abilities as parents, that they helped us bring these children into our family. I’m grateful that many of those same people took the time and care to educate us, as much as they could, about the racial issues our children would face, and that we would face as a family. Those lessons have proven valuable again and again.

I love the peaceful, quiet evenings when I can sit on the front porch or walk around my neighborhood, just listening to the quiet murmurings of people going about their lives, sometimes catching a whiff of someone’s dinner or hearing a snippet of their music.

My life is substantially better because of the diversity of the country and the area where I live. My family’s life is richer and more varied. And, I might add, as a multicolored family, we are safer here than we would be almost anywhere else in the world.

Someone I know was claiming online this week that his life would be essentially unchanged regardless of who the president was. Lucky for you, I told him. But for me, I feel absolutely different. The incoming president troubles me, a lot, both for what he has explicitly said and what he has alluded to or implicitly endorsed. His supporters scare me even more, especially the ones who feel emboldened to speak their racism, misogyny, and homophobia more openly now, and to express it ever more hatefully.

This — this diversity — is exactly what we stand to lose if America becomes a more hateful, more intolerant, more exclusive nation. This, I am here to tell you, would be a loss not just for black people, immigrants, gay people, transgender people: It would be a loss for white people too. It would be a loss for all of us.

And I’ll be damned if I’m going to just sit back and let that happen to the country I love.

5 Ways to Disrupt Racism

There have been a disturbing number of racist incidents in the wake of Trump’s election. This video, filmed in response to a similar reaction after Brexit, is really helpful.


Arthur Brooks is the head of a conservative think tank, but his NYT op-eds have been tending in a decidedly Buddhist direction the past year or two. Today, he shares a byline with the Dalai Lama.


Everyone has something valuable to share. We should start each day by consciously asking ourselves, “What can I do today to appreciate the gifts that others offer me?”

Leaders need to recognize that a compassionate society must create a wealth of opportunities for meaningful work, so that everyone who is capable of contributing can do so.

6 financial facts would-be entrepreneurs need to know

Photo of an empty wallet with an IOU slip inside

So you’re considering quitting the rat race and becoming an entrepreneur — congratulations. Whether you’re working on a killer startup with a few pals or embarking on a career of self-employment, you’re about to discover what life is like when you have maximal control.

In many ways, it’s awesome. I’ve been self employed, running Tweney Media, for a bit more than a year. It’s not my first rodeo: I was a self-employed freelance writer for about 4 years from 1999–2003. Self-employment is way better now than it was the last time, mostly because of the internet, which gives me access to a kind of social interaction that was difficult to come by in the early 2000s. So, it’s less lonely. It’s also easier to network, find new business opportunities, work with people around the world, and to educate yourself.

Self-employment and early-stage entrepreneurship is also an excellent exercise in self-determination. You realize that everything you do has meaning. If you find yourself doing bullshit, you can just stop. Do something else that’s meaningful, or makes you money, or both. If you find yourself working with assholes, you can stop. Life’s too short. Find different partners or clients. If you have an idea for something amazing, you can do it. Why not? You’re an entrepreneur! This attitude leads me to new realizations about my life, the world, and how they intersect almost every day. I have never felt more awake.

But to be successful you’re going to need to know a few things about financing a life of entrepreneurship. I’m not going to give you the usual crap advice: “Skip the $3 lattes at Starbucks.” If you’re drinking so many lattes that it’s impacting your finances, you have a serious caffeine and foamed milk addiction and you may need medical help. No, the real issues facing you are much more serious: Health care, debt, taxes, and housing are all extremely expensive. Cash flow is a bitch. Doing accounting is necessary and hard. And, unfortunately, the U.S. economic system is not going to help you with any of those. In fact, you could say that the U.S. economy actively discourages entrepreneurship.

Here are some things you need to know if you’re considering becoming an entrepreneur.

Health care will fuck you.

Seriously, the U.S. health care system is a travesty. It is the opposite of a functioning free market: It’s a completely opaque market where you don’t know what you’re buying, you don’t know what it will cost until you get the bill, and you can’t compare options. This is as true for a band-aid in the hospital as it is for the insurance that supposedly covers it. And insurance costs more, and covers less, every year. The result: Everything is insanely expensive.

This is not just an Obamacare problem. This is far deeper than that. And even with employer-sponsored health insurance, you may already be spending tens of thousands of dollars on uncovered health expenses. If you’re self employed, it’s just that much starker.

As an example, my family of four in California spends $20,000 a year on insurance, and about as much again on uncovered health care costs. And we’re fairly healthy people. (So far.)

Credit cards will fuck you.

You’re not going to get VCs to back you at first unless you’ve already had a successful startup under your belt. Banks won’t loan you money unless your business has several years of records to show. Unfortunately for you, you’re going to need to fund your business out of your own pockets. Unless you’ve built up a big nest egg, that probably means credit card debt. Once you have it, credit card debt is very hard to get rid of.

Granted, if you have good credit, you can take advantage of low-interest-rate offers and turn credit card debt into very low percentage loans. Pay attention to when those offers come up and how long they last, and you can move the debt around as needed to keep the rates insanely low (for now). That’s a reasonable way to fund your business at first. But just remember, it’s still debt. You need to pay it back. And as long as you’re paying it off, that adds to your monthly overhead.

Housing costs will fuck you.

Especially if you want to live where the opportunities are, like Silicon Valley/San Francisco, or New York, or someplace else where there are creative people doing interesting things and investors fueling companies that might want to pay for your product or services. But housing costs are insane in these places. A 2-bedroom rental in SF or the East Bay goes for $4,000 a month these days. If you have a family, you’re going to be paying. A lot.

Taxes will fuck you.

I’m not talking about the tax rate, but about the process of paying taxes as a self-employed person. You will need to make quarterly estimated tax payments. That means every three months you need to estimate how much money you’re likely to make for the whole year, calculate approximately how much of that will be taxable, figure out what your estimated total tax will be for the year, and then based on that figure how much you ought to pay this quarter so your four quarterly payments wind up being pretty close to the correct total. And then write a check to the IRS. A big check.

Cash flow will fuck you.

In order to write that check to the IRS (and your monthly rent or mortgage check, and your medical bills, etc) you will need to pay close attention to your cash flow and ensure that you’re saving enough money from whatever you’ve got coming in so you make all those payments when they come due. If you don’t manage your cash flow intelligently, it’s entirely possible to go completely bust even while you are making great money. That’s because it always takes the money longer to come in than you expect it to, especially if you have a service business that involves invoicing people. (This is a strong argument for building a SaaS business where you get recurring monthly revenues without having to send invoices, btw.) Some months the incoming cash will be great. Some months it will be terrible, or zero. You need to plan things out to deal with those lumps. And that brings us to accounting.

Accounting will fuck you.

I would be lost in this whole process if it weren’t for my wife, who is also our CFO. She spends hours with spreadsheets figuring out the optimal tax strategy, the optimal health insurance choices (modeling different policies against what we actually use), figuring out our cash flow, and making sure bills get paid on time. It’s an enormous job that she spends many hours on every week. If you aren’t lucky enough to have a partner like this, you’re going to need to do it yourself, or pay an accountant.

Oh, and by the way? Mint is useless for most of this. There are no financial management systems out there that accommodate self employed people’s needs, such as budgeting for uneven cash flow. As far as I know, there’s no financial management system that can deal with the need to manage significant credit card debt either. If you are self-employed, your finances are more complex than most, and you need to do most of the work manually. Google Sheets is your friend. (Update: a friend tells me that You Need a Budget, aka YNAB, is designed for helping manage credit card debt.)

Accounting may be a pain, but you need to do it. The amount of expenses involved in being an entrepreneur — just to stay alive and keep a roof over your head — are not trivial. The complexity of managing those expenses is a pain. But there are significant opportunities for savings if you’re willing to dive in. Just remember that diving in will take a lot of time, or money, or both.

Like I said at the top, entrepreneurship is great. I’m happier than I ever have been in my career, and I’m building a growing business that is starting to generate work for other people too. I’m making more money (on a gross revenue basis) than I ever earned in a day job. I love the flexibility and the self-awareness. I am proud to be supporting my family.

But it is financially challenging. It takes a lot of determination to fight into the headwinds like this. If you’re considering going independent, you need to know what you’re getting into.