to get unstuck on your next project, start with a frame

I’m at World Domination Summit in Portland this weekend. (My visit to the City of Roses is especially poignant having just finished watching the final season of Portlandia. Goodbye, Fred and Carrie!)

Chris Guillebeau (author of The $100 StartupSide Hustle, and The Art of Non-Conformity) launched WDS in 2011 to celebrate community, adventure, and service. The vibe? Warm, vulnerable, and open. I’ve been resolutely resisting all efforts to get me to cry, stand up and shake my money-maker, or otherwise emotionally engage with the event since 2013. It hasn’t always been easy. (“Honey, one day I hope you can give another baby squirrel the opportunity to break your heart.”)

Lately, I’ve been thinking about frames. A frame is a powerful, valuable constraint. If we’re stuck trying to make something new, it’s usually because we haven’t put a good frame around it first. 

This doesn’t have to be an actual, literal frame with gilded edges. My wife and I attended her friend’s art opening years ago. They were still setting up when we arrived at the gallery. In the middle of the pristine white floor sat a half-eaten hamburger on a crumpled fast-food wrapper. To this day, I’m not sure whether the burger was part of the show or just the guy’s hamburger. Either way, it made for a pretty striking image.

(If you’ve never seen Yasmina Reza’s play Art, an extended, hyper-articulate argument between friends about the merit of an all-white painting, it’s well worth a read. And if you like all-white paintings, Dia:Beacon has a ton. They’re like the world headquarters of “Is it art?”)

Last week, I quit Twitter. (I first quit in 2008, but they tricked me into returning. I won’t be fooled twice.) Partly, I did this because it made my phone a depression machine. Partly, it was because they doubled the size of a tweet, diluting the dwindling remnants of Twitter’s value to me.

Originally, a 140-character limit allowed tweeting by SMS, but this limit became a powerful and useful frame for creativity. Whoever you were, no matter the size of your ad budget, you had to make 140 characters work. No tricks, no SEO, no splashy graphics. 140 forced you to be creative and clever. Over time, as the power and flexibility of tweets grew—images, etc.—their value sank.

Frames are supposed to make things harder. This does not mean you should abandon them.

Speaking of frames, I had an idea for a new social network yesterday. Now that I’m off Facebook and Twitter, I need a new network, but only a minimal one. Really, just a series of flags:

Living [Y/N] Marital Status [M/S] Children [#] Opportunity [O/C] Location [ ]

This is the information I’m going to miss without Facebook and Twitter. I trawled through all that sewage just to get these key facts for the people in my social network:

  1. Are you still alive?
  2. Are you married, i.e. should I ask about your spouse when I email you, or would that create awkwardness?
  3. How many kids are you up to now?
  4. Are you up for a new opportunity? Employment is a tricky area to share about publicly. Realistically, no one’s going to admit on a social network that they’re looking for a new job if they’re employed full-time. So there’s no point in trying to get detailed info about the opportunities people are interested in hearing about. Instead, this flag is set either to Open or Closed. Open means you’re interested in hearing about new opportunities: full, part-time, freelance, side hustle, whatever. Closed means you’re not open for business: you’re busy, retired, don’t bother me. Simple, and unlikely to set off alarm bells with the boss.
  5. Are you nearby? Is it physically possible to meet up for coffee?

That’s it. That’s the whole social network. Maybe it pings you every week to update your settings. Or every month.

Just imagine how useful this would be. You could look at all of your hundreds or thousands of connections on a single page as a series of color-coded dots, quickly identify patterns and opportunities:

“All my tech friends just lost their jobs.”

“Wow, a lot of divorces among my West Coast peeps.”


When someone entered your geographic area, you would automatically be notified. Invite them to lunch. That sort of thing. Josh Kaufman had the excellent idea of integrating your fitness tracker: If your heart rate goes to zero, the Living flag automatically updates. Thanks, Josh! 

We struggle with our online personas and the creative work we share online because there aren’t many good frames. Sharing feels dangerous without them. TinyLetter is an underwhelming service, sorely neglected by MailChimp, but it provides a useful frame by removing all your choices around the formatting of your newsletter. That’s what creative people like about using it. Newsletters are hard to write (emotionally, cognitively) because you have so little real control over how they end up looking to the recipients, even down to whether your images will be visible. Frames help.

This is why PDFs were created in the first place: to exert some control over what people saw when you sent them documents. For the first few months of my freelance business, I was using a Word template with a couple of fonts that most people didn’t have installed on their computers. Needless to say, my stuff looked really weird and unprofessional on their end.

One of the reasons the photography site 500px took off was because it made your resolution decision for you. It’s right in the name.

Creative people need frames to create their best work. It isn’t enough to make a video. You need to know how people will experience it: the big screen, a pristine image with perfect sound? An iPhone with subway noise drowning out the audio? It matters. Josh uses Prince to preview the typeset pages of his next book as he writes them in plain text. I use Marked for the same reason. Creative people need frames.

If you’re stuck on your next project, ask yourself: do I have a frame yet? If not, can I find one or make one?

Take the “tap essay” frame Robin Sloan used to create Fish. It had been lost to digital entropy but Sloan re-created the app with the help of a few faithful fans, updating the text for 2018. Go check it out. (h/t Guillaume Athenour) I think a tap essay makes for a terrific frame. It doesn’t require much in the way of coding knowledge to create. Would your next project work better as a tap essay, too?

calling for a renaissance

Together with his wife, Georges Borchardt has run his eponymous literary agency since 1967; his career as an agent stretches back to his arrival in the United States shortly after the Second World War. Magnificent list, naturally: John Gardner, John Ashberry, Ian McEwan, Tracy Kidder, Elie Wiesel, Eugene Ionesco…

I never had the opportunity to work with Borchardt, but thankfully he took the time to sit down for a marvelous conversation with his client, Michael Meyer, for The Paris Review. Borchardt thinks back fondly to his childhood in Paris:

[In] those days, when you gave a book to a child, it was not an insult. If I didn’t ask for a book for Christmas, I asked to have one of my favorite books bound. They came uncut, with paper covers. I would go to a place and select the end papers and the leather for the binding, and then I would have this beautiful object to take home.

The war put an end to all that, and to all of Borchardt’s beautifully bound books, too.

I would love to see a shift back to binding one’s own library. Publishers could offer an “uncut” edition—would that be feasible? After all, bookbinders still practice their craft. The New York Times profiled one still working out of a cramped shop on the Lower East Side. I’m tempted to tear the cover off David Lynch’s Room to Dream before I finish it and bring it down there. There are some books you enjoy so much they demand nothing less than Corinthian leather. Or perhaps the pages could be wrapped in plastic.

Borchardt is an excellent conversationalist. Is it just me, or is the capacity for good conversation increasingly rare? Should I blame social media? I don’t know. Have you ever had one of those conversations with someone where you’re not only dissatisfied with the conversation but you actually start to doubt conversation itself? Not just “this is boring” but “have I ever really enjoyed talking to another person before? I mean, I must have, but those memories seem very hazy right now…”

I feel that way about the Internet all the time now. I bounce around Reddit and Twitter, sift half-heartedly through my RSS feeds, watch some clips on YouTube…it’s not only “this isn’t that fun” but “was this ever fun? I remember being excited about the Internet, at some point. It felt like a revelation. Didn’t it? I don’t know. Maybe it didn’t.”

In 1994 or so, I visited my sister at the University of Pennsylvania. In the computer lab, she pulled up something she called a webpage. She’d created it herself using a special code of some kind called HTML. She showed it to me. I could kind of read it. This was a “homepage”: some text about her favorite TV shows at the time (Cheers and Seinfeld, as I recall) and some photos from the shows. How did she get those onto the computer? It wasn’t clear. At the time, I was a big CompuServe chatroom user who dabbled in the occasional MUD, but this was something else. It wasn’t an enclosed digital playground with an hourly fee. This was somehow out there, unleashed, a world wide web of information. That summer, I attended a summer science program at Syracuse University. Imagine my thrill when I learned we had unlimited access to the Web. I was beyond hooked. Anything was possible.

No longer. Even clickbait has lost its addictive luster. It used to be that marketing copy had this irresistible sparkle and lure, every word chosen by specialists to create the maximum psychological draw. Now I feel like even the lifestyle brands and course creators and purveyors of creative entrepreneurship retreats and what-not are simply going through the motions like the rest of us.

The Web has entered its Darkest Timeline.

Can it come back? Sure. Podcasts died. Apple killed them when it introduced its podcast store. Suddenly all the weird, cool, indie, niche podcasts were drowned out by the repackaged NPR shows that suddenly dominated the various Top 10 lists. The air went out of the room and many cool podcasts—including my own—cut transmission. Then Serial came along and things are have gotten good again. Maybe I should bring the podcast back.

In this case, I can’t point to any one thing responsible for sucking the air out of the Web. But we’re long overdue for a renaissance. Where will it come from?

Like Georges Borchardt, I’m caught looking back fondly at a lost era. But it’s time for action, not nostalgia. Any ideas?

why you should never, ever finish your book

Formerly, when anyone said music I presented was experimental, I objected. It seemed to me that composers knew what they were doing, and that the experiments that had been made had taken place prior to the finished works, just as sketches are made before paintings and rehearsals precede performances.

—John Cage, Silence: Lectures and Writings

If any new work is experimental, every work is. Whether you’re Yoko Ono or Stephen King, you make something, you put it out there, and you wait to see: did it work? That’s the experiment, every time.

You never know if it’ll work. Even if you dutifully follow every “rule”—rules are overrated. They’re just a starting point. Learn them, practice them, break them. The only thing worse than trying something and failing is letting the rules dictate what you try and still failing. Which happens far too often.

My book-in-progress is as “experimental” as any book of writing advice is going to get. I’m writing it using Leanpub, a cutting-edge iterative publishing tool. That said, writing this way hearkens back to a long history of serialized publishing. Book serialization waned long ago, but the industry’s been trying to kick off a renaissance for years. Even Jim Cramer agrees that subscription businesses are the future.

While there are lovely book subscription services like Quarterlane, they still only sell ordinary titles. Many authors, given the option, would greatly prefer writing for loyal subscribers who paid for regular installments of a single work. Nothing beats a steady audience. You can start tuning in to its preferences, tailoring your work to meet its needs. TV writers take this power for granted. Books are due for a return to serialization, too. The tools are all there. It’s just a matter of doing it, making it work. Experimenting.

For example: why not a neverending story? (Sort of disappointing that The Neverending Story clocks in at only 448 pages.  That’s half a Harry Potter and the Goblet of Fire.) Seriously, though, in a digital landscape without spine width or weight, why do books ever have to end? Why do Tony and Angela ever have to get married? A story can last as long as its author, and even longer.

My so-called friends Josh Kaufman and Tim Grahl introduced me to Worm. That’s because they hate me and want me to fail in life. Worm is a book, published in blog form by its author John C. “Wildbow” McCrae, that runs 1.6 million words long. That’s 7,000 pages, more than 15 Neverending Stories back to back. Wildbow’s take on teenage superheroes is smart and dark and fun—wonderfully addictive. I had to stop after only a few hundred thousand words just to get back to living my life and earning a living. Tread with caution. The sequel is in progress.

I’m encouraging you to experiment. Nothing “works” until it’s been tried. Every successful book is, in a way, a Black Swan. A 1.6-million-word book couldn’t work, until it did.  What are you going to try?

be patient and pay close attention

Learn to look; compare what is before you with your familiar or secret ideas. Do not see in a town merely houses, but human life and history. Let a gallery or a museum show you something more than a collection of objects, let it show you schools of art and of life, conceptions of destiny and of nature, successive or varied tendencies of technique, of inspiration, of feeling. Let a workshop speak to you not only of iron and wood, but of man’s estate, of work, of ancient and modern social economy, of class relationships. Let travel tell you of mankind; let scenery remind you of the great laws of the world; let the stars speak to you of measureless duration; let the pebbles on your path be to you the residue of the formation of the earth; let the sight of a family make you think of past generations; and let the least contact with your fellows throw light on the highest conception of man. If you cannot look thus, you will become, or be, a man of only commonplace mind. A thinker is like a filter, in which truths as they pass through leave their best substance behind. [emphasis mine]

—A. G. Sertillanges, The Intellectual Life

Several years ago, an acquaintance enthusiastically introduced me to the work of author Robin Sloan through Sloan’s iPhone app, Fish. The app is essentially a digital essay/PowerPoint presentation. You tap your way through it. It summarizes this original account of the profound teaching method of Jean Louis Rodolphe Agassiz, a 19th-century Harvard zoologist. Agassiz’s approach was very much in line with that of good old Father Sertillanges, above.

To learn, look. Pay attention, to all of it. Be patient. And, as Sertillanges and Agassiz would both have added today: put down the damn phone. (Unless you’re using it to read innovative interactive essays like Fish. I’d like to see more of those.)

Sloan emailed his mailing list a few weeks back. Apparently, Fish needs to be re-compiled for the new iOS App Store and Sloan no longer has the source code. Digital entropy strikes again! Thankfully, you can buy paper editions of Sloan’s other books. I’ve enjoyed several of his short stories as well as his debut novel, Mr. Penumbra’s 24-Hour Bookstore. I’ll read Sourdough one of these days.

Speaking of books, my own experiment with “lean publishing” continues apace. Thanks to those of you who’ve already purchased a copy of Book Into Battle, my guide to writing books that need to be written. (As opposed to the other kind.) Having an actual paying readership from the start helps my brain tremendously. I hope you enjoy what you find in its burgeoning pages whenever you choose to dip in. I won’t ask for feedback because, let’s be honest, feedback is hard work. I’m just glad you’re reading it! That said, if you have thoughts about the direction I’m taking, it would be very valuable to hear them. Using this tool, I’m supposed to “pivot” a lot. You know, like a startup. Depending on the customer response, it might end up being a religious tract, or an autobiography of James Polk. Lean publishing! 

This week, I added a new introduction as well as a cover designed by my lovely wife, Samantha Hahn, who should really be spending her valuable time on actual book covers like these.

How does it look?

Book Into Battle: How to Write What You Mean So It Matters

Book Into Battle will continue to be updated weekly. I’m using Pacemaker to stay on track. It lets you set goals and track progress on large writing or editing projects. I’m targeting 40,000 words by October 1. In 2018, 40K feels like a good number. That’s just enough book.

Leanpub takes an interesting—and underappreciated—approach to publishing, one worthy of investigation and experimentation. Even if readers in general aren’t interested in keeping up with an iterative book, the “live” method really does change the way you write. And I needed a change. It took me a few days to get the hang of the site itself, but I’ve got a solid workflow now: I write using Atom—avoid Ulysses for this purpose—with some Markdown-friendly modifications. The text files sync via Dropbox; when I’m done writing, I click Publish and updated PDF, MOBI, and EPUB are automatically generated. Neat, right?

When I’m done, I’ll do a small print run of a hardcover edition. All on my own, including typesetting and proofreading. That cover deserves a nice glossy jacket, don’t you think? Plus, I wouldn’t want to fall prey to digital entropy like Robin Sloan did. In fact, I’ve been preparing for a GoldenEye-style EMP attack since 1995. That’s why I print all my tweets. (Come to think of it, GoldenEye was probably the last big spy movie to feature Russians as the bad guys. That streak is ready to be broken, sadly.)

Where was I? Books! Books, guys. Read them, closely. Write one, with an end in mind. This struck me the other day: Of the many things on my phone, all of them (!) leave me feeling worse. News, email, social media, Reddit, Hulu, all of it. My phone is a depression machine. I come out of using it in a degraded mental state. Except for the Kindle app. When I read books, I feel better. Even sad books. Even bad books. How easy it is to forget this simple and obvious truth and open a browser instead.