Questions OR Rosencrantz and Guildenstern at 40

Yale has a wonderful writing class called Daily Themes. This class has been taught at Yale for over 100 years and requires students to write a story each day of about 500 words. I always wanted to take the class but never did. So I started to do some of the writing on my own based on the prompts my friend Aaron Gertler online from the 2015 class.  My favorite one so far is:

Create a conversation between two characters in which everything said on either side is in the form of a question and every question advances the conversation. Avoid rhetorical questions and repetitions.

I hadn’t realized this but the instructor had put in a link to Rosencrantz and Guildenstern’s “Questions” game — which was what popped into my head as well. With that preamble, I now give you…

Rosencrantz and Guildenstern at 40

How did we get here?

Weren’t we promised a happy and fulfilled life if we just gave our life to the company?

Isn’t that why we went to business school?

Wasn’t that the promise once we got out?

Do you feel likely we have climbed a giant mountain up through the clouds only to see more mountain?

Do you think we are at the top of the mountain and can finally see clearly?

Are we getting close to the end?

Do you feel like we are in that Tom Stoppard play “Rosencrantz and Guildenstern are Dead?”

Or maybe Godot?

So what do we do now?

Should we change our focus and get off the hedonic treadmill?

But what would we do then?

Don’t Zen monks talk about this problem?

Could we leverage some of that?

Why do you always have to talk in business speak?

Aren’t you afraid of death?

Aren’t we dying every minute?

Do you think that’s the secret – living completely in the moment?

Is there any other way?

Why don’t we treat every moment as our last by being fearless and vulnerable and not afraid to fail?

Are you saying failure is good?

How can you have anything valuable without failure?

What about love and courage and accomplishment?

Isn’t that what I’m saying?

A Better Way to Write OR Why You Don’t Need to Write About the iPhone 5

There’s an old saying that the best way to learn something is to teach it. That’s certainly true when working with Blake on a school project. Blake is writing a chapter book at school. At most, it’s going to be 20 pages long. In Blake’s mind this is huge. Like infinitely large.

Blake‘s topic is Apple — a topic that he’s passionate about. He wants to write everything in the world about Apple in his up to 20 pages. He wants to explain all the iPhones, iPods, iPads, Macs and everything else that’s ever existed within the Apple oeuvre. I thought it might be more useful to take a historical perspective and highlight the important parts of Apple history. He wanted to stick with his original plan of writing the encyclopedia of Apple.

So I tried to prune some of the low hanging fruit.  “What about the iPhone 5?”

“Of course we have to write about the iPhone 5,” Blake said.

“Why?” I said.

“Because it’s important. That’s where Apple started using Touch ID.”

“No,” I reminded him, “that didn’t happen until the iPhone 5s.”

So we got rid of one Apple product. But the real question here is how to make writing the most productive and fun, While Blake is working on his writing project, I was trying to think about how to optimize my own writing.

I thought about some of the principles we’re using in Agile software development at work and how they could help when writing:

  • Limiting the work in progress  (WIP). It’s much easier to start things than to finish them. I remember someone at Google once told me that “If you have 10 apples, don’t take one bite from each of them.” And it’s the same thing with writing. I only want to have 3 items in progress at any given point. That gives me some flexibility on what to work on but any more than that I start to feel overwhelmed with the work I need to finish.
  • Develop iteratively and refine. Jeff Patton gives a great example of this when thinking about the creation of the Mona Lisa. Da Vinci didn’t sit down and start drawing pieces of the Mona Lisa.
    Tbe Mona Lisa Wasn’t Put Together Piece by Piece…

    …It Was Refined in an Iterative Fashion
  • He drew the basics. Then he drew the outline. Then he made refinements.
  • Do the most important thing first. In order to develop iteratively, I need to prioritize. By prioritizing the work, it breaks things up into manageable chunks. I’ve also done the biggest things first so I can stop much earlier and still have something that holds together. Then I can edit and refine only the parts I really want to. 
  • Time Box. I give myself a certain amount of time upfront to finish something. If I say I’m going to finish this piece in 2 hours it really helps me prioritize and make sure I’m focused.
  • Split up the planning and the doing. Most people don’t like planning so they mix up their planning and their actual writing. It’s much easier to split up the work into multiple bite-sized chunks. This relieves a lot of the cognitive stress and makes the writing more fun.

Here are the steps I use to implement these principles:

  1. Topics. This is really just the very high level of topics that I want to write about. I keep a list in Evernote. It’s good to try to keep this list prioritized because the items on the top become the most exciting ones that I want to tackle. Possibly I might put in a very high-level outline at this point.
  2. Story Bits. This is when I start to flesh out the idea. This can be done on index cards, post it’s, or just a piece of paper. My favorite way of brainstorming is Mind Mapping. There’s a great book that taught me how.
  3. Organizing. Then it’s time to create a broad outline. Some good ways of building the outline are user story mapping and the pyramid principle (summary here). These days when I’m writing a blog post I just write out my the paragraph order and my topic sentences.
  4. Write. Once I’ve done he organizing, the writing is fairly easy. It’s just fleshing out the idea. Each paragraph really should only be one idea and I’ve already written that idea down in the last step.
  5. Refinement. This is where I go in and make sure that spelling is correct and that everything makes sense. This is best to do once I’ve had some time to rest and take a look at it. There’s normally some silly mistakes but in general I’m happily surprised with what I wrote.

By following these steps I’ve been able to write a lot more and have a lot more fun doing it. Give it a try!

My Mobile Payments Writing

Ashwin Shivaikar from Citi’s Equity Research group and I joined forces to write two reports Upwardly Mobile I and Upwardly Mobile II. The pieces were very well received and we had the honor of giving out 2000 of these at Money 2020. I also gave a 10 minute summary of the paper at a payments conference. Kate Fitzgerald wrote it up in surprising detail in American Banker in an article called Simplicity, Usefulness Should Guide Mobile Wallet Development.