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Cheerleaders and Eyerollers

​Big projects need big backers. These aren’t the kind of backers that make giant contributions to your Kickstarter (although those are great, too); these are the backers who will not only contribute to your Kickstarter, but who will also provide enthusiastic support when your project needs it most.

The role of cheerleader is frequently derided (everywhere, but also in business management circles). A cheerleader denotes a sideline position—someone who isn’t actually playing the game and whose input is therefore superficial. But a cheerleader doesn’t have to be a mouthpiece for empty and purposeless praise, and cheerleading doesn’t need to come at the cost of the real-talk that gets things done.

The best cheerleader is an empathic listener who supports a project by considering possible throughways through challenges. A cheerleader responds to a crisis not by ignoring it and hoping it can be rah-rah-ed away. A cheerleader responds to a crisis by listening and offering positive feedback and a few tactical suggestions for a way forward.

When undertaking a big (or team-based or many-stepped or project-managed) project, a cheerleader is indispensable.

But big projects also benefit from eyerollers. Austin Kleon, responding (sort of) to Jon Lovett and George Lucas, recently wrote about that critiquing voice that helps keep projects in check. Although Kleon writes more specifically about artists and the undermining efforts of outsized egos, eyerollers also play an important role in making sure projects fulfill their goals. An eyeroller does not naysay for the joy of expressing cynical skepticism; an eyeroller (a good, useful eyeroller, that is) acts as an editor and a critic, deploying skepticism to ensure that a project reaches its stated goals.

 
Cheerleaders and eyerollers can benefit any project. When assembling your team—whether formally or informally—decide who will cheer you on and who will keep you in check. ​
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Pocket + Pinterest + Evernote + Presentation + Collaboration = Webjets?

If you’re like me (meaning a tech-curious but otherwise regular computer user), new web apps can inspire a bit of excitement. New always promises to be more fun or beautiful or useful than old, but I usually realize and pretty quickly that the new app doesn’t address a need I have, and it quickly disappears into the ether.
Not so with Webjets! Webjets, which I first read about in Kai Brach’s newsletter Dense Discovery, is a mood-board-esque desktop for your desktop. It’s a bit like Pinterest, or Pocket, or Evernote, or a variety of other visually organized bookmarking and note-taking tools. But it’s also broader and much more dexterous. Basically Webjets is an easy-to-use interactive canvas that lets you drag, drop, and arrange images, videos, live links, docs—any type of file—and then organize, connect, and annotate everything in a (limited) variety of different ways.
 
For example, if you’re working on a speech or a presentation, you could fill your canvas with thumbnail links of your subject matter. You could then attach other links (like particularly apt comments or tweets or relevant op-eds), other images (like a grabs from previous presentations), and text-based responses (like lists of audience questions) onto the images themselves.

This is helpful, and in some surprisingly deep ways. If you’re looking to repurpose or refresh a project, Webjets provides an engaging format through which to envision your work. If you’re looking to gain insights or access points into stubborn questions, Webjets can help you reorganize your files in new ways (like lists, cards, folders, or mind maps). If you’re looking to collaborate with a partner or a team, Webjets lets you share your screen for pretty efficient (and frankly very fun) collaborative brainstorming sessions.
 
Did I need a new way to envision and brainstorm new projects? In fact, yes! My old way of brainstorming cannot even be called a “way”; it’s certainly not efficient; and it’s not at all conducive to structured collaboration. As we work on bigger, more collaborative projects at MWS, Webjets offers a narrative snapshot that is more comprehensive and more dynamic than a linear or written description.
 
The question of whether or not Webjets aids productivity is harder to answer. On the one hand, it will undoubtedly add to the bottomline of time spent brainstorming and collaborating. On the other hand, if it means the end result is a smarter and more creative project, then I’ll happily take it. Have you used Webjets? Tell me more.

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​Don’t Waste Your Time: Lessons from a Recent Classic

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As part of the Do-More/Do-Less banner I’ve unfurled for 2019, I’m revisiting Jane Friedman’s book The Business of Being A Writer. Friedman, whose Twitter bio declares that she knows “far too much about the publishing industry,” is the cofounder and editor of The Hot Sheet, the call-is-coming-from-inside-the-house newsletter about publishing.

​​​Her book gives a comprehensive overview of professional writing and pragmatic, utterly helpful advice. While it’s an ideal reference for anyone dipping a toe into the world of professional writing, the insight and advice ripples outward to other professionals, too.
 
Take, for instance, Friedman’s injunction to avoid wasting someone’s time. For writers, a pitch to an unresearched editor, to an ill-chosen agent, or to an unsuitable publication is not a hail-mary strategy—it’s a waste of the reader’s time and a waste of the writer’s time.
 
This is the case for all types of pitch-makers. You might be pitching a report to shareholders, a book to an agent, an argument to an audience, a grant to a grantor, or a professional background to an interviewer. In each case, your aspiration should be for your audience to consider the time they spend with you and your work to be worthwhile.
 
You will gain their appreciation by knowing that audience not as an indistinct bulk but as a single person. Recognizing your audience as a single (and actual) person makes it easier to undertake the work of understanding their professional background, needs, and aspirations. Only then can you determine if your work (or your speech or your grant) really is a good fit. Can you give this person something they need? If yes, then you can succinctly and persuasively explain what you have to offer.
 
This type of reconnaissance isn’t as fuzzy as it sounds. You don’t have to divine motivations (though you may want to). You simply have to turn to Google to trace your audience’s past work and current efforts. The time you spend—no matter your pitch, no matter your audience—will always be well-spent.

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