Just because work is digital now doesn’t mean there’s no paperwork.

In fact, there’s probably more than ever: email, instant messaging, project management, databases, shared drives — the list goes on and on and on.

Organizing your workflow in and across platforms is a task in itself, and a bigger one than I’m going to delve into here.

[Here’s “GTD (Getting Things Done) in 15 Minutes,” visualized, if you’re curious. HT to Khe Hy of RadReads for this.]

Rather, I’m here to argue for diligent digital-paperwork hygiene in general — and to propose a few basic principles for starters:

• Develop, maintain, and enforce a good document titling protocol. [Bare minimum: have one for yourself. Lead by example.]
• Craft effective subject lines.
• Ditto body text. (It can be shorter. Where?)
• No agenda, no meeting.
• No minutes/actions, don’t expect follow-up or follow-through. (Don’t repeat the meeting itself, either.)
• Know who and what you’re writing for.

Surely you can think of others. When in doubt, turn being peeved into better practice. Show, then tell if necessary.

But whatever you’re working on, in whatever workflow you use, be sure to see to the basics of good process. People rarely need more bits and bytes. What they need is something they can really sink their teeth into.

[Note: This isn’t a call for more bureaucracy. Nobody needs that. It’s ultimately about effectiveness — which might mean shipping fast, but might also mean having the empathy, creativity, and professionalism to make life easier on the people you work with (and your future self) in the way you write, share, meet, decide, and — yes — act.]

One of the best ways to secure long-term advantage from a system is to design it yourself, according to your preferences.

Undoing long-standing advantages for the long-term good of society is a painful and fraught process.

But seeking short-term advantage at the risk of the system itself is a grave risk indeed. If you wrote the rules of the game, you have to more or less follow them yourself — or other people might build a new sandbox to play in. And the rules over there might not be as advantageous as the ones you wrote yourself.

Rather than articles, here’s a list of books I’ve been reading lately:

• Too Big to Fail, by Andrew Ross Sorkin
• Rubicon, by Tom Holland
• The Art of Gathering, by Priya Parker
• Educated, by Tara Westover (finally!)
• Systems Thinking: A Primer, by Donella Meadows

As usual, the themes seem to be how systems and societies work, when and how they don’t work, and how it’s possible to intervene to make things better.

A deceptively simple question, isn’t it?

It’s not easy to answer in general, and it’s far too easy to overthink.

What if I change my mind? What if I don’t like it once I get there? And what about that other wild scheme that always seems to come up whenever I consider this question?

I can’t begin to count the number of people I know who have been stumped or stymied by this question at one point or another. Plenty of people would rather not face it at all (some for good reason).

There are a thousand million ways to avoid this question. A show to watch, a dollar to make, a person to please, a job to do.

But, sooner or later, the question will come around again. And it’s worth having an answer — or at least consciously deciding that someone else gets to answer for you.

The future — a healthy future, anyway — is small, local, and connected.

The implications of this are substantial:

• Conferences that are just as good (or better) but don’t require travel
• Teaching the people you can reach (online and off)
• Aiming for sustainability and sufficiency in a community rather than extracting the most from a global economy
• And on and on

If you want to be famous, if you want to have influence, if you want to make things better … it’s never too soon to get really, really clear who exactly you’re trying to reach and serve.

There’s a fine line between cynicism (which doesn’t help) and clear-eyedness (which does).

“When hell freezes over” is just as unhelpful as faith in tabula-rasa “disruption.”

But there there’s also a career-planning equivalent of throwing good money after bad.

If the system is the problem, is greater leverage to be found inside or outside?

As a general rule, it’s best to finish what you start.

(That, of course, puts a high premium on choosing what to start and when it’s going to finish. Most of us discount both of those pretty heavily.)

But there are two big exceptions:

First, projects that intentionally never finish. A daily blog, pushup regimen, or yoga practice is a good example. The point isn’t to touch your toes once; it’s to become more flexible over the years.

Second, projects begun on behalf of the community and designed to devolve. You can’t delegate a daily blog post, but you could start a movement that others can lead if it turns out to be popular.

What needs to finish? And what would you like to start?

These are two different roles, and it’s important to distinguish them.

Chiefs of staff are operators. They work a leader’s will, ensuring that what an executive has decided is actually executed.

Consiglieres are counsellors. They also need high executive function, but their role is about deciding which trains ought to run and where, rather than keeping them running on time. (That’s the chief of staff’s job.)

Both great roles, but worth knowing which is which — and which you want.

It’s worth designing healthy and sane on- and off-ramps into a project right from the get-go.

Especially if it’s a modular, remote, at-will, generosity-fueled project.

The future of work, and particularly good work that starts, runs, or scales largely on goodwill, depends on letting people come in and contribute their talents, then gracefully cycle off when it no longer makes sense for them to be on board.

Design these early and they’ll save a lot of heartache, ego, and reputation, later.

[Note: designing these is one thing, but learning to use them is another. Just like asking for what we want, tapping out when that’s the right move is often a learned skill. If you want in, we want you — but if and when you want out, we want you to ask. It’s better for everyone.]

***

HT to the amazing Lisa Lambert for this idea.

We all know the stats on new year’s resolutions.

Statistically speaking, they don’t work.

Most people will say that’s because we’re not very good at habit-building. And I’d say that’s true — brute force and best intentions don’t often translate into habits.

But I’d also say it’s because we generally don’t prepare to instill habits.

It really is remarkable what you can accomplish in a year if you set your mind to it — and especially if you do some stretching and route-mapping before you run the marathon.

If 2020’s going to be truly different for you, it’s worth reflecting now about what’s going to happen in January. (Hint: “everything” probably won’t be.)

Without further ado, four resources that have helped me the most with reflection and direction-setting over this past, most unusual year:

“The Pact” — Seth Godin
“At some point, you’ll need to make a deal with yourself.”

“Prototyping a New OS for 2019” — Sara Kalick
From chaos through control to controlled chaos.

21st Century Creative Foundations Course — Mark McGuinness
If you’re going to make a resolution for the coming year, why not make it truly a year-long commitment? In 28 brilliant lessons over 52 weeks, Mark will walk you through what matters and how to create it. (Free, self-paced, by email.)

Habit Secrets — Michael Bungay Stanier and Box of Crayons
How to build rock-solid habits, as demonstrated with a Barrel o’ Monkeys, claymation, and sparklers. Really.