Although I’m writing this from the same couch where I began 2019 by reading Steve Pressfield’s The War of Art and Turning Pro and then writing a 10-part interactive curriculum/summary of what I’d learned in the previous year or so, I’m in a totally different place in life and work.

Here, without further ado, are the first five of 10 reflections on a momentous year.

(1) Don’t underestimate what you can do in a year.
Attention and intention matter: January is as good a sort-of-arbitrary time as any to chart a new course. The trick, of course, is to keep steering that heading for an entire year — but, if you can manage that, a lot of long days and short weeks will put you several horizons beyond what you could see when you first fixed your direction.

(2) There’s really nothing like going out on your own.
And, no matter how much you read about it, you can’t know until you try. Truthfully, there’s probably no way not to feel unprepared for the journey in some way or ways. And that leads directly to …

(3) You can ask for help.
In fact, you have to. And the sooner you start, the better it’s likely to work. This is one of the ways in which I felt worst prepared for this year: after almost three decades of optimizing for reproducing the right answers on homework and tests, I had to learn a lot about working with other people to create interesting and original assertions. I still have a lot to learn there.

(4) Boundaries are essential.
I’m a keep-my-options-open kind of person. I love thinking about new opportunities and their follow-on effects. And I hate to disappoint people or shut them out. All well and good — but I’ve finally seen how important boundaries are. Without getting very, very clear about who it’s for, what it’s for, and what constraints it has to be produced within, it’s extremely difficult to get anything done.

[Note: there’s still a place for unframed thinking. It just needs to have boundaries, too: for this hour, we’re all blue sky — no need to worry about implementation. Next week, no more bells and whistles — we’re all about implementing whatever vision we create.]

(5) Everyone’s faking it.
Yes, everyone. Everyone has days when they don’t feel like it. Everyone has moments they have no idea how to explain. The best-laid plans are constantly being overtaken by reality. And the answers we’re all desperately seeking will only yield new and deeper questions. The art is not to double down on bluster, indulge in cynicism, or cower in fear. The art is to see that all the world’s a stage and then to act your part as generously and effectively as you can.

Over the past couple of months, I’ve been slowly making my way through Tom Holland’s Rubicon: The Last Years of the Roman Republic.

It’s a powerful reminder of Rome’s first fall — from the Republic into the Empire with the coming of Caesar and then Augustus.

And, naturally, it’s raised some tough questions, such as:

• Is it possible to arrest the decay and division of a democratic society?
• What happens when a superpower goes through a convulsion that utterly changes its internal governance yet does not reduce its external power?
• Can a culture of striving avoid being strode over by generation upon generation of ambition?

The story of the fall of the Roman Republic is worth knowing — and contemplating. Rubicon is a pretty good one-volume telling, but it would probably be better as an audiobook. (Holland is a radio personality, and writes like it.)

Luckily, that’s where Dan Carlin’s Death Throes of the Republic series on his podcast, Hardcore History, comes in. A couple weeks’ worth of commutes will provide you with some excellent fodder to focus your mind for 2020.

One year ago, I asked my brother for two little books.

He came through — and I spent the couple of days after Christmas reading The War of Art and Turning Pro by Steven Pressfield.

Like plenty of people before me, those books changed my life.

Steve’s big insight is that there’s a force in the world that opposes creative energy, which he calls Resistance. And, since we’re not taught to see or name it, we struggle to fight it: we go on building castles in the air without getting down to the hard work of laying their foundations.

The gift of these books is the naming of Resistance. For once it’s described so clearly, it can be named. And once it’s named, it can be called out.

And that turns out to be the simplest and most effective way to fight Resistance: “Oh, it’s you again. I know who you are and what you want. But I don’t want what you want. I’m getting back to work.”

That’s the simple-but-difficult work of turning pro. As Steve himself says, it’s free and available to everyone, but it’s sure not easy.

The legend goes that Ernest Hemingway would give some possessions away at the end of each year just to show that he in fact possessed them and not they him.

Today, I’ll return from Christmas vacation with a small pile of new treasures in hand.

Tomorrow’s a good day to clean out the closet and retire or give away some stuff rather than adding new presents to piles of old possessions that still hold me too tightly.

An uncle of mine refers to spiritual self-sustainment as “connecting to source.”

No matter how you fill your cup (or which metaphor you choose), it’s important to figure out which people and activities do that for you and to make time for them.

Taking a walk with my dad yesterday afternoon, he recalled going to the pub in Ireland with my friends and me after a hike and thinking that there’s something in that gathering that reflects how people are meant to live.

And that’s true: a shared experience followed by shared meaning-making — whether it’s coffee hour, pints, or any other story-crafting setting of your preference — is a formula that’s worked for lots of people over many years.

Some communities still organize around such activities and some don’t, but it’s worth finding or creating a practice that provides connection to source.

Sliding this one in under the wire after a very nice Christmas following a very tough year.

A very happy and healthy — and much easier — new year to you and yours.

The world doesn’t need more noise today.

Find a little moment of stillness amidst the busyness.

Savor it.

The Art of Possibility, by Roz and Ben Zander

***

This was easily one of the most influential books I read this year. It’s certainly the one that I’ve playfully quoted the most, and one that I keep turning over in my mind.

The Zanders’ thesis is that the world is alive and filled with much more possibility than we’re accustomed to seeing — and all it takes to realize it is some subtle-yet-powerful shifts of mind and speech.

Two memorable examples are trading “and” for “but” and responding to mistakes by smiling, raising one’s hands, and saying, “How fascinating!”

Those shifts might not sound like much, but consider the difference between the statements “I’m OK for now, but I don’t know what I’m doing,” and “I’m OK for now, and I don’t know what I’m doing.”

These concepts have to be handled with care (“How fascinating!” isn’t the appropriate response to all mistakes), but they have brought a lot of consolation during a year when it felt like the training wheels came off.

You can’t stay upright on the bicycle by positive thinking alone, but it is possible to choose to pedal with a smile.

It’s the day after the solstice and the beginning of the holiday week, which means it’s time to take a break from assertions about work, life, and culture.

Instead, I’ll round up some of my favorite resources and reflections from the past year — starting with some of the music that’s carried me along through 2019. Consider these “cheerful chants against the dark,” as Brian Doyle wrote.

[Each artist is followed by a favorite lyrical snippet.]

***

Josh Ritter — Hello blackbird, hello starling / winter’s over, be my darling

John Prine — And when the angel on the treetop requested a song / we sang Silent Night all day long

Jason Isbell — I heard enough of the white man’s blues / I sang enough about myself / so if you’re looking for some bad news / you can find it somewhere else

Mark Erelli — All the others who tried fell by the wayside / I wanna walk all the way with you

Lake Street Dive — If you’re gonna tell them everything / don’t leave out the good part

Tedeschi Trucks Band — No more mysteries, baby / no more secrets, no more clues / the stars are out there / you can almost see the moon

What’s normal is what’s normal for you.

And it usually takes a while to get that way.

Hard as it might be to imagine, no one is born believing that Cinnamon Toast Crunch is in fact normal — or even food.

Just think for a moment about how much, ahem, “education” that takes.

Why isn’t tofu the regular kind of breakfast? Or even something more “normal” like salad?