2019 Year in Review (Pt. 1)

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.