I was looking at an early draft of an article a few weeks ago — a rough one, still finding its shape — and I caught myself doing something I do almost every time. I wasn’t reading it as a beginning. I was reading it against the finished piece already sitting in my head, the one it wasn’t yet, and marking every place it fell short. The opening wasn’t strong enough. The structure felt off. A sentence sounded ordinary. My hand was already moving to fix it before I’d let it simply be unfinished.
Writing has become my creative pursuit in this stage of life, and I don’t think I fully admitted that to myself until I caught myself doing this. Not painting, not woodworking, not anything with my hands — just the plain, quiet work of putting words together, sentence after sentence, trying to say something true. That moment at the keyboard, staring at a rough draft and wanting to fix it before it had a chance to simply exist, was the moment I recognized it as a genuine creative practice, with all the discomfort that comes with one.
I sat with that draft longer than I needed to, honestly, just noticing what I was doing. I wasn’t reading to see what the piece might become. I was reading the way I used to review a contract — hunting for the flaw, the thing that would cause a problem later if I let it slide past me now. Word by word, sentence by sentence, checking for weakness the way you’d check a foundation. It didn’t occur to me, in that moment, that a rough draft isn’t a foundation with a crack in it. It’s closer to a pile of lumber that hasn’t decided yet what it wants to be built into. But that’s not how I was trained to look at unfinished things.
That instinct has been with me a long time. It didn’t come from writing. It came from thirty-eight years of real estate and a career in journalism before that, both of them built on getting things right the first time. In real estate, a missed deadline, a wrong figure, something overlooked in a contract — these weren’t small matters. People were trusting me with one of the largest financial decisions of their lives. You learn to check things twice, anticipate the problem before it happens, treat a mistake as something that should have been prevented. That habit doesn’t retire when you do, and it doesn’t know the difference between a legal document and a rough paragraph. It just wants everything to be right, immediately.
I came across a phrase recently that named this better than I could have myself. Bernard Wood, a retired architect who spent his career drafting precise technical lines, took up painting after he stopped practicing. In an interview recorded for a study on how older adults come to art later in life, he described his real challenge not as learning a new skill, but as undoing an old one. He’d spent a lifetime drawing straight lines. Now he was trying to learn how to stop.
He was talking about a canvas. I recognized it instantly as my own blank page.
I understood that immediately, though it took me a while to see it clearly in my own writing life. The Encore Project might be the closest thing I have to Bernard Wood’s canvas. I want the articles well researched. I want the site to look right, the categories organized properly, the photography and the podcasts to meet a real standard. Those aren’t bad instincts — they’ve served me well for most of my life. But creative writing doesn’t always cooperate with that kind of structure. I’ve discovered you can build an excellent source library, write a careful brief, follow a sound process from start to finish, and still not end up with a better article. Sometimes all that scaffolding gets in the way of finding out what the story actually wants to be.
I’ve felt this most sharply, oddly enough, in how I’ve been working with my team to write these very pieces. When a draft isn’t good enough, my instinct isn’t to sit with it and let it be bad for a while, the way a painter might sit with a muddy first layer of color. My instinct is to fix the system. Rewrite the brief. Add another research step. Tighten the outline. I am, quite literally, trying to engineer my way to creative writing — which is almost a perfect modern echo of Bernard Wood’s straight lines. He drafted buildings. I draft processes for drafting words. Both of us, in our own ways, have spent a long career believing that if something isn’t working, the answer is a better structure, not a looser hand on the pen.
There’s real science behind why this shift is so uncomfortable, and it isn’t just stubbornness. The psychiatrist Gene Cohen, who spent much of his career studying creativity and the aging brain, described something like a transition from one-sided to fully integrated thinking as we get older — moving, in his own words, from something like two-wheel drive to all-wheel drive. The logical, sequential left hemisphere increasingly works in tandem with the more associative, synthesizing right hemisphere, supporting a kind of thinking that’s less linear and more integrative than what drove most of our working lives. In plainer terms: the very mental machinery that made me good at contracts and deadlines may not be the machinery good writing actually rewards. Learning to trust the other kind of thinking, later in life, is its own real education — not a failure of discipline, but a different discipline altogether.
The photographer Sally Mann has written about a similar idea from her own creative work, though from the opposite direction. An imperfect attempt, in her view, isn’t a wrong turn to be avoided — it’s often exactly what moves you toward the version you were actually trying to make. Work that falls short of what you pictured isn’t wasted; it’s frequently the very thing that shows you where to go next. I think the same is true of a rough paragraph. In my working life, an imperfect attempt was still a miss, and misses had consequences. In writing, I’m slowly learning, an imperfect attempt might be doing something closer to the opposite: not costing you the outcome, but leading you to it.
An imperfect attempt might be doing something closer to the opposite: not costing you the outcome, but leading you to it.
I think about the actual stakes of a mistake now compared to what they were then. If a real estate deal went sideways because of an error, someone could lose real money — sometimes a great deal of it. A transaction could collapse. Trust, once damaged, was hard to earn back. There was no redo, no second version to try once the first one failed; the consequences landed on someone else’s life, not just mine. If a paragraph in one of these articles doesn’t work, I delete it. If a whole approach to a piece falls flat, we start over. Nothing is actually lost — no one’s closing gets delayed, no one’s savings are at risk, no one is disappointed in a way that follows them home. I know that intellectually. But I’m not sure my instincts have fully caught up to it yet. My default is still to treat a wrong turn in a piece of writing as something that should have been prevented, rather than as part of how the good version gets found.
There’s an irony in all of this that I don’t think I should smooth over. This entire monthly writing operation — the research libraries, the interview process, the production packages, the workflow steps my team and I have built together — is, in its own way, a fairly elaborate structure built around the act of writing. I’ve sometimes wondered lately whether we’ve built more system than the writing actually needs. That question makes me uncomfortable in a very specific way, because my instinct, when something isn’t working quite right, is almost always to improve the system further — add a step, tighten a brief, build a better process, rather than simply write badly for a while and see what turns up. Maybe that instinct is exactly the straight line I still need to unlearn as a writer.
I haven’t mastered any of this. I’m not sure “mastered” is even the right goal. What I’m learning, slowly and a little unwillingly, is to tolerate the period when a piece of writing isn’t very good yet — to let a draft be rough without immediately reaching to fix it, to let an idea wander before deciding what it’s about, to treat a wrong turn as part of the process instead of a problem I failed to prevent. After a lifetime spent trying to get things right the first time, that’s a genuinely different way of writing, and it doesn’t come naturally to me even now. I don’t know that I’ll ever fully undo the straight lines Bernard Wood spent his whole career drawing, or that I even should undo all of them. But I’m starting to notice when I’m drawing one, in real time, in the middle of a sentence. That noticing feels like the actual beginning of the unlearning — not the finished thing, just the first honest look at the habit itself, and at the writer I’m still learning to become.
