Most people see a rustic, weathered old barn, its red coat faded by sun and wind, its paint chipped in a perfect mosaic of time and history, and they think, How beautiful.

I look at the same barn and think, Needs paint.

One evening last summer, I saw such a barn. I was walking in a field with some friends and their dog on land I know well. We stood in the green grass taking in the view as swallows dipped and weaved through the dusk. The barn stood at the far end of the field soaking in the last of the light, assuming the sense of purpose old structures often do—a purpose larger than that for which they were built. Its silhouette seemed to outline the passage of time itself, a symbol of endurance and ingenuity and utility.

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And yet, man, did it need a coat of paint.

Landing on the right color for a barn is trickier than you'd think.

Barns, the simplest of wooden structures, need paint. Each time you seal a barn with a solid coat of good paint, you buy it ten years of life, I say. And yet, as easy as it would seem to paint a barn—four flat, red sides, some white trim if it's fancy—with the wrong equipment it can be a chore.

I've worked at this magazine for nearly three decades and I can't remember a story about painting a barn. And it's probably been twenty years since we did a major painting story at all. It was time.

We talked to the owner, said we wanted to paint his barn. He didn't resist. I and a small team immediately inspected the structure and laid out a plan. The thing needed window sashes, repair carpentry, and some general sprucing up. We'd do the paint job and enough repair carpentry to achieve a nice look. Everything else was the owner's problem.

Landing on the right color for a barn is trickier than you'd think.

Too light a red and in the wrong combination of light, a barn can appear orange or, worse, pink. To get the color just right, I took pictures of the barn in early morning, afternoon, and at dusk on my iPhone 7—this is a good idea to do before visiting your paint dealer. We settled on Benjamin Moore's Country Redwood in a high-quality Regal Select Exterior, a high-quality all-acrylic coating that provides a much thicker film than a typical coating.

With the paint lined up, I set out to find the best new tools on the market—there had to have been some improvements in the past twenty years. You don't want to mess with homeowner-grade equipment, especially on big jobs. Good tools pay for themselves on the first job and help you complete the work in half the time.

We selected Purdy Power Lock extension poles in two sizes, equipped with eighteen-inch-wide frames and a Purdy Marathon roller cover with a 3/8-inch nap. Most of us are familiar with applying paint with a nine-inch roller. You can't believe how fast painting goes when you use products like this. The paint goes on more than twice as fast.

Some parts of the barn were not accessible with hand tools. While the north, east, and west are shiplapped vertical cedar siding, the south side is weather-beaten board-and-batten. Worse, the rafter tails are exposed on the north and south faces, and many of the bays are studded like a cactus with nails poking out in every direction, just waiting to bite your hand or snag a roller.

The answer was simple: We would spray as much of the barn as possiblae.

We were ready to paint—but the barn was dirty, one of its main doors was off its hinges, and the bottom edges of all the doors looked like they had been chewed by rats.

So I did what any sensible editor would do, I called Richard Romanski, contributing editor and Guy Who's Good at Everything, and asked if he could lend a hand. "That's more work than two guys can handle," Richard said. "Call Andy."