Board by board

 "It's been my experience that you can nearly always enjoy things if you make up your mind firmly that you will." - L.M. Montgomery, from Anne of Green Gables

Why bother?  Lots of things are enjoyable without all that work.

That's a very sensible objection.

What Montgomery is describing is not really pleasure, but attitude. If a thing is already enjoyable—a good meal, a favorite piece of music, a conversation with an old friend—there is no need to decide to enjoy it. The enjoyment arrives on its own.

The quotation is more applicable to things that are neutral, tedious, uncomfortable, or unavoidable. Anne is talking about finding delight in circumstances that don't naturally provide it. The effort is not directed toward increasing the enjoyment of a symphony from 90% to 95%; it's directed toward turning a dreary afternoon, a tedious chore, or an unwelcome situation into something bearable or even pleasant.

There is also a limit. Some things are not enjoyable, and pretending otherwise can become absurd. You can choose your attitude toward a tooth extraction, but that doesn't make the extraction fun. Human beings are remarkably capable of reframing experience, but reality eventually pushes back.

The quote probably resonated in Montgomery's era because life contained more unavoidable drudgery than many people experience today. If you're living on a farm in rural Prince Edward Island in 1900, there may be long stretches when your choices are not between several attractive alternatives. The question is not "Which enjoyable thing shall I do?" but "How shall I approach the thing I must do anyway?" In that context, deciding to enjoy it has practical value.

There is a Buddhist flavor to it as well, which I suspect you may recognize. Much suffering comes not from the event itself but from the mental resistance to the event. If you must sit through a long rainstorm, you can spend the day wishing it were sunny, or you can listen to the rain. The rain is unchanged; the experience is different.

Still, I think your question exposes the weakness in the quote. If life offers a choice between naturally enjoyable things and things requiring sustained mental effort to enjoy, most people will sensibly choose the former. The quote is really advice for when there is no such choice.

In a way, it is less a recipe for enjoyment than a strategy for reducing misery. That's a more modest claim, and probably a truer one.

If something tedious has to be done, then it has to be done.  One can sometimes make a game of it, fine, but if not, just do it.

That is much closer to my own reading of the situation.

There is a certain Victorian and early-20th-century optimism in Montgomery's quote, a belief that character can transform experience. Sometimes it can. But there is also a danger of spending more energy trying to enjoy a task than the task itself requires.

If the fence needs painting, paint the fence. If you happen to find satisfaction in doing a neat job, excellent. If not, the fence still gets painted.

What you are describing is a kind of stoicism—not the modern popular version, but the older practical sort. The task presents itself. One evaluates it. If it must be done, one does it. The emotional state accompanying the task is secondary.

Oddly enough, this can sometimes produce more contentment than the determination to enjoy everything. The person who insists on enjoying the fence painting may become disappointed when enjoyment fails to appear. The person who simply paints the fence has no such expectation.

I am reminded of something often observed among older people. The young sometimes ask, "How do you stay motivated?" The answer is frequently, "I don't. I just do the thing." Motivation, enthusiasm, and enjoyment are treated as welcome visitors rather than prerequisites.

That strikes me as a very durable philosophy, especially over a long life. Enjoy what is naturally enjoyable. Endure what must be endured. And every so often, a tedious task unexpectedly becomes interesting without any conscious effort at all. The surprise is more pleasant when it isn't demanded.

One can always divide the task into sub-tasks.  I don't know why, but it helps as each sub-task gets done.

That's a well-known phenomenon, and psychologists have spent a fair amount of effort trying to understand it.

Part of it seems to be that the brain is much better at dealing with finite, clearly defined objectives than with large, vague ones. "Clean the house" is a burden. "Wash the dishes" is a task. Once the dishes are done, there is a small sense of completion and progress. Then comes the next step.

There is also the satisfaction of closure. Human beings seem to have a strong preference for finishing things. A completed sub-task moves from the category of unfinished business to finished business, reducing mental load. The effect is sometimes called the Zeigarnik effect: unfinished tasks tend to linger in awareness more than completed ones.

I suspect there is another element that isn't discussed as often. A large task exists mostly in imagination. It can acquire all sorts of unpleasant qualities there. But a sub-task is concrete. You stop thinking about the project and start interacting with reality. Instead of "I have to organize years of paperwork," you are simply sorting the papers in one drawer.

Programmers have known this for decades. A project that seems impossible is often transformed by breaking it into pieces small enough that each piece looks almost trivial. The miracle isn't that the pieces are easier—they often aren't—but that you can see where you are and what comes next.

Your observation that "each sub-task gets done" may be the key. Every completion provides evidence that progress is actually occurring. A mountain climbed one step at a time is still a mountain, but from the climber's perspective there is always only the next few feet of trail. That perspective can make an enormous difference to how difficult the journey feels.

One of my teenage duties each spring was to paint our house.  The first time was a task, then it came to be fun, conquering, as it were, each board.

That sounds less like "making yourself enjoy it" and more like discovering a naturally satisfying structure within the task.

Painting a house board by board gives you hundreds or thousands of small victories. Each board starts out weathered and unfinished and ends up neat and complete. The feedback is immediate and visible. You can literally see your progress stretching behind you.

I suspect that's why many people enjoy activities that, viewed from a distance, seem monotonous: gardening, knitting, woodworking, polishing brass, even some forms of data entry. The work provides a constant stream of completed units. The brain seems to like that.

There's also an element of conquest, as you say. The house initially appears as one enormous job. But after a while it ceases to be "the house." It becomes that board, then the next board. Eventually you look back and realize half the house is done. The task that seemed overwhelming has been steadily retreating before you.

The interesting thing is that your enjoyment emerged after experience. The first year it was simply a duty. Later it became a game of sorts. That strikes me as more authentic than deciding in advance that one will enjoy it. Familiarity allowed you to find the rewarding aspect hidden inside the work.

A lot of life's satisfactions seem to work that way. As a young person you endure the task because it must be done. Years later you realize there was something pleasant in the rhythm of it all along.

I wonder whether what you enjoyed was not the painting itself so much as the visible evidence of efficacy: I did that board. Now I'll do that one. Human beings seem to take deep satisfaction in seeing the world yield, however slightly, to their efforts. A freshly painted board is a very tangible proof that one's actions matter.