Like most haiku poets back in the day, Issa didn’t have a lot of money. Then, as now, art didn’t pay so well. Issa usually embraced his poverty with humor, as he is doing here.
風吹や穴だらけでも我蚊帳
kaze fuku ya ana darake demo waga kachō[1]
the wind blows—
ragged, full of holes
my mosquito net
—Issa[2]
Back in the day, the mosquito net was an essential item. Issa here is giving us a simple image: his mosquito net blowing back and forth in the breeze. Littered with holes and tears as it was, it was still a mosquito net, albeit likely not a very effective one. This was written in 1803, a handful of years before he married for the first time. Without a wife to sew up the holes for him, we can imagine he wasn’t very good about doing it himself. He was always making jokes about his own laziness as well.
Making fun of himself or his circumstances was something Issa did often. What good is life if we can’t laugh at ourselves, after all? Issa always kept that sense of humor, despite what life threw at him.
The kigo (season word) here is mosquito net, which is a kigo for all of summer.