He that observeth the wind shall not sow! - The man that is too scrupulous is never likely to succeed in any thing. If a man neither plough nor sow till the weather is entirely to his mind, the season will in all probability pass before he will have done any thing: so, if thou be too nice in endeavoring to find out who are the impostors among those who profess to be in want, the real object may perish, whom otherwise thou mightest have relieved, and whose life might have been thereby saved. Those very punctilious and scrupulous people, who will sift every thing to the bottom in every case, and, before they will act, must be fully satisfied on all points, seldom do any good, and are themselves generally good for nothing. While they are observing the clouds and the rain, others have joined hands with God, and made a poor man live.

He that observeth the (d) wind shall not sow; and he that regardeth the clouds shall not reap.
(d) He who fears inconveniences when need requires will never do his duty.

He that observeth the wind shall not sow,.... Who before he sows his seed is careful to observe where the wind is, from what corner it blows, and forbears sowing until it is down or changes, lest it should be troublesome unto him in sowing, or blow away his seed, and waits for a better season; such a man may lose his seedtime and never sow at all, and his grain in his barn may be devoured by vermin, or be destroyed by one accident or another, and so he may lose both his seed and his crop;
and he that regardeth the clouds shall not reap; which are uncertain signs of weather; and if a man gives heed to them, and puts off his sowing from time to time, for the sake of better weather, as he may never sow, so it is impossible that he should reap; and if he sows, and when his grain is ripe and forbears to reap because of the clouds, lest his grain should be wet, may never reap at all: and so it is with respect to liberality; if a man will raise difficulties, and make objections, and attend unto them; if he puts off giving till such an affliction is removed from him and his family, or that is grown up; or such an estate is obtained, or he has got to such an amount of riches, or till more proper and deserving objects present, with twenty things more of the like kind; if he defers giving on such accounts, or through fear of want, which may possess his mind for various reasons, he may never give nor get, yea, never do any good work; for, if nothing is done till all difficulties are removed, no good thing will ever be done.

Therefore sow thy charity in faith, without hesitancy or speculation as to results, because they may not seem promising (Ecclesiastes 9:10). So in Ecclesiastes 11:1, man is told to "cast his bread corn" on the seemingly unpromising "waters" (Psalm 126:5-6). The farmer would get on badly, who, instead of sowing and reaping, spent his time in watching the wind and clouds.

"He who observeth the wind shall not sow; and he that regardeth the clouds shall not reap." The proverb is not to be understood literally, but in the spirit of the whole paraenesis: it is not directed against the provident observation, guided by experience, of the monitions and warnings lying in the present condition of the weather, but against that useless, because impossible, calculation of the coming state of the weather, which waits on from day to day, from week to week, till the right time for sowing and reaping has passed away. The seed-time requires rain so as to open up and moisten the ground; he who has too much hesitation observes (שׁמר) the wind whether it will bring rain (Proverbs 25:23), and on that account puts off the sowing of the seed till it is too late. The time of harvest requires warmth without rain (Proverbs 26:1); but the scrupulous and timid man, who can never be sure enough, looks at the clouds (cf. Isaiah 47:13), scents rainy weather, and finds now and never any security for the right weather for the gathering in of the fruits of the field. He who would accomplish and gain anything, must have confidence and courage to venture something; the conditions of success cannot be wholly reckoned upon, the future is in the hand of God, the All-Conditioning.

He - He who neglects the necessary works of sowing and reaping, because the weather is not exactly suitable to his desires will lose his harvest. Whereby he intimates, that men will never do good here, which is expressed by sowing, and consequently not receive good hereafter, which is called reaping, if they be discouraged from it by every doubt and difficulty.