He who hesitates looks before he leaps.

Proverbs 22:1-2, 8-9, 22-23

Context
The book of Proverbs is a collection of wisdom sayings from ancient Israel. There are a few extended passages, but the majority of the book contains brief sayings. They sound better in Hebrew than in English - most are very short word plays.
As with proverbs from any culture, they cannot be taken absolutely. Consider two of English proverbs: "Look before you leap" and "He who hesitates is lost." Both are true - and they contradict each other! Be equally careful of ignoring the Proverbs and of treating them as physical laws.

Listening to the writer
The Proverbs, as a whole, teach conventional wisdom: good behavior and hard work are rewarded, laziness and evil is punished, and those in power should care for the weak. The selections emphasize the latter, although the former does peek out in verse 8. Read the entire chapter for a better feel of the breadth of the Proverbs.

Listening to God
Pick one of the proverbs that you don't like (or like the least), and meditate on it. Where is the truth in it? Why don't you like it? Allow God to challenge your behavior and/or prejudices.

Miscellaneous Meanderings
Like James, many people I know either love or hate the book of Proverbs. I think both feelings come from underestimating the book.
If we treat Proverbs as a list of simple commands and absolute truths, we will either love it (for reinforcing our ideas and being easy to understand) or hate it (by railing against its untruths and "oversimplifying" reality). But the book is not really that simple.
Some of the originators of the Proverbs may have seen the world in "black and white", but the collectors of the Bible did not. They included books like Job, and Ecclesiastes, and the Gospels - all of which make clear that a simple "good is rewarded, evil is punished" outlook on life is unsatisfactory.
But if we allow the book to speak in its full complexity, it has much to say. I think most of us have built-in tendencies towards one of the main messages of Proverbs - either the "reward/punishment" side, or the "care for the weak" side. Try listening to the side that rubs you the wrong way.
A one-sided "reward/punishment" view of the world leads to a cruel conservatism. If the good are always rewarded, and the evil always punished - especially in monetary terms, as much of the Proverbs imply - it follows that wealthy happy people have been good, and poor sad people have been punished. This leads to questions like "who sinned, that this man has been born blind?" (John 9) - questions which Jesus fought against.
A one-sided "always give" view leads to sloppy liberalism, which can encourage lazy and wicked behavior. Are we to always love? Yes. But encouraging people to be lazy - or ignoring the reality that good behavior generally does have good consequences, and bad behavior bad consequences - is not loving, it's "spoiling", quite literally. God doesn't want us to bring out the worst in people.
I tend towards niceness, and need to be reminded from time to time that it's good to ask people to do things for themselves. And some of my friends occasionally need me (or the Proverbs) to remind them that there are a lot of people hurting because of what's been done to them, not what they've done to themselves.


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