Let’s look at each of the three verses:
First, Proverbs 27:1 tells us not to boast about tomorrow. Why? Because you don’t even know what today is going to bring. Wisdom does not brag about what we will accomplish without considering all the unknown factors. I do think we need to keep this balanced by remembering the usage of the word “boast” here. This verse does not decry planning—far be it for anything in Proverbs to be seen as anti-planning. Rather, this is about claiming that you will be, do, or become super-awesome tomorrow.
And we see this in movies as they reflect life, don’t we? Right after the extended monologue about his awesomeness and plans to rule the world, the villain then slips and falls off his horse. Or a superstar proclaims their great and amazing talent just before their next rehab stint. We see politicians blather on and on about how they are going to pass great laws or force great actions, and the next day a court, Congress, or President shuts down that plan.
The wise have intentions followed by actions, which will someday see results. They do not have boasting. Consider William Wilberforce: he never knew what day would bring forth the end of the slave trade in the British Empire, and I find nothing that indicates he boasted of his success in its demise. This showed wisdom: he never knew, until the law was signed, whether the day would bring forth success.
Second, Proverbs 27:11 encourages wisdom from a son, which will answer the criticism of the father. This connects right back to 27:1—do not boast about what you are doing, until you know what it brings forth. Does your parenting produce wise offspring? You don’t actually know that for years, do you? Does your education system work? Your philosophy? Your governing practices?
Perhaps we would be wise to not judge a system until we see its fruit. This is not to say we turn a blind eye to abuse and sin: waiting to see if the next generation of Nazis was still evil would have been horribly wrong. Likewise, abusive parenting should be stopped. But what of the debate about less hostile governing plans?
I think the same can be seen in education. We have to evaluate based on the results, but to judge, for example, a professor on the end-of-semester evaluations of students is pretty silly. Sure, I thought Drs. Vang, Hays, Carter, and Duvall were mean people at the end of the semester. Yet now, I think very differently. A teacher that can get students to pass a test may not be a teacher that inspires life-long learning and growth.
Finally, Proverbs 27:21, which points out that we are tested by our praise. We are tested by what people say about us. When praised, do we become puffed up? What about pursuing people’s praise?
Do we seek wisdom and to avoid reproach, or do we pursue praise? What drives our boasting about tomorrow and our planning?
All three of these interact well together. They speak, ultimately, to our need to trust in God for tomorrow. To entrust God with the results of walking in obedience, and to let His “well done, good and faithful servant,” be the praise we desire.