6213b. עָשָׂה asah (796b); a prim. root; to press, squeeze:—handled(3).
6119. עָקֵב aqeb (784a); from an unused word; heel, footprint, hind part:—footprints(1), footsteps(1), heel(4), heels(3), hoofs(1), rear guard(1), steps(1), trail(1).
So we see Jacob going along his merry way and he decides to send messengers to his brother in Edom. He tells the messengers to tell his brother what he has been up to and how he has prospered but notice how Jacob tells them to relay the message. He uses terms of respect; “My lord, Esau” and “your servant, Jacob.” Because Jacob had received the birthright and the blessing he should have been known as “lord” of the family not as Esau’s “servant.” But Jacob knowing full well the depravity of his own nature and past actions humbles himself even though he wasn’t bound by law to do so. The messengers come back and inform Jacob that not only did they relay the message to Esau but that Esau was on his way to meet him.
Funny, how the appearance of supernatural angelic beings did not strike fear into Jacob but the news that his older brother was coming to see him makes him cower. Interestingly, the messengers did not give any indication to Jacob that his brother was coming to do harm to him. But nevertheless, Jacob takes immediate precautionary action. He divides all that he has into two groups and then sends them in different directions. His strategy was that if Esau attacked and destroyed one group the other would remain safe. He then calls out to God and picks the fight.
Oh, God, you told me this would work out and now look at the mess I’m in. Now I know I don’t deserve what you have done for me so far but you said return and prosperity and now look. My brother is on his way and I am divided into two different groups for safety. God, he’s gonna hurt me. This doesn’t look or feel like prospering. You said You would prosper me remember! (my own humorous paraphrasing)