It's absolutely possible to outgrow the blessings of a previous season. As we grow on our walks with the Lord, we can outgrow the environment where we were planted, just like plants outgrow their pots.

Matthew 9:17
Neither do people pour new wine into old wineskins. If they do, the skins will burst; the wine will run out and the wineskins will be ruined. No, they pour new wine into new wineskins, and both are preserved.”