Thou shouldest not have entered into the gate of my people in the day of their calamity; yea, thou shouldest not have looked on their affliction in the day of their calamity, nor have laid hands on their substance in the day of their calamity;
Obadiah 1:11 In the day that thou stoodest on the other side, in the day that the strangers carried away captive his forces, and foreigners entered into his gates, and cast lots upon Jerusalem, even thou wast as one of them.
Obadiah 1:12 But thou shouldest not have looked on the day of thy brother in the day that he became a stranger; neither shouldest thou have rejoiced over the children of Judah in the day of their destruction; neither shouldest thou have spoken proudly in the day of distress.
Obadiah 1:13 Thou shouldest not have entered into the gate of my people in the day of their calamity; yea, thou shouldest not have looked on their affliction in the day of their calamity, nor have laid hands on their substance in the day of their calamity;
Obadiah 1:14 Neither shouldest thou have stood in the crossway, to cut off those of his that did escape; neither shouldest thou have delivered up those of his that did remain in the day of distress.
Obadiah 1:15 For the day of the LORD is near upon all the heathen: as thou hast done, it shall be done unto thee: thy reward shall return upon thine own head.
The verse centers on "thou", "shouldest", "entered", "gate", "people", and "calamity". It is saying that the verse draws attention to "thou" and "shouldest", so its meaning should be read from those terms before moving to application.
The nearby context moves from verse 12's "But thou shouldest not have looked on..." into verse 14's "Neither shouldest thou have stood in the...", so "thou" and "shouldest" belong inside that flow. In Obadiah context, the local focus is covenant, worship, and faithfulness.
A plain takeaway is to answer the verse's own emphasis on "thou" and "shouldest" with trust shaped by these words, not by a vague optimism outside the passage.