Travel to the United Nations building. It is on the east side, slightly northeast above Grand Central Station. Stand on one end of the flagpoles so that you are facing them in a long row in front of you. Take one step back if you are standing next to them. Charge a jump and land on the first one. Use standard jumps and only press the Analog-stick Forward. With some luck, you should have landed about four or five flagpoles from the first one. Repeat this about four times to get the achievement.