As for when to check your blood pressure, the most important thing is to do it consistently the same time of the day (ask the doctor which time he prefers and also what time in relation to taking your medication). The following article has a lot of good information for someone just starting to monitor their blood pressure: https://www.drugs.com/cg/how-to-take-a-blood-pressure.html


The guidelines also redefined the various categories of hypertension. It eliminated the category of prehypertension, which had been defined as systolic blood pressure of 120 to 139 mm Hg or diastolic pressure (the lower number in a reading) of 80 to 89 mm Hg. Instead, people with those readings are now categorized as having either elevated pressure (120 to 129 systolic and less than 80 diastolic) or Stage 1 hypertension (130 to 139 systolic or 80 to 89 diastolic).
Healthcare professionals use a stethoscope and a manual sphygmomanometer to measure your blood pressure. Typically they take the reading above your elbow. The sphygmomanometer has a bladder, cuff, bulb, and a gauge. When the bulb is pumped it inflates the bladder inside the cuff, which is wrapped around your arm. This inflation will stop the blood flow in your arteries. The stethoscope is used to listen for sound of the heartbeat, and no sound indicates that there is no flow. As the pressure is released from the bladder, you will hear the sound of the blood flowing again. That point becomes systolic reading. The diastolic reading is when you hear no sound again, which means that the blood flow is back to normal.
"Blood pressure guidelines are not updated at regular intervals. Instead, they are changed when sufficient new evidence suggests the old ones weren't accurate or relevant anymore," says Dr. Paul Conlin, an endocrinologist with Harvard-affiliated VA Boston Healthcare System and Brigham and Women's Hospital. "The goal now with the new guidelines is to help people address high blood pressure — and the problems that may accompany it like heart attack and stroke — much earlier." 

Typically, more attention is given to systolic blood pressure (the first number) as a major risk factor for cardiovascular disease for people over 50. In most people, systolic blood pressure rises steadily with age due to the increasing stiffness of large arteries, long-term buildup of plaque and an increased incidence of cardiac and vascular disease.
Imagine a garden hose hooked up to a spigot. When the hose is flexible and there are no kinks in it, you can turn on the water full blast and it will flow easily through the hose. But if there’s a kink in the hose, the water doesn’t flow as well beyond the kink. And the pressure inside the hose builds up behind the kink. Or imagine there is gunk inside the hose blocking the path of the water. Your arteries are a lot like that garden hose.
Imagine a garden hose hooked up to a spigot. When the hose is flexible and there are no kinks in it, you can turn on the water full blast and it will flow easily through the hose. But if there’s a kink in the hose, the water doesn’t flow as well beyond the kink. And the pressure inside the hose builds up behind the kink. Or imagine there is gunk inside the hose blocking the path of the water. Your arteries are a lot like that garden hose.
A nurse takes your blood pressure at your annual physical. The numbers are recorded and the checkup continues. But do you know where on the blood pressure chart your levels are? Are they healthy? Too low? Too high, meaning you have hypertension? If you have high blood pressure or are heading in that direction, you should know that hypertension is among the primary enlarged heart causes, and a major risk factor for heart failure.
Blood pressure readings fall into four general categories, ranging from normal to stage 2 high blood pressure (hypertension). The level of your blood pressure determines what kind of treatment you may need. To get an accurate blood pressure measurement, your doctor should evaluate your readings based on the average of two or more blood pressure readings at three or more office visits.
×