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

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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. 

If your blood pressure remains high for a long period of time, you run the risk of damaging your blood vessels. Your stroke risk rises significantly, too. And because your heart is working harder to push blood through your system, that very valuable muscle can become overworked and grow thicker. An enlarged heart causes further complications, including heart failure. Medications and special implantable pumps can help boost heart function. But if you can manage your blood pressure before it gets too high and puts your heart at risk, you may be able to avoid a lot of complications down the road.
The brain requires unobstructed blood flow to nourish its many functions. Very high, sustained blood pressure will eventually cause blood vessels to weaken. Over time these weaken vessels can break, and blood will leak into the brain. The area of the brain that is being fed by these broken vessels start to die, and this will cause a stroke. Additionally, if a blot clot blocks a narrowed artery, blood ceases to flow and a stroke will occur.
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). 

If your blood pressure readings are consistently high, you and your doctor will probably discuss treatment strategies. Treatment for high blood pressure often begins with lifestyle changes such as a weight loss and exercise program as well as a low sodium diet. In fact, the AHA recommends adopting these strategies as a means of preventing the development of high blood pressure and heart disease. If these strategies are not successful in lowering your blood pressure, medications may be recommended.
Some heart attacks are sudden and intense, however most heart attacks start slowly with mild pain and discomfort. Most heart attacks involve discomfort in the center of the chest that lasts more than a few minutes, or that goes away and comes back. It can feel like uncomfortable pressure, squeezing, fullness or pain. Shortness of breath may occur, as well as nausea, or lightheadedness. It is vital to get help immediately if any of these symptoms occur.
If you had previously been diagnosed with high blood pressure, the new guidelines don't affect you too much, says Dr. Conlin, as you still need to continue your efforts to lower it through medication, diet, exercise, and weight loss. "However, based on new information in the guidelines, your doctor may propose treating your blood pressure to a lower level," he says.
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.
The new guidelines stem from the 2017 results of the Systolic Blood Pressure Intervention Trial (SPRINT), which studied more than 9,000 adults ages 50 and older who had systolic blood pressure (the top number in a reading) of 130 mm Hg or higher and at least one risk factor for cardiovascular disease. The study's aim was to find out whether treating blood pressure to lower the systolic number to 120 mm Hg or less was superior to the standard target of 140 mm Hg or less. The results found that targeting a systolic pressure of no more than 120 mm Hg reduced the chance of heart attacks, heart failure, or stroke over a three-year period.
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