"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."
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 

High blood pressure, also known as hypertension (See blood pressure chart below) is called the “silent killer” for a reason — there are no obvious symptoms but it can result in heart attack, stroke and even death. The good news is there’s a lot you can do to maintain healthy blood pressure or get back to one, often without the need for medications.
Your total blood pressure reading is determined by measuring your systolic and diastolic blood pressures. Systolic blood pressure, the top number, measures the force your heart exerts on the walls of your arteries each time it beats. Diastolic blood pressure, the bottom number, measures the force your heart exerts on the walls of your arteries in between beats.
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.
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