Make no mistake; smoking a pipe successfully is somewhat of an art form. As with anything you want to be good at, it will take some practice. I can't tell you how many times I've watched a new pipe smoker struggling to keep his pipe lit. This can be very frustrating and may turn what should be a pleasant and enjoyable experience into an out right battle. But with a combination of patience, practice and very importantly, a properly broken in pipe anyone can become an expert.
I've been fortunate to be around pipe smokers most of my life and have, and continue to, pick up pointers as I go along. It really is a never ending journey. So remember, don't get frustrated and don't give up.
When you smoke your pipe the moisture in the tobacco is released by the heat. This moisture forms into a flavored resin and works into the pipe. Over time the resin turns into a dark insulating cake which helps keep your pipe lit as you smoked it as well as protects the bowl from being scorched if smoked to hot.
How you pack your bowl plays a key role in the caking process. If the bowl is packed too tightly it will block the air passage and the tobacco will not burn properly. If it is packed to loosely it may create a hot spot and you run the risk of scorching your bowl. The traditional method of breaking in a new pipe is to only pack and smoke half bowls for the first few smokes. This ensures that you start the cake at the bottom of the bowl and it will work its way up the bowls walls evenly. When packing your bowl place your tobacco into the bowl with a circular or twisting motion. This will assist with the air flow through the tobacco as you pull gently on the pipe.
Once the bowl is packed pull some air through the pipe so you know you haven't blocked the air passage. If you're using a flame to light the bowl use a circular motion. Don't take short quick puffs off the pipe; instead take long, even, gentle, pulls, this helps to light the tobacco evenly and helps to keep the bowl from overheating. The tobacco will have the tendency to expand and rise after you light it. You will want to push the tobacco back down to give the unlit tobacco a chance to catch. After doing this you will want to re-light your pipe quickly. This is what is meant by tamping the pipe.
What is done after the smoke has a large effect on how long your pipe will last, as well as how well it will stay lit in the future. The most important thing to do when you have finished with a smoke is to blow forcefully through the stem. This will force any resin that has built up inside the stem back into the bowl. This not only will clean any loose resin out of the pipe it will also help keep it in the bowl where it will be useful. Doing this is a great way to help build up the cake in the bottom of your bowl, which again will help keep your bowl lit during your smoke and add years to the life of your pipe. Also, to help eliminate clogging make sure you clean out your stem and bowl.
Or at least this is what I've been told. I hope you become better at this than I.