This is not a tobacco pipe smoking tutorial. It's also not a pipe tobacco smoking tutorial. I am unsure which of those it is the least, but at that point, I suppose I'm splitting hairs. When we decide to light up a cigar, once it's lit, we typically have a certain ease insofar as smokeability and smoke ability. Smokeability because they tend to hopefully smoke themselves barring some light trouble-shooting; and smoke ability because perhaps we've smoked similar products before.
When we first grab a pipe, however, many of us are in uncharted environs. Again, I won't be playing at cartographer here, but perhaps I'll be a bit of a coach. I once had a terrible little league coach whose advice was to "throw harder." Seeing as I already threw hard, his advice to me was to "throw strikes." He never told anyone how to accomplish the former, or me how to accomplish the latter. All told, he was fairly adamant though. It might've been better for him to have said, "Calm down."
I once had another little league coach who yelled at me from dugout to mound "Calm down!" And then, after another pitch, "Throw harder." The two bits of advice seemed in conflict with one another. He never got around to "Throw strikes," maybe that was the other coach's trademarked pearl of wisdom. I didn't have a great amount of luck with little league coaches. Truthfully, I didn't give them a whole lot to work with.
Advice tends to be contextual. Perhaps their words were sound but their timing and topic were off. Let's see if now is the right time and place then, shall we? "Throw harder." Well, that could simply speak here to don't let up. As said, smoking loose-leaf tobacco in a pipe is not as easy as smoking cigars. Don't quit (unless you really want to). You will have to adjust the way your chamber is packed, you'll have to re-light frequently, and you might even have to unjam a jam. It's OK.
"Throw strikes." Don't waste your time or metaphorical arm on pitches that don't count. Don't drop a fortune on fancy pipes or lighters or tampers. Get a corn cob, a disposable soft flame lighter, or matches (lots), and grab yourself a cheapie Czech tool. Make your efforts and tools count. Also, stick with OTC blends, no need to get cutesy with blends and/or cuts.
Captain Black if you want aromatics and Half and Half maybe Carter Hall if you do not. I make further tobacco recommendations in Cigar and Pipe Tobacco Recommendations Reaching Across the Aisle: A Kaplowitz Media. Quick-Take (but hold off on that till you're a bit comfy. It ain't a race--it's actually quite the opposite.
That brings us back to "Calm down." Do that. While doing that, give yourself a break because, once more, you'll probably need a ton of relights and adjustments. One bit of direct advice I would give is don't throw only with your arm. Use your legs and follow through. See? Context matters. Grab a pinch of tobacco and fill the chamber. Press it down with the strength of a child. Do it again, this time with the strength of a woman. Do it a final time with the strength of a man.
That should get you off on somewhere near the right foot. The left foot is jamming the nub of a cigar into the thing and cursing everyone you've ever met through gritted teeth... but I'm more addressing myself there. Pipe smoking is an art all its own; each pipe is another drawing or song, or poem. Stick to your first one for a good bit, so get a decent cob with a hardwood plug (which will still be affordable, so that's neat). Get the lay of that land, it'll help future journeys.
Is it all worth it? I think so. I'd tell you why but it maybe won't matter to you. Maybe you could tell me why but it probably won't matter moving in that direction either. I'll give you this much, exploration seems no small part of the human experience--much like little league coaches who work long hours at hard jobs and are nice enough to give their free time to kids who think they can pitch.
::: very :::