I often read about newcomers to this hobby learning the ropes of what it's all about, so I thought I would write an entry about my journey through the waters of how we do this.
Let's dispel some myths first. Deep sky objects are faint, no matter what size scope you use, and the sky is a large place to find a small object. The joy of finding a new object is akin to discovering a needle in a haystack, or a gem in a mountain of rock. But unlike those experiences, this one comes with some tools to help make the job easier. I came to this hobby in the 70's, and back then things were a little different when it came to learning the sky. But those experiences are still the same today, the technology will only help you to a certain extent, and beyond that, it is this root level knowledge that gets a griphold and kicks in when everything else can't bail you out.
Begin with a basic planisphere. Some will say to use Stellarium, but then you are lugging a laptop outside, and ruining your dark adapted eyes with it. A simple planisphere will get you in the ball park of what's up and where as far as constellations are concerned. Put away the telescope for now, just use a planisphere, grab a chair, and a red covered flashlight, and begin to learn the constellations. Start with a really prominent one, like Orion in the Winter, easy to find, and then work your way out from there in larger and larger circles. Once you've grown the circle a bit, familiarize yourself with those constellations that lie on the ecliptic, the series of constellations that the sun and planets follows. Use software if you like to use the moon's position in the sky to determine the rough location of some of the constellations. You can watch the moon move across the sky on a monthly basis, and it is a highly visible indicator that can be very helpful.
If you are really bent on using a telescope, stick to easy targets like the moon or brighter planets that you can identify. Enjoy the craters, practice changing eyepieces, centering targets, print a moon map and enjoy the thrill of first hand discovery. It never quite goes away, even years later, so don't think mastery at this stage. And don't forget to use the locations of those planets to learn the constellations and vice versa. If you are going to use your telescope's finder, aim at a distant daytime object and set the crosshairs dead on between the finder and main scope at a medium to high magnification. The finder will be hard enough to use at night without it being accurately pointed. Learning how to point a telescope properly is an exercise in growth itself, how to deal with the mount, it's motions, damping after movement, etc, all are important. Aim it at stars, learn the names of a few bright ones as you learn the constellations, begin to memorize their names. Night after night and time after time this begins to grow as the stars in the east gradually wander to the south and finally the west and the seasons pass onward. In 12 months you will have come full circle with the plane of the ecliptic and learned many new constellations. And don't think you will learn it all in one year, but that first year will bring a lot of growth.
This hobby takes time, patience, practice, a little gear, more patience, some mistakes, some success, a bit of reading, and some interaction. Good luck in your great new endeavour.