Had always been into nature / hiking since childhood. Had a variety of decent binoculars and spotting scopes.
At age 20, bought a K1000 with a 50mm f/2. Shot mostly landscapes and some flora... and, of course, obligatory sunsets.
3 years later, bought F65 and a cheap 70-300mm f/4.5-5.6 zoom, and moved toward wildlife, my true passion. Took lots of crappy shots, but a few gems.
4 years after that, bought a D90, initially still using the cheap 300mm zoom, but eventually variety of DX and FX lenses.
Digital really allowed for gaining lots of experience. Made every mistake in a hurry; figured out the do's and dont's, and got much better at tracking wildlife.
Age 31, using mainly D7100 and 600mm f/4. GF uses D5100 and 80-400mm f/4.5-5.6 zoom or 105mm f/2.8 macro, and we spend most weekends in the brush together.