This a big question that cannot easily be answered. Sort of like many Quora responses, the answer can be long, with a lot of caveats stating - it depends.
GIS has evolved into far more than anyone imagined in the late 1960's when first implemented. During a US SOUTHCOM lecture I gave a few years ago, the ability to map almost any kind of dataset opened up a Pandora's box of where to start. It's interesting that how we learn and new 'technology', is often determined by what questions we want answered in order to determine GIS objectives and goals. I don't say this lightly. This is because I doubt you are actually a novice by asking yourself, the right questions. It starts with a premise and what your objectives are.
There is good news on the learning front. GIS is available in a variety of online formats using video, lectures, online course materials, illustrations and real world tutorials. It's important to always remember what your macro AND micro objectives intend to illustrate and plot. Is it to enable analysis, awareness, dynamic news events, distribute information, collect data.... is it strategic, tactical or real time? This is important stuff to always be aware of. I find that many "novice" GIS users are in fact, very good at understanding what they are looking at, how to interpret and come to conclusions when viewing GIS datasets.
As odd as this may sound, documenting the 5 W's of your objectives in learning GIS is a good way to literally, map it out. Below are some resources for your review. All are free to browse and learn from. In my opinion, ESRI's apps and tutorials are not difficult if one takes the time to master them.
www.google.com/.../
http://learnosm.org/en/
msdn.microsoft.com/.../ff428643.aspx
gisgeography.com/.../
grass.osgeo.org/.../
www.qgistutorials.com/.../learning_resources.html
dotspatial.codeplex.com/
mannlib.cornell.edu/.../gis
I wrote a paper on the use of GIS technology, data and imagery for the National Defense University in 2012, which you may find useful. It is used as course material and freely available for download.
ctnsp.dodlive.mil/.../
Hope this helps. If I can be of further service, let me know.