My 'learning curve' (over 20 years or so) has gone something like this:
1. Buy nice, new, wicked sharp knife. Buy 'whatever' sharpening stone/hone that 'seems' to look useful (I had no clue at that point), and quickly ruin the edge on nice, new, wicked sharp knife. Buy more, nice, wicked sharp knives to appease my frustration. Amass very large collection of nice, new, wicked sharp knives that I still don't know how to properly maintain.
2. Buy guided sharpening system. Become frustrated at my own apparent inability to make it work. Put it away and forget about it for about 15 years. Buy more knives.
3. Buy ceramic pocket stone. Finally figure out how to 'freehand' a decently touched-up edge on my knife. Keep doing this for about 5 years. Still buy more knives.
4. Accidentally stumble across old guided system, which was previously stashed away and forgotten about. Decide to give it another go.
5. Using newly acquired knowledge of things like using LIGHT pressure and making sure I've formed a burr before moving to finer grits, I FINALLY put an 'OH MY GOD' edge on my knife using guided sharpener. Round up as many knives as possible, so I can put an 'OH MY GOD' edge on them, too. Don't quite feel the need to buy too many more knives. Starting to actually believe I can now sharpen the ones I've already got.
6. Decide to learn about stropping. Spend hours and hours stropping my 'OH MY GOD' edge, hopefully without making it duller. Do this for about 2 -3 years, to develop the 'feel' of the bevel being properly flush on the strop.
7. Out of the blue, one day just decide to put some sandpaper on my strop block and try convexing. Epiphany moment. Finally realize that all that time spent with previous gadgets & such had, in it's own convoluted way, paid off. Realize that I now have some decent 'feel' and muscle memory for maintaining proper angle and pressure.
8. After the previous epiphany moment, now 'experimenting' with freehanding on diamond hones. After all these years, have come full circle. Can finally, actually IMPROVE the edge on my knives using freehand technique, still applying the universal fundamentals of maintaining proper angle and pressure. This is where I am today.
Now, it's just a matter of PRACTICE, PRACTICE, PRACTICE to make sure I never forget.