Let's try and answer the question in terms of a rigid ruler. The first question one need to ask is "is there such a thing?" The answer is yes, more or less, with some interesting limitations that I won't get into much. The concept is a rather advanced one, called "Born Rigidity". See for instance the
<wiki link>.
Given this rigid object, our "born rigid" object, we can describe how the object accelerates. In it's own instantaneous inertial frame, the object always has a constant length. But as it accelerates, it appears to shrink. How does this happen? That's a question we can answer.
Basically, the front of the object, in order to maintain rigid motion, accelerates less, a lower "proper acceleration", than the front of the rocket.
This is closely related to Bell's spaceship paradox, but the details are different. Bell's spaceship paradox covers the case of two rockets with the same proper acceleration, and discusses how the proper distance between them increases with time.
The rule for the proper acceleration reading is that the product of the distance from the so-called "Rindler horizon" and the proper acceleration is constant. So the acceleration vs distance is not a linear curve, it's a hyperbola.
So, if we have a point accelerating at 1 light year/ year^2, which is approximately 1 Earth gravity, (whcih I'll henceforth cal 1G), the Rindler horizon is 1 light year behind the object.
The acceleration needed for an object to keep up in rigid motion approaches infinity at this Rindler horizon, 1 light year behind the point that is accelerating at (roughly) 1G. And it drops to half a G 2 light years away from the horizon, which puts it 1 light year ahead of the part that's accelerating at 1G.
Again, this is fairly advanced stuff, not really a good idea for an intorduction to SR, but the wiki entry on the Rindler coordinates and rindler horizon is at
<wiki link>.
I would suggest a different approach than the whole "shrinking rulers" idea to learn special relativity. My general advice is to focus on things that remain the same (this includes proper time, proper distance, and proper acceleration) rather than things that vary with different observers. Probably the place to start is to learn about the difference between proper time and coordinate time, and go on from there. Exactly where to learn about prop;er time is a good question, though - I'm not sure of the best resource here.