Learning to escape side control can be a pretty frustrating task. The bad news is that once you "know how", it can still be very difficult to do. One thing that can make escaping difficult is confusion of objectives. The classic frame for physical conflict and contests is a) we are going to have an event (fight, match, contest), and b) one of us is going to win. In a sporting contest, of course you want win, however your foundation should always be the Jiu Jitsu order of operations: 1) stay safe, 2) don't allow your position to be degraded, 3) advance your position, 4) finish.
That frame of reference gives us the understanding that it is possible to meet half the objectives without ever escaping. This is a bit of a different focus as most people want to win the contest. With a little training it is not very difficult to hold side control on an equally skilled person. Advancing position or finishing is a different story. The space and momentum given by the top players attempt to move forward often gives the opportunity needed to escape. Similarly, efforts made by the bottom player attempting to escape gives the top player the space to attack or advance position.
For the most part our basic side control escapes are escapes of opportunity - escaping at a key moment or opening given by the top player. The frame escape generally occurs prior to a solid side control being established while the pummel escape occurs when the top person tries to hold the position without shutting down that escape route. Our hand position is initially the same for both escapes. It is one hand on the bicep by the elbow and the other on the shoulder with both elbows tucked in, in an effort to prevent chest/chest contact. If possible the bottom person should use their outside leg to make space.
When we teach the basic one arm pass the guard drill in the intro class an effort is made to get students moving just a little bit most of the time. Reason being, if any movement from you signals the beginning of your attempted technique then your partner knows when you are trying to perform a technique. If however, in the example of the open guard pass, the top player is always moving a little it becomes significantly more difficult for the guard player to know when or what to defend. Similarly, but worse, many beginning attempts to escape involve the bottom person "winding up", holding their breath, and then predictably exploding into the escape. When working with an inexperienced practitioner this might work. However the fine folks at Praxis Brazilian Jiu Jitsu will simply read the move and advance their position when that opportunity is given.
The player in bottom side control is better served by many small movements and feints or faux escapes. This way you can establish movement and start trying to read your partner and time your escape correctly. The best time to do the frame escape is before side control is established. The second best time is when you catch the top partner lightening up on their pressure as they move. We practice the frame escape as it is shown below; 1-2-3-4 all big movements with a definitive beginning and end. In real time you often just need enough space to get your nearside knee between you and your partner, just enough of purchase to allow you to back extension away and replace your guard.
Typically though the top player tries to mob the bottom player. Power has an immediately addictive draw to it. Gravity has power and when you are about to pass the guard there can be an urge to try and help it. Many top players, even very experienced players, attempt to pounce on their partner, (side note: please do not pounce on your partner - it is rude, or hilarious depending upon the partner). You don't wake up in side control. Typically you pass guard to get there. As we all know passing guard can be difficult. In the half guard series we just covered the set up was achieved not just by replacing the knee shield with the pummel, but by moving your torso forward into the pummel. There is a similar motion with the side control escape where you use the space created by your bridge to drop forward into the pummel. Then as your partner still has momentum you use the pummel to accelerate them along that line and escape.
Sometimes you don't need to bridge to make that space. Often times the top player will pass guard hastily or leave too much space in their side control transitions. If you are franticly trying to escape or otherwise not paying attention you might miss it. However if you are focused on staying safe and making a little bit of motion you will see it and find the room to escape. If your partner is posted up and not moving then you do need a good initial bridge to get things moving, once space is made and the "scramble" ensues - the person with the best body positioning and awareness is going to come out on top.
In our basic side control escape set up we assign two hands to guard against the head control arm, why? Because escaping side control, (which is difficult by itself), is much more difficult when the top player can wrap your head with their arm. I teach how to properly use shoulder pressure when it is supposed to be shown: after you know how to hold side control without it. Often times when people show heavy handed shoulder pressure as a means of holding side control it is because they don't really know how to hold side control without it.
Oddly enough, in Jiu Jitsu class I tend to show Jiu Jitsu. There is a very versatile and useful set of controls at your disposal from top side control. It takes awhile to learn them, however once you do the bottom person never feels like they are escaping. Their efforts to escape are met with them falling deeper and deeper into a trap that ends in submission. Once you have that skill set down AND THEN learn why and how to hold proper shoulder pressure you will end up with an enviable top game. Until then, (advanced class), you can wrap the head and hold your shoulder static against your partners upper chest/lower trap. For now don't press into your partners jaw - but do not yield if they turn into you. Your shoulder should feel a bit like a wall where it's not crushing your partner, but they cannot turn to face you.
Just that simple control can still cause for a long day. To escape bridge/bump to make enough space to grab the shoulder solidly with both hands, then bump again to bring your elbows close together. Then you bridge into your partner to make space underneath you. To free your head you need to keep their shoulder held up in place while you use the space to free your head. Part of the motion to free your head is caused by moving your head, part of the motion is from moving your hands, and gravity is helping you move your head away at the appropriate time.
The speech I often give with any moves that involve putting pressure on or near the face is as follows;
"Look around at all of your friends here. No one has a fat lip or a bloody mouth. They should all look the same way when you are done training".
I am going to add to that. Shoulder pressure, to me, is one of the first "jerk tests" in Jiu Jitsu. it's like the spider man thing - with great power comes great responsibility. The immediate goal is to learn how to apply the basic escapes. The next goal is to use the basic controls of side control. Don't be afraid to play with the shoulder, (on the chest - not the jaw), but understand that it's a little like wearing floaties in the swimming pool. You're not learning how to swim, you're learning how to not drown.
Getting light head control down isn't something to stress about. Everyone here is going to pick it up just fine. Along that road though many people are bound to hold a little too much pressure - that is part of learning. Fluctuating between boundaries is how you figure out how techniques work, (too much pressure, not enough pressure, just right). What I don't like to see is a student who selectively picks techniques like shoulder pressure and then hall passes on the rest of the material. Those students rarely last long in the academy as they get confused and frustrated when they aren't progressing.
Learning Jiu Jitsu takes a lot of diligent effort. There aren't any short cuts, but powerful techniques can make you feel like you found one. The basic drill we use when learning these two escapes is to place your hands as shown in the first slide above. The reason we set the drill up the way we do, (top person hops over butterfly guard - bottom person prepares the escape), is so you can get 100 or more reps in a single class of establishing that base to escape from. Focus on that, focus on purposefully creating movement and space from the bottom and you will quickly starting seeing a lot of escape opportunities where previously you were just being held down.