I've noticed that in a lot of my interactions with women, I'm too scared to push forward. I know that I can get a kiss or have her sit on my lap or something like that, but I chicken out and don't follow through. My question is not just "when do I know it's time to escalate" but also how do I make myself escalate and what to do if she responds badly to the escalation. For the record I haven't had too many kisses and find myself uncomfortable when trying to get one and I feel women feel that as well. Any help would be greatly appreciated.

you start escalating compliance as soon as you open, and you know it's time to escalate the compliance when you see compliance, but it doesn't nessicarily have to be linear, you're just testing her out to see what she's ok with so you can guess how receptive she is towards you physical advances
do more approaches and escalate, if you have alot of anxiety around this really only you can fix this, and to do that you have to challenge your self and consistently do the things that terrify you, just so you can get over it and realize it's not really a big deal
when you're starting out, just appologise and leave her alone, go meet a new girl, a non-compliant girl = not interested/available so you just saved yourself from wasting time and can go test a different girl by escalating
no pua e-book and no response over a pua forum will make you feel comfortable with this, you are going to have to make yourself uncomfortable to get used to doing this, do it enough, eventually you will become desensitized

You have to be able to read the IOIs. If you haven't gotten ANY IOIs, then moving in for a kiss close or kino isn't going to work out. I get real flirty and stare into her eyes and give her a seductive look. If she gets an awkward expression on her face and looks away, that's an IOD and I know she's not ready yet. If she keeps the gaze and smiles or does something cute, that's an IOI telling me I can progress further.

I will use words along with my kino as a distraction. As I touch a lock of her hair I'll tell her she has really nice hair. As I touch her leg I'll tell her she has cool jeans. As I caress her arm I'll tell her that her skin is really cold (not as a neg either). And if the kino doesn't go over well, then I'm already talking and prepared to keep talking to distract her from it. That's so much better than putting your hand on her, having her move it away, then sitting there silently and staring off into space awkwardly.

Kino usually comes naturally for me, so you may have kino anxiety or something. Because kino is done once you get passed your open and are already into your routine, and by that point the girl should be IOIing you a little bit and is ready for you to escalate.

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“Nothing is impossible, the word itself says 'I'm possible'!” ~Audrey Hepburn

Ok thank you for your advice. I have one last question though, how do you get kiss closes, do you just go for it or do you have a routine you use?

chiefs-guide-to-outer-game-vt75887.html

this should give you a basic idea of how to build compliance

For a kiss close, there are some classic ones.

When you are in the moment, and you can feel it's on, you can start ignoring what she is saying and what you are saying. Don't let words or content distract you. You will both know what's about to happen.

Take her arms and place them over your shoulders. She will probably clasp her hands together behind your head. Wait for it. Lead the moment. Don't burst the bubble. Then go in for the kiss.

Other method:

You whisper something in her left ear. Move your head slowly past her mouth and whisper something into her right ear. Then move towards her left ear again with your lips. If at any point she leans in to kiss you, then you can kiss her. If you feel the time is right to kiss her independent of that, then kiss her. If you don't feel it's ready, then don't kiss her and wait for a better time. But while you keep moving your lips past her lips, it's a really good method to get yourself the kiss. I also like to pull away first.

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What you sow is what you reap