How does one develop the concentration necessary to do contemplation/Philosophy?

[julienw]

I feel that if I sit to do contemplation, I would just enter daydreaming and mental games with myself. Is it best to pick a question I've asked and then focus on answering that question in a contemplation session?

To be honest, I have never tried contemplation or self-inquiry, just basic mindfulness meditation. Would you recommend re-visiting Leo's videos about contemplation and self-inquiry?

[Thought Art]

Try downloading the free version of the timer app Tao Mix. Set the timer for 15 minutes. Pick one question you want to contemplate and then simply do it for 15 minutes. Doesn’t matter how it goes just try it and then note how that experience went. Use a pen and paper and put the phone on airplane mode. 
 

Start small, and just practice. I have similar fears but how I feel after an hour or two of not only contemplating but, doing exercises such as my morning pages/ brain dumps feels so much better and it’s amazing all the insights you generate. Start small, low pressure and build up a regular practice that is consistent.

[julienw]

@Thought Art Awesome! Great tips. Thanks for the advice--I'll give it a shot.