The Mind Illuminated by John Yates (aka Culadasa) helped me a lot on how to structure my practice and how to deal with specific issues arising during meditation. I also find it quite well-written.

I’ll second this recommendation. It makes meditation feel more accessible.

Thirded. It reads like a ~500 page technical manual for the mind. I don't know of any other book that states things as plainly, or in as much detail.

I did learn the distinction between focused and surrounding~ attention. Felt a bit different.

Mindfulness in Plain English by Henepola Gunaratana[1] is a classic intro. Altho the free version at the link is called "rather dated" -- really, how "dated" can meditation instructions be? Anyway, I found that edition helpful.

[1] https://www.urbandharma.org/udharma4/mpe.html

I think Headspace is quite a good fit for someone looking for 10 minute (or shorter or longer) sessions. Since you have meditated before, I would skip the "Basic" sessions.

The "Pain Management" facet of Headspace has been the most rewarding and I think its focus on breath movement through the body (even if you don't have pain or discomfort) is brilliant.

As far as reading goes - I've recommended Jon Kabat-Zinn's Full Catastrophe Living before and still do. I read it before starting a guided meditation program (I didn't buy his CDs) and eventually added Headspace.

I like how this talk explains meditation and it's progression, with variations on the practice: http://centerforsacredsciences.org/podcasts/Listening%20to%2...

Warning: on the talk, meditation is explained in a mystical context, but the practice is the same whether you share or not that perspective.

For mindfulness awareness in the moment I would recommend Mindfulness:a practical guide to finding peace in a frantic world by Williams (Oxford University). It takes you through a course in Mindfulness Based Cognitive Therapy. MBCT is aimed as anti-depression. I like the standardised approach used which means that clinical trials are possible. Another interesting angle is Mindful Self Compassion - best starting point Kristin Neff.

"Three pillars of Zen" by Phillip Kapleau. Contains chapters on practice and main concepts of Zen.

I've heard good things about the dhamma.org 10-day Vipassana retreats. The sessions seem to require registering months in advance for new students, though.

10 days is a bigger commitment than I feel comfortable making at the moment.

10 days is a big commitment, and it may be something you want to explore in future. While I do not agree with all the philosophies and can do without all the evening talks, the fact that you can do long sessions of meditations and everything is taken care of is excellent. I like to compare ten days course to a marathon - it is hard, you need to be open, and you learn a lot about your mind.

I have also found "Black Lotus App" (http://blacklotusapp.org/) to be a good source for myself. It is free, has some good guided sessions, allows you to attend global sessions and gives access to other resources.

Practical Zen by Julian Diazan Skinner

Waking Up with Sam Harris. It's an app for iOS. Sam Harris is a very insightful philosopher and neuroscientist. He explains things in a very concise and concrete way that I value above my experience with Headspace.

Is Sam Harris actually a philosopher? I got the impression he isn't, not in the academic sense, anyway. Daniel Dennett is a philosopher.

He has a B.A. in Philosophy from Stanford, so he at least has the foundation.