Headspace is a nice app that does some timed guided meditation - you can start by aiming to do five minutes each night. It's free for some level of use, I don't remember the restrictions but the free version is definitely enough to begin a decent meditation habit.

A pragmatic guide, that's been mentioned on HN a few times, is 'The Mind Illuminated' [0]. The subreddit [1] is a great resource as well.

[0] https://www.amazon.com/Mind-Illuminated-Complete-Meditation-...

[1] https://www.reddit.com/r/TheMindIlluminated/

I'm not sure what I'm going to say will be helpful, but this is my experience: knowing myself, there is absolutely no way I could've done it alone. I went to some sort of camp for couple of days, where there is nothing to do but meditate. At the beginning not only I thought that it's too hard for me to do, but that it's simply impossible. After the first 2 days it went better. It's not magic, but it does have a very positive effect on my life. The way I see it it's like any other sport: it's very hard to get yourself to start, but it's amazing how fast you're getting better

I found this blog post (http://drewscanlon.com/meditation-for-beginners/) from Drew Scanlon to be helpful.

He used to be a member of the Giantbomb team and discussed his experience with meditation on their podcast. He wrote the post after they received an influx of email about the aforementioned discussion. It was nice to see meditation described by an amateur practitioner; I found the advice useful, and it spurred additional interest.

Insight timer is a good free app. I had some free time recently and need to get away so I did a 1 week mindfulness retreat which I found very helpful. I was finding it hard to stick with it since returning but the app gives me a little structure to work with and I'm enjoying it so far.

“The Mindful Geek” by Michael Taft is great for someone with a programming background. I think you can download it for free from his website.