But how would it work for me?
Knowing this was a new habit I was attempting to form, I started with something very simple: I listened to my favorite three-minute song. That's a Tim Ferriss technique: If you look forward to hearing the song, you'll start to look forward to meditating, too.
I set a goal of daily meditation for 10 to 15 minutes every night using Headspace. Over a span of 45 days, gradually I progressed until I reached it.
These are the rough stages I went through:
Stage 1, days 0-3: Before using Headspace, I just listened to my favorite three-minute song. It worked: Because it was an enjoyable experience, it was easy to keep doing, and it made me look forward to meditation.
Stage 2, days 4-6: Drawing from research on the concept of priming written about by Dan Ariely, Malcolm Gladwell, Daniel Kahnemen, I modified my habit. I began listening to a set of upbeat songs in the morning and a set of slower songs, a mix of "Kentucky Rain," "In the Ghetto" and "Clair de Lune," before bed.
This primed my body to wake up or go to bed when I heard these songs.
Stage 3, days 6-45: Using Headspace's free trial, I began to add a 10-minute guided meditation to the end of my evening meditations. Later I progressed to a 15-minute, and then a 20-minute, session, while slowly weaning myself off of the evening music.
Stage 4, day 45 and onward: By this point, I had almost completely eliminated the music as well as the morning routine. The evening routine alone gave me the same alertness in the morning, and it also make it easier for me to go to bed.