As is anything – meditation is all about practice practice practice. I can sit for long stretches on the cushion. But it doesn’t mean that I’m meditating. More like wrestling with elephants or chasing monkeys.

I would characterize my own meditation in two phases – the first is settling in and finding my anchor. It’s usually my breath. Sometimes my seat and posture. I’ll count my breath if the elephants are really rattling around.

After I settle in I usually experience a “drop”. Sometimes it is gradual or sometimes more pronounced. Things slow down a bit and I’m not chasing anything. Just barely watching. I become more of an observer – and I don’t attach or react. I love the drop. It doesn’t happen for very long and I get caught up in my thoughts again and off I go wandering – again. And then I come back. It’s hard not to criticize or judge. I try to bring myself back to my anchor – gently.

I’d recommend not relying on an app to help you learn how to meditate. I’ve downloaded and tried most of them and haven’t found them helpful. Especially for a first time meditator. Find a weekend retreat to go to or go to a class. Better to do a retreat. Especially at these places; House, NY Meditation Center, NY – Insight Meditation Society in Barre, MA. – New York Insight Medication Center – Garrison Institute, Garrison, NY – Zen Mountain Monastery, MT Tremper, NY Center of NYC – Zen Center Village Zendo – Blue Cliff Monastery, Pine Bush, NY – Menla Mountain Retreat, Phoenicia, NY – Dhamma Dhara Vipassana Meditation Center, Shelburne, MA

You can go shallow with a weekend retreat or you can go really deep really fast at Dhamma Dhara in Shelburne, MA. It’s a ten day silent retreat. Silent. Like no talking. For ten days. Once you’ve taken your first intro course or have gone on your first weekend retreat then you can dip into the apps. They are;
Headspace – $$
Stop, breathe, think – $$
10% Happier

And a bunch more here on HuffPo. Download a few and find the one you like. I use Insight Timer. They’ve got tons of guided meditations when I do need them. It’s a terrible design but it works. When I do use a guided meditation or do look for a dharma talk I go to Audio Dharma. I’m a big fan of Gil Fronsdal. I discovered him years ago. He’s like the Woody Allen of dharma teachers. He has a bunch of “intro to meditation” classes that you can download and listen to. All free. As they should be.
I also recommend Tara Brach – she’s a powerhouse and is always very popular.

I’ve just recently discovered Shinzen Young who seems very awesome. He has this – He also does this – He’s claimed to have found a style of practice that will work more quickly than most.

I also would highly recommend Dr. Kristin Neff. She strips it down bare and has some really great guided mediations.

There is also Sharon Salzburg,  Joseph Goldstein, Pema Chodron and a whole bunch of others.

This looks super interesting – By the founders of Buddhist Geeks. Loved the podcast.

If you are into podcasts listen to any of these from the Secular Buddhists.

This looks super trendy – never have been – Buddhism and mediation is getting way over the top trendy now.