The guide below is meant to be followed casually. Take your time, and let meditation enter your life at whatever pace feels right to you.
1) Do your first guided meditation.
Find a comfortable place to sit, where you won’t be distracted for a few minutes. Silence your phone. Sit comfortably. Then, follow this guided meditation. (Here’s a good text version of the meditation in case you’d rather read it before trying it.)
2) Don’t be hard on yourself when you inevitably get lost in thought or sleepy.
Being lost in thought or sleepy does not mean you’re a bad meditator. The mind does an amazing job of staying busy! And it’s natural to become sleepy when you relax. Be kind to yourself — do not judge yourself. There is no such thing as a bad meditator.
When your mind runs and you eventually notice you’ve been lost in thought, pause for a moment, be aware that you were just thinking, and kindly and gently bring your attention back to your body and breath. You can’t stop the thought or sleepiness, but you can react with kindness and love.
When you notice you’re feeling sleepy, try opening your eyes and resting your gaze on a neutral object, like the floor. If you’re still sleepy, stand up and continuing meditating, either with your eyes open or closed.
3) Try other guided meditations.
There are a wide variety of free, online guided meditations that you should experiment with. Guided meditations can be about awareness, loving kindness (metta), forgiveness, the breath, and many other topics. Experiment and see what you like.
Start with short meditations — 3-10 minutes. As you get more comfortable, experiment with longer meditations — 15, 20, 30, 45 minutes.
Below you will find my favorite guided meditation resources:
- UCLA Mindfulness Awareness Research Center
- Dr. Robert Foster
- Dharma Seed — note, many of these are talks, not meditations. Look specifically for meditations. Talks will be covered later in this guide
- Six Essential Practices by Jack Kornfield (for purchase) 
- Nine Guided Practices by Tara Brach (for purchase)
4) Experiment with different postures.
Try sitting on a couch or chair. Try sitting on a cushion or bench — your local Sangha (see below) will have these available to try for free. Try standing (this is especially helpful when you’re sleepy). Try walking meditation. And try lying down.
5) Learn the Buddhist principals behind meditation — known as the Dharma.
There are several ways to learn the Dharma. My suggestions are below:
These are talks given by Buddhist teachers. My favorites are listed below:
- Wisdom by Jack Kornfield
- Who am I? The Question of Identity by Jack Kornfield
- Awakening from Trance – Embracing Unlived Life by Tara Brach
- Respect and Dignity by Jack Kornfield
- You Can’t Stop the Waves by Jack Kornfield
- Real But Not true: Freeing Ourselves from Harmful Beliefs by Tara Brach
- Planting Beautiful Seeds by Jack Kornfield
- Loving Kindness by Jack Kornfield
- Seeing Thru Eyes of Love by Vinny Ferraro
- That Bird Got My Wings by Tara Brach
- Stress and Everyday Nirvana by Tara Brach (and part 2)
- Spirituality and Politics (post 2016 election) by Jack Kornfield
- “Play a Greater Part” – Bodhisattva for our Times (post 2016 election) by Tara Brach (and part 2)
- The Calling of the Bodhisattva in Our Times (post 2016 election) by Donald Rothberg
- Trusting Our Awakening Heart (touches on confidence) by Tara Brach
- The Joy of Virtue (morality, ethics, virtue) by Jack Kornfield
- Realizing Your Deepest Desires (finding what you really want) by Tara Brach
My favorite books on this topic are:
6) Experiment with unguided meditations.
Once you’re comfortable with guided meditations, experiment with unguided meditations. Start short — 5 or 10 minutes. Lengthen them as you get more comfortable. Choose whatever type of meditation feels right — open awareness, breath awareness, loving kindness, etc.
Meditation timers are very useful for unguided meditations. This is a great one. You can also use one of the many apps available on the iOS and Android marketplaces. Unfortunately I don’t have a recommendation.
You may also consider getting a singing bell to ring at the end your meditations. I’m not familiar with a good online purchase option. I bought mine at a local Tibetan store.
Also, here’s a great meditation FAQ from Tara Brach.
7) Attend a meditation/Buddhist community evening in your area — known as a Sangha.
Your area likely has at least one Buddhist community, known as a Sangha, that meets once a week in the evening. Usually during these meetings, a teacher will guide you through a 30-45 minute meditation, which is followed by a 45-60 minute Dharma talk.
Experiment with attending a nearby Sangha. Try going two or three times to start. Don’t make a judgment after just one visit — you may get unlucky and attend an off night.
8) Go on a multi-day, silent meditation retreat.
Your area likely has a retreat center. Google to see what’s available. Ensure the day-to-day schedule, including food and accommodations, will be comfortable for you.
 Jack’s CD collection comes with two CDs, each with three meditations. The three meditations are combined into one long audio track, making it hard to jump around between meditations. To help with this, I’ve copy-pasted the start and end of each meditation below.
Loving Kindness (Metta):
end: (end of session)
Working with Difficulties:
Gratitude and Joy:
Mind like sky
end: (end of session)