session: 1 start: 5:17 end: 28:15
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.
Your first meditation should be a guided meditation, where a recording takes you through the process. There are several places you can find free, guided meditations. I recommend this one as a place to start. Various mobile apps are also great places to start. I like Insight Timer.
When you’ve chosen a guided meditation to follow, find a comfortable place to sit, where you won’t be distracted for a few minutes. Silence your phone. Sit comfortably. Then, follow the guided meditation.
Here’s a good text version of the meditation in case you’d rather read a bit before trying it.
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.
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:
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)
There are several ways to learn the Dharma. My suggestions are below:
These are talks given by Buddhist teachers. My favorites are listed below:
Mindful Loving Awareness by Jack Kornfield
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
Planting Beautiful Seeds 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
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
On Dying by Jack Kornfield and Frank Ostaseski
Patience (original title: Monday Night Meditation Talk) by Jack Kornfield. Talk starts at 37:15
The One Who Knows by Jack Kornfield.
Practicing with Darkness and Light by Donald Rothberg
Mindfulness to One (good introduction to mindfulness) by Kittisaro
The Bodhisattva Leaves a Retreat (about how to bring our meditation practice into the world with compassionate and loving action. Skip the practice from 15:15 to 31:09.) by Jack Kornfield
My favorite books on this topic are:
Fear by Thich Nhat Hanh
The Issue at Hand by Gil Fronsdal
The Wise Heart by Jack Kornfield
Art of Mindfulness by Thich Nhat Hanh
The Miracle of Mindfulness by Thich Nhat Hanh
The Body Keeps The Score (on trauma) by Bessel van der Kolk
Waking the Tiger (on trauma) by Peter Levine
The Wisdom of No Escape by Pema Chodron
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.
I like mindfulness of breath, using a three-part breath. First I focus on the body sensations of the inhale, then the exhale. During the pause between breaths, I focus on a body sensation, for example my feet on the floor or my butt in the chair. Usually the pause is where distraction starts, hence the focus on the body to stay focussed. This is a way to use the busy mind to stay focussed and present.
Meditation timers are very useful for unguided meditations. I use Insight Timer's mobile app to time my unguided meditations.
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.
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.
In Redwood City and Santa Cruz, Insight Meditation Center is great.
In the East Bay, East Bay Meditation Center is great.
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.
In the Bay Area, I can’t recommend Spirit Rock strongly enough. Every experience I’ve had there, whether a day-long retreat or a residential retreat, has been amazing.
You can use RetreatList to find retreats and follow teachers.
 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.
session: 1 start: 5:17 end: 28:15
Loving Kindness (Metta):
session: 1 start: 33:47 end: 55:45
session: 1 start: 1:00:37 end: (end of session)
Working with Difficulties:
session: 2 start: 1:19 end:
Gratitude and Joy:
session: 2 start: 15:00 end: 27:25
Mind like sky:
session: 2 start: 29:20 end: (end of session)