How To Finally Start Meditating

7 ways to make the habit stick.

Transcendental Meditation is the Rolls Royce of practices,” they said. The irony of a meditation practice describing itself as an extravagant material possession aside, I figured six million devotees couldn’t be wrong. They weren’t. In my first session, I felt what can only be described as “dropping in;” a spectral, TV-static feeling enveloped my body.

One hit of stillness in the zen-like, Far East setting of my first meditation lesson and I was an addict on a furious (if not paradoxical) hunt for more. Back home, however, the zenith of peace remained elusive. Clearly, something was wrong with me. I slipped into a perverse meditative practice: sitting for twenty minutes, twice a day, beating myself up. I’m not good at this. I can’t do this. Six million stupid people. Eyes closed, I pawed around for my iPhone. It was time to call in reinforcements. Unfortunately, my teacher was no help. “All of that stuff didn’t get there overnight and it’s not going to disappear overnight,” she said. “Just stick with it.”

Four months of meditative masochism followed. I began to feel like a toddler with a diurnal time-out. Sit there and think about what you’ve done!” Meditation had become a dreaded task instead of a respite, and the more I practiced, the further I ingrained this counter-productive belief into my neural wiring. Instead of dropping in, I was dropping out.

In an effort to reframe my perception, I began researching various methodologies, taking classes, and testing apps. Still, nothing stuck. There wasn’t a specific reason for quitting; as spirit-guru Deepak Chopra has said when it comes to abandoning meditation, “it’s not that a new habit didn’t take hold, but that an old one did.” (1)

Old habits die hard.

A few months after these failed attempts, I ran across an assortment of meditation paraphernalia in my closet of habits lost. Deciding to give it one last shot, I signed up for Vipassana, a 10 day silent retreat in the quiet wilderness of Wisconsin. 10.5 hours of meditation a day. No cell phones. No entertainment. No speaking. The experience was as difficult as it was life-changing.

We tend to think of transformation as uncommonly hard but powerful events change our sense of self all the time. (2) A death, a birth, a chance encounter, and what began an ordinary day becomes “the moment everything changed.” Vipassana was just that, a radical, metamorphic experience. After 130 hours, 20 minutes a day seemed relatively painless.

But if we don’t have someone to hold us accountable (or in the case of Vipassana, tell you not to leave), expecting to self-enforce a new, intensive daily habit is setting ourselves up for failure.

Yes, there are plenty of badass meditators who dive straight into a daily practice and succeed, but for me, even a simple regimen became excessive when applied to an already ambitious daily protocol. While it went against every cell in my type-a body, it’s only when I lowered the bar that the habit could truly take hold.

Change happens best when it’s not forced.

And so, through Vipassana, Headspace, Calm, Vedic, TM, mindfulness, guided hypnotic meditations, and a whole host of other methods which I cannot recall or spell, here’s what I’ve learned about how to make meditation a lasting habit:

  1. Start Small
    Begin with 5 minutes, every other day. You’ve probably heard this advice before. The problem is that no one ever takes it. In our eagerness for peace, we look at 5 minutes and think, “Eh, that’s too easy.” That’s the point. We live in a society that equates time and effort with usefulness but things don’t have to be difficult to be worthwhile. Look at it this way: It will be easier to build off of a small habit than to create a brand new one out of nothing.
  2. There Is No On Or Off The Wagon
    Our brains love categorization. Labeling a habit a “failure” makes it finite and known, providing a foundation from which we can start over. We stopped here. We’ll begin again here. It’s in the vague purgatory in between when we’ve missed a day or two that our mind gets confused, leaving us unsure whether to declare the effort a wash or keep going. Keep going. Just knowing that your desire to drop out is simply your brain’s misguided attempt at understanding will help you get back on track asap.
  3. Trick Your Mind
    The amazing thing about human beings is that we never stop when we reach our goals. Not only will you be more likely to hit your target if you set the bar lower- say four times a week- but the prospect of mental reprieve will allow you to exceed your expectations: You’ll find yourself adding in the extra days you would have skipped had you aimed for a daily practice.
  4. Get Guidance
    “Am I… am I doing this right?” Often, we quit meditating because there’s no palpable result. If this is you, a guided practice might be your answer. The two most popular apps tend to be Calm and Headspace, the latter a fan favorite due to the narrator’s comforting, mellifluous voice. Personally, I love this Meditation Minis Podcast. Be forewarned: With titles like “Buffalo In A Storm,” they’re on the woo-woo side. The benefit of these short tracks, though, is that they’re hypnotic: The applied visualization techniques carry you into a different state, offering a bit of instant gratification that’s sure to keep you coming back for more. That said…
  5. Focus On The Process
    You will not become Buddha overnight. Focus on the sitting, not the result. I’ve had a few amazing meditations in my life. I mean, out-of-body, can’t-believe­-this-is-happening-moments. TM failed for me because I began craving transcendence. It may seem counterintuitive, but it’s only in giving up the goal of enlightenment that you’ll begin to progress down the path.
  6. Create an Anchor 
    Ever notice how every time you walk through the door to a yoga studio or spa, you immediately feel calmer? While the peaceful color scheme and incense helps, your brain has learned to associate that environment with imminent relaxation. Every time you walk through the door into a certain friend’s nice apartment, or the door to a spa, you immediately feel relaxed? While the peaceful color scheme and incense helps, it’s not just the environment, but the fact that your mind has learned to associate it with upcoming relaxation. By creating a spot dedicated to your practice, you’ll teach your mind to expect quietude and mindfulness, letting you to “drop in” more quickly, and gain more from your practice. Yet…
  7. Keep It Loose.
    You’re 3 for 4. It’s Sunday am. But everything’s haywire and there’s no time. When all of the above goes out the window (and it will), know that sitting in silent mindfulness for 5 minutes contributes to your practice. Even if it’s small, just doing something will give your mind the pleasure of checking it off the list, helping you to keep the habit going.

To sum it up, be kind to yourself. Many teachers will tell you to just sit, no matter what, but it’s okay to take a break sometimes. Your meditation practice will happen in its own time. Remember, there is no shortcut to peace. If there were, it would just be the way.

  1. Chopra, Deepak. Super Brain: Unleashing the Explosive Power of Your Mind to Maximize Health, Happiness, and Spiritual Well-Being. Harmony: 2012. 249
  2. Chopra, Deepak. What Are You Hungry For?: The Chopra Solution to Permanent Weight Loss, Well-Being, and Lightness of Soul. Harmony: 2013. 225
Like what you read? Give Cat Castellanos a round of applause.

From a quick cheer to a standing ovation, clap to show how much you enjoyed this story.