I started mindfulness meditation in 2008, sitting cross-legged to watch the arising and passing of my thoughts. It was a lie. The truth was, I didn’t want my thoughts to pass. I had so much to prove to the world. I wanted to get a worldwide book deal. I wanted to become a CEO. I wanted to backpack around the world. For months, I struggled until I read more and switched to a concentration based meditation approach. Immediately, something clicked. I’d meditate for only 30 minutes but would feel the effects for the rest of the day. I wasn’t checking Facebook and Quora in the middle of work, I didn’t get up every five minutes to get coffee, I was sharper, more productive, in everything. Now many years later, my meditation practice has changed again to mindfulness meditation. And that’s how meditation works. Don’t get sucked into writing in gratitude journals and burning incense sticks and repeating “I’m complete”/”I love myself” affirmations if you aren’t there yet. Change how you meditate based on where you are in life as below:

How to meditate based on your life stage

I find the most complete definition of life in The Yoga Sutras: first, evolution, then involution. Like an eagle, first you flap your wings high, as high as you can flap them, then you bring them down gracefully. How do you know which phase you’re in?

Evolution (growth): You’re thirsty for experiencing the world to the fullest: travel, advancement, success, family, starting your own company, meeting new people, getting new perspectives etc.

Involution (silence): The world starts to lose its pull. Something always seems missing even in moments of great achievement. You crave a deeper, more permanent reality, but not in a static depressive way, more as an active quest.

In 2008, I wanted to be the CEO of Procter & Gamble. Now, I want to no external marker of success at all, just dissolve myself in my work everyday, so I have no sense of self left.

Then, I took a sabbatical and back-packed across South America and Central Asia, hungry to see every notable place in every country. Now when Kerry and I travel, you’ll have to pay us to see a museum or a cathedral. We spent most of 2013 in forest ashrams and silent meditation retreats.

Then, I was an extrovert. Now, I don’t have much to say, and often talk more about life with Leela, our 20 month old daughter and Coconut, our pup, than with real people.

You change and your meditation practice should reflect where you are.

Concentration-based meditation approaches (mantra, image, breath) are excellent for the evolution or growth phases of life. You learn focus, concentration, single-mindedness, everything you need to achieve your goals in this world with excellence.

Insight meditation approaches (vipassana, mindfulness) work for the involution phase as they help you observe how transient your obsessive worldly thought patterns are and break free from them.

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Defining types: the pyramid of meditative experience

In every ashram or meditation retreat, you meet people who’re in neither evolution nor involution stage. They’re stuck. They don’t like their jobs, the credit card bills are piling, their parents didn’t love them, their fiancée doesn’t understand them, their pet parrot died. Learning meditation is a noble idea but know this:

Meditation will not help with personal drama.

The foundation of meditation is morality or love. Without a basic level of love for yourself (and a result, others), you’ll never shift focus away from yourself, the basic requisite of meditation. Over time, your meditation practice should evolve like this:

Of course, it’s never as simplistic as this. Each stage has stages within it and you keep going up and down the ladder but a quick, broad definition as below:

Morality

Morality is basic self-love and love for others so you’re approaching meditation from a position of some mental stability. You can learn morality by leveraging the abundant self-help industry resources–“love yourself”, “practice gratitude”, “follow your dreams,” kind of stuff or skip it entirely if you don’t have any personal drama that needs resolution.

Concentration Based Meditation

Once you’re not obsessed with yourself, you’re ready to start concentration-based meditation. The basic construct here is that you’re training your mind to go from scattered to one pointed by concentrating on an object external to your mind, be it your breath, a mantra, an image, or a deity. Within six months times of practicing concentration based meditation, you should see a tangible difference in your performance in the world. In my case, I was suddenly able to calculate numbers faster than before among other things so I knew my focus and attention was improving (Detailed concentration-based meditation instructions here).

Insight Based Meditation or Mindfulness Meditation

With a one pointed mind, you become mindful of reality as it is—the constant, helpless arising and passing away of thoughts. Anger arises, then disappears. Lust arises, then disappears. Happiness arises, then disappears. Now, when I sit down and meditate, here is what happens: A stray thought arises: “I want my book to be a bestseller”, I make a mental note. The thought goes away. Then, “I should take up that job”, noted, gone, “Jason shouldn’t have said that”, noted, gone, “Leela’s cough medicine is in my coat”, noted, gone. You’re just aware, observing this constant arising and passing of thoughts without judgment, without getting sucked into them and reacting to them, an understanding that slowly creeps into every phase of your life. (Detailed insight-based meditation instructions here).

Enlightenment

Months, years, perhaps lifetimes of insight meditation later, a deep, visceral realization arises that all that exists is the arising and passing of thoughts. There’s no permanent self at all. Just selfless phenomena—happiness, anger, love, sorrow, desire, lust, everything you experience is passing phenomena. Your sense of static self, the “I”, the experiencer, dissolves, so that there’s no difference between the observer and the observed. Everything is just one _____.

Fill in the blank with God, Brahman, Shunyata, nothingness, Purusha, Tao, consciousness, energy, awareness, whatever your mystical tradition says. They’re all fingers pointing to the same moon though I like Nagarjuna’s definition the best since it acknowledges the un-acknowledgeable nature of the ultimate reality: “it both exists and does not exist; it neither exists nor doesn’t exist .”

Bonus: Learn meditation in 7 days by signing up for my Learn meditation in 7 days by signing up for my free short video course here

I meditate. Why am I still not happy?

Have you truly internalized these two realities of the human experience?

Impermanence: Every thought, every emotion, every experience that arises will pass. Are you still trying to hold on to the pleasant ones? Incompleteness: The relative pre-enlightenment reality we’re living in will always be incomplete. Are you falsely assuming a baby, a new friend, a job, or a bestselling book will complete you?

Without acceptance of the limitations of the human experience, you’ll keep chasing the infinite in a finite world rather than looking for completeness within. That’s why most self-help books fail. No gratitude diary and affirmation practice can mask the truth of our incompleteness. Nor should they because a thoughtful inquiry about happiness starts from accepting that discontent.

In summary, what is the purpose of life?





Evolution, then involution. Be in each phase completely. Push the boundaries of experience in the growth phase. Turn inward and experience deep silence when going within. Meditating is your companion in both stages. Will you join me in maintaining a steady practice in 2016?