Spiritual bypass: The dark side of meditation

The productivity bros are back. With a vengeance.

First it was cold showers.

Then it was monk mode.

More recently, “testicular tanning.”

What’s their latest invention to maximize output, financial independence and unleash beast mode?

Rawdogging a flight.

I’m not kidding.

Have you ever gotten this freaky on an airplane?

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Help me focus bro

Like its brethren, the rules of raw dogging a flight are pretty simple:

  • Not using headphones or watching movies
  • Avoiding snacks and drinks (some even abstain from water)
  • Refraining from reading books or magazines
  • Not sleeping
  • Simply staring ahead or at the flight map for the entire duration

Why would anyone choose to suffer this way?

Well, there are supposed benefits to this approach.

Some broskis view it as a challenge to their mental endurance and their ability to cope with boredom.

Others claim it allows for uninterrupted thinking time and can lead to creative ideas.

The source of humanity’s problems?

The French philosopher Blaise Pascal was ahead of this trend when he proclaimed:

“All of humanity’s problems stem from man’s inability to sit quietly in a room alone.”

And while I’m no raw-dogger, I’ve come to appreciate stillness and quiet through a decades-long meditation practice.

When I left Wall Street at 35 years old, one of the first things I did was take a meditation class at the Transcendental Meditation (“TM”) center in Manhattan.

If I’m honest, it was during the days when Ray Dalio was fervently praising the practice. So I said to myself, “If it helped Ray, it’ll probably help me.”

Like many Type A’s, meditation appealed to me through the lens of “performance.”

I also loved how simple TM was – you effectively repeat a mantra for 20 minutes, twice a day.

So I went on and did TM for 7 years for 40 minutes a day before exploring new practices.

In 2022, I started an insight practice in the mornings and a concentration meditation in the evening.

And earlier this year, I realized that I may have been doing things wrong – so once again, I pivoted the meditation playbook.

Meditation is like flexibility

I’ve meditated approximately 112,320 minutes (or 1,872 hours) in the past decade.

It’s a huge time commitment (that often comes at the expense of watching TV and leisure) which begs the obvious question:

What are the benefits?

I won’t bore you with the details you’ve already heard a million times:

  • Reduces anxiety
  • Improves sleep
  • Better decision-making
  • Deeper concentration
  • Enhanced emotional regulation

And while all of these are true, there’s something way more powerful happening beneath the surface.

Yet it’s not easy to explain with words.

Let me use the analogy of flexibility. Imagine you exercise regularly but don’t stretch. You chip away at your workouts and runs and see continued improvement.

Then you decide to inject stretching into the mix. You probably won’t notice a direct change in your workouts. But your body may feel better, you may avoid more injuries – yet you’ll never know for sure when the benefits kicked in.

When it comes to meditation, I’ve noticed things that used to really agitate me now just dissipate.

I used to beat myself up over any mistake, and now I’m kinder to myself – without impacting my performance.

When my business got punched in the face from every angle – I didn’t panic and executed with calmness and clarity.

I used to fear the devastation of losing a friend or a family member – now I can honor my grief without it destroying me.

I can’t pinpoint the date – yet I can’t imagine my life without this practice.

But it’s not all pretty roses

Meditation can be pretty sneaky though.

And this year, my teacher Jess Morey showed me that I might have been subconsciously partaking in an activity known as Spiritual Bypass.

It’s when you use the practice “to avoid facing or dealing with difficult emotions, unresolved psychological issues, or real-life problems.”

You know how some people (ahem) cope with the everyday challenges of being a human with work, doomscrolling, video games and alcohol?

Well you can do that with meditation too.

Derek Haswell, co-founder of the Ten Percent Happier Mediation app directed me to the book I Don’t Want to Talk About It: Overcoming the Secret Legacy of Male Depression. In this book the author chronicles the many ways men are taught to suppress their feelings, and the fallout this creates — i.e. many many men struggling with unacknowledged depression, which can manifest as alcoholism, workaholism, anger issues, and difficulty in maintaining close relationships.

And while meditation can be a powerful part of the solution,

it can also be leveraged as a tool to remain emotionally distant from whatever is happening. Like the parent of a crying child who stops at seeing the kiddo without actually comforting them with a hug and reassuring words. What’s tricky is that this can seem like progress (“how can meditation be a bad thing??”) when in reality it can actually be distancing one even more from their feelings, and possibly even entrenching the covert depression even more (“I must really be broken if I’m doing all this meditating and still feel depressed”).

Spiritual bypass showed up for me in two ways.

First, I tried to suppress reality, rather than coming to terms with it.

Then, I “detached without compassion,” confusing indifference for equanimity.

Thankfully, through a new set of teachings (specifically around metta or “loving-kindness”) I’ve been able to reconnect and love myself in a truly sincere way.

And, heck, I can even do it on a plane.

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