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Yes, I think meditation pointed out my self-discrepancy. I thought I was and wanted to be person X, but really I was acting like person Y. It wasn’t limited to technical leadership though, but many other areas of my life. It has been a uncomfortable and immensely rewarding journey.
Gerald Weinberg talks about “congruence” (taken from Satir): http://www.satirworkshops.com/wp-content/uploads/2009/06/TowardsCongruence.pdf
For whatever reason, after each session I would feel very uncomfortable. I would be confronted with emotions that made me feel worthless and embarrassed. My mind was bringing forward all these painful memories and feelings.
I think this is a natural result of removing the suppression mechanisms we practice throughout the day (i.e. staying consciously busy to avoid subconscious discomforts). To anyone interested in going for a deep dive in this, I’d also recommend doing a week of silent meditation in leu of your next vacation.
As a person who has never meditated, but is interested, what would this (a week of silent meditation) entail?
I guess there are about a dozen different answers you could receive here. And there are dozens of traditions (best thought of as like philosophical traditions than religious ones, IMO, although there is certainly religious buddhisms - but harder to find in the more straightforward & to the point Vipassna or Zen lineages - but just like every walk of life - there are crazies about too :) What follows is just my opinion..
As a person who has never meditated,
I wouldn’t be so sure of this. It might be that when you find out what ‘it’ is, you find that experience matches experiences you’ve had before, or not - everything changes.
“The empty mind is the mind of compassion.” S. Suzuki. 
I don’t know about meditating in order to gain something or something else. I’m a beginner with a practice known as Shikentaza, aka “Just sitting”,“Sit & face the wall. Sit sincerely.” From the Soto Zen tradition - I’m not kidding when I say this is the practice, it’s amazing anything has been written about it at all.
“Zazen that makes your life busier, that’s ridiculous!” - S.Suzuki.
Meditation is “good for nothing”.
And yet, in the form of djhana/chan/zen - buddhism - a 2500 year old tradition,
How is something a 2500 year old tradition that amounts to “Sit. Sit sincerely.”
“To assume the Zazen posture is itself enlightenment.” - S. Suzuki
Three Pillars of Zen: Philip Kapleau
“Zen Mind, Beginners Mind.” - S. Suzuki.
Maybe it’s not for you, who knows. You know what is for you.
what would this (a week of silent meditation) entail
A person sitting, facing a wall.
“People say Zazen is difficult, but there’s a misunderstanding as to why. It’s not difficult because it’s difficult to sit in the cross legged posture or attain enlightenment. It’s difficult because it’s difficult to get rid of "something extra” from our practice.“ - S. Suzuki in "Zen Mind, Beginners Mind” (paraphrased from memory)
Essentially the goal of Shikentaza is to sit, “just sit”, until there is a person sitting facing a wall. Watch your thoughts come & go, etc, in the midst of all of this, a person sitting and facing a wall, but how sincere & close can you be to just sitting and facing the wall - this is an experience of reality, as it is, unpoluted by notions, thoughts and ideas - just A person sitting facing a wall. You’ll see the truth of how exactly “the mind of emptiness is the mind of compassion” but until you see this, it all sounds like new age woo woo, probably.
Other Zen practices involve Koans: “What did your face look like before your parents were born?”
Anyway, all of this is “just my opinion, man”. :)
The way I got here was actually listening to the talks of Joseph Goldstein on youtube, but in the end I’ve found the Soto Zen tradition is more concise & vivid for me. YMMV.
So what do you do?
Look up the Zazen posture - there’s a few, pick which is most comfortable.
Set a timer - perhaps 10 minutes at first.
Count the breath, 1 to 10, counting on the exhalation. If you find you’ve lost count or go over, or counting on the inhalation go back to 1.
“Sit. Just sit. Sit sincerely.” and “Let it go.” don’t “stop” thoughts, don’t suppress: instead, acknowledge & let go. Other words might be “accept things as they come, and as they go” or instead of trying to stop or look for anything in particular, “put it down” and simply return to focusing on the breath & sitting sincerely.
Notice how thoughts come & go, just like sensations. “Everything changes.”
When the time is up, the time is up.
“Don’t be too interested in Zen. Interest in Zen that involves some excitement or adds some busyness to your life is not true interest.” - S.Suzuki :)
 In all the statements I’ve heard, this particular statement is the one that on the surface, seems to posit two ideas that are unconnected “empty mind” and “compassion” but, through experience, is true. This is the “theory” if you will, that can only be found true in the light of experience & experiment. The experiment? “Sit & face the wall”. But its worth noting expecting anything is not a very skillful way of finding what ‘empty mind’ is :) So, in this case, it’s an introspective psychology - something for which there’s a 2500 year history in the east, but in the west we have, perhaps the Stoic tradition, some of the medieval theologian system builders & William James, others, perhaps.
Maybe you would like Alan Watts talks/writings interesting ?
I just signed up and the first comment I see is about Alan Watts. This is my kind of community.
I stumbled across this playlist on YouTube a while back and watch it regularly. https://www.youtube.com/playlist?list=PL02D3110151849463
Great! I had never seen him so young.
… Vipassna or …
(There are also many blog posts online about retreat experiences.)
The one I did, having not really meditated before, was a week long one from dharma.org.
There are daily sittings / lectures about random stuff. Chas had some good ones, although they are a little abstract: http://dharmaseed.org/teacher/43/
In between daily sittings, you can walk around the woods nearby or sit around in gazebos or benches. There are lots of people there, but almost no talking between students. “Almost” because there are chores that everyone gets assigned (cleaning, cooking, waking people up), some of which, e.g. pot duty, involve talking quietly if you can get away with it ;)
The most intense and enlightening part for me was being completely separated from all of the stimulus I’m used to throughout the day for a whole week. There’s no reading or writing or music allowed, and a lot of stuff “comes up” when you’re just thinking by yourself all that time — from memories to melodies. I recommend it.