BACKGROUND

I learned the basics of mindfulness meditation in April 2013, which was five years ago to the month.

The type of meditation I learned and would go on to practice would be closing one's eyes and concentrating on one's breath.

The goal would be to literally have one's concentration follow one's breathing — literally directing one's attention to the experience of inhaling and feeling air pass through one's nostrils when breathing through the nose, feeling the air pass through the throat/trachea, and feeling the air settle into one's lungs.

Then I'd hold the breath for ever so slightly, and follow the path of the air as I exhaled out the nose or mouth.

I meditated every single day for a few years, at first for a mere five minutes a day in the morning, and eventually ten minutes per day, and sometimes twice per day. Occasionally I'd do longer sessions in the 20-30 minute range, and sometimes I adopted somewhat similar mindfulness practices in the gym or when unable to fall asleep promptly.

I was never particularly strict in the position I'd meditate — sometimes I'd be sitting down, or sometimes I'd be laying down. I'd meditate wherever was convenient given the furniture layout of where I was at — often laying flat on top my bed after I'd gotten up for the day and made the bed, sometimes sitting at the kitchen table or at the sofa.

After a few years of this, one day I came to feel something like, "You know, I've gotten everything I can get out of this, and it's not very valuable any more." From there, I mostly stopped meditating for a couple years before picking the practice back up a couple months ago.

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OBSERVATIONS

Here's a few simple observations I've taken from meditation, without commentary or lessons, which I'll get to in a moment —

1. Bringing Awareness to Automatic Practices: We're breathing constantly, but most of the time, we don't notice it. It happens more-or-less automatically without any conscious thought.

2. Constant Streams of Thought: It might sound simple, when described, to just concentrate on one's breath. Not so! Thoughts constantly arise, sometimes very quickly and sometimes less quickly. I never counted the frequency of thoughts unrelated to breathing that came into my awareness and concentration, but I reckon it was often 30+ thoughts even in just five minutes. Five minutes is 300 seconds; just 30 arising thoughts would be a new thought every 10 seconds... and this is when I was attempting to bring my full concentration to bear.

3. "Streaks" of Thinking: With that said, it seemed that my meditation was "streaky" — there'd be minutes where thoughts were nearly constantly arising. Sometimes, though, I'd settle into a rhythm and all the unrelated thoughts would seem to entirely stop for 2-3 minutes until the timer went off and the meditation session ended. So in a session with 30 unrelated thoughts, it might be experiencing those 30 thoughts in the first 120 seconds or so (a new thought every 4 seconds), followed by 180 seconds of seemingly no thought arising.

4. Inconsistent Perception of Time: Though I always attempted not to do so, during subjectively perceived difficult meditation sessions, I'd sometimes check how much time was remaining. Oftentimes, I'd have a subjective perception of incredible difficulty and lots of time passing... only to check the clock and see that only 30 seconds passed! Alternatively, when things "settled down," then often anywhere from 3+ minutes would pass seemingly instantly.

5. Subjective Experiences of Discomfort or Calm: For seemingly no reason and often unpredictably, sometimes I'd experience a lot of discomfort when meditating. Sometimes the reason would be obvious — maybe a nagging sports injury that actually felt painful — but oftentimes, there'd be discomfort for seemingly no rhyme or reason. My mind, for lack of a better phrasing, "didn't want to be there." Sometimes, even in a single sitting, that would give way to calm — again, seemingly with nothing changed and for no particular reason.

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LESSONS

Following from those five observations, here's some points I learned that I think apply to all of life —

1. We can bring attention to otherwise unquestioned patterns of living.

Zvi Mowshowitz wrote about an experience he had,

"I was walking home from class along my usual route I had made a habit while doing this of stopping into Famiglia Pizza and ordering garlic knots. I like garlic knots quite a bit, but I also hated being fat and the way being fat made me feel. Things weren’t quite as bad on that front as they’d been a few years before but they were still extraordinarily bad. I thought about my impending solace and thought to myself: You wouldn’t be so fat if you didn’t keep buying these garlic knots every day."

I thought about that for a second, realized it was trivially true and then wondered to myself whether it was worth it. If I never stopped for the knots I would weigh less and feel better, but I wouldn’t have any knots. Even worse, I wouldn’t have any garlic. But would I rather enjoy today the full effect of never having had the knots, in exchange for not having any? Once I asked the question that way the answer came back a resounding yes. I didn’t know how much it would matter, but the calculation wasn’t remotely close. I walked right past the pizza place and never stopped in there for a snack again."

In my experience, the general lessons learned and trained during meditation made it ever-so-slightly more frequent and ever-so-slightly easier to notice similar situations — around food, around leisure activities, around internet usage, around procrastination and fight or flight reactions.

Often these things happen more-or-less automatically, and are unexamined. Meditation seems to have made me more aware of impulses, behavioral patterns, and decisions being made in real-time with minimal thinking, which has then made it easier to adjust behavior going forwards.

2. Concentration can be shaped and directed, but it isn't easy or free.

The simple act of attempting to concentrate on my breath showed me just how often random thoughts arise when attempting to concentrate. I don't think this will sound too counterintuitive when written down like this, but it was actually quite surprising for me.

We're up against a lot of self-created mental distraction in our lives. Concentration is possible and beneficial, but is more expensive and harder to attain than most people think — at least, it has been for me. It's somewhat expensive to train and get a mastery on.

Once I realized this, I eventually settled on a two-pronged approach in my life — first, I'd look to make better decisions a little more often. Second, I'd look to curate and shape the environment around me much more strongly. For instance, I don't have a web browser on my smartphone at all, and usually block the internet on my laptop for 12 hours when I go to bed — meaning the internet will be blocked when I wake up.

At the highest levels of developed concentration, I imagine it might be possible to get by without any shaping and curating of the environment. But seeing everything I was up against, I tried to shape and curate the amount of behaviors and choices available to me. Knowing that in highly distracted periods, I'd be facing new thoughts and pulls on my attention multiple times per minute was something surprising and, frankly, a little bit concerning.

3. Dealing with streaks of thinking is important.

I realized three things in this regard — (1) being able to trigger something like flow state more often was valuable, (2) being able to maximally utilize periods of high concentration and agency was valuable, and (3) being able to hit some baseline of not terrible performance during scattered times was valuable.

The last point is the one I'll highlight the most — I think a lot of people figure out sooner or later that they should get into a good zone of performance more regularly, and take advantage of those times. But for me, being able to put up non-negative performance on scattered days was probably the most important.

I think a lot of people have days that are a strict negative for their life — days they backslide, break otherwise good habits, make minimal progress on what's important in their lives, get behind schedule on duties, etc, etc.

My experience is that if you can turn a day that would otherwise be destructive to long-term well-being into a neutral or slightly positive day, everything else starts working much better.

4. Careful study is the only way to get a correct calibration of time.

At least, for me — it seems like sense of time and estimation ability varies naturally from person to person, but mine wasn't very good. Often, I'd think aversive tasks would take much longer than they actually took. Very often, I'd think that a given task I didn't want to be doing "was taking forever"... when it was only 20 minutes, 40 minutes, or 90 minutes. Even some really ugly unpleasant large projects only came out to a grand total of 3-6 hours of focused work.

After a few years of batting this concept around mentally, I eventually started estimating how long every task would take in 30-minute blocks. I made a low estimate and a high estimate, and then I recorded how long things actually took and compared.

For instance, for doing the final lingering details and submitting my American federal income taxes for 2017 a few days ago, I estimated it would take between 3.5 and 9 hours (7 to 18 blocks of 30 minutes)... it turned out to be only 90 minutes. I had overestimated the time required by 130% on the low end to 600% on the high end!

I've found that in order to understand how long it actually takes to get things done, I basically need to go through a process of (1) estimating time required beforehand on tasks, and (2) recording actual time taken to complete it. At least for me personally, my subjective perception of time has shown itself to be unreliable and untrustworthy.

5. Subjective experiences often varies for no good reason, and negative subjective experience shouldn't be given too much weight.

Some days I'm having a great day — other days, not so much.

Crazily, this seems to vary even completely independently of objective factors. Sure, a day on extremely low sleep or when nursing an injury or illness might feel worse, that's to be expected. But sometimes, for no good reason, Wednesday and Thursday are basically exactly the same in objective circumstances, but Wednesday feels great and Thursday feels not great.

I've learned — and keep learning — that it's possible to be feeling bad for no particular reason, and to ignore it and get on with whatever my duties and goals are. I do check in and think for a moment to make sure I'm not missing anything from the basic details (nutrition, sleep, hydration, fitness, etc) to the strategic (is what I'm doing effective, is it efficient, will it produce the results I hypothesized when I drew up the actions) and occasionally at the more philosophical level (am I doing the right things broadly in life? am I missing anything important?) — but once I check in, sometimes everything is fine, and yet I don't feel great that day anyways.

So be it. Noted. Any given day might not feel like a good day, but if there's nothing to course-correct on, then I just get on with whatever I wanted to concentrate on and do.

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GENERALIZATION AND UNIVERSALIZATION

Finally, I'll point out that I don't think mindfulness meditation is the only way to learn these lessons or train these skills. My good friend and business partner, Kai Zau, meditated for years — but eventually he transformed his morning meditation sessions into morning physical fitness sessions, specifically focused on doing planks, an exercise that's far more intellectually challenging than physically challenging.

I think the general skills of concentration and navigating distraction, as well as the lessons around time, arising thoughts, and subjective experience can be learned a variety of ways — certainly through fitness, which is a common one, but probably also through bringing similar concentration to artistic or productive endeavors.

The reason I took meditation back up, specifically, is because I find it a very good "calibration" mechanism to see where is at in the mornings. It's nice to see and experience the training benefits again, but the biggest ongoing benefit is that I know a day with a very scattered or unpleasant meditation session to start is likely to be a harder day, and I take appropriate measures.

That's my experience and a few lessons. If you get started in meditation, I recommend you start small — a five-minute timer goes a long way. It can also be very helpful to sit down and have someone who is an experienced meditator talk you through a first session or two — you can probably figure out the nuances on your own, but getting some basic instruction and guidance can answer a lot of little questions and potentially lead to more fruitful sessions earlier on.

Questions and similar observations are welcome.