Working Meditation

Observations on Human Connection & Contribution

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#87: The actual distance

If we zoom out enough on any interactive map, the cities of Seattle and Portland seem to merge. The ~180-mile, multi-hour driving distance gets erased. Someone planning a visit solely from the zoomed out view of a map might think they can cover key West Coast hubs from Vancouver, British Columbia all the way down to San Diego, California quickly. They might dream of popping in and out of Seattle, Portland, San Francisco, and Los Angeles along the way to get a feel. But of course, no one really does that. We know a trip like that would require more planning, time and resources. We know this because we have experienced the reality of navigating our own cities and countries, with their roads and delays. If we’ve left home base to explore, we’ve likely experienced upset stomachs from novel food sources, we know that the same piece of luggage can feel heavier as the days go by, we get the strain of finding and relying on an unknown doctor or mechanic mid-travel. In short, we understand the physical, mental and emotional fatigue that accompanies any significant exploration.

But we seem to forget this wisdom while planning explorations related to daily life. In imagination mode, our mind seamlessly zooms out to dreamily plan our days with vibrant work and social life. On a bright and sunny Saturday morning, after we are well rested, it can daydream that we’ll go from epiphany to functioning business in a couple of years. That from here on, we’ll wake up fresh and early everyday. That we’ll have energy to meditate and move in the morning, then give our utmost focus to work, and have energy left over in the evening for family and friends. We might even imagine everyone around the table sharing a lovely meal with laughter. In those moments, the mind is doing what interactive maps do. It zooms out to see the highlights but doesn’t factor in the actual lived-distance between them. It doesn’t see us getting offroaded by home maintenance, echos of grief, unexplained allergic reactions or a sick child. It doesn’t factor in those happy faces needing our support or that meal needing our effort.

It’s a silently harsh experience to fail ourselves because our dreams took longer than imagined to manifest. When in our life’s geography, the highlights aren’t happening so close together one after another. Our daydreams should come with a caution like some maps do: “This map is not to scale”.


“If you can dream — and not make dreams your master
If you can think — and not make thoughts your aim,
If you can meet with Triumph and Disaster
And treat those two impostors just the same”― If by Rudyard Kipling: writer, poet and journalist

#82: Nested commitments

Recall a time when you really wanted to start doing something. Maybe workout a certain number of days a week, learn to ride a bike as an adult, experiment with building a robot, or see friends more consistently. There would have likely been a moment of intense and condensed emotion that helped you imagine and ache for the new normal. Then, if you followed up this imagination with action, you might have encountered initial roadblocks. It’s likely that the imagination was still strong enough to help you summon willpower and bust through a few initial bumps. Hope was still strong and you powered through and did well; maybe for even a few months. Results came but so did more twists and turns on the path. You had a baby, busted your knee, a loved one passed leaving you shattered and scared, and you had little energy to give to this thing you still crave from deep within. Life happened and it feels like you took a few steps back and are now seemingly exactly where you started.

Then you come back to the practice after the break but this time your desire is less acute, more chronic. It’s transitioned from soft youthful hope to a more subtle, less shiny but a deeper-felt hardened goal. Brute willpower won’t cut it anymore because you’ve seen how things out of your control can easily keep interfering. As if imagination and hope held your hand early on in the path but their arms aren’t long enough and as you walk further and further, their fingers slip from your hands. This is when you let go of imaginary perfection and summon adaptation. You ease your clutch on over-monitoring against a set plan and develop a radar for in-moment adjustments. The practice now seems to have a cycle, a going and coming, a breath-like timbre. It’s not actually one foot in front of the other, more like one hop to the side, one step diagonally. Enough of these steps, jumps and hops and you meet another ally called self-compassion, who reminds you to ease your grip on the dream and let joy and ease flow as you get to do this thing you value.

The commitment to begin comes from imagination, the commitment to push through from willpower, but the commitment to stay on the path comes from adaptation and self-compassion.

“The only journey is the one within.”― Rainer Maria Rilke, poet and novelist

#70: Thresholds and pauses

There seem to be two ways of orienting to any new task. The first way is to jump in head-first without a pause and the second is to pause and understand the structure of the task, and our role and skills in relation to it. The pause-less action may be because of well-earned confidence or lack of awareness. If we take a pause, it may be short or long, noticeable or invisible even to us.

Like everyone else I’ve followed both approaches at different times but I’ve never really reflected on this because my approach to a task wasn’t the noteworthy part, the task was. I’ve recently experienced the comfort of doing something hard without thinking much and the discomfort of feeling unprepared and stuck mid-task. I’ve had to perch above my shoulders as I worked to observe what I was doing and what needed to change. I’ve had to pause and reflect on whether I had the tools, skills, information, context and mindset that I needed.

How do we know that a pause is in order and how can we make this process instinctive without overthinking? Two tell-tales have been helpful to me:

  1. Is the next task sufficiently different from what I’m doing or anything I’ve ever done? In other words, am I crossing a threshold? 
  2. Am I stuck spinning my wheels?

“People who wonder whether the glass is half empty or half full miss the point. The glass is refillable.”— Simon Sinek, author

#68: Room for doubt

There are times where even a hint of doubt is undesirable. For example, high-stakes situations with immediate consequences; like landing an aircraft or performing life-saving surgery. For a lot of other things however we carry more doubt than we show and we tend to hide it even from ourselves. Maybe because action requires certainty and commitment to follow through and we fear if we dwell too long in doubt, we’ll melt our resolve to act. But suppressing doubt doesn’t nullify it. We carry uncertainty, hesitation and indecision perpetually.

A particularly poignant example for me is Mother Teresa, who continued in her good works despite a 50-year crisis of faith. She says in one of her letters to her spiritual advisor – “When I try to raise my thoughts to heaven, there is such convicting emptiness that those very thoughts return like sharp knives and hurt my very soul. I am told God loves me, and yet the reality of darkness and coldness and emptiness is so great, nothing touches my soul.” This is was written in the 1940s, relatively early in her work and roughly 30 years before her Nobel Peace Prize in 1979. These doubts never abated but she didn’t abandon her belief or her work.

It’s a difficult place to operate from…when something speaks to us intrinsically enough that we commit to it but know on some level that we know little and will never know the full picture. Parenting, faith, and entrepreneurship are some common examples but the biggest example is the human life itself. Most of our discomfort is tied to the existential questions. Can any of us say with 100% certainty, without any doubt why we are here, what the purpose of a human life is, and what happens after we die? We fill in the blanks with high-judgment estimates and go about focusing on our daily life and goals. We let the act of living guide and consume us enough to create a sense of certainty in aspects: “I don’t know what happens after but know I was made for this work”. “The only thing I’m certain of is that I love my kids”. “Math has always made sense to me”. “I feel at home when I play the piano”. And so on. Micro doses of certainty on the macro path of unknown. Moments of clarity interwoven with moments of doubt, fear and loss. 

My evolving theory on doubt is this:

  1. The clearest indicator of what we should pursue and how we should live is a faint and sometimes hard to hear signal that we carry somewhere inside. Even though we carry it within, it comes across only when we silence the noise of daily pursuits, and listen without judgment. Because we may resist what we hear.
  2. We have to act despite doubt. The action doesn’t need to be big or all at once.
  3. A shared space with other people doing similar work is a huge boost, especially if we aren’t comfortable with what we’re being called to do. If this space or collective doesn’t exist, we need to create it.

#3 is perhaps the most important part in working alongside doubt. It ensures that in difficult moments, we have the wisdom of others doing  their own but similar work. That we have a safe space to air doubt, gain perspective and courage to keep going. It’s important that they understand this specific practice we have chosen. Its nuance, its promise, its fear, its draw and terror, the joy of having taken this path and the ache of having given up other options. If we want to keep going, it’s important we create a space that helps us recommit when we stumble. 

“It’s not necessary to be a saint to do good. You need willing hands, not clean ones. If we wait for our souls to be totally clean, our time on Earth may slip away.”― Mother Teresa: Roman Catholic nun

#66: Prototyping the everyday

I haven’t published in two months. I was building other parts of life that left little brainpower to review and edit. Or so I thought.

Over the last year, I saw my writing-voice take shape. But behind the scenes I was observing and getting to know myself through this part that likes to write. I saw how ideas arrive, which ones I select, how I process them, but also what I observe, what I care to write about and how I string together language. I was not only finding my writing-voice, I was finding my voice and wisdom. And because I sought discernment, I wanted to think things through a bit more before I published. I didn’t post last two months because I didn’t have time to think things through to the degree I would have liked.

I also noted that I had pieces at various stages of readiness. Some thoughts were supported only by quick scribbles to help me recall later while others were over 90% written, just needing final edits. Simultaneously, the inflow of observations and thoughts never stopped (I am thankful for this). So a mental traffic jam occurred. On one side, incessant mental downloads knocked on my brain waiting to be unfurled and on the other side half-written notes awaited attention. And there I was crushed in the middle…wanting to publish when my personal standards had been met. This act of turning off the publishing faucet created a creativity backlog so instead of flowing, my words felt like a tangled mess on my Notes app.

I’ve been learning prototyping tools and mindsets over the last couple of weeks. Today I realized that the prototyping mindset applies even to my writing. A prototyping mindset frees startups to experiment in front of potential users without being ashamed of failures and imperfections. The prototype only has one goal: learning. So it’s developed just enough to gain learnings and not an ounce more. Prototypes aren’t meant to be perfect, they are meant to be iterative. Each prototype a fertilizer for the next.  

The act of writing over the last year has been learning in motion for me. I write about this and then about that. An addition here and a deletion there. Sometimes poetic and sometimes prose but always a learning. When I stopped posting, I stopped learning. The desire for better got in the way of doing.

Thinking like a prototyper, I might have published more. Published more imperfect work that would have been enough to get the point across and taught me lessons not only for my writing but also other work and life. This writing isn’t meant to be perfect; it’s meant to teach me something and be of use to others. One prototyped post at a time.

“What would life be if we had no courage to attempt anything?”― Vincent Van Gogh: Dutch painter