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Taking meditation seriously

July 12, 2024 @ 12:22pm – Mission Dolores Basilica, CA As soon as one believes a doctrine of any sort, or assumes certitude, one stops thinking about that aspect of existence. – Robert Anton Wilson
Belief is a toxic and dangerous attitude toward reality. After all, if it’s there it doesn’t require your belief- and if it’s not there why should you believe in it? – Terrence McKenna
I recently finished my second 10-day silent Vipassana retreat.
As I said my goodbyes, I got into conversation with Vishal, the man I’d been sitting next to in the meditation hall every day. Since there’s no talking or eye-contact allowed, the other meditators (about 24 men and 24 women) are more like blurry shapes of energy than actual personalities. You can’t help but think about what they are like in the outside world, but we’re reminded that this is just another distraction.
Yet, with only occasionally glances at him in my peripheral, I’d noticed his quiet determination. Compared to others, he took every sitting as seriously as possible. Sometimes you can just tell.
When I said this to him, he smiled politely. “You take it seriously too.”
Two years prior, I had signed up and sat my first retreat quite spontaneously. I had no meditation practice or even theoretical knowledge to prepare me. But after a short ‘dark night of the soul’ on Day 3, where I was close to packing my bags, I was suddenly all-in. When the gong was struck at 4am, I didn’t flinch. I was often first in and last out of the hall. I started to deeply enjoy the simple, vegetarian meals. 10 days went by in a blur. On the final day, when ‘noble silence’ was lifted, others came up and congratulated me. “You were sitting like a statue.” “How did you do that?” I felt surprised and sheepish. I didn’t have an answer. I shrugged, “I guess I just took it seriously.”
I shared some of this with Vishal, who nodded. He was tall, and pious looking, with carefully groomed hair. It had been ten years since his last retreat, due to a busy family life, part of the reason he’d tried to make the most out of the last ten days.
“We’re serious because we’ve done this before.”
Due to his beliefs, karma and previous lives explained my disciplined almost reverent approach to meditation, something relatively unfamiliar to me and not connected to my parents or society I grew up in.
In 2023, encouraged by a Taiwanese co-worker, I booked ‘Tour de Taiwan’, and rode around the island in 9 days. Having never visited before, I felt strangely at home with the strange people and places we discovered. Why was that? As we made our way along roads that snaked over mountain passes and rice paddies, familiar faces crossed my mind.
There was Emily, a Creative Director at a tech startup. She was high energy, put on art shows in her spare time and was half Taiwanese. In 2014, after a summer of unsuccessful interviews, my US visitor visa had run out and I’d travelled to London. I was calling her from a loud Starbucks with dodgy wi-fi. But she hired me, and I ended up living in America for the next 6 years.
Four years after that call, another Taiwanese woman took a chance on hiring me, and so I moved from New York to San Francisco. She was also a Creative Director, a single mum, loud, un-filtered and Taiwanese.
At that job, the Taiwanese-American Head of Content, who moonlit as a spin class instructor, encouraged me to sign up for a triathlon, which would become an interest for me over the following years.
Finally, my girlfriend in New York. One weekend we took a trip to upstate New York where we stayed at her family’s house. She was born in the States but her parents were from Taiwan and seemed to be Buddhists by the look of some of the paintings and sculptures dotted around the house. On the way back to the city we stopped at a temple. “We’re not really that serious about it” she said as I gawked at a giant statue of Buddha.
Do these coincidences make me believe in reincarnation? The short answer is no. I like to remain open and flexible in my thinking, which is just not compatible with being certain about stuff like that. But I think it is worthwhile to consider and be grateful for our unique strengths, preferences and affinities – whether you know where they came from or not.
This was also posted on Substack
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Writing rightly

February 12, 2022 @ 12:56PM – Freeport, Bahamas Last August I posted a note to Substack that outlined my criteria for publishing writing. It should be:
- Interesting (to me)
- Communicated as clearly as I can
- Useful to the reader
I mostly still agree with these but wanted to include my general ethical attitude/approach toward my writing. Here it is, in no particular order.
- I think what I’m writing about is valuable in some way. I wouldn’t share it otherwise.
- My intent therefore is to share that with the reader. That’s basically it. I don’t want to inflame emotions, get you to buy something, troll or make you feel bad.
- I’m not writing for a specific audience.
- Writing is both a means and an end for me.
- I only write what I’d also be comfortable saying, or defending if need be, in person.
- I’ll try to write as clearly as I can. I might use certain words or techniques but my intent is never to manipulate. This is obviously a balancing act, but I’d rather someone be bored and leave than to be tricked.
- I won’t lie or make things up.
- I’m mostly interested in things that you can point to or that seem intuitively right. I don’t make metaphysical claims.
- I want to write as truthfully as I can, but don’t expect exactitudes. That’s not the point of my writing. I might say something like: “we’d be better off drinking water instead of Fanta or whiskey.” One could pick apart that sentence endlessly, but you get what I’m trying to say. This is why I use a lot of words like ‘might’ or ‘probably’. I don’t ever want something I write to be misconstrued or misunderstood as an absolute claim.
- I have opinions but I won’t ever try to force them on you. I try not to write moralistically or judgmentally. For example, although I don’t think it’s a good idea to lie, I will never say that people who lie are evil or that you should never lie. If you want to read what I write, great! If you don’t, great!
- I write about topics I feel confident enough to explore and perhaps offer something valuable to the reader. That said, writing about something doesn’t ever mean I know what I’m talking about.
- Aside from minor tweaks, I don’t dramatically rewrite articles once they’ve been published. If I do seriously change my mind, I might remove the post.
- I occasionally use LLMs for writing support.
- I’m often thinking or relating to real people, places and things that happen in my life, but in almost all cases I won’t use names or details of real people.
- I’ll occasionally quote books or articles, and if I do I’ll make a footnote. But I’m not a good fact-checker. For example, if I quote Socrates or a Wikipedia article, I’m not doing deep research to make sure it’s correct. I go by intuition, and if I feel unsure about the source, I won’t quote it.
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Are designers making design hard for themselves?

These days, whether it’s gen AI or the overall death of the industry, there’s no shortage of problems flying around for designers. And that’s what I expected to read about when I picked up this short book titled Why Design is Hard.
But instead, I was surprised to see the argument made that design is hard because of an internal problem, rather than an external one; that the profession of design has flaws in how we think about what we do.1
So why is design hard?
- Designers tend to think of design as a solo activity, when it’s clearly not
- Designers tend to think others should just trust their design decisions
- Designers tend to overvalue creativity over bottom-line value for the business
The authors suggest that this type of attitude lands designers (of all levels) in all sorts of trouble. Designers are then surprised when priorities change, offended by constructive critique or resentful that their skills are undervalued or misused.
With a bit of a reality check, designers can stop tripping over themselves and basically get back to designing.
This made me wonder, does every profession struggle with these sorts of attitude problems, or is it only design? Maybe because UX design is a relatively new profession (~100k UX designers in the U.S), it never had much time to solidify its identity, and maybe never will.
The latter half of the book shares a few ideas for ways of working more effectively, particularly focused on designers within large organizations. Here are three that stood out to me:
If you can’t sell it, did you even design it?
In order for your precious work to see the light of day, a designer needs to not only deliver well designed solutions but articulate how the design solves it in a way that is compelling and fosters agreement.2 Like a politician running for election, what’s almost equally important to their ideas is how those ideas are communicated to the voters. For designers, whether it’s explaining a problem, or the results of a successful experiment, if your communication isn’t clear, it’s like it never happened.
The system is working (just not for you)
Have you ever been really surprised by something, like a project that was cancelled at the last minute, or user behavior that clashed with the data? It turns out that often what can seem like stupidity is often a constraint you can’t see.3 Rather than reacting blindly, or waiting for the perfect internal process to materialize, designers should learn to use system thinking (eg. 5 Whys) to help us understand our environment better and anticipate future hiccups.
The one thing designers forget to do…
Let’s face it. No one ever says ‘involve me as late as possible.’4 Whether you are an engineer, or product marketer, a lack of trust and collaboration with design is a recipe for disaster. That’s why it’s critical for designers to shepherd the work through the organization5 and lead their core team along the design process. In a way, showing the same care for coworkers as you might for the end-users you design for. Again, I think soft skills like active listening, empathy & communication do most the heavy lifting here.
Overall, Why Design Is Hard is a short, slightly bitter perspective on how to be effective as a designer (especially within a large organization).
Thankfully, there’s not too many grand proclamations or predictions on the future of design, just good advice on how to stop getting in your own way.
- Why Design Is Hard by Scott Berkun and Bryan Zug ↩︎
- Why Design Is Hard by Scott Berkun and Bryan Zug ↩︎
- Why Design Is Hard by Scott Berkun and Bryan Zug ↩︎
- Why Design Is Hard by Scott Berkun and Bryan Zug ↩︎
- Why Design Is Hard by Scott Berkun and Bryan Zug ↩︎
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Being wrong for the right reason

March 15, 2025 @ 9:30am – Richmond, Victoria Last year, I DNF’d a difficult bike race.
It was painful for me in many unexpected ways and I wrote about it a lot.
I compared it to a temper tantrum:
You kick up a big fuss because things aren’t going your way.
I got existential:
You start questioning yourself. Why am I here? What am I doing this for? When all you need to do is ride your bike to the finish line, asking “what’s the point?”, is not very helpful.It’s the type of question that invariably creates more questions. Do I even like this? Why do I do this to myself? Who do I think I am? What am I getting out of this?
I blamed my ego:
It was dramatic (I’ve lost the love, I’m quitting.) It was proud and sought validation (I’ve done a lot of training, but it wasn’t enough). It was dismissive (Things change. I’m interested in different things now. Cycling is not for me)
I blamed my body:
When we run low on water or nutrition, our mind goes crazy. I was bonking, dehydrated and out of carbs. I hadn’t planned enough, paced enough or trained enough, and paying the price.
I blamed masochism:
No one told me to grit my teeth. Although it gives me a certain kind of energy, it doesn’t feel very pleasant. And if I’m honest, it rarely helps with whatever I’m trying to do. It doesn’t make me smarter, faster, funnier, kinder.
Even in my dreams I was questioned, prodded and mocked by satisfied race finishers who demanded I take responsibility for my result.
Once the psychic dust had settled, the diagnosis was blindingly obvious. I hadn’t prepared enough.
A year later, I was back and ready to ride again. My determination was still there to finish the job.
But this time, I had a plan. I mean, I literally had a training plan, a single PDF page which told me very simply what to do and when to do it. On Monday I rested. On Tuesday, I rode my bike.
I had one rule. Stick to the plan as best as you possibly can.
As the race loomed closer in my calendar, I noticed how much I resisted following a structured plan that was almost guaranteed to help me.
I started to resent ‘grinding‘ through it day by day and wanted to invent my own approach. I hated to defer to a ‘stupid’ ‘rigid’ instructions and wanted to ride with vengeance, ‘destroying’ my previous time.
Famed San Francisco 49ers coach Bill Walsh calls these distracting ego-traps ‘faulty reasons’. It’s when “your logic is skewed by emotions, pride or arrogance.”1
In other words, when your ego gets in the way and tries to run the show.
Like what happened last year to me.
He noticed early in his career that he consistently got into trouble when he was “trying to prove you’re right and trying to prove someone else is wrong. Of course, they amount to the same thing and often lead to the same place: defeat.”2
Outside of the football field, Bill points to Ernest Shackleton as an example of the ego trying to “force a plan past the point of reality.”3 Before Shackleton set off on his mission to cross Antartica by foot, whalers told him that the Weddell sea was unusually packed with ice that season and advised waiting. Sticking to his plan turned into an epic disaster.
On race day, I rode with a clear head, fresh legs and surprising ease. My boring plan and preparation freed a huge amount of bandwidth to enjoy the car-free roads, nature, meet strangers and help teammates.
I reigned in all point proving, theatrics or anything else stupid.
My ego suffered, but I finished the race.
It’s not a surprise that decent planning and preparation helped. Of course it did!
But sticking to the plan rather than the tempting demands of the ego, meant that even if I had failed, I would have failed for the right reasons.
This journal is also published on Substack.
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Where should people begin if they want to have a more friendly inner voice?

February 21, 2025 @ 8:13am – Richmond, Victoria This question was originally asked of Alain de Botton. You can listen to his answer here.
Here’s the problem, and it’s a big one. Most inner voices are not noticed.
The most helpful and important thing one can do with an inner voice is to nudge it into the daylight. There, one can deal with it simply, like an incorrect charge on your credit card bill.
If you can see it, an inner voice will reveal itself as non-complex. It’s just a bit of commentary.
But when it is left in the dark, it’s dangerous.
A personal example. I’m getting ready to leave my house to go camping for the weekend. I need to brush my teeth, eat breakfast and pack my bags. But as I do these tasks, a critical voice follows me.
- “You forgot to turn off that light again.”
- “Toast is taking too long, you should have made cereal instead.”
- “You’re making a mess. Slow down.”
- “You’re not thinking very clearly are you?”
I could go on, but I think you get the picture. Lots and lots of negative commentary.
Heres’ the kicker:
When one is not aware of an inner voice, we implicitly agree with it.
In one smooth, habitual action, we’ve listened, agreed and responded to something that might not be worth responding to.
We might reason to ourselves, “I know it’s a mess, but I’m in a rush.” Can you see how ‘mess’ has been folded into that thought without question?
And that’s how most of us live with an unfriendly voice. It sets the scene for every moment of our lives and narrows the scope of the actions available to us.
You didn’t answer the question. Where should people begin if they want to have a more friendly inner voice?
With a little awareness of an inner voice, one has many great options to deal with it. Instead of responding to an inner voice automatically, don’t. Pause. Question it. Get it a cold drink. Suggest that there are nicer, kinder ways of speaking (or thinking) that the voice may not have considered. Point out the invariably faulty logic and contradictions. If you are being critical of the quality of someone’s cooking, ask this unfriendly voice if it thinks it is a Michelin star chef.
A nasty inner voice doesn’t have the ability to introspect or to seek balance. It’s a hot headed 14 year old with a keyboard, an anonymous comment section and a point to prove.
It’s not about making an inner voice friendlier. It’s most important to make it conscious, so it can be seen for what it is, a weak, repetitive bit of commentary that you respond to without flinching. Then, with an appropriate amount of objectivity, one can form a more mature relationship, whether that’s ignoring, tempering, laughing or even (gasp) showing some compassion.
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Don’t imitate entropy

February 15, 2025 @ 5:11pm – Hawthorn, Victoria Everything you do has a consequence.
“Consequence” might make you think of detention, jail, guilt, regret.
But consequence is as simple as cause and effect.
Are you aware that everything you do has a consequence?
The other day, I took a cardboard box down to the bin area of my apartment building. Instead of crushing it, I tossed it into a corner. We always have reasons for doing things like this. No matter what the action is, we can justify it.
The next few trips to the bins, I saw my box still sitting there. I ignored it.
Then, one day, I saw another box next to it. Now there were two.
Someone copied me.
René Girard says we are imitative beings. We watch each other. We look up. We show off. We mirror. We are born and then we start to watch other people.
Instead of eating the healthiest food or wearing the most appropriate clothes, we copy the habits and style of others, often making our lives more difficult.
We resemble our parents not just because of genetics, but because we watched, listened, and learned from them – a lot.
But even if you don’t have a family to care for or a company to run, you still can’t separate yourself from others.
No matter how unique, reclusive, or separate we feel, a microscope proves there’s no barrier or border containing us.
We can feel deeply responsible for what we have influence over.
I listened to a podcast about a guy who went into a depression because of the troubles his son was facing. Because of something stupid the son did, the father blamed himself and slid into a depression for three years.
This is a natural.
So what do we do?
We could drive ourselves crazy over making sure we only have a positive influence on our surroundings.
But we can’t really know all the ways we will ‘effect’ others. It’s impossible. The variables are too complex.1 Just like you’ll never really know what is ‘effecting’ you.
Take out the recycling, or don’t. But once in a while, I hope a small sign reminds you—somewhere, someone is watching.
Originally published on Substack
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Don’t die on a hill

January 27, 2025 @ 10:31am – Mt. Donna Buang, Australia Do you know the difference between struggling and suffering?
A hot day on a bike might show you the difference. One moment you’re quietly complaining to yourself about the dwindling water in your bidon and the next moment you’re a martyr.
Historically, a martyr was someone who would volunteer to die rather than renounce their religion. They chose to take a bullet for a belief.
Martyrs don’t take the easy way out:
- Instead of asking for help, they grit their teeth in isolation.
- Instead of trouble shooting they resigns themselves to endless frustration.
- Instead of easing up they doubling down, as if suffering is a good thing.
On a long gravel bike ride with far and few stops for refueling, I caught myself in this martyr frame of mind. I’d been there hundreds of times before without much recognition.
When our group finally pulled up at a 7-11, passive aggression, bitterness and resentment had almost entirely consumed me.
I rushed past my friends to the fridge, burning with righteousness. But before I cracked open my drink, I managed to catch myself.
I asked myself a simple question. This question stops the martyr in its tracks.
What do I need right now?
The false-selflessness, the white knuckling, the relentlessness, the self-destruction all came crashing to a halt.
What do I need?
What do I need? I need to sit down for a few minutes and cool down. That’s it. That’s all. There’s no point to prove. No badge of honor. I simply need to sit down.
I slowly sip my drink and gently tune back into a conversation about the fires in L.A. I finish my drink. My heart rate steadies.
What do I need?
I needed that.
Being a bit of a martyr can fuel us because there’s always someone or something to rail against. It can stroke our ego and make us feel falsely superior and falsely selfless, because the ego is always right.
Martyrdom feels powerful, but problem-solving actually is.
When we let the martyr go and ask ourselves what we need, we come back to neutral reality. We can gain focus on the actual problem to solve. And when we do that, we open ourselves to real, simple solutions. A purple gatorade. Borrowing sunscreen from a friend. A detour. A conversation.
We all have hills to die on. Martyrdom is likely not completely unavoidable for some us (more stubborn) folks. But life is too short to rip ourselves to shreds over a belief.
So next time you find yourself dragging yourself into a personal war,
Just ask:
👉 What do I need?
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Don’t grind your teeth

July 11 2024 @ 3:32ppm – Yerba Buena, CA I don’t train for races like normal people do.
Normal people sign up for a race for a particular reason, train and prepare and then do their best effort on the day.
I don’t do that.
For some strange reason I avoid research, training plans, coaches. I do my own thing. Instead of calmly and happily sticking to a plan, I grit my teeth and take on an attitude that the world is against me. Sometimes I summon the energy to take on tough physical challenges that raise the eyebrows of others, but don’t really help me get ready.
When I hear about my friends clocking miles on their trainer, I roll my eyes, generally resentful of their progress.
And if I don’t perform like I hoped I would, I heap the blame back on myself. I wasn’t disciplined enough. Not motivated enough. I throw around ultimatums like “I’ll quit cycling forever.”
It’s a mess.
But I’ve been thinking.
I believe something strange.
And this belief is what likely messes with my training, and perhaps every other aspect of my life.
I believe everything has to be hard.
Or put another way…
I believe I have to grit my teeth in order to get to a good result.
I believe that if something is hard, unpleasant and requires a lot of grit teeth, it must be good, or the right thing to do.
I have to admit, I feel morally superior when I grit my teeth.
And I believe if I grit my teeth hard enough, I can control the outcome.
Strange isn’t it.
No one told me to grit my teeth.
Although it gives me a certain kind of energy, it doesn’t feel very pleasant.
And if I’m honest, it rarely helps with whatever I’m trying to do.
It doesn’t make me smarter, faster, funnier, kinder.
It just makes me want grit my teeth more.
Last year when I was bonking, it suddenly became clear that the tooth grinding wasn’t moving my bike forward. It’s a reaction that I’ve told myself is important, rather than a causative force.
Of course my ego didn’t want to hear that. So it came up with all sorts of other excuses, to assure me that I hadn’t lost control.
- I’m not really into this sort of thing anyway.
- Everyone else is obsessive and freakish, and I’m the only normal one.
- I didn’t work hard enough (this time).
It’s all bullshit.
I have a theory that perfectionists are afflicted by this ‘tooth grinding’ disease more so than others. Most people just don’t care that much about being good or perfect. They’re too busy having fun.
The harsh reality for perfectionists is that no one is perfect. No one can make anything perfect. There’s no points handed out the more you suffer, or feel hard done by.
The best one can do is to acknowledge the straining attitude, and if you can bear it – to laugh.
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Dream symbols of 2024

Sunlight and Shadow Study, 1855, Albert Bierstadt – July 13, 2024 @ 11:10am – De Young Museum, San Francisco Dreams are usually dismissed as “nothing other than very vivid thoughts” with limited benefit to your waking life.
And if you’ve ever taken the time to remember and record your dreams, you’ll probably agree that they don’t make much sense. (Learn how AI can help to decipher your dreams.)
But occasionally you’ll pick up a clear message, a directive or an understanding about someone you care about. So even though I don’t always learn something from dreams, I like to think of them as educational. The fact that they might need to repeat themselves lots of times for the message to sink in is more a comment on my learning style. I’m sure most of my high school teachers would agree.
In 2024, I made a habit of drawing one image or symbol that stood out from my dreams of the night before. Since most dreams are blurry or are about people, they can be hard to draw. So, I biased towards images that were easy to draw. If a dolphin appeared as an element in any of my dreams, I’d draw that the next day. In most cases this would only be one symbol. If there was a few, I’d pick the more interesting one, or one that I hadn’t dreamt of before.
When the year wrapped up, I had drawn about 260 unique symbols. My symbols neatly fit into three broad categories: Personal, Nature and Conceptual. Each of these had a few sub-groups. Let’s take a look!
Personal
Food & Drink

Let’s face it, we are all food obsessed. We spend all day planning our next meal. So I’m not surprised my unconscious made use of chicken drumsticks and bagels. Unfortunately, it’s not the most appetizing collection of food (onion, old bread, eggs). Beer was the most common drink.
Home

Although most of these items look domestic, it’s because we’ve lost the context of the dreams. The t-shirts for example were part of an elaborate dream set in Israel, where t-shirts indicated your political stance. Cigarettes and pills (ecstasy or otherwise) repeated quite often for me.
Hobbies

I’m pretty active, so images of tennis balls and bikes makes sense to me. But I haven’t skateboarded or played guitar since I was 14 or so. Images like footy or fishing trips felt like they related to social groups and male friends.
Technology

My psyche loves boats. And submarines. And ‘colossal’ ships. For some reason, the sight of big container ships floating across a red horizon filled me with hope and joy. The bigger the better. The other big theme was guns and bombs. Impending nuclear strikes and Uzis pointed in my face were obviously my least favorite dreams.
Natural
Body

Two celebrities made an appearance here, Tony Robbins and Woody Harrelson. One of my favorite dreams involving my body was the ‘headstand’, claimed by Yogis “to destroy all diseases. to increase the digestive fire, and to banish signs of ageing.”
Animals & plants
There’s a wide variety here, and I always appreciated a dream animal because they seem to easily convey feelings. Finding caged birds in the trash broke my heart and a wolf filled me with primal fear. They also taught me lessons about myself. A ‘guilty’ dog that wanted to be hand-cuffed and sent to jail for some unknown crime was both funny and prompted me to consider my own tendency to blame myself. The only interesting dream about plants was a specific reference to a large ‘Banyan’ tree, maybe a good symbol for life itself.
Elements

Dreams can forecast the future. I think 10,000 years ago we’d be experiencing a sort of early warning system every night: a lot of storms, rivers overflowing and hungry animals that might directly threaten our tribe. We take in so much information everyday that we’re not conscious of. Instead of discarding it all, perhaps we sometimes receive it repackaged in dreams. One example of this was a dream about a powerful storm that caused spot fires. I took this as a warning of ‘extreme weather’ for an upcoming bike race, where it turned out to be over 45 degrees on the road.
Conceptual
Cultural

I’d occasionally have dreams which I started to call ‘future backwash’. These weren’t particular warnings, but rather just images that I would come across that day or the next. For example, the neon sign of a burger store was part of a dream plot, and I noticed something very similar on a walk home from work (not my usual way home).
Spiritual

I had a dream where I’m staring at a book by candlelight. We’ve all probably had reading dreams where we are looking at letters but not able to absorb anything. In this case, I recognize ‘NUIT’ and some Egyptian looking drawings. Wikipedia suggests this is a reference to Nut (close enough), the goddess of the sky, starts, cosmos, mothers, astronomy and the universe in ancient Egyptian religion. I’m happy there was no sign that I had disturbed or angered her. 😅
Overall, I’m somewhat disappointed at how vanilla my unconscious is. Where are the shrieking devil monkeys, the green aliens or the fire-breathing dragons? I’ll have to try harder in 2025.

