a changing world: observations for my future self.
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hi. i'm wil.

hi. i’m wil.

we moved around a lot...

my earliest memories were probably when we lived on a farm in california.
from there, we moved often. every new town taught me to quietly pay close attention. to listen first, read the room and align signal from noise.

i built a career in technology, leadership and communications, helping organizations bridge people, processes and tools so they get things done.

what i've learned is that most companies focus on efficiency while neglecting alignment. they talk about innovation but forget that people make it possible. that imbalance continues to fascinate me.

today i help companies launch products and businesses faster by getting teams on the same page. i’m not a guru or an expert. just someone who’s seen a lot of change and learned how to navigate it.

i also walk around with a camera and a mic, taking photos and video while i talk to myself. these days, in new york city.

stuff i’m (generally) curious about...

→ the future of rich media.
→ the future of organizational structure.
→ audio capture, production, distribution.
→ film and photography.

stuff i’m (professionally) curious about...

→ ai readiness. auditing the "guts" to ensure ai adoption drives margin.
→ narrative alignment. syncing product specs with buying logic.
→ operational sync. building process-based workflows to prevent drift.
→ business visibility. measuring decision-making effectiveness.

professional roles I’ve held...

→ head of marketing | ai software development | new york, ny & london, uk
→ enterprise business development | telecommunications | montana
→ head of marketing, media relations | data centers | new york, ny
→ head of sales and marketing | software development | washington, dc
→ business development | b2b software | sydney, aus & san francisco, ca
→ investment banking analyst | boutique m&a advisory | san francisco, ca
→ network, systems admin | integrated circuits | silicon valley, ca

my formal education...

→ bsc, business computer telecommunications: csu east bay (hayward, ca)
→ mba, marketing: ageno school of business, ggu (san francisco, ca)

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observations.

i'm an observer, likely the last one to jump into a conversation. i'd much rather get a better understanding of context before shooting my mouth off. (though, there are times...)the following observations are short pieces–audio, text, video–usually captured while i'm on one of my walks. observations are really letters to my future self, capturing how i thought about a topic today.


2026

jul →     aug →     sep →     oct →     nov →     dec →    

observations

july 2026.

01 →     02 →     03 →     04 →     05 →     06 →     07 →    
08 →     09 →     10 →     11 →     12 →     13 →     14 →    
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29 →     30 →     31 →

 

observations →     july 2026

july 20, 2026.

organizations:
substack
topics:
social media, relationships


“whatever, i’m done.” 1i’ve struggled with social media. personally and professionally.i assumed it simply wasn’t for me. yet the longer i go, the less i'm convinced that’s the real reason.


to say social media is “bad” would be inaccurate.it's connected people, launched businesses and given countless creators a voice they never would have had otherwise.yet something about it has always felt off.at work, i never understood people who seemed to spend all day posting on linkedin. “shouldn’t you be working?” was my instant reaction.lately, i’ve started wondering if that’s the wrong question.maybe somewhere along the way we confused visibility with contribution.


for a while i thought maybe i just didn’t like sharing my work. yet, that doesn’t really hold up.i write.i publish.i photograph.i record myself walking through new york.i send email newsletters.i’m clearly willing to share. perhaps the better question isn’t:do i like sharing?rather:who do i want to share with?the answer feels much more intimate: people who enjoy thoughtful conversations. people who appreciate photography. professionals interested in leadership, technology and how organizations change.and, most importantly, my future self.


the more i think about it, the more i wonder whether this is really a question of trust. i don’t completely trust the platforms.or, maybe, i don’t always trust the incentives they create: algorithms reward speed. feeds reward novelty. attention becomes the product. relationships become secondary.maybe that’s why i keep gravitating toward slower places.email. personal websites. long-form writing. communities that develop over months instead of minutes.perhaps this is partly generational.i am part of the last generation to watch the internet arrive. back then, relationships felt like the point. today, platforms often feel like the destination.and i still believe relationships matter more.


that belief shapes how i think about business, too: relationships and people first, technology second.the tools should strengthen relationships, not replace them.maybe that’s why substack has become interesting to me. not because it’s another publishing platform. rather, it feels more like a community.wiljr.org can remain the permanent archive. substack can become the conversation around it.the observations live in one place.the discussions happen somewhere else.


i’m beginning to think the future isn’t better social media. it’s smaller communities built around people who genuinely enjoy one another.maybe the internet didn’t become worse. maybe it simply became too large for relationships to matter.


1:
inspired by this discussion on reddit... https://www.reddit.com/r/GenX/comments/1ujq1a8/anyoneslowlyditchingsocialsafteryearsof/

audio via video

me saying the words above.

Video

 

observations →     july 2026

july 16, 2026.

organizations:
fifa world cup
topics:
leadership

yesterday felt heavy with the noise of real-time reaction. everything around us continues to be optimized for the immediate: instant feedback, instant metrics, instant pivots.watching the fifa world cup semi-final between argentina and england was a jarring reminder of a different, slower way of operating.i’m writing this down because i want to remember the specific tension of that match. it wasn't just about football; it was about the terrifying reaction of watching in real time when a leader sticks to a plan and waits to see if it works.scaloni, the argentine coach, looked almost archaic in his refusal to panic. tuchel, the england coach, cut the exact opposite appearance.i wonder if, five years from now, we will have completely lost the ability to remain calm, believing in our approach, no matter how hectic the world around us is becoming.

photos

i took these photos at 5:20am on thursday, july 16, while walking and talking to myself about the focus of your own conviction.

video

i strapped a small 4k camera to my chest, added a mic and hit record.

Video

 

 

observations →     july 2026

july 14, 2026.

organizations:
u.s. government
topics:
self

i am still trying to make sense of how i used to think about the world. i have been looking back at the first gulf war and our modern day war with iran. i am struck by how distant the person who formed my initial opinions on foreign v. domestic policies feels to me now.have i actually grown wiser, or have i just grown tired. it feels like the latter can be disguised as the former.i don't know if my current, more pragmatic views are "right." in fact, i suspect they are just as flawed as my youthful idealism, just in a different direction in a different time.i don't want to look back and think I had it all figured out.rather, i want to remember that i was actively reflecting on the simplicity of the convictions i once held.(even as i was, unknowingly, letting them go.)

photos

i took these photos at 5:30am on tuesday, july 14, while walking and talking to myself about the balance of heads and hearts as we age.

video

2.5 mile walk around central park and the upper west side. no talking, just pov photography with some background music.

Video

 

 

observations →     july 2026

july 13, 2026.

organizations:
u.s. government
topics:
policy     war     change

i’ve been thinking a lot about a quote from françois guizot: "… not to be a republican at twenty is proof of want of heart; to be one at thirty is proof of want of head.”.the term republican has taken on many definitions, at home and abroad.i’ve been thinking about the quote in more of an age manner.are we brave and foolish in our 20s and intellectual and “c”onservative in our 40s? do we expect our representatives to take on the world when we are younger, a reflection of our own invincible attitudes? while in our later years, we slow our “hearts” to show the wisdom of our years?am i even able to remember what my 20s-year-old-self envisioned of the world at my feet? was i even able to construct internal rationalism between foreign and domestic policies?if i believed i actually had answers in my 20s, is it because i want to recognize my own growth? or is my memory of my 20s-year-old self a retrospective fiction, shaped by how i want to appear to myself now?am i reacting to the iran war (head) the same way that i presumably reacted to the first gulf war (heart)?

photos

i took these photos at 5:30am on monday, july 13, while walking and talking to myself about heads and hearts.

 

 

observations →     july 2026

july 12, 2026.

organizations:
open ai     chatgpt     microsoft
topics:
leadership     product

i can’t stop thinking about this past week’s product release from open ai, especially as it relates to internal organizational culture.the product changes feel big in both interface and implication. (as of 8:32am est this morning, i’m unable to log into the chatgpt ios app, however i am able to log into the chatgpt web app.)users, including me, are confused by the change in app names, app functions and how to continue using the apps in the same manner we have been using the apps.it just seems that overnight, poof, everything is gone or changed with zero education and zero notice.and the confusion makes me think about the fragility of organizational and leadership trust in fast-moving ai companies.with 1 billion reported monthly users of chatgpt, it feels like the brand is wobbling in a way that could sink revenue, leadership confidence and the ipo narrative.i don’t know if this is the first crack in a larger pattern or just a blip highlighted by my own frustration. (the tech world is full of moments that felt seismic and faded quickly, however this fu@$ up feels really big.)given open ai’s already-riddled past of leadership changes, which leader takes the fall for this change? maybe they pin it on the outgoing apps person? even if they do, do investors ask for a reset of top leadership, similar to the changes at uber a few years ago?has microsoft’s patience run out?has the product update rollout only impacted a small set of users, where there is still time to reverse course and pin the problem to poor messaging/positioning?the line between product, leadership and strategy feels unusually thin.

photo

i took this photo at a little after 5am on saturday, july 11. i’m facing north in taking this photo, which was odd to me. normally when i’m walking in the mornings, i see the moon over midtown, which is south.

hi. i’m wil.

 

 

observations →     july 2026

july 3, 2026.

organizations:
 
topics:
photography     video

i very much enjoy the early mornings, especially walking and taking photos in big cities.videoon this morning, i walked around central park and the upper west side, with a dji osmo nano attached to my digital camera (with zoom lens), filming what i saw as i found compositions and snapped photos.here's the result, background music included if you so choose.

Video

 

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cover photo.

on july 4, 2026, i walked down to pier 1 on the west side of manhattan.

it was a very hot and humid weekend and since there wasn't much shade on the pier, there weren't many people waiting on the pier for the airshow.

i found a good spot on the bridge and positioned myself facing the george washington bridge, assuming the airshow would fly up the hudson river.

between 10am and 12p, i clicked the shutter button 399 times.
only 35 photos were flagged as 'favorites'.

this was one of them.

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