Upon Consideration...

I have a few of these shorts lined up. While these are my first attempts at creating short(er) videos, I'd like to try doing some narrative voiceovers to add a little context to the video. (Maybe, like, read a piece from a book or poem or song?)Note: Initially posted on YouTube: https://www.youtube.com/watch?v=SD_61Isu3Vc. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Only 30% of enterprises have fully moved to the cloud, yet we are already sprinting toward AI. The result? A 95% failure rate for AI initiatives. In this episode, I talk about why high-performance teams are failing at the finish line and why “team onboarding” must include a consistent decision-making framework to protect your margins and your sanity.Links:• Ben Evans: www.ben-evans.com• The Governance Partner: hialex.cc• Strategic Consulting: thenewcommunicate.com• Weekly Insights: uponconsideration.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Join me on a walk across Central Park from the West Side to the Met (and back again).In this episode, we explore the ancient Persian city of Nishapur (a hub of the Silk Road), the hidden engineering history of Park Avenue’s most "unstable" skyscraper, and the somber reality of why we must record our thoughts during times of war.Key moments* How Central Park hides its traffic via "below-grade" thoroughfares* The Silk Road: Trade artifacts from the 1930s now at the Met* The Journaling Pivot: Why our memories of the Iraq and Afghanistan wars are unreliable* The Citicorp Center: The building that almost toppled in the 1970s* The "hilly" origins of ManhattanSign up for my newsletter at https://uponconsideration.com.For the full experience (videos, images, transcript), visit wiljr.substack.com. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

In this week's dispatch, we brave the "crunchy snow" and mud of Central Park to uncover the layers of history hidden between 96th and 72nd Streets. Beyond the scenery, we dive into the functional difference between embassies and consulates and take our time at the Alexei Navalny memorial.For video and images, see: https://wiljr.substack.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode descriptionWill winter never end? Come walk with me through Central Park after the February blizzard and hear me talk about Alex, a new product I’m launching to help make executive-level decisions before doing dumb-ass things.Episode references* Alex (my new product): www.hialex.cc* Photos from this walk: wiljr.substack.com* The full walk-and-talk-and-photo-taking video at wiljr.substack.comListener responseIf this episode made you notice something you hadn’t before, you can leave a short voice message or text.Messages may be referenced anonymously unless you say otherwise. All are read or listened to.https://uponconsideration.com/#listener-responseRelated workI share examples of how early misalignment shows up inside organizations. Not at the breaking point. Before momentum makes it expensive.https://thenewcommunicate.comFollow Upon Consideration* Podcast: https://uponconsideration.com/* Newsletter: https://uponconsideration.com/* Author: https://uponconsideration.com/#more* Support: https://uponconsideration.com/#support-listener* Alex: https://hialex.cc Photos!More photos!Video! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

On another cold New York morning, I walk down to the Hudson River, take some photos and talk about artificial intelligence and the collision with humans.There’s video (see below)!VideoEpisode references* Alex (my new product): www.hialex.cc* Photos from this walk: wiljr.substack.com* The full walk-and-talk-and-photo-taking video at wiljr.substack.com* Dario from Anthropic: https://www.nytimes.com/2026/02/12/opinion/artificial-intelligence-anthropic-amodei.html* Nick Thompson: Listener responseIf this episode made you notice something you hadn’t before, you can leave a short voice message or text.Messages may be referenced anonymously unless you say otherwise. All are read or listened to.https://uponconsideration.com/#listener-responseRelated workI share examples of how early misalignment shows up inside organizations. Not at the breaking point. Before momentum makes it expensive.https://thenewcommunicate.comFollow Upon Consideration* Podcast: https://uponconsideration.com/* Newsletter: https://uponconsideration.com/* Author: https://uponconsideration.com/#more* Support: https://uponconsideration.com/#support-listener This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode descriptionI went for a walk around Central Park with my camera in -14° weather. There’s a video, too:Listener responseIf this episode made you notice something you hadn’t before, you can leave a short voice message or text.Messages may be referenced anonymously unless you say otherwise. All are read or listened to.https://uponconsideration.com/#listener-responseRelated workI share examples of how early misalignment shows up inside organizations. Not at the breaking point. Before momentum makes it expensive.https://thenewcommunicate.comFollow Upon Consideration* Podcast: https://uponconsideration.com/* Newsletter: https://uponconsideration.com/* Author: https://uponconsideration.com/#more* Support: https://uponconsideration.com/#support-listenerSome photosVisit all photos at www.wiljr.photos. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode descriptionApple and OpenAI are on a collision course.References* Apple AAPL Q1 2026 Earnings Call Transcript: https://www.fool.com/earnings/call-transcripts/2026/01/29/apple-aapl-q1-2026-earnings-call-transcript/* Apple Financial Results - Q1 2026: https://www.apple.com/investor/earnings-call/* OpenAI’s “secret” new device is coming. Here’s what we know so far: https://www.axios.com/2026/01/23/openai-device-earbuds-sweetpea-altmanListener responseIf this episode made you notice something you hadn’t before, you can leave a short voice message or text.Messages may be referenced anonymously unless you say otherwise. All are read or listened to.Listener response: https://uponconsideration.com/#listener-response Related workI share examples of how early misalignment shows up inside organizations. Not at the breaking point. Before momentum makes it expensive.https://thenewcommunicate.comFollow Upon Consideration* Podcast: https://uponconsideration.com/* Newsletter: https://uponconsideration.com/* Author: https://uponconsideration.com/#more* Support: https://uponconsideration.com/#support-listener This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode descriptionSepp Blatter. St. Pauli. DFB. Government of France. All are talking about boycotting the 2026 World Cup. And Gianni Infantino? He’s touring and meeting with city mayors to “lock in support”. With a little more than 120 days from the start of the tournament... that can’t be good.Related links* “Infantino takes World Cup charm offensive to US mayors”: https://apple.news/AgHMdbgBaTZWfNW3ZVXghGA * The Beautiful Game: https://en.wikipedia.org/wiki/The_beautiful_game* Sepp Blatter has something to say: https://apple.news/AKk9RPny5Tv6ZQytQfY-V4g* St. Pauli has something to say: https://apple.news/APt4Fd3hzSm6mvkqs1NHG_A* The German Football Federation) has something to say: https://apple.news/AiqsoNMVAS5WPRFpQIxbDeg* The French Government has nothing to say (yet): https://apple.news/AiqsoNMVAS5WPRFpQIxbDegListener responseIf this episode made you notice something you hadn’t before, you can leave a short voice message or text.Messages may be referenced anonymously unless you say otherwise. All are read or listened to.Listener response: https://uponconsideration.com/#listener-responseRelated workI share examples of how early misalignment shows up inside organizations. Not at the breaking point. Before momentum makes it expensive.* https://thenewcommunicate.comUpon Consideration* Follow: https://uponconsideration.com/* https://uponconsideration.com/* Author: https://uponconsideration.com/#more* Support: https://uponconsideration.com/#listener-support This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode descriptionOn a windy New York morning, I walk past one of my favorite locations in New York City (Lincoln Center) towards West End Avenue on my way to run an errand.After listening to Ben Thompson and John Gruber this week, in addition to reading about the Google / Apple AI partnership, I wonder how afraid Apple is of OpenAI (given what’s not being said about the partnership).This episode reflects on a single phrase in a quote from the Financial Times via 9to5Mac: ““OpenAI declined to comment. But a person close to the company said it had taken “a conscious decision to not become the custom model provider for Apple” in the autumn of last year and instead focus on building its own AI device to leapfrog the big tech companies.”It’s this piece of that quote that has me wondering if Apple is scared of OpenAI (and Jony Ive): “instead focus on building its own AI device”.Listener responseIf this episode made you notice something you hadn’t before, you can leave a short voice message or text.Messages may be referenced anonymously unless you say otherwise. All are read or listened to.Listener response: https://uponconsideration.com/#listener-response Related workI share examples of how early misalignment shows up inside organizations. Not at the breaking point. Before momentum makes it expensive.https://thenewcommunicate.comMore Upon Consideration* Podcast: https://uponconsideration.com/#follow* Newsletter: https://uponconsideration.com/* Author: https://uponconsideration.com/#more* Support: https://uponconsideration.com/#support-listener* Partner: https://uponconsideration.com/#brand-partnerships This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode descriptionOn a cold New York morning, I walk past the Simón Bolívar statue near 59th Street and Sixth Avenue and think about why a 19th-century Venezuelan liberator still feels relevant today.Bolívar fought foreign rule, resource extraction and the impossible task of unifying competing interests across Latin America—problems that sound uncomfortably familiar in 2026.From Venezuela, oil and modern regime politics to America’s fixation on strategic resources, and from global power plays to the quieter leadership battles inside cities and businesses, this episode reflects on how history doesn’t repeat—but it definitely rhymes.Listener responseIf this episode made you notice something you hadn’t before, you can leave a short voice message or text.Messages may be referenced anonymously unless you say otherwise. All are read or listened to.Listener response:https://uponconsideration.com/#listener-responseRelated workI share examples of how early misalignment shows up inside organizations. Not at the breaking point. Before momentum makes it expensive.https://thenewcommunicate.comFollow Upon Consideration* Podcast: https://uponconsideration.com/#follow* Newsletter: https://uponconsideration.com/* Author: https://uponconsideration.com/#more* Support: https://uponconsideration.com/#support-listenerPhotos This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Podcast title: Upon ConsiderationEpisode title: 032: A missed moment.Thoughts:Everyone watched the shot. No one noticed the moment the season shifted.Strong teams rarely fall apart all at once. The shape starts to change long before the headlines do.On a morning walk through Central Park, I’m thinking about Liverpool, leadership, grief, new systems and the small, easily missed moments that tell you more than the scoreline ever will.This episode is about the signals most people ignore—the gesture, the frustration, the shift that doesn’t register on a stat sheet but explains everything that follows.If you’ve ever watched a team, a company or a project still look fine while something underneath felt off, this is for you.Call me?* Send me a voice mail or text about this episode!* tel:+13476945202* More info here: https://uponconsideration.com/#listener-responsePsst: By leaving a message, you’re giving permission for excerpts to be referenced anonymously unless you explicitly say otherwise. Not every message is shared. All messages are read or listened to.Links: * Recent weekly email: https://mailchi.mp/uponconsideration.com/2025-12-31-wednesdays * From listeners like you: https://uponconsideration.com/#listener-response * Support Upon Consideration: https://uponconsideration.com/#support-listener * Get Upon Consideration: https://uponconsideration.comThank you! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode title: 031: We were in Brooklyn with Maduro.Notes: * Talking politics* We were in Brooklyn when Maduro was being flow in (A post-episode realization)* Change is coming for us allCall me?* Send me a voice mail or text about this episode!* tel:+13476945202* More info here: https://uponconsideration.com/#listener-responseHey: By leaving a message, you’re giving permission for excerpts to be referenced anonymously unless you explicitly say otherwise. Not every message is shared. All messages are read or listened to.Links: * Recent weekly email: https://mailchi.mp/uponconsideration.com/2025-12-31-wednesdays* From listeners like you: https://uponconsideration.com/#listener-response* Support Upon Consideration: https://uponconsideration.com/#support-listener* Get Upon Consideration: https://uponconsideration.comThank you! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Podcast title: Upon ConsiderationEpisode title: 030: “This is intentionally boring.”Notes:* End of year banger* A five-mile walk, across Central Park and back, in the frigid cold* New lens on the film camera!* What’s changing at Upon ConsiderationCall me?* tel:+13476945202* Click/Tap the link above* Send me a voice mail or text!* More info hereNote: By leaving a message, you’re giving permission for excerpts to be referenced anonymously unless you explicitly say otherwise. Not every message is shared. All messages are read or listened to.Links:* Recent weekly email* From listeners like you* Support Upon Consideration* Get Upon ConsiderationThank you! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode title: Not quite graupel.Episode summaryIt’s a little cold and a little rainy. Not quite graupel. In this episode, I walk around a very busy and noisy New York City talking about some behind the scenes planning for this podcast, my agency and the new year in addition to how aligning your teams create a better foundation for strategy and success. Links to stuff in this episode* The guy walking around NYC with a camera: https://www.youtube.com/@WalkingCommuter* My agency: https://thenewcommunicate.com* This podcast overview page: https://uponconsideration.com/#podcastSubscribehttps://uponconsideration.comAbout this podcast Upon Consideration… is a project about intentional alignment, deliberate thinking, focused productivity and better decisions.It began as a set of personal letters, and became a study of how leaders and creators can work deliberately, even when the world demands chaos.I write, record and publish to connect ideas, people and outcomes. Join a growing group of professionals and leaders slowing down to think more clearly.About the authorWe moved often while growing up, and every new town taught me to quietly pay close attention. To listen first, read the room and align signal from noise.That skill–separating and aligning the real from the rehearsed–became the through line of my career (and my life).Learn more: https://uponconsideration.com/#moreMore links* Subscribe: https://uponconsideration.com/#podcast * Sponsorships: https://uponconsideration.com/#sponsor * Donations: https://uponconsideration.com/#donate Thank you!Thank you for listening to Upon Consideration...! If you found this episode useful, please leave a review and share it with your community. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode title:Wait, that’s not a dog.Episode summaryIt’s the weekend! With my digital camera in hand, I’m walking around Central Park and the Upper West Side as I talk about the weather, Daniel Webster, AI + Automations to find fund stuff to do in New York City and starting over with my watch and phone.Links to stuff in this episodePaperclips game: https://www.decisionproblem.com/paperclips/index2.htmlDaniel Webster statute in Central Park: https://www.nycgovparks.org/parks/central-park/monuments/1692Daniel Webster: https://en.wikipedia.org/wiki/Daniel_WebsterDeath by Lightning: https://en.wikipedia.org/wiki/Death_by_LightningSubscribehttps://uponconsideration.comAbout this podcastUpon Consideration… is a project about intentional alignment, deliberate thinking, focused productivity and better decisions.It began as a set of personal letters, and became a study of how leaders and creators can work deliberately, even when the world demands chaos.I write, record and publish to connect ideas, people and outcomes. Join a growing group of professionals and leaders slowing down to think more clearly.About the authorWe moved often while growing up, and every new town taught me to quietly pay close attention. To listen first, read the room and align signal from noise.That skill–separating and aligning the real from the rehearsed–became the through line of my career (and my life).Learn more: https://uponconsideration.com/#moreMore linksSubscribe: https://uponconsideration.com/#podcast Sponsorships: https://uponconsideration.com/#sponsor Donations: https://uponconsideration.com/#donateThank you!Thank you for listening to Upon Consideration...! If you found this episode useful, please leave a review and share it with your community. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode summaryIs finding common ground the key to makeing decisions? When will I get the zipper on my jacket fixed? Links to stuff in this episode* ‘All chaos and panic’: Nilay answers your burning Decoder questions: https://www.theverge.com/podcast/846750/decoder-mailbag-qa-nilay-patel-interview-2025* Zohran Mamdani on FDR, LaGuardia—and Trump: https://www.thenation.com/article/politics/zohran-mamdani-interview-donald-trump-laguardia/Thank you!Thank you for listening to Upon Consideration...! If you found this episode useful, please leave a review and share it with your community.About this podcastUpon Consideration... Slow thinking for better outcomes–practical insights for leaders navigating change.Some episodes are recorded while I’m walking, capturing raw thoughts before they’re fully formed (*In the field*). Others are in the studio, with reflections after I’ve thought them through (*In the studio*). Together, they tell a fuller story of how I think, work and lead.More* Subscribe: https://uponconsideration.com/#podcast* Sponsorships: https://uponconsideration.com/#sponsor* Donations: https://uponconsideration.com/#donate* About me: https://uponconsideration.com/#more This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode summaryTwo recorded/published episodes in a row! That’s not normal! Nor is the business model for CoreWeave. Bondi Beach, Rhode Island and Lake Mead.Links to stuff in this episodeLake Mead: https://en.wikipedia.org/wiki/Lake_MeadRhode Island on map: https://www.mapsofindia.com/world-map/usa/rhode-island/location-map.htmlBondi Beach: https://en.wikipedia.org/wiki/Bondi_BeachCoreWeave: https://www.coreweave.comSomething Ominous Is Happening in the AI Economy (Rogé Karma, The Atlantic): https://apple.news/A22zeiJ40Rca1rtJKV25AQwThis weekend’s...errr... Monday’s premium podcast episode: https://wiljr.substack.com/p/giuseppe-mazzini-zohran-mamdani-andA survival guide for Heads of Marketing operating under pressure. (That field book I mentioned.): https://uponconsideration.com/#alignmentGo Knicks! https://knicksfilmschool.substack.com/p/winning-the-cupThank you!Thank you for listening to Upon Consideration...! If you found this episode useful, please leave a review and share it with your community.About this podcastUpon Consideration... Slow thinking for better outcomes–practical insights for leaders navigating change.Some episodes are recorded while I’m walking, capturing raw thoughts before they’re fully formed (*In the field*). Others are in the studio, with reflections after I’ve thought them through (*In the studio*). Together, they tell a fuller story of how I think, work and lead.MoreSubscribe: https://uponconsideration.com/#podcastSponsorships: https://uponconsideration.com/#sponsorDonations: https://uponconsideration.com/#donateAbout me: https://uponconsideration.com/#more This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode summaryThis weekend, I walked by the bust of Giuseppe Mazzini. After taking a few photos, I dove into what made Giuseppe so dedicated to his cause of unifying Italy, then discussed how Giuseppe and Zohran Mamdani, in a current sense, would get a long with each other. I touched on other topics like leadership, Benito Mussolini and Stephen Miller.Links to stuff in this episode* Giuseppe Mazzini: https://en.wikipedia.org/wiki/Giuseppe_Mazzini* Bust of Giuseppe Mazzini in Central Park: https://www.centralparknyc.org/locations/giuseppe-mazziniThank you!Thank you for listening to Upon Consideration...! If you found this episode useful, please leave a review and share it with your community.About this podcastUpon Consideration... Slow thinking for better outcomes–practical insights for leaders navigating change.Some episodes are recorded while I’m walking, capturing raw thoughts before they’re fully formed (*In the field*). Others are in the studio, with reflections after I’ve thought them through (*In the studio*). Together, they tell a fuller story of how I think, work and lead.More* Subscribe: https://uponconsideration.com/#podcast* Sponsorships: https://uponconsideration.com/#sponsor* Donations: https://uponconsideration.com/#donate* About me: https://uponconsideration.com/#morePhotos This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode summaryMore thoughts on leadership with a focus on end of year subjective bonuses. Links to stuff in this episode* No one leaving New York City because of Mamdani, say two top real estate CEOs: https://www.cnbc.com/2025/11/14/new-york-city-mayor-zohran-mamdani-real-estate-ceos.html* Office Recovery Strengthens As Vacancy Drops: https://www.credaily.com/briefs/office-recovery-strengthens-as-vacancy-drops/Thank you!Thank you for listening to Upon Consideration...! If you found this episode useful, please leave a review and share it with your community.About this podcastUpon Consideration... Slow thinking for better outcomes–practical insights for leaders navigating change.Some episodes are recorded while I’m walking, capturing raw thoughts before they’re fully formed (*In the field*). Others are in the studio, with reflections after I’ve thought them through (*In the studio*). Together, they tell a fuller story of how I think, work and lead.More* Subscribe: https://uponconsideration.com/#podcast* Sponsorships: https://uponconsideration.com/#sponsor* Donations: https://uponconsideration.com/#donate* About me: https://uponconsideration.com/#more This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode summarySome thoughts on leadership, especially in the wake of Mo Salah’s rant this weekend. Some sort of vortex is coming our way and it’s likely the last full week of work in 2026 for most folks.Links to stuff in this episode* Liverpool’s Stance on Arne Slot Sack ‘Revealed’ After Stu…: https://apple.news/APU8bdQx2Sd-WHD8Huu-OyAThank you!Thank you for listening to Upon Consideration...! If you found this episode useful, please leave a review and share it with your community.About this podcastUpon Consideration... Slow thinking for better outcomes–practical insights for leaders navigating change.Some episodes are recorded while I’m walking, capturing raw thoughts before they’re fully formed (*In the field*). Others are in the studio, with reflections after I’ve thought them through (*In the studio*). Together, they tell a fuller story of how I think, work and lead.More* Subscribe →* Sponsor →* Donate →* About me →* My photos →Episode photosI record many of my episodes as I’m walking around New York City. From Central Park to midtown to the Upper West Side, my walks (and bike rides!) are accompanied by photos of the surrounding areas. Here are photos from this episode. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode summaryThis morning I walked around Central Park, heading towards Bethesda Terrace and Fountain talking about how AI + Apple Automations is helping me build a smarter research process. Amid our first snowfall, it was very cold out.Also, I take pictures (see below and in your favorite podcast player)!Links to stuff in this episode* Bethesda Terrace and Fountain: https://en.wikipedia.org/wiki/Bethesda_Terrace_and_Fountain#Bethesda_Fountain* Johno Verity (YouTube): https://www.youtube.com/@johnoverityThank you!Thank you for listening to Upon Consideration...! If you found this episode useful, please leave a review and share it with your community.About this podcastUpon Consideration... Slow thinking for better outcomes–practical insights for leaders navigating change.Some episodes are recorded while I’m walking, capturing raw thoughts before they’re fully formed (*In the field*). Others are in the studio, with reflections after I’ve thought them through (*In the studio*). Together, they tell a fuller story of how I think, work and lead.More* Subscribe: https://uponconsideration.com/#podcast* Sponsorships: https://uponconsideration.com/#sponsor* Donations: https://uponconsideration.com/#donate* About me: https://uponconsideration.com/#more* My photos: https://www.wiljr.photosPictures This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode summaryCome walk with me up Fifth Avenue, into Central Park and over the Upper West Side of Manhattan where I talk about New York City and the challenges of being a decision–making leader. Also, I take pictures (see below and in your favorite podcast player)!Links to stuff in this episodeMeta’s Metaverse Cuts Aren’t What Investors Need: https://apple.news/AXs9q-VkbRSKLwE_FNhuZAAThank you!Thank you for listening to Upon Consideration...! If you found this episode useful, please leave a review and share it with your community.About this podcastUpon Consideration... Slow thinking for better outcomes–practical insights for leaders navigating change.Some episodes are recorded while I’m walking, capturing raw thoughts before they’re fully formed (*In the field*). Others are in the studio, with reflections after I’ve thought them through (*In the studio*). Together, they tell a fuller story of how I think, work and lead.More* Subscribe: https://uponconsideration.com/#podcast* Sponsorships: https://uponconsideration.com/#sponsor* Donations: https://uponconsideration.com/#donate* About me: https://uponconsideration.com/#more* My photos: https://www.wiljr.photos Pictures This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode summaryA new schedule is coming! I also talk about planning for the end of the year and beginning of the year, using Ferrari’s terrible planning for the F1 2025 and 2026 seasons as an example.Links to stuff in this episode* Updated schedule: https://uponconsideration.com/#podcast* Ferrari reveals when it decided to switch attention to F1 2026: https://www.motorsportweek.com/2025/11/28/ferrari-reveals-when-it-decided-to-switch-attention-to-f1-2026/Thank you!Thank you for listening to Upon Consideration...! If you found this episode useful, please leave a review and share it with your community.About this podcastUpon Consideration... Slow thinking for better outcomes–practical insights for leaders navigating change.Some episodes are recorded while I’m walking, capturing raw thoughts before they’re fully formed (*In the field*). Others are in the studio, with reflections after I’ve thought them through (*In the studio*). Together, they tell a fuller story of how I think, work and lead. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode title: Unpack first.Episode summaryI walk around the neighborhood talking about the challenge of doing back-end work.Links to stuff in this episode* Johno Verity: https://www.youtube.com/@johnoverity* The New Communicate (my agency): https://thenewcommunicate.com * A Box of Corn Dogs (websites for humans): https://aboxofcorndogs.com* Community advocacy: https://dontdonothin.xyz* My photos: https://wiljr.photos This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode title: Lights in trees! Episode summary I walk around Central Park, however I walk to and around the Great Lawn, taking photos and pointing out how cars go across the Park, the Museum Mile and different colored trees. Links to stuff in this episode Empire Hotel: https://www.empirehotelnyc.comFormer ABC Campus Set for Major Transformation: Extell Plans 1,200-Foot Mega-Tower: https://www.ilovetheupperwestside.com/former-abc-campus-set-for-major-transformation-extell-plans-1200-foot-mega-tower/ Thank you! Thank you for listening to Upon Consideration...! If you found this episode useful, please leave a review and share it with your community. About this podcastUpon Consideration... Slow thinking for better outcomes–practical insights for leaders navigating change.Some episodes are recorded while I’m walking, capturing raw thoughts before they’re fully formed (*In the field*). Others are in the studio, with reflections after I’ve thought them through (*In the studio*). Together, they tell a fuller story of how I think, work and lead. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode summaryI walk around Central Park, however I walk to and around the Great Lawn, taking photos and pointing out how cars go across the Park, the Museum Mile and different colored trees.Links to stuff in this episode* Museum Mile: https://www.wonderfulmuseums.com/museum/one-museum-mile-new-york/* The Great Lawn: https://www.centralparknyc.org/locations/great-lawn* Seneca Village: https://en.wikipedia.org/wiki/Seneca_Village* How to Find Your Way Out of Central Park Using Lamp Posts: https://www.centralpark.com/news/how-to-find-your-way-out-of-central-park-using-lampposts/* Shakespeare in the Park (New York City): https://en.wikipedia.org/wiki/Shakespeare_in_the_Park_(New_York_City)* Belvedere Castle: https://en.wikipedia.org/wiki/Belvedere_Castle* New York City Council Votes to Reform Scaffolding and Sidewalk Shed Rules to Reduce Their Presence, Improving Public Safety and NYC’s Streetscapes: https://council.nyc.gov/press/2025/03/26/2824/Thank you!Thank you for listening to Upon Consideration...! If you found this episode useful, please leave a review and share it with your community.About this podcastUpon Consideration... Slow thinking for better outcomes–practical insights for leaders navigating change.Some episodes are recorded while I’m walking, capturing raw thoughts before they’re fully formed (*In the field*). Others are in the studio, with reflections after I’ve thought them through (*In the studio*). Together, they tell a fuller story of how I think, work and lead. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode summaryThat episode where I walk around the Upper West Side talking about Thursdays, a recent roll of black & white film I had developed and how James Gibson viewed the world from a train.Links to stuff in this episode* James J. Gibson: https://en.wikipedia.org/wiki/James_J._GibsonThank you!Thank you for listening to Upon Consideration...! If you found this episode useful, please leave a review and share it with your community.About this podcastUpon Consideration... is available for free. Find recent episodes in your favorite podcast player and subscribe today!Some episodes are recorded while I’m walking (In the field) with raw thoughts before they’re fully formed. Others are in the studio, with reflections after I’ve thought them through (In the studio). Together, they tell a fuller story of how I think, work and lead. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode summaryThat episode where I walk around Central Park in sub-feels-like-freezing temps moaning about not wearing a beanie, the impact of higher insurance rates on politicians and microphone magnets. Something about ambient optic array, too.Links to stuff in this episode* Ambient optic array: https://en.wikipedia.org/wiki/Ambient_optic_arrayThank you!Thank you for listening to Upon Consideration...! If you found this episode useful, please leave a review and share it with your community.About this podcastUpon Consideration... is available for free. Find recent episodes in your favorite podcast player and subscribe today!Some episodes are recorded while I’m walking (In the field) with raw thoughts before they’re fully formed. Others are in the studio, with reflections after I’ve thought them through (In the studio). Together, they tell a fuller story of how I think, work and lead. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode summaryThat episode where I walk around Central Park blabbing about the weather, recapping my trip to Atlanta, sidewalks, Andy Byford, Madison Square Garden and Penn Station.Links to stuff in this episode* Amtrak’s Andy Byford outlines next steps to get Penn Station under construction by the end of 2027: https://www.archpaper.com/2025/10/andy-byford-next-steps-penn-station-construction-2027/Thank you!Thank you for listening to Upon Consideration...! If you found this episode useful, please leave a review and share it with your community.About this podcastUpon Consideration... is available for free. Find recent episodes in your favorite podcast player and subscribe today!Some episodes are recorded while I’m walking (In the field) with raw thoughts before they’re fully formed. Others are in the studio, with reflections after I’ve thought them through (In the studio). Together, they tell a fuller story of how I think, work and lead. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode summaryThat episode where I walk around mid-town Atlanta and talk about, um, leaving Atlanta.Links to stuff in this episodeNone!Thank you!Thank you for listening to Upon Consideration...! If you found this episode useful, please leave a review and share it with your community.About this podcastUpon Consideration... is available for free. Find recent episodes in your favorite podcast player and subscribe today!Some episodes are recorded while I’m walking (In the field) with raw thoughts before they’re fully formed. Others are in the studio, with reflections after I’ve thought them through (In the studio). Together, they tell a fuller story of how I think, work and lead. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode summaryThat episode where I walk around Central Park a few days before heading down to Atlanta for the week. Something about the Cleveland Browns, servant leadership, expectations and star performers.Links to stuff in this episodeNone!Thank you!Thank you for listening to Upon Consideration...! If you found this episode useful, please leave a review and share it with your community.About this podcastUpon Consideration... is available for free. Find recent episodes in your favorite podcast player and subscribe today!Some episodes are recorded while I’m walking (In the field) with raw thoughts before they’re fully formed. Others are in the studio, with reflections after I’ve thought them through (In the studio). Together, they tell a fuller story of how I think, work and lead. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode summaryThat episode where I walk around Central Park before a few days before heading down to Atlanta for the week. Something about tour buses, swans and drizzle.Links to stuff in this episode* Hop on/Hop off bus tours: https://loving-newyork.com/hop-on-hop-off-bus-new-york/Thank you!Thank you for listening to Upon Consideration...! If you found this episode useful, please leave a review and share it with your community.About this podcastUpon Consideration... is available for free. Find recent episodes in your favorite podcast player and subscribe today!Some episodes are recorded while I’m walking (In the field) with raw thoughts before they’re fully formed. Others are in the studio, with reflections after I’ve thought them through (In the studio). Together, they tell a fuller story of how I think, work and lead. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Episode summaryI’m traveling this week.Links to stuff in this episode* None!Thank you!Thank you for listening to Upon Consideration...! If you found this episode useful, please leave a review and share it with your community.About this podcastUpon Consideration..., the podcast, is available for free. Find recent episodes in your favorite podcast player and subscribe today!Some episodes are recorded while I’m walking (In the field) with raw thoughts before they’re fully formed. Others are in the studio, with reflections after I’ve thought them through (In the studio). Together, they tell a fuller story of how I think, work and lead. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Podcast summaryThe first episode of me in the studio. Check your podcast player for a picture of not me in the studio. Sales. Marketing. Legacy. Gatekeeping.Links to stuff in this episode:* None!Thank you!Thank you for listening to Upon Consideration...!If you found this episode useful, please leave a review and share it with someone who leads under constraint. Ranking this podcast as three stars would mean the world to me. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Podcast summarySomething about a super moon, blue hour and golden hour. In the field episodes v. In the studio episodes. How to we stop the legacy rot of responding with “We’ve always done it this way.)? Change. Lots of change.Links to stuff in this episode:* Supermoons! https://science.nasa.gov/moon/supermoons/Thank you!Thank you for listening to Upon Consideration...!If you found this episode useful, please leave a review and share it with someone who leads under constraint. Ranking this podcast as three stars would mean the world to me.Upon Consideration..., the podcast, provides reflections on leadership, technology, change from me, Wil. This podcast is released twice-monthly and is available for free. Subscribe today! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Podcast summaryThat episode where I walk around the Upper West Side and Central Park on election day. Some photos of the New York City Marathon finish line (it’s still up!) and some jibber jabber about why traditional marketing culture sucks for successful sales.Links to stuff in this episode:* None!Thank you!Thank you for listening to Upon Consideration...!If you found this episode useful, please leave a review and share it with someone who leads under constraint. Ranking this podcast as three stars would mean the world to me.Upon Consideration..., the podcast, provides reflections on leadership, technology, change from me, Wil. This podcast is released twice-monthly and is available for free. Subscribe today! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Podcast summary That episode where I walk around the Upper West Side on the first day of November, the last day of the Daylight Saving Time, the day after Halloween and the day before the New York City Marathon. I took my camera along with me and added random images to random timestamps (check your podcast player!). I also talk about the challenges of your running your own business (or, podcast, as the case may be). Links to stuff in this episode Josh Blumenfeld of YouTube on creators' role in the economy: https://youtu.be/LyE-0qHjrFk?si=vOzgR_xhOcPxKEmJ Thank you! Thank you for listening to Upon Consideration...! If you found this episode useful, please leave a review and share it with someone who leads under constraint. Ranking this podcast as three stars would mean the world to me. Upon Consideration..., the podcast, provides reflections on leadership, technology, change from me, Wil. This podcast is released twice-monthly and is available for free. Subscribe today! Subscribe: https://uponconsideration.com/#podcast Sponsorships: https://uponconsideration.com/#sponsor Donations: https://uponconsideration.com/#donate About me: https://uponconsideration.com/#more      This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

Upon Consideration…Reflections on leadership, technology, change.The shorty episode where I walk around Central Park and the Upper West Side a few days before the 2025 New York City Marathon. Slow productivity. Digital photography. Film photography. Leadership.That Substack link I mentioned: https://substack.com/home/post/p-176569745  This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

How amazing is the Upper West Side? New York Marathon, Thanksgiving Day Parade (balloons), When Harry Met Sally, Seinfeld, The Beacon, American Museum of Natural History. (Pretty amazing!) Talking Kool-Aid and how leaders and individual contributors shouldn't drink too much corporate culture.  Upon Consideration..., the podcast, provides reflections on leadership, technology, change from me, Wil. This podcast is available for free. Subscribe today! Subscribe: https://uponconsideration.com/#podcast Sponsor: https://uponconsideration.com/#sponsor Donate: https://uponconsideration.com/#donate  AI note: I used ChatGPT for reformat the transcript. Which, if I'm honest, I don't feel great about. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

The episode where I walk around a foggy Central Park after a nor'easter misses the city. Extreme phone minimalism, OpenAI, Sam Altman. Something about opposites attract.Articles mentioned in this episodeA group of us ditched our smartphones for a month. It changed us. https://apple.news/A0MJSYy7iSRaewo2NAtSH6wTech CEOs weigh in on OpenAI chief Sam Altman's leadership. https://apple.news/ATaE8nCcRQRyLsO9-OjkydAUpon Consideration... provides reflections on leadership, technology, change from me, Wil. This podcast is available for free. Subscribe today! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

The episode where I walk around Central Park and the Upper West Side before a nor'easter lands on the city. Letters to Me. Brand. AI slop. Airplanes. Business. Upon Consideration..., the podcast, is released twice-monthly and is available for free. Find the link to your favorite podcast player and subscribe today! Sponsorships: https://uponconsideration.com/#sponsor  Donations: https://uponconsideration.com/#donate  Episodes: https://uponconsideration.com/#podcast  This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

The episode where I walk around Central Park and the Upper West Side before a nor'easter lands on the city. Starting something new. Upon Consideration..., the podcast, is released twice-monthly and is available for free. Find the link to your favorite podcast player and subscribe today! Sponsorships: https://uponconsideration.com/#sponsor  Donations: https://uponconsideration.com/#donate  Episodes: https://uponconsideration.com/#podcast  This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com