Hey. It's Wil.

Wil A.

Notes and observations on work, leadership, technology and life. wiljr.substack.com

  1. 🎧 043: Expectations, New York Knicks, World Cup, 50mm lens.

    May 14

    🎧 043: Expectations, New York Knicks, World Cup, 50mm lens.

    May 14, 2026 I walk around New York City and Central Park in the morning, taking photos with a newly added 50mm lens. Personal operating systems, expectations, case studies, photos and sports. * Referenced case study: https://thenewcommunicate.com/#alignment-in-practice * Contact me: hello@uponconsideration.com * No guest requests. It’s a solo joint. 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

    23 min

  2. Apr 13

    Mornings in New York City.

    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

    2 min
  3. 🎧 042: The $100k Salary with a 10% Success Rate: Solving the Decision Gap.

    Mar 26

    🎧 042: The $100k Salary with a 10% Success Rate: Solving the Decision Gap.

    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

    8 min

  4. Mar 18

    🎧 041: Why I Regret Not Journaling (And How I’m Processing Today’s Conflict).

    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 Manhattan Sign 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

    26 min

  5. Mar 16

    🎧 040: From Ancient Egypt to Modern Geopolitics: A Walk Through Central Park.

    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

    45 min

  6. Feb 25

    039: Walking through a Snowy Central Park.

    Episode description Will 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.com Listener response If 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-response Related work I share examples of how early misalignment shows up inside organizations. Not at the breaking point. Before momentum makes it expensive. https://thenewcommunicate.com Follow 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

    25 min

  7. Feb 18

    038: Let’s take some POV photos of a partially frozen Hudson River.

    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)! Video 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.com * Dario from Anthropic: https://www.nytimes.com/2026/02/12/opinion/artificial-intelligence-anthropic-amodei.html * Nick Thompson: Listener response If 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-response Related work I share examples of how early misalignment shows up inside organizations. Not at the breaking point. Before momentum makes it expensive. https://thenewcommunicate.com Follow 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

    1h 3m

  8. Feb 9

    037: Let's go for a walk and take some photos.

    Episode description I went for a walk around Central Park with my camera in -14° weather. There’s a video, too: Listener response If 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-response Related work I share examples of how early misalignment shows up inside organizations. Not at the breaking point. Before momentum makes it expensive. https://thenewcommunicate.com Follow Upon Consideration * Podcast: https://uponconsideration.com/ * Newsletter: https://uponconsideration.com/ * Author: https://uponconsideration.com/#more * Support: https://uponconsideration.com/#support-listener Some photos Visit 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

    33 min
See All (44)

About

Notes and observations on work, leadership, technology and life. wiljr.substack.com

Information

  • Creator
    Wil A.
  • Years Active
    2025 - 2026
  • Episodes
    44
  • Rating
    Clean
  • Copyright
    © Wil A.
  • Show Website
    Hey. It's Wil.