hey. it's wil.

Podcast summary

The 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 summary Something 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/
• This podcast's web page: https://uponconsideration.com/#podcast

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

Episode transcript

• Raw transcript provided by Voice Memos
• Formatted transcript reviewed by ChatGPt

Recorded during an early morning walk through Central Park, this episode captures that fleeting blue hour before sunrise — when the city glows between night and day. As the skyline softens under overcast light, I talk through a few things on my mind: the New York election results, the marathon setup still lingering in the park, and the beauty of slowing down long enough to notice both.

Then the conversation shifts. From observing the city to examining something that's been stuck in my head lately — the dangerous comfort of doing things "the way we've always done them."

I explore why that mindset quietly kills innovation inside small and growing B2B firms, how leadership hesitancy stifles change, and why founders often resist the very transformation their teams need.

You'll also hear a quick behind-the-scenes look at how this show is made:

• "In the Field" episodes like this one — spontaneous recordings captured while walking through the city.

• "In the Studio" episodes — more structured sessions, recorded at home with a professional mic for deeper dives.

A few quiet minutes from the Upper West Side. A few thoughts on what it takes to adapt when everyone around you says, "we've always done it this way."

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 summary

That 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 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:

>

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

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 episode

A group of us ditched our smartphones for a month. It changed us. https://apple.news/A0MJSYy7iSRaewo2NAtSH6w

Tech CEOs weigh in on OpenAI chief Sam Altman's leadership. https://apple.news/ATaE8nCcRQRyLsO9-OjkydA

Upon 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