<![CDATA[The Creative Pragmatist: The Grey Area Podcast]]>https://www.thecreativepragmatist.com/s/the-grey-area-podcasthttps://substackcdn.com/image/fetch/$s_!Lpln!,w_256,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F6113c41a-fbd0-4828-b0b4-453e372b4cee_256x256.pngThe Creative Pragmatist: The Grey Area Podcasthttps://www.thecreativepragmatist.com/s/the-grey-area-podcastSubstackMon, 11 May 2026 07:10:41 GMT<![CDATA[1.9 - Are We Really Supposed to Be Here?]]>https://www.thecreativepragmatist.com/p/19-are-we-really-supposed-to-be-here-031https://www.thecreativepragmatist.com/p/19-are-we-really-supposed-to-be-here-031Mon, 04 May 2026 12:00:00 GMTThe Grey Area is where Gen Z talks about the stuff that doesn't have clean answers — business, culture, identity, and everything in between. In Episode 9, Gabe and Stella start with a deceptively simple question: when's the last time you changed your mind about something? Gabe's apartment flooded and he's temporarily on the Upper East Side — and within a week he realized he actually missed the dirty streets and broken glass of Soho. Stella spent her teenage years counting down the days until she could escape small-town Virginia, and now she wants a farm. Then they get into imposter syndrome — what it feels like to pull up to a historic LA studio with three iPhones and a GoPro, wondering if anyone's going to take you seriously, and why the lo-fi setup might actually be the whole point. And they close by pulling up their camera rolls from exactly a year ago — Gabe at Stagecoach, Stella on a solo walk through Brooklyn with no furniture and a full album — and realizing how unrecognizable they are from the people in those photos. New episodes every Monday. Part of the Almost Reckless universe from CP Media.

]]><![CDATA[1.8 - Hawaiian Punch and Hidden Skills]]>https://www.thecreativepragmatist.com/p/18-hawaiian-punch-and-hidden-skills-24ehttps://www.thecreativepragmatist.com/p/18-hawaiian-punch-and-hidden-skills-24eMon, 27 Apr 2026 12:00:00 GMTEpisode 8 of the Grey Area Podcast pulls from two recent Substacks that Gabe and Stella wrote for The Creative Pragmatist and turns them into a conversation. First: stealth skills — the ones you collect without knowing it. Stella traces hers back to a Hawaiian Punch heist she pulled on her grandmother at five years old. Gabe traces his to a restaurant kitchen and the systems that taught him how to think under pressure. Then they get into the wave — the idea that when your life shifts overnight, it was never actually overnight. It was building beneath the surface for years, and the break is just the arrival. And they close on manifestation — not the kind where you stare in a mirror and hope. The kind where you train your mind to give yourself a real shot, and then trust that what comes is what's supposed to.

The Grey Area is where Gen Z talks about the stuff that doesn't have clean answers — business, culture, identity, and everything in between. New episodes every Monday. Part of the Almost Reckless universe from CP Media.

]]><![CDATA[1.7 - Proactively Reacting]]>https://www.thecreativepragmatist.com/p/17-proactively-reacting-692https://www.thecreativepragmatist.com/p/17-proactively-reacting-692Mon, 20 Apr 2026 17:46:37 GMTIn Episode 7 of The Grey Area, Gabe and Stella dive into the difference between being proactive and being reactive — and why the best moments of their careers have come from the chaos they didn't plan for, including a runway show where the collection truck tipped over on the highway four hours before showtime. Then they talk about what "right" actually feels like — Gabe tells the story of an RV trip through Joshua Tree that changed his entire career path, and why the signs you're looking for aren't always written in the sky. They close with the question they keep circling back to: what would you do if money, society, and industry pressure weren't in the way? Turns out they both want the same thing — peace, nature, and the work they love without the noise.

The Grey Area is where Gen Z talks about the stuff that doesn't have clean answers — business, culture, identity, and everything in between. New episodes every Monday. Part of the Almost Reckless universe from CP Media.

]]><![CDATA[1.6 - Looking in The Wrong Mirror]]>https://www.thecreativepragmatist.com/p/16-looking-in-the-wrong-mirror-a47https://www.thecreativepragmatist.com/p/16-looking-in-the-wrong-mirror-a47Mon, 13 Apr 2026 11:47:21 GMTIn Episode 6 of The Grey Area Podcast, Gabe and Stella get into what happens when you're putting all your energy into fixing the wrong thing — going to the gym twice a day when the real problem is how you see yourself, spiraling over a typo in an email to 200 people when no one's dying, and the feedback loops that have been telling you you're not enough since you were a kid. Then they build their Mentor Man — the idea that your mentor isn't one person but a composite, assembled from everyone who shaped how you think, feel, trust your gut, and keep moving. Head, heart, gut, arms, legs — each one a different person.

The Grey Area is where Gen Z talks about the stuff that doesn't have clean answers — business, culture, identity, and everything in between. New episodes every Monday. Part of the Almost Reckless universe from CP Media.

]]><![CDATA[1.6 - Looking in The Wrong Mirror]]>https://www.thecreativepragmatist.com/p/16-looking-in-the-wrong-mirror-0c4https://www.thecreativepragmatist.com/p/16-looking-in-the-wrong-mirror-0c4Mon, 13 Apr 2026 11:47:21 GMTIn Episode 6 of The Grey Area Podcast, Gabe and Stella get into what happens when you're putting all your energy into fixing the wrong thing — going to the gym twice a day when the real problem is how you see yourself, spiraling over a typo in an email to 200 people when no one's dying, and the feedback loops that have been telling you you're not enough since you were a kid. Then they build their Mentor Man — the idea that your mentor isn't one person but a composite, assembled from everyone who shaped how you think, feel, trust your gut, and keep moving. Head, heart, gut, arms, legs — each one a different person.

The Grey Area is where Gen Z talks about the stuff that doesn't have clean answers — business, culture, identity, and everything in between. New episodes every Monday. Part of the Almost Reckless universe from CP Media.

]]><![CDATA[1.5 - The Frontal Lobe Has Arrived]]>https://www.thecreativepragmatist.com/p/15-the-frontal-lobe-has-arrived-debhttps://www.thecreativepragmatist.com/p/15-the-frontal-lobe-has-arrived-debMon, 06 Apr 2026 12:00:00 GMTThe Grey Area is where Gen Z talks about the stuff that doesn't have clean answers — business, culture, identity, and everything in between. In Episode 5, Gabe and Stella get into what creativity actually means when you strip away the performance of it, why the friendships that survive your mid-20s are the ones built on honesty instead of agreement, and what happens when your priorities flip and you barely recognize who you were six months ago. The frontal lobe at 25 is real, FOMO is a phase, and the best show they've been to all year was the one where nobody reached for their phone. New episodes every Monday. Part of the Almost Reckless universe from CP Media.

]]><![CDATA[1.5 - The Frontal Lobe Has Arrived]]>https://www.thecreativepragmatist.com/p/15-the-frontal-lobe-has-arrived-5a9https://www.thecreativepragmatist.com/p/15-the-frontal-lobe-has-arrived-5a9Mon, 06 Apr 2026 12:00:00 GMTThe Grey Area is where Gen Z talks about the stuff that doesn't have clean answers — business, culture, identity, and everything in between. In Episode 5, Gabe and Stella get into what creativity actually means when you strip away the performance of it, why the friendships that survive your mid-20s are the ones built on honesty instead of agreement, and what happens when your priorities flip and you barely recognize who you were six months ago. The frontal lobe at 25 is real, FOMO is a phase, and the best show they've been to all year was the one where nobody reached for their phone. New episodes every Monday. Part of the Almost Reckless universe from CP Media.

]]><![CDATA[1.4 - Assume the Best, Clear the Noise]]>https://www.thecreativepragmatist.com/p/14-assume-the-best-clear-the-noise-0c8https://www.thecreativepragmatist.com/p/14-assume-the-best-clear-the-noise-0c8Mon, 30 Mar 2026 11:27:56 GMTThe Grey Area is where Gen Z talks about the stuff that doesn't have clean answers — business, culture, identity, and everything in between. In Episode 4, Gabe and Stella unpack a failed college startup and what it taught about drive, why assuming the best in people is harder than it sounds (especially if you grew up with three sisters or a middle school that destroyed you), and the mental clarity problem nobody talks about — when the thing you're doing to decompress is actually making it worse. Plus: ego deaths, people pleasing, contract negotiations, and the TikTok algorithm you built brick by brick.

A CP Media production, born from the world of Almost Reckless. New episodes every Monday.

]]><![CDATA[1.4 - Assume the Best, Clear the Noise]]>https://www.thecreativepragmatist.com/p/14-assume-the-best-clear-the-noise-ce4https://www.thecreativepragmatist.com/p/14-assume-the-best-clear-the-noise-ce4Mon, 30 Mar 2026 11:27:56 GMTThe Grey Area is where Gen Z talks about the stuff that doesn't have clean answers — business, culture, identity, and everything in between. In Episode 4, Gabe and Stella unpack a failed college startup and what it taught about drive, why assuming the best in people is harder than it sounds (especially if you grew up with three sisters or a middle school that destroyed you), and the mental clarity problem nobody talks about — when the thing you're doing to decompress is actually making it worse. Plus: ego deaths, people pleasing, contract negotiations, and the TikTok algorithm you built brick by brick.

A CP Media production, born from the world of Almost Reckless. New episodes every Monday.

]]><![CDATA[1.3 - Growth in Discomfort]]>https://www.thecreativepragmatist.com/p/13-growth-in-discomfort-8b5https://www.thecreativepragmatist.com/p/13-growth-in-discomfort-8b5Mon, 23 Mar 2026 15:08:39 GMTEpisode Three of the Grey Area Podcast, hosted by Stella Pyles, Gabriel Smilovic, and Matthew Blackman, looks to answer three new questions this week through the Gen-Z lens:

  1. What does "authenticity" mean to you? How does it appear, or not appear, in your daily life?

  2. Describe your relationship with "discomfort" - elaborate.

  3. What are the driving forces in your life that tempt you to take risks? What are the forces that discourage you to take risks?

]]><![CDATA[1.3 - Growth in Discomfort]]>https://www.thecreativepragmatist.com/p/13-growth-in-discomfort-04ehttps://www.thecreativepragmatist.com/p/13-growth-in-discomfort-04eMon, 23 Mar 2026 15:08:39 GMTEpisode Three of the Grey Area Podcast, hosted by Stella Pyles, Gabriel Smilovic, and Matthew Blackman, looks to answer three new questions this week through the Gen-Z lens:

  1. What does "authenticity" mean to you? How does it appear, or not appear, in your daily life?

  2. Describe your relationship with "discomfort" - elaborate.

  3. What are the driving forces in your life that tempt you to take risks? What are the forces that discourage you to take risks?

]]><![CDATA[1.2 - Who is Your Hero?]]>https://www.thecreativepragmatist.com/p/12-who-is-your-hero-a1chttps://www.thecreativepragmatist.com/p/12-who-is-your-hero-a1cMon, 16 Mar 2026 12:00:00 GMTEpisode Two of the Grey Area Podcast, hosted by Stella Pyles, Gabriel Smilovic, and Matthew Blackman, looks to answer three new questions this week through the Gen-Z lens - 1) Identify a list of individuals that you admire - style, career, character. What are the specific attributes that you admire? Is there a throughline between them? 2) Which to you is more important: experience, or common sense? 3) When you get dressed, how do you want to feel? Is there a connection between this craving and other aspects of your life?

]]><![CDATA[1.2 - Who is Your Hero?]]>https://www.thecreativepragmatist.com/p/12-who-is-your-hero-38dhttps://www.thecreativepragmatist.com/p/12-who-is-your-hero-38dMon, 16 Mar 2026 12:00:00 GMTEpisode Two of the Grey Area Podcast, hosted by Stella Pyles, Gabriel Smilovic, and Matthew Blackman, looks to answer three new questions this week through the Gen-Z lens - 1) Identify a list of individuals that you admire - style, career, character. What are the specific attributes that you admire? Is there a throughline between them? 2) Which to you is more important: experience, or common sense? 3) When you get dressed, how do you want to feel? Is there a connection between this craving and other aspects of your life?

]]><![CDATA[1.1 - Welcome to The Grey Area]]>https://www.thecreativepragmatist.com/p/11-welcome-to-the-grey-area-5b2https://www.thecreativepragmatist.com/p/11-welcome-to-the-grey-area-5b2Mon, 09 Mar 2026 12:00:00 GMTWelcome to The Grey Area Podcast hosted by Stella Pyles and Gabriel Smilovic. On this week's episode, we introduce the catalyst for TGA – "Almost Reckless: A Creative and Pragmatic Approach to Taking Risks" by Amy Smilovic. Riffing off the concepts and principles outlined in the book, we dive into a list of questions that prompt us to think beyond the black and white and embrace ambiguity. We certainly don't have all the answers, and we won't always agree – but we do know that when you open up the floor to good, honest discourse...good conversations happen.

]]><![CDATA[1.1 - Welcome to The Grey Area]]>https://www.thecreativepragmatist.com/p/11-welcome-to-the-grey-area-67chttps://www.thecreativepragmatist.com/p/11-welcome-to-the-grey-area-67cMon, 09 Mar 2026 12:00:00 GMTWelcome to The Grey Area Podcast hosted by Stella Pyles and Gabriel Smilovic. On this week's episode, we introduce the catalyst for TGA – "Almost Reckless: A Creative and Pragmatic Approach to Taking Risks" by Amy Smilovic. Riffing off the concepts and principles outlined in the book, we dive into a list of questions that prompt us to think beyond the black and white and embrace ambiguity. We certainly don't have all the answers, and we won't always agree – but we do know that when you open up the floor to good, honest discourse...good conversations happen.

]]>