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Confessions of CoWorking

Career Blindspot

Release Date: 11/10/2025

Community Tiers show art Community Tiers

Career Blindspot

Why did I build the Blind Spot Community? Because I want to help more people than 1:1 coaching allows — and because most of us already know what to do… we just don’t keep doing it. In this episode, Courtney and I break down the purpose of the community and how the three tiers are designed for different stages: Tier 1: practical handouts + monthly updates for people who want tools they can actually use Tier 2: DIY coaching + hiring resources, a 1:1 call, and the weekly group for support and momentum Tier 3: year-long check-ins, deeper assessment work, and an AI consult with...

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Rejection Hurts/Helps show art Rejection Hurts/Helps

Career Blindspot

Why did you dump me in 2004? That’s how this episode starts. But this isn’t just a relationship story. It’s about rejection — in love, in leadership, in sales, and in career growth. We talk about: Why rejection feels isolating (even when it’s necessary) The difference between being rejected and being freed How rejection forces the next chapter Why leaders must normalize “no” Sales, negotiation, and the flinch test The shame that keeps people silent Why if you’re not getting rejected, you’re probably not swinging big enough Rejection hurts. But it...

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AI Leader Credibility show art AI Leader Credibility

Career Blindspot

What does a leader need to know about AI — if they’re not planning to become an expert? More than you think. Less than you fear. In this episode, we unpack what actually builds credibility around AI for leaders: Embracing the fact that you don’t know everything Avoiding the “curse of knowledge” Why curiosity beats certainty How fast iteration changes leadership expectations Why technical expertise doesn’t automatically equal strategic leadership AI is not just a technical shift. It’s a mindset shift. The leaders who will thrive aren’t the ones pretending...

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BS Model: Stop Being Busy, Start Being Intentional show art BS Model: Stop Being Busy, Start Being Intentional

Career Blindspot

For years, I’ve coached leaders using a framework I never fully explained — until now. The BS Model (Blind Spot Model) reveals where your attention goes and what it produces: Intentional Presence Task Execution Reactive Distraction Avoidant Coping Most people live externally focused and call it productivity. But without internal clarity, busyness turns into burnout. This episode breaks down: Why “I’m busy” is a warning sign How reactive distractions quietly take over The difference between being productive and being aligned Why burnout isn’t accidental...

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Why Is It So Hard To Work With Creatives? show art Why Is It So Hard To Work With Creatives?

Career Blindspot

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Revenge of Sleep Training show art Revenge of Sleep Training

Career Blindspot

Why aren’t our babies sleeping? That’s the question. But this episode isn’t just about sleep. It’s about leadership, ownership, energy, and what happens when a system that once worked starts slipping after a new variable is introduced. Sleep training is project management. Regression is iteration. Exhaustion changes your standards. We talk about: ·       Why knowing what to do isn’t the same as doing it ·       How depletion impacts decision making ·       Ownership vs resentment ...

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Giving Someone An Attitude Adjustment show art Giving Someone An Attitude Adjustment

Career Blindspot

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reFresh Tradition show art reFresh Tradition

Career Blindspot

“Make your own traditions. Do not do things just because everyone else does.” – Courtney   CBQ: Why are there white Christmas trees in our bedroom and the kids’ rooms?   Summary: Juan and Courtney talk through why traditions should evolve with your life—and how choosing intention over obligation turns holidays into something you actually enjoy instead of just survive.   HIGHLIGHTS “Nothing says Palm Springs like white Christmas trees.” – Courtney “We want traditions, but we do not want to be beholden to traditions.” – Juan “Avoiding something is a start,...

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Fine… Networking Is Not That Terrible show art Fine… Networking Is Not That Terrible

Career Blindspot

“I did not understand what networking was. I thought it was just, ‘Here is my job, help me.’” – Courtney CBQ: How much do you hate networking today?   Summary: Juan and Courtney break down why traditional networking felt like a “negative 34” and how getting clear on your talent, value, and curiosity can turn awkward events into intentional, energizing collaboration.   HIGHLIGHTS “You are more excited to network because you are more clear on what you are talented at and where it is valued.” – Juan “People do not know how you could help them. You have to...

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Vasectomy!? Vasecta-You!! show art Vasectomy!? Vasecta-You!!

Career Blindspot

“It lifted a weight off your shoulders I did not realize I was holding.” – JK   CBQ: Why did you get a vasectomy?   Summary: Juan and Courtney use a very personal story to expose an overlooked leadership truth: responsibility shared is pressure reduced, and sometimes the smallest physical procedure removes the biggest emotional load. HIGHLIGHTS “It was a pinch for you. It was surgery for me.” – Courtney “I did not realize I wasn’t lifting weight off your shoulders.” – Juan “Men get praised for showing up. Women get questioned.” – Juan “Sometimes the...

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More Episodes

"Getting out of the house makes us do work better.” – Courtney

 

CBQ: Why are we in a phone booth at Industrious?

 

Juan and Courtney pull back the curtain on their recording setup to unpack the modern co-working experience—why intentional environments matter more than trendy spaces, and how isolation quietly kills creativity.

 

HIGHLIGHTS

  • “Getting out of the house makes us do work better.” – Courtney
  • “I chose co-working because I wanted human experience.” – Juan
  • “Just because I do not get energy from people does not mean I should avoid them.” – Courtney
  • “Until you are intentional about it, you will be stuck in an office or stuck at home—with lonely company.” – Juan
  • “Who do you actually want to run into?” – Juan

 

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