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, but leaning into a celebration is different." – Juan "They are not going to remember any of this. We are." – Courtney "This is permission to mess around and find out." – Juan

*]:pointer-events-auto scroll-mt-[calc(var(--header-height)+min(200px,max(70px,20svh)))]" dir="auto" tabindex="-1" data-turn-id= "75a0a129-e3e3-4f5e-b73e-b810c6aaa0e6" data-testid= "conversation-turn-36" data-scroll-anchor="false" data-turn= "assistant">

• CareerBlindspot.com
• LinkedIn | Instagram | Youtube
• Juan | Courtney

→ Your listening perspective matters - 5 min survey.

"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 tell them what you do well." – Juan
• "If you are not excited to be there, stop going. Go where you would actually get on a plane to meet people." – Juan

• CareerBlindspot.com
• LinkedIn | Instagram | Youtube
• Juan | Courtney

→ Your listening perspective matters - 5 min survey.

"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 leadership move is doing the thing that makes life easier for someone else." – Juan

CareerBlindspot.com

LinkedIn | Instagram | YouTube

Juan | Courtney

→ Your listening perspective matters – 5 min survey.

"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

• CareerBlindspot.com
• LinkedIn | Instagram | YouTube
• Juan | Courtney

→ Your listening perspective matters – 5 min survey.

"It is not the content. It is the intention behind it." – Courtney

CBQ: What is the difference between doom-scrolling and researching on your phone?

Summary: Juan and Courtney dissect the blurry line between learning and avoidance—why "research" can be productive curiosity or just another flavor of self-distraction.

HIGHLIGHTS

"Doom-scrolling is when I am not actually going to apply what I learned." – Courtney "Body-doubling helps neurodiverse people get things done." – Courtney "Investing in yourself is different from retail therapy." – Juan "I do not deserve this notebook? Yes you do. Start using it." – Juan "Repurpose something you already have - intention beats novelty." – Juan

• CareerBlindspot.com
• LinkedIn | Instagram | Youtube
• Juan | Courtney

→ Your listening perspective matters - 5 min survey.

"DIY starts with ego, but ends with humility." – Juan Kingsbury

CBQ: Why is DIY a mixed bag of fun and frustration?

Juan and Courtney break down the trap of "doing it all yourself." From home projects to leadership habits, they reveal how ego fuels the start, but humility gets the job done.

HIGHLIGHTS

• "When you DIY, you eventually have to delegate."
• "The real skill is knowing who to delegate to."
• "Letting go of control is not weakness, it is awareness."
• "No one will care for your baby the same way you do."
• "If your projects are unfinished, check your ego."

• CareerBlindspot.com
• LinkedIn | Instagram | Youtube
• Juan | Courtney

→ Your listening perspective matters - 5 min survey.

"The egos are shaping the meeting — and whether your mission is accomplished or not." – Juan

CBQ: What Egos are shaping your meetings? (*Why does Juan love Inside the NBA?)

Juan and Courtney break down the leadership lessons hidden inside Inside the NBA. From Barkley's bluntness to Shaq's dominance, Kenny's analogies, and Ernie's calm structure, it is more than sports talk — it is a masterclass in team dynamics. When strong personalities collide, who leads, who listens, and who actually moves the mission forward?

HIGHLIGHTS

• 03:54 - "These are egos, and it reminds me of meetings where people hijack — not just executives, but anyone leading a team." – Juan
• 11:05 "Silence can be just as deadly to progress as too much talking." – Juan
• 10:50 "That's what it is, you got to appeal to people's motivations." – Courtney

• CareerBlindspot.com
• LinkedIn | Instagram | Youtube
• Juan | Courtney

→ Your listening perspective matters - 5 min survey.

"When's the last time you thrilled yourself?" – Juan Kingsbury

CBQ: When you find out someone has read A Court of Thorns and Roses, what are you instantly doing?

Juan and Courtney unpack the joy of nerding out — from fantasy novels to comics to leadership. Leaders often chase productivity, but when is the last time you chased thrill?

HIGHLIGHTS

• 1:09 "It is not just reading it, it is the joy of nerding out with someone else." – Juan
• 2:39 "Nostalgia comforts, never thrills."
• 4:38 "Everybody's just looking to find where they belong." – Courtney
• 9:48 "When's the last time you instigated thrill?" – Juan

• CareerBlindspot.com
• LinkedIn | Instagram | Youtube
• Juan | Courtney

→ Your listening perspective matters - 5 min survey.

#thrill #nerdingout #leaderswhoread #fiction #community #culture #purpose #belonging #growth #careerblindspot

"Whenever I hear the word networking, I feel scuzzy. I don't want to schmooze people, but the way you describe it makes it feel easier — it's about really getting to know people." - CK

CBQ - What is your love language?

Juan and Courtney discuss the resistance people feel in reaching out for advice or support, reframing networking as an act of offering value instead of seeking it.

HIGHLIGHTS

• [00:04:16] "Leadership should not be lonely. Leadership isn't lonely — it's the opposite. You're collaborating with people, delegating, and trusting them to deliver." - JK
• [00:05:23] "It's always a no if you don't reach out." - JK
• [00:10:14] "Call not just your best friends, but the ones you can truly be yourself around. Those friends remind you who you are, and we avoid them because they hold us accountable." - JK
• CareerBlindspot.com
• LinkedIn | Instagram | Youtube
• Juan | Courtney

→ Your listening perspective matters - 5 min survey.

"I wanted it. I was just doing the work to have that job, and I didn't even know what the freaking job was." – JK

Juan's Disney Internship

CBQ: How come you never talk about what it was like to work at Disney?

Juan reflects on his Disney internship 24 years ago, the risks he took despite his parents' doubts, the odd jobs and lessons along the way, and how that leap helped shape his confidence to take risks in his career.

HIGHLIGHTS

• 1:39 "Working at Disney World was like college without classes." – Juan
• 4:52 "I can't keep this medal…" – Juan
• 8:40 "I don't think I'm gonna be an artist anymore." – Juan
• 10:02 "The biggest lesson was like, I need toothpaste." – Juan
• 13:45 "Reflect on your big risk in the past when you did something that other people were like, no, don't do that. And you're like, I'm doing it anyway." – Juan

Follow

• CareerBlindspot.com
• LinkedIn | Instagram | Youtube
• Juan | Courtney

→ Your listening perspective matters - 5 min survey.