Art is Hard

Reclaim your artist mindset

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5-Second Summary

  • The Red Thread Why your day job is closer to art than you think.

  • The Unlock — Three simple shifts to reframe your work as art.

  • Creative Edge — Sharing your work is part of the art.

  • Prompt Playground — The “Am I Hiding?” audit for leaders and creators.

  • Industry Pulse — New AI music genres, news podcasts breaking records, TikTok live music contests, Hank Green’s new app, and more.

  • Creator Tools — Free podcast hosting, recipe AI, photo editor, and conversational agents.

  • Open Opportunities — New roles at Lower Street and Warner Music, plus top industry job boards.

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"Art is lunging forward without certainty about where you are going or how to get there." Mark Vonnegut

The Red Thread This Week

Art is Hard

Ask a room of kindergartners, “Who here is an artist?” and nearly every hand will shoot up.

Ask 6th graders, and maybe a third will raise their hand.

Ask the high school kids, and you’ll be lucky if more than a few will admit it.

What changed?

Well, we trained art out of ourselves.

We decided “art” meant paintbrushes, or playing the violin, and everything else became “work.”

Work with instructions. Work with a rubric. Work that leads to predictable, measurable outcomes.

But there’s a problem: predictable, task-based, interchangeable, repeatable “work” (the very definition of industrial-age labor) is exactly what machines do best.

And AI is demolishing the need for this type of work to always require us human folk.

So the work that matters most now looks different.

It’s the pitch with no guarantee of success. The new project or proposal that might fall flat. The tweak to team strategy that could fail. The product launch that’s on-deck.

That’s art.

Whether you’re leading a school district, running a VC firm, recruiting warehouse staff, managing engineers, coaching high school baseball, or steering a media company, your real work isn’t just “checking the boxes” all day long.

It’s leading people. Building products and businesses. Pushing projects forward. Creating change when, and where it’s needed.

And that’s the essence of art: bringing work and ideas into the world that might not work.

This week’s Red Thread is about reclaiming the artist’s mindset. Not as a luxury, but as the only way to do work that matters.

Let's dive in.

~ Jaime

🔑 The Unlock

Why Leaders Need the Artist Mindset

When we hear “artist,” we picture a painter, a musician, a writer. But art is any work where outcomes aren’t guaranteed.

And if you’re building, leading, or managing? That’s the world you live in every day.

Here are three ways to shift your frame:

1️⃣ Redefine “Work” as Creation When Possible

Ask yourself: Am I just following instructions, or am I creating something that didn’t exist yesterday?

  • Updating the spreadsheet to spec? Assembly work.

  • Designing a new process that saves your team hours? Creation.

2️⃣ Recognize Resistance for What It Is

Steven Pressfield calls it The Resistance: the voice in your head that whispers, “Don’t risk it. Don’t speak up. Don’t try.” 

  • That’s your lizard brain doing its job, keeping you “safe.”

  • But safe isn’t always what you, or the situation, might actually need.

Effective leaders and professionals don’t try to silence the resistance, they mark it. They say Ah, that’s a signal that this work right here…it’s probably worth doing, and it matters.

3️⃣ Expand Your Definition of Art

If the outcome is uncertain, if it might fail, if it requires judgment, courage, or vision—congratulations, you’re making art.

  • Pitching investors is art.

  • Leading a classroom is art.

  • Rallying the team with an email is art.

The minute you see your work this way, you stop waiting for perfect instructions and start showing up as a maker, not just a task-manager.

📌 Remember: Industrial work is about minimizing risk. Artistic work is about having courage enough to sign up for it.

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Your voice is your strength. Typeless turns it into a superpower.

💡 Creative Edge

If It Might Not Work, You’re Doing It Right

Think about the best idea you've had in the last year. The one that could actually change how your team works, or how your industry thinks about a problem.

Now ask yourself: Who outside your head knows about it?

  • The brilliant strategy nobody hears.

  • The game-changing idea parked on your desktop.

  • The product that dies behind “Let’s get more data first.”

That's not humility, or professional wisdom. That's hiding.

The musicians who change culture? After the record is out, they know that getting the songs heard is part of the creative act. It’s an extension of their craft. It requires the same muscles.

Your work is the same.

📌 Mindset shift: If your work feels risky or makes you uncomfortable when you share it, you’re on the right track.

🎲 Prompt Playground

The “Am I Hiding” Audit

Sometimes as builders we mistake fear for wisdom. Use this prompt help approach your next project with the mindset of an Artist (with a capital A.)

Copy + paste the prompt below into ChatGPT, Claude, Gemini, or Perplexity, and fill in the blanks.

Prompt:
I need an honest assessment of where I might be hiding behind "professionalism" instead of doing the risky work that could actually matter.

Here's my situation:

  • My role: [your position/influence]

  • The idea I keep thinking about but haven't acted on: [describe it]

  • Why I tell myself I'm waiting: [your official reason]

  • What I'm actually afraid might happen: [be brutally honest]

Now help me see clearly:

  • First, rewrite my "official reason" for waiting. What would this sound like if a 5-year-old said it?

  • Second, what's the worst realistic outcome if I actually try this idea and it doesn't work perfectly?

  • Third, what might happen to this idea in 6 months if I keep waiting for perfect conditions?

  • Finally, what's the smallest version of this idea I could test this week that would teach me something real?

Give me one specific action I can take in the next 48 hours that moves this from "someday" to "started."

 Bonus Prompt:
"What would I do with this idea if I knew I couldn't fail? Now what would I do if I knew failure was temporary?"

📡 Industry Pulse

  • AI experiments are spawning entirely new music genres, according to a new Stability AI study — Music Business Worldwide.

  • News podcasts have reached record audience levels, cementing their role as a trusted source of information — Signal Hill Insights.

  • How MD Foodie Boyz, a podcast built by 4 middle schoolers, is making waves — Tubefilter.

  • The Golden Age of Social Media is Over says The Trade Desk’s John Tegnér — The Current.

  • Hank Green’s new productivity app Focus Friend quickly topped the App Store charts — Tubefilter.

  • TikTok is expanding its live music contests with Music on Stage ’25Music Business Worldwide.

🛠️ Creator Tools

  • Pinwheel – Newly launched FREE hosting services for podcasters.

  • ElevenLabs – Build text-only conversational agents using ElevenLabs new Chat Mode.

  • GrubPick – Your personal AI recipe companion. Plan meals and discover new dishes instantly.

  • Nano Banana – New AI photo creation and editor…likely from Google (shh…)

💼 Open Opportunities 

Head of Audience Development  Lower Street (remote) View Role →

Director, Digital Marketing – Warner Music Group (Los Angeles) View Role →

Your next move in Music
Explore the MBW Job Board →

📌 Know someone looking? Forward this to them!

Your Next Move

I run JMedia, an advisory firm helping companies and creatives bring their ideas to life. Here are a few ways we can work together when you’re ready:

  1. 🗓️ Get 1:1 Support from Me: Need a thought partner to help shape what's next for your project or team? Let’s talk.

  2. 🎙️ Audit Your Podcast: Get pro-level eyes on your podcast without hiring a full-time producer.

  3. 🚀 Speaking Engagements & Workshops: Looking for a speaker for your next live (or virtual) event? Or someone to lead your next strategic workshop? Drop me a note!

NEW! The Red Threads Podcast: Apple | Spotify

Thanks for spending time with Red Threads this week, I’m glad you’re here :)

~ Jaime

P.S. My weekly Red Threads newsletter goes out every Friday. Move my emails to your primary inbox so you see the next edition!

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