Unconventional Leaders – Details, episodes & analysis

Have you ever been told that in order to succeed, you need to pick one lane and narrow your focus?

Meet Natasha Pearl Hansen. She’s a touring comedian and startup founder who is successfully embracing two worlds unapologetically. From launching her own tech company to navigating the business side of entertainment, she has always been intentional about creating her own path. Pretty unconventional, hmm?

In this conversation, Natasha shares how she manages relationships and networking, stays productive without burning out, and makes smart decisions about which opportunities to pursue. She also talks about the moment she turned her canceled wedding into a comedy special, her approach to producing shows, and what it really means to build a portfolio-style career.

WATCH EPISODES ON YOUTUBE: https://www.youtube.com/heatherparady 

TOPICS FROM THIS EPISODE:

• How to maintain relationships and build your network (even when you are super busy)
• How to make strategic moves: Knowing when to say “yes” and when to say “no.”
• How to create a “portfolio career” (balancing entrepreneurship with a creative career)

CONNECT WITH NATASHA PEARL HANSEN:

• Website: nphcomedy.com
• Instagram: https://www.instagram.com/nphcomedy/
• Hustle and Chill: https://hustleandchillwithnph.beehiiv.com/subscribe

CONNECT WITH HEATHER:

• Ask Heather a Question: https://www.heatherparady.com/ask 
• Follow Heather on IG: https://www.instagram.com/heatherparady/ 
• Access full show notes here: https://www.heatherparady.com/blog/79

Feeling Overwhelmed by Too Many Ideas? Try This Trick Used by Professional Creatives

TOPICS FROM THIS EPISODE:

• How innovation thrives within structure
• Why setting rules can actually make you more creative
• How to use structure to grow your platform

EPISODES MENTIONED:

• Improve Your Short Form Video by Doing This | ‪@BrendanKane‬
• https://www.youtube.com/watch?v=wiC8GU_ycmw&t=129s
• How to Produce Better Content as a One-Man Show | George Sidiropoulos https://www.youtube.com/watch?v=oGBRZHeyFHo&t=17s
• The Creative Process of Adam Rose https://www.youtube.com/watch?v=aTsYFUMx5oU&t=2s

WATCH EPISODES ON YOUTUBE: https://www.youtube.com/heatherparady 

CONNECT WITH HEATHER:

• Ask Heather a Question: https://www.heatherparady.com/ask 
• Follow Heather on IG: https://www.instagram.com/heatherparady/ 
• Access full show notes here: https://www.heatherparady.com/blog/78

Feeling behind in your business or creative work? As the year wraps up, it’s easy to feel down if you didn’t meet your goals or feel off track from where you want to be. If that sounds like you, here’s a little pep talk for ya.

WATCH EPISODES ON YOUTUBE: https://www.youtube.com/heatherparady 

CONNECT WITH HEATHER:

• Ask Heather a Question: https://www.heatherparady.com/ask 
• Follow Heather on IG: https://www.instagram.com/heatherparady/ 
• Access full show notes here: https://www.heatherparady.com/blog/60

If you struggle with telling your story—whether it’s fear of being judged or labeled, or maybe exposing others that you love—this episode is for you. Today, I connected with Irene from Irene’s Entropy, a musician and content creator. She’s built a big ol’ community around her journey of leaving Mormonism and rebuilding her life and career after leaving literally everything behind and having to start all over.

Although her story is complex, she has mastered a way to communicate it through her music and short-form content.

And my guess is, maybe you have a complex story too. There is a way to communicate it effectively, but it’s going to require something. Like Irene says, “It really all comes back to self-awareness, emotional awareness, and understanding your goals and where you’re headed. And then being okay if the public doesn’t see you for who you are yet—knowing that they will if you keep moving toward your goal.”

Well, this is a good one, y’all. This is Irene.

WATCH EPISODES ON YOUTUBE: https://www.youtube.com/heatherparady 

TOPICS FROM THIS EPISODE:

• How to share your story despite fear of judgment or appearing like a victim
• How to share deeply personal experiences without exposing others
• How to keep your story engaging without it feeling gimmicky or repetitive

CONNECT WITH IRENE: https://www.instagram.com/irenes.entropy/

SERIES OF MUSIC VIDEOS SHARING HER STORY: https://www.youtube.com/watch?v=nj_qq_wDnHg&list=PLv49btAcOU0IMix14DxFZCpwlK9nCA-Y_

CONNECT WITH HEATHER:

• Ask Heather a Question: https://www.heatherparady.com/ask 
• Follow Heather on IG: https://www.instagram.com/heatherparady/ 
• Access full show notes here: https://www.heatherparady.com/blog/68

In today’s episode, we are answering a question from Conner: “How do you get your creative work ‘out there’?” I had a few thoughts and then brought in my friend Jay, who is an Emmy Award-winning filmmaker, to help answer this question.

WATCH EPISODES ON YOUTUBE: https://www.youtube.com/heatherparady 

• Previous Interview with Jay: https://www.youtube.com/watch?v=pnKyZ92DXWo&t=1s
• Connect with Jay: https://www.instagram.com/jayworsley/

CONNECT WITH HEATHER:

• Ask Heather a Question: https://www.heatherparady.com/ask 
• Follow Heather on IG: https://www.instagram.com/heatherparady/ 
• Access full show notes here: https://www.heatherparady.com/blog/67

If you are ambitious, it can sometimes be challenging to relate to others who don’t share that ambition. You may also wonder how to maintain healthy relationships when you choose to work more than the average person.

In this episode, I sat down with Stefanos Sifandos, a relationships expert with an extensive background in psychology, philosophy, and ecology, to explore the delicate dance between ambition and connection. In this conversation, you’ll hear why Stefanos believes that "most people's ambition is a compensatory strategy to avoid the pain they don’t want to feel" and how "ambition doesn’t have to disappear, but it should evolve."

If you’re curious about how to reconcile the drive to build something amazing while maintaining healthy relationships, this episode is for you.

WATCH EPISODES ON YOUTUBE: https://www.youtube.com/heatherparady

Topics from this Episode:

• Why ambitious people often feel misunderstood or unseen
• How to balance the energy required to build something big while nurturing relationships
• What to do when your partner doesn’t share your passion or enthusiasm

CONNECT WITH STEFANOS SIFANDOS: https://stefanossifandos.com/

CONNECT WITH HEATHER:

• Ask Heather a Question: https://www.heatherparady.com/ask 
• Follow Heather on IG: https://www.instagram.com/heatherparady/ 
• Access full show notes here: https://www.heatherparady.com/blog/66

One of the biggest challenges I’ve faced lately as a creator is finding the balance between “being consistent” and not putting out something I don’t fully believe in. How do we stay professional and "show up," as Seth Godin says, while keeping our work honest and meaningful?

TOPICS FROM THIS EPISODE:

• Understanding why you're creating and who it’s for.
• Accepting that inspiration doesn’t come on demand—and that’s normal.
• Using structure and deadlines to create space for creativity.
• Reusing ideas in fresh, exciting ways to ease the pressure of constant innovation.

WATCH EPISODES ON YOUTUBE: https://www.youtube.com/heatherparady 

Overview of the 4 Stages of Flow: https://www.facebook.com/share/v/17xVsZbw3P/

CONNECT WITH HEATHER:

• Ask Heather a Question: https://www.heatherparady.com/ask 
• Follow Heather on IG: https://www.instagram.com/heatherparady/ 
• Access full show notes here: https://www.heatherparady.com/blog/65

PSybYL8nuetKDcNNAyAQ

You might think content from a project management company would be dry, right? Think again.

Today I sat down with Chris Cunningham, a founding member of ClickUp and the head of their social media marketing, to explore their unconventional approach to content creation. Believe it or not, ClickUp isn’t just making business content—they’re breaking all the rules by taking inspiration from comedy and entertainment (think Saturday Night Live) while still delivering value to their audience.

Chris shared how their team takes their content strategy seriously—investing in talent, writing teams, and a creative vision that’s anything but boring. We also talked about how creators can adopt scrappier methods, why it’s important to “take bets off data,” and how reframing embarrassment can unlock your creative potential.

WATCH THIS EPISODE ON YOUTUBE: https://www.youtube.com/heatherparady 

TOPICS FROM THIS EPISODE:

• Scrappy ideas for content creators
• Documenting your journey and leveraging that content
• How to “think in pictures” to spark better ideas
• Ryan Reynolds’ approach to newsjacking (and what you can learn from it)
• How to reframe “embarrassment” as a creator and push through doubt

CONNECT WITH CHRIS CUNNINGHAM:

• Instagram: https://www.instagram.com/cunningham/
• LinkedIn: https://www.linkedin.com/in/chrisclickup/

CONNECT WITH HEATHER:

• Ask Heather a Question: https://www.heatherparady.com/ask 
• Follow Heather on IG: https://www.instagram.com/heatherparady/ 
• Access full show notes here: https://www.heatherparady.com/episodes/64

Jimmy asked for marketing advice, and I gave a couple of answers he might not have expected.

WATCH EPISODES ON YOUTUBE: https://www.youtube.com/heatherparady 

CONNECT WITH HEATHER:

• Ask Heather a Question: https://www.heatherparady.com/ask 
• Follow Heather on IG: https://www.instagram.com/heatherparady/ 
• Access full show notes here: https://www.heatherparady.com/episodes/63

There isn’t a straightforward career path for creatives. You’re often figuring it out on your own and facing resistance. When is it "too lofty" of a dream? Where’s the line between "This isn’t for me" and just needing patience?

Today, I connected with Jay Worsley, an Emmy Award-winning filmmaker, here to share what it took to build a career (and life) telling stories. In this conversation, he shares his decision-making process and why he "says no as much as he can" (and sometimes says yes for reasons beyond the project). Jay also dives into finding emotion in a story, building a team, networking (even if you’re not extroverted), and his bold ideas about marketing indie films. And he shares why it’s crucial to get still and ask, How does this move me?

This, my friends, is Jay Worsley.

WATCH EPISODES ON YOUTUBE: https://www.youtube.com/heatherparady 

TOPICS FROM THIS EPISODE:

• When should you say “no” to a project?
• Developing a strong vision in your work
• Finding and conveying emotion in a story
• You might not need social media (try this instead)

CONNECT WITH JAY WORSLEY: 

• Instagram: https://www.instagram.com/jayworsley/
• Website: https://sonderstorytelling.com/

CONNECT WITH HEATHER:

• Ask Heather a Question: https://www.heatherparady.com/ask 
• Follow Heather on IG: https://www.instagram.com/heatherparady/ 
• Access Full Show Notes Here: https://www.heatherparady.com/episodes/62