The Creative Penn Podcast for Writers

Host: Joanna Penn
Guest: Pilar Orti
Episode: How to Pivot Careers, Co-Write Books, and Stay Connected As a Remote Creative
Date: October 6, 2025
Theme: Writing craft and creative business—focusing on career pivots, co-writing, remote work, and finishing creative projects.

Overview

This episode centers on navigating creative and professional change. Joanna Penn hosts Pilar Orti—non-fiction/memoir author, voiceover artist, podcaster, and Pilates instructor—for an in-depth conversation about pivoting careers, wrapping up life phases with books, the nuances of co-writing, strategies for meaningful connection as a remote/independent creative, and the discipline of finishing projects. With candid stories and specific strategies, the episode offers actionable guidance for writers and creatives juggling multiple interests or evolving career paths.

Key Discussion Points & Insights

1. Pilar Orti’s Creative Journey and Career Pivots

Timestamp: 36:58 – 44:26

• Pilar’s writing roots began in childhood, crafting plays for friends, and always with a public-facing intent: “Looking back, I think for me writing has always been about sharing. All the writing I've done, I've always wanted it to be public. So I've never journaled or anything like that.” (37:24, Pilar)
• Transitioned through various careers: theater, voiceover, and then remote work consultancy.
• Discovered self-publishing after traditional gatekeepers deemed her translations too niche, leading her to increased creative output and self-direction.
• Major life changes often get “wrapped up” with a book project—each new book embodies a phase, e.g., leaving theater, reflecting on voiceover work, and now summarizing remote team consultancy experience.

Memorable Insight:

“I think I'm wrapping up parts of my life with books.” (40:48, Pilar)

2. Why and How to End Projects or Careers

Timestamp: 42:28 – 44:26; 64:40 – 68:35

• Pilar ended her consultancy because the post-pandemic market no longer needed her services in the same way, and she no longer resonated with the type of work coming in.
• The decision was a mix of market forces and personal satisfaction:

  “The clients I would end up working with were not the ones I should be helping or at least I couldn't help them in the way I wanted ... I wasn't comfortable anymore with what I was finding when I was going in. At the same time, let's be honest, the work started to dry up.” (42:35, Pilar)

• Joanna reflects on the importance of recognizing when a project has served its purpose and allowing for a positive ending rather than seeing it as a failure.
• Ending something can be as much about having nothing left to say as it is about external drivers.

Pilar’s marker for ending:

“For me it's when I really don't want to do something anymore or when something is a bit of a drag ... if it's a creative project that you keep doing, and suddenly you're like, I don't know why I'm doing this. I have nothing more to say. I'm getting tired of the sound of my own voice in whatever way.” (64:40, Pilar)

3. Connection and Disconnection as Remote Creatives

Timestamp: 44:26 – 54:17

• “Connection” encompasses different needs for different people:
  • Across the work (collaboration)
  • Around the work (discussion about the process, like this podcast)
  • Away from work (personal stories, hobbies)
• Self-awareness is crucial: understand your own best ways to connect, and be aware of others’ preferences.
• Technology offers various ways to connect but can complicate things—important to clarify and explicitly state preferred modes and expectations, especially in collaborative projects.

Practices discussed:

• Use of personal manuals in remote teams (stating preferences for communication and collaboration)
• Try different modes (forum, Zoom, Google Docs, email) to find what’s sustainable
• Regularly ask, clarify, and respect collaborators’ needs

Quote:

“You need a high level of self-awareness to really find how you connect with others and then a level of awareness about how other people like to connect.” (45:18, Pilar)

4. Co-Writing Across Continents—Process, Challenges & Tech Tools

Timestamp: 53:55 – 62:36

• Pilar and her co-author, Bri Kajati, co-wrote their new book, Connection and Disconnection in Remote Teams, entirely remotely, rarely meeting on video.
• Their method:
  • Heavy reliance on Google Docs for everything—notes, drafts, project updates (even personal check-ins).
  • They kept a running record of their process, which became a valuable project archive.
  • Used generative AI (Claude) to help manage and synthesize their massive trove of transcripts, reduce blank-page anxiety, and help smooth their different writing voices.

Memorable Moment:

“We created a project in Claude which had all the transcripts. So you could say, ‘Oh, at some point we talked about ... who was that? What episode was that in?’ And instead of having to dig through all these transcripts, suddenly we had an assistant.” (57:23, Pilar)

On overcoming a stalled start:

• The first attempt at writing failed due to time constraints and overwhelm.
• Second attempt succeeded due to process changes (starting from AI-generated summaries), and using tech platforms that suited their brains, not whatever was “trendy.”

Joanna’s point:

“You don’t have to use what someone else says transformed their process. If it doesn’t work for your brain, it doesn’t work.” (61:29, Joanna)

5. Strategies for Pivoting and Managing Multiple Careers

Timestamp: 68:35 – 77:13

• Combining overlapping or sequential careers:
  • Pilar’s income streams shifted for reasons outside of her control (e.g., remote voice talent market changed due to better tech, which made it easier to hire directly from Spain instead of London, and AI began taking small contracts).
  • She proactively developed new skills (consultancy, Pilates instructor) while existing income sources still partially functioned.
• Advice for other creatives facing diminishing prospects in one area:
  • Test out new interests or income streams before taking the full leap.
  • Scale back the old as the new (if viable/enjoyable) scales up.
  • Be comfortable with experimentation: “Try little experiments before you decide to take a big plunge.” (70:29, Pilar)
• Don’t be afraid to step back if something isn’t working.
• Maintain an “ideas list” or “for later” folder; give yourself permission to let go, or pause, or just dream for now.

6. The Importance of Finishing Energy

Timestamp: 73:04 – 77:13

• Both Joanna and Pilar identify as “finishers” rather than people awash in open projects.
• Not finishing isn’t failure; sometimes, finishing means putting something aside after honestly assessing that it’s not the right time or fit.
• Advice for multi-passionate creatives: Track ideas, do “deep research” to test willingness, and commit only when you feel sustained energy/enthusiasm.

Pilar:

“Finishing for me sometimes is not doing it anymore. It doesn't mean I've completed the project ... It means I've gone, you know what, in one year, how much have I enjoyed this? How successful ... did it bring an income? ... Put it away. And that's okay.” (74:06, Pilar)

Notable Quotes

• “I think I'm wrapping up parts of my life with books.” (40:48, Pilar)
• “I have nothing more to say. And I thought, well, that's it.” (66:10, Pilar)
• “You need a high level of self awareness to really find how you connect with others.” (45:18, Pilar)
• “Try little experiments before you decide to take a big plunge.” (70:29, Pilar)
• “Finishing for me sometimes is not doing it anymore...Put it away. And that's okay.” (74:06, Pilar)
• “You don't have to use what someone else says transformed their process. If it doesn’t work for your brain, it doesn’t work.” (61:29, Joanna)

Timestamps of Key Segments

• 36:54–44:26 – Pilar’s creative background, life phases marked by books, and entering writing/publishing.
• 44:26–54:17 – The science and art of connection as remote creatives; self-awareness in collaboration.
• 53:55–62:36 – Practicalities of co-writing remotely, using Google Docs and generative AI to manage and shape collaborative work.
• 62:36–64:40 – The importance of analyzing failures/process misfits and adjusting course.
• 64:40–68:35 – Motivation for ending projects and reframing “quitting”; how to conclude positively.
• 68:35–77:13 – Navigating career pivots, managing multiple interests, and the discipline of finishing projects.

Resources and Further Reading

• Pilar’s website: pilarwrites.com
• Joanna’s podcast backlist and resources: thecreativepenn.com/podcast
• Mentioned AI tools: Claude, Notebook LM, Google Docs

Final Thoughts

This episode is an encouragement for creatives to embrace change, be intentional about how and why they end or pivot projects, and to balance the joy of starting new things with the discipline of thoughtful finishing. If you’re navigating a career in flux or seeking ways to build meaningful connections (and endings) as a creative, Joanna and Pilar’s candid discussion will resonate.

Contact and Credits:

• Pilar Orti: pilarwrites.com, LinkedIn: Pilar Orti
• Joanna Penn: thecreativepenn.com

“Hold some of them lightly until you decide to commit. And then if you're going to commit, absolutely commit.” (77:13, Joanna)