Today I'm sharing ten more of my favorite recent GPT4 prompts and experiments for creative business owners.

This episode originally aired as a bonus episode for the private BFF community, as a follow-up to a case study on how ChatGPT has helped me draft a few solo podcast episodes.

Want more where this came from? Join us in the private BFF community and/or Free Time Operations Dashboard with promo code PODCAST.

🏝️ I’m also opening up ten Voxer coaching spots to work with me 1:1. Enrollment closes when the 10 spots are filled or by EOD June 4, whichever comes first. Learn more and sign-up » (Apply promo code PODCAST at check-out)

💬 As always, I'd love if we could crowd-source on this one! What are the most interesting GPT prompts that you've tried? Join BFF so you can share with us in the comments! 🎧 Or if you're listening on Spotify, answer the question prompt at the bottom of this episode's page :)

✅ Do (or Delegate) This Next: Try just one of the ideas above!

🌟Enjoying the show? The best way to thank us is by leaving a rating or review

❤️ Join our BFF community for Heart-Based Business owners

🛠 Get instant access to the Free Time Toolkit: http://itsfreetime.com/toolkit

☎️ Submit a voice question or comment for future episodes: http://itsfreetime.com/ask

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The average American worker gets 11 days of paid vacation per year. Among those with unlimited paid time off (PTO), the average person takes 19 days off per year, yet 48% of Americans say they still check their work email while away.

What about business owners? Although it seems like we have more free time, the reality is that life as a business owner can be a 24/7 unceasing, all-consuming task. Even if you’re not at the computer, your passing thoughts probably drift toward what you need to do, projects to tackle, revenue gaps to make up for.

Today’s guest, DJ DiDonna, is an advocate for taking more abundant time off—ideally measured in months, not days or weeks. By DJ’s definition, sabbaticals should go beyond recovering from burnout; instead offering extended time to learn more about yourself in unstructured, even “unproductive” ways.

More About DJ: DJ DiDonna is a Senior Lecturer in the Entrepreneurial Management Unit at Harvard Business School, where he teaches the required first-year course: The Entrepreneurial Manager. In 2019, he founded The Sabbatical Project to define, explore, and research sabbaticals. He is currently working on a book based on this research, called Time Off Well Spent: A Sabbatical Manifesto.

📝 Permission: Take four to six months off, even if it’s two years from now to give you enough time to prepare. Entrepreneurs often grasp their role in their companies too tightly, and inadvertently create a business that will fail without them.

✅ Do (or Delegate) This Next: Look for the area of your business that would fail without you. What small step could you take today to bolster that area for the future?

📝 Check out full show notes from this episode and share it with a friend: https://itsfreetime.com/episodes/193

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Today I'm sharing five creative ways to better organize your phone contacts. I hope it’s helpful and time-saving toward a very important end: feeling less overwhelmed by relationships!

🏝️ Friendly Reminder: I’m opening up ten Voxer coaching spots to work with me 1:1 (asynchronously). I’d love to help you take a step back from the day-to-day operations of your business and set even more of your time free this summer! Enrollment closes when the 10 spots are filled or by EOD June 4, whichever comes first.

Learn more and enroll » (Apply promo code PODCAST at check-out)

📝 Permission: Not to create a full-on CRM or pay for expensive overly complicated software.

✅ Do (or Delegate) This Next: Spruce up your ability to keep in touch with people who are important to you by implementing just one of the ideas above.

🌟 Enjoying the show? The best way to thank us is by leaving a rating or review

❤️ Join our BFF community for Heart-Based Business owners

🛠 Get instant access to the Free Time Toolkit »

💬 I’d love to hear what’s on your mind! Take the Free Time listener survey

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“Small hinges move big doors.” That one thought helped Karen Allen pick herself up from the depths of grief after losing her husband in a tragic, senseless act of violence nearly a decade ago. Shortly afterward, she lost her house, her car, and then one year later — her job.

Getting fired followed just a few months after an intuitive hit that corporate wasn’t the best fit for her any longer was a blessing in disguise that precipitated the founding of her now-thriving business, one where she puts her son front-and-center as her North star.

In this conversation, Karen shares how she navigated overwhelming grief while parenting, structuring her business for free time as a single parent, and how her business has evolved as she continues gaining clarity about who she wants to be and how she wants to serve.

More About Karen: Karen is a super-mom, healthy eater, and keynote speaker. After experiencing the tragedy of losing her husband, she picked herself up and set out to thrive for her son’s sake. She is the founder of the 100% Human movement, helping others develop a mindset of joy and abundance through her community. She also hosts the In the Details podcast.

📝 Permission: Do what your soul is calling you to do, and create it in a way that supports you.

✅ Do (or Delegate) This Next: Identify your triad (or duo or quad) of life/work categories you want to be entirely present for; for example, time with family, for your business, for your community. Make sure each have their own dedicated (and inviolable!) space in your schedule.

💻 Access Free Time episode transcripts on Podscribe »

🌟Enjoying the show? The best way to thank us is by leaving a rating or review

❤️ Join our BFF community for access to a monthly Q&A call, a private podcast feed with bonus content, and a forum to exchange ideas and feedback with fellow Heart-Based Business owners.

💌 Subscribe to the Time Well Spent newsletter: http://itsfreetime.com/join

🛠 Get instant access to the Free Time Toolkit: http://itsfreetime.com/toolkit

💬 I’d love to hear what’s on your mind! Take the Free Time listener survey

☎️ Submit a voice question or comment for future episodes: http://itsfreetime.com/ask

🎧 Make sure you’re subscribed wherever you listen to podcasts

📝 Check out full show notes and share it with a friend: https://itsfreetime.com/episodes/191

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Hi friends! A quick in-beteween-isode to let you know about a special opportunity to work with me 1:1 :)

Back by popular demand, I'm opening doors again for my 1:1 Voxer coaching pop-up. Summer is the perfect time to take a step back from your business and set even more time free through smarter systems—while freeing yourself from screens and coordinating extra calendar entries.

We piloted this program last year with members from my private BFF community, and it was a big hit! It was so nice to connect asynchronously to help you focus on the big picture and make meaningful progress on the projects that matter most. 

✅ How it works:

*Make sure to apply promo code PODCAST at check-out!

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Time- and money-based targets don’t always serve the purpose we intend. In fact, sometimes, they actively work against us. Today we’re spelunking into a few related principles like Goodhart’s Law, The Cobra Effect, and why vanity metrics are often no more than a hungry ghost lurking in the shadows of your business. I couldn’t resist sprinkling pop culture clips throughout to illustrate these concepts, so I hope you enjoy the ride :)

📝 Permission: Stop chasing the hungry ghost of vanity metrics in your business. Get clear on your more meaningful metrics and core values, and aim for a holistic picture of those instead.

✅ Do (or Delegate) This Next: To more clearly see the tradeoffs you are willing to make, write your own “even over” statements, like the originators of the Manifesto for Agile Software Development have inspired many businesses to do. As in: “We value {important quality A} even over {important quality B}.”

💻 Access Free Time episode transcripts on Podscribe »

🌟 Enjoying the show? The best way to thank us is by leaving a rating or review.

❤️ Join Jenny’s private BFF community for Heart-Based Business owners

🛠 Get instant access to the Free Time Toolkit: http://itsfreetime.com/toolkit

☎️ Submit a voice question or comment for future episodes: http://itsfreetime.com/ask

📝 Check out full show notes and share this episode with a friend: https://itsfreetime.com/episodes/190

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In episode 181: Be Irreplaceable, you heard from my creative coach, Jay Acunzo about how to prioritize resonanceover reach. I’ve been working with Jay for about six months now, and it has transformed the way I think about creating content.

One of the videos he shared with us in his new community, Creator Kitchen, is a walkthrough of his Intellectual Property (IP) Development OS: how he collects ideas, chooses which one/s to pursue, and decides which channel they belong in.

I loved it so much — and I know you will too — that I asked for special permission to share it here on the pod. Learn more at creatorkitchen.com and apply promo code FRIENDOFAFRIEND for $100 off your membership for life.

🎧 If you're listening on Spotify—or just want to pop over there to share your biggest insight—answer the question prompt at the bottom of this episode's page :)

💡 View the diagram of Jay Acunzo’s IP Development OS here »

💻 Jay’s IP Development Trello board has the following columns: Ideas, Chef’s Table (Community), Playing Favorites (Newsletter), Unthinkable (Podcast), Strongest Ideas (categorized as either Problems, Change, or Solution/s), Strongest Stories (Lead or Supporting), and Frameworks + Models (Diagrams)

More About Jay: Jay Acunzo is one of the world’s most sought-after business storytellers and brand consultants. He’s hosts the award-winning podcast, Unthinkable, and has authored multiple books on creativity, including Break the Wheel: Question Best Practices, Hone Your Intuition, and Do Your Best Work. He helps creators learn to increase the power of their creative work, not just the volume, through his membership platform, the Creator Kitchen. Jay’s grandest aspiration-slash-delusion is to be the Anthony Bourdain of workplace storytelling.

✅ Do (or Delegate) This Next: Map out your own IP Development process. What does the life of a new frustration, question, or insight look like? How would it move across a Kanban-style content production board?

🌟Enjoying the show? The best way to thank us is by leaving a rating or review

☎️ Submit a voice question or comment for future episodes: http://itsfreetime.com/ask

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When today’s guest, Kelli Thompson, was overwhelmed by opportunity—a level of success she had been dreaming of and working diligently toward—she knew she needed a roadmap to better manage her time and energy, stat.

In this conversation, we unpack how she created an Energy Capacity Plan (a woman after my own spreadsheet-loving heart!), how to create yours, why it doesn’t need to be a detailed calendar grid sliced into specific 15-minute increments, and how that plan can inform your pricing.

In the second half, we also talk about masterminds — when to join, what to watch out for, and how to determine which one/s are right for you. If you haven’t already, be sure to check out our conversation for the Pivot podcast on 315: Intuition-Building, Spotting Pedestal Syndrome, and Closing the Confidence Gap.

More About Kelli: Kelli Thompson is a women’s leadership coach and speaker who helps women advance to the rooms where decisions are made. She has coached and trained hundreds of women to trust themselves, lead with more confidence, and create a career they love. She is the founder of the Clarity & Confidence Women's Leadership Program, and a Stevie Award winner for Women in Business—Coach of the Year. She is the author of Closing The Confidence Gap: Boost Your Peace, Your Potential & Your Paycheck, which was selected as a must-read by The Next Big Idea Club.

📝 Permission: Drop anything that drains your energy!

✅ Do (or Delegate) This Next: Do an energy audit, and perhaps even create your energy capacity plan mapping out what each week looks like at a high level (day by day, rather than hour by hour) and the time-value of different types of activities.

💻 Access Free Time episode transcripts on Podscribe »

🌟Enjoying the show? The best way to thank us is by leaving a rating or review

❤️ Join our private BFF community

🛠 Get instant access to the Free Time Toolkit: http://itsfreetime.com/toolkit

💬 I’d love to hear what’s on your mind! Take the Free Time listener survey

☎️ Submit a voice question or comment for future episodes: http://itsfreetime.com/ask

📝 Check out full show notes from this episode and share it with a friend: https://itsfreetime.com/episodes/188

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Today’s episode is the second half of an in-depth Licensing Q&A prompted by BFF Al Dea, host of the MBA Insider podcast. If you haven’t already, listen first to 140: How to Licensing Your IP (Intellectual Property), followed by 186: Licensing 201 — Q&A (Part One) on Product Development, Attracting Clients, and Sales Process.

Al submitted a series of wonderful questions that span five categories; in this episode I’ll be addressing the latter three: selling and packaging, delivery (including Train-the-Trainer), and legal considerations. A caveat, as always, when it comes to this notoriously opaque arena: this is not the way, it’s just what I’ve learned along the way in nearly a decade of setting my mind to licensing as a revenue stream.

📣 Join us in our private BFF community for a related workshop this week! We’ll be diving deeper into Certification and Licensing on Thursday, May 11 at 1pm ET. Even if you can’t make it live and/or if you’re listening after that date, you’ll get instant access to the entire private podcast feed with years of special content archives. 

In this special BFF bonus workshop, my longtime friendtor Pamela Slim—who taught me the early ins-and-outs of licensing—will walk us through: how to know if/when adding a certification or corporate licensing program to your business makes sense, the first steps involved in creating them, ways you can work with her team on build-out, and anything you can think to ask during Q&A! You can also hear Jenny on Pam's Widest Net podcast in episode 005: From Friction to Flow and Finding Joy in Systems.

❤️ Learn more and join us at http://itsfreetime.com/bff (apply promo code PODCAST)

📝 Permission: Start tiny. Plant a few little conversational seeds here and there with current and prospective training clients, and see what starts to blossom.

✅ Do (or Delegate) This Next: Create a page on your website that shows the path from one-off workshops or keynotes to full-on licensing and Train-the-Trainer, even if you haven’t fully built out your programs yet. And join us in BFF to learn (and develop your materials) alongside fellow Heart-Based Business owners who are also on the certification and licensing journey!

🌟 Enjoying the show? The best way to thank us is by leaving a rating or review »

🛠 Get instant access to the Free Time Toolkit: http://itsfreetime.com/toolkit

💬 I’d love to hear what’s on your mind! Take the Free Time listener survey

☎️ Submit a voice question or comment for future episodes: http://itsfreetime.com/ask

Learn more about your ad choices. Visit megaphone.fm/adchoices

“A shoe is just a shoe until my son steps into it.” —Deloris Jordan

When negotiating Michael Jordan's famous shoe deal with Nike, his mom Deloris “made an additional demand: Her son must receive not only a $250,000 fee, but also a cut from every sneaker sold,” making her case with that mic drop moment above (as retold in the movie Air via The New York Times article ‘Air’ and the Argument for Letting the Talent Share in the Profits).

That, my friends, is the power of licensing :) Today’s episode is the first of a two-parter — an in-depth addition to 140: How to License Your IP (Intellectual Property), thanks to a set of wonderfully thorough follow-up questions from BFF member Al Dea.

Al is the founder of MBASchooled.com, author of MBA Insider, and host of the MBA Insider podcast. He asked a series of questions across five categories, and in this episode I’ll be addressing the first two: product development and client attraction strategies. A caveat as always, when it comes to this notoriously opaque arena: what I’m sharing is not the way, it’s just what I’ve learned along the way in nearly a decade of building out licensing as a revenue stream.

Check out episode 140 if you haven't yet, paired with 135: How to Rapidly Prototype a Course, 016: IP Licensing with Lee LeFever, 185: How Licensing Helps Serve the Queen Bee Role with Mike Michalowicz, and 045: Behind the Free Time Brand with Adam Chaloeicheep.

📆 Join us in the private BFF community for a related workshop coming up! We’ll be diving deeper into Certification and Licensing on Thursday, May 11 at 1pm ET. Even if you can’t make it live and/or if you’re listening after May 11, you’ll get instant access to the entire private podcast feed with years of special content archives.

In this special BFF bonus workshop, my longtime friendtor Pamela Slim—who taught me the early ins-and-outs of licensing—will walk us through: how to know if/when adding a certification or corporate licensing program to your business makes sense, the first steps involved in creating them, ways you can work with her team on build-out, and anything you can think to ask during Q&A! You can also hear Jenny on Pam's Widest Net podcast in episode 005: From Friction to Flow and Finding Joy in Systems.

❤️ Learn more and join us at http://itsfreetime.com/bff (apply promo code PODCAST)

📝 Permission: To be overwhelmed. Even if you need to listen to this three times, even if you're still scratching your head, it will start to make more sense, slowly over time.

✅ Do (or Delegate) This Next: Join us in BFF to learn more and develop your materials alongside fellow Heart-Based Business owners!

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