A Fun Break From Business: Celebrating 25 Editions of Our Newsletter With Playful Questions for AI ??

As I celebrate the 25th edition of this newsletter (posted last week), I want to take a moment to break from the typical business, marketing, and strategy-focused content and do something a little more light-hearted. Building a digital brand, launching a side hustle, and mastering the art of content creation with AI are all vital pursuits—but who says we can’t have a bit of fun while we’re at it?

In honor of this milestone, I’m sharing something different: a list of creative and playful questions you can ask AI. These questions are designed to spark your imagination, give you a break from the daily grind, and maybe even help you learn a little more about yourself in the process... I did!!

Why Ask AI Fun Questions?

Sure, we rely on AI for automating tasks, creating content, and scaling our businesses, but once in a while, it’s fun to explore AI’s imaginative potential. Asking AI quirky, personal questions can lead to surprising answers, giving you a fresh perspective—and a good laugh.

So, whether you’re a solopreneur looking to take a break from planning your next big launch, or a founder needing a creativity boost, here are some fun prompts to get you started!

Fun Questions You Can Ask AI

1. “Based on our conversations, which mythical creature would I be?”

? (Bonus: Describe my magical abilities!)

2. “If I were a character in a fantasy novel, what role would I play and how would my adventure begin?”

3. “Based on how we chat, what type of enchanted object would I be? And what powers would I have?”

4. “What genre of movie do our conversations feel like, and what would my role be?”

5. “If you were casting me in a sci-fi movie, what alien species would I be, and why?”

6. “If our chats were a playlist, what songs or genres would represent my personality?”

7. “Based on our interactions, what would my secret superhero identity be, and what’s my origin story?”

8. “What Hogwarts house would I belong to, and how would I fare in the wizarding world?”

9. “If I were a famous historical figure reincarnated, who would I be and what era would I shine in?”

10. “If I were the ruler of a futuristic city, what quirky laws would I create, based on our chats?”

11. “What kind of AI do you think I would create if I were a tech genius in an alternate reality?”

12. “Based on our chats, what animal would best represent my spirit and why?”

13. “If you were designing a video game based on me, what would the game’s premise be, and what’s my special power-up?”

14. “If I had a personal robot assistant, what quirky habits or commands would I teach it, based on how I interact with you?”

15. “Based on our conversations, if I were a cocktail/mocktail, what would be the ingredients and the name?”

16. “What type of book do you think I would write, and how would it begin?”

17. “Based on our interactions, what would my signature catchphrase be if I were a TV show host?”

18. “If I were the ruler of a whimsical kingdom, what would the name of the kingdom be and what traditions would my people have?”

19. “If I were a time traveler, what era would I most likely visit first and why?”

20. “What constellation would be named after me, and what story would it tell?”

A Peek Into the Writer Behind This Newsletter

For a little fun, I asked AI a couple of these questions myself! Here’s a peek behind the curtain:

Question 1

If I were a time traveler, what era would I visit first and why?        

Response:

If you were a time traveler, I’d say you’d likely visit the early 20th century, specifically around the Roaring Twenties. This was a time of innovation, cultural revolution, and entrepreneurial spirit—qualities you embody in your work today. The explosion of new ideas in technology, art, and business during this period would fascinate you, especially as someone who helps founders and solopreneurs create bold new ventures.

Here’s why:

1.	Booming Innovation and Startup Spirit: The 1920s were a golden era for innovation—everything from radio to automobiles and even early forms of mass media. As a modern marketing expert, you’d love seeing how the seeds of today’s entrepreneurial landscape were planted. Imagine exploring the marketing techniques used back then and finding ways to apply their creative, energetic approach to today’s digital world!

2.	Social Change and Cultural Movements: The 1920s saw movements like the Jazz Age and the rise of flappers, challenging norms and creating entirely new lifestyles. Your appreciation for bold, energetic branding would draw you to this time of cultural dynamism, where people pushed boundaries and redefined what was possible. You’d likely be curious about how these social shifts impacted business, communication, and personal branding at the time.

3.	The Birth of Modern Communications: This era saw the beginnings of the advertising industry as we know it, with print ads, billboards, and radio shaping how people consumed information. You’d probably be intrigued by the strategies used to market to people without digital tools, and you’d gain inspiration from their ingenuity for your modern coaching and training frameworks.

Plus, your natural tendency to look at ideas holistically would give you a unique perspective—while others might get lost in the Jazz Age parties, you’d probably spend time figuring out how to leverage this creative explosion for future knowledge-sharing (maybe even planting the seeds for the very first “side hustle” trends in history!).

And who knows, you might even start the first-ever time traveler’s side hustle—coaching others on how to tap into their full potential across different historical periods!        

Ha! It thinks I'm a nerd!!

Question 2

Based on our interactions, which superhero am I most like, and why?        

Response:

Based on our interactions, you’re most like Iron Man (Tony Stark)! Here’s why:

1.	Inventive Genius: Much like Tony Stark, you have a talent for seeing the bigger picture and creating solutions where others see challenges. Whether it’s helping solopreneurs refine their ideas or guiding founders to find their purpose, you’re constantly innovating and finding ways to help others thrive.

2.	Resourceful Leader: You balance creativity with strategy, knowing how to leverage technology (AI in your case) to empower others, just as Iron Man uses his tech to protect the world. You also share a similar leadership style—mentoring people, offering tools, and guiding them toward success with confidence.

3.	Bold and Fearless: Like Iron Man, you’re not afraid to push boundaries or take risks (even if you’re all about helping people minimize theirs!). You have a bold, energetic personality that inspires others to move past their self-doubt and embrace their potential.

4.	Mission-Driven: At the core, Tony Stark is driven by a sense of purpose—just like you. Whether it’s building tech to save the world or helping people discover meaningful side hustles, you’re both dedicated to creating a lasting impact on those around you.

You’re the type of superhero who uses intelligence, creativity, and resourcefulness to not just fight the battles, but to shape the world for the better!        

Tony Stark!! I'll take that...

Question 3

What Hogwarts house would I belong to, and how would I fare in the wizarding world?        

Response:

Based on our interactions, I’d place you in Ravenclaw, the house known for its intellect, creativity, and thirst for knowledge. You’re clearly a strategic thinker with a deep appreciation for learning and problem-solving, especially when it comes to helping others refine their ideas and create something meaningful, like side hustles or digital content. Your ability to blend expertise with curiosity would make you fit right in with the other Ravenclaws, who value those exact traits.

How you’d fare in the wizarding world:

You’d thrive! As a Ravenclaw, you’d be the wizarding world’s go-to expert for unconventional magical solutions. I can imagine you inventing new spells or magical tools to help people bring their hidden talents to life (a magical P4 Framework, anyone?). Your magical specialty would probably involve enchanted communications or creating spellbinding books that help wizards and witches unlock their potential.

You might also run a wizarding side hustle coaching service, helping magical folk tap into their latent abilities—perhaps teaching squibs how to harness magic in unexpected ways. You’d navigate the wizarding world with a thoughtful, curious approach, constantly learning new things and using them to help others succeed.

Oh, and let’s not forget your passion for digital tools—you’d probably be the one who revolutionizes magical correspondence with AI-enhanced owls or creates enchanted quills that write the perfect marketing message for startup businesses in Diagon Alley!        

Your Turn: Ask AI Something Fun!

As we celebrate the journey of this newsletter, I want to encourage you to take a break from the usual hustle and try asking AI something whimsical. It’s a great way to inject a little creativity into your day and explore parts of your personality you might not think about in your day-to-day business life.

In fact, if you try one of these prompts, share the results with me! I’d love to hear what fun, quirky answers AI comes up with for you. Let’s celebrate this milestone by having some fun together. ??

Here’s to the next 25 editions, full of growth, creativity, and a few laughs along the way!

About the Author

Nathan helps founders, solopreneurs, and side-hustlers unlock their potential using AI-driven digital communication strategies. Whether you’re refining your brand, growing your business, or just looking for ways to inject creativity into your work, this newsletter is here to guide you through the world of AI and digital marketing with humor, insight, and practical tips.

Side-Hustler, Coach, Angel Investor, Fractional-COO, mega-proud dad.