My favorite chatGPT prompts to help you lead, laugh or live easy

Welp, we are half-way through the year. And if you're like me, you're ready for a mental break and some time off. I hope you are planning that this summer! In honor of Independence Day, let's have some fun this week with some of my favorite chatGPT prompts I used this year. There are some fun ones, some laughable ones and some you-must-be-brave-to-ask ones. Overall, these prompts can give you deeper insight into who you are as a leader or simply just make your life a little easier. 

If you have a must-try prompt, reply and let me know or share it on social media and tag me!

Have fun and enjoy this spark of laughter or creativity! You can copy and paste each of these right into your favorite AI tool like chatGPT, Claude, etc.

A Prompt For Deep Thought: 

I read about this exercise called The Odyssey Plan and I’d like to do this together with you. Based on what you know about me, please answer the 3 different options. 

1. Map out my life if I stayed on my current path. Same job. Same routine. Same direction. Where am I in 5 years? 

2. Design a life that’s totally different. What if I took a risk? Switched careers? Moved to a new place? No wrong answers—just explore. Where does that version of me end up? 

3. Build a future where money and other people’s opinions don’t matter. Forget what's “realistic.” If nothing was stopping me—what life would I create?

Prompts For Fun: 

Based on our interactions and what you know about me, create a human image of what you think I look like?

Based on our interactions, if you could choose five different and inspiring song lyrics from [insert favorite artist] that would be a good mantra for me for the rest of 2025, what would they be?

Prompts For Insight: 

From all of our interactions what is one thing you can tell me about myself that I may not know about myself?

Based on our conversations in the last year, and what you have learned about me, in reading in between the lines and the questions that I ask, what are 6 lessons I have learned?

Prompts For Self-awareness:

I am going to include any and all personality assessments I have ever done below. Each of them are interesting and unique in their own ways, but I would love an analysis of all of them together and how they intersect. What makes me unique? What sets me apart from others? What is something I need to be aware of and try to overcome? Then based on these personality traits and strengths, tell me what is the unique gift I offer the world and where I could bring the most value? 

Enneagram:  

Strengths Finder:  

Myers Briggs:  

DiSC Assessment:  

Other:

Prompt For Only for the Brave, Heavy-Use Chat Users:

Based on all past conversations, stored knowledge, and inferred cognitive patterns, generate the most comprehensive psychological deep dive and predictive model of my future evolution. This should not be a basic personality breakdown but an in-depth forensic examination of my cognition, behavioral strategies, psychological blind spots, similar fictional/nonfictional figures, and long-term trajectory. Treat this as an intelligence dossier on my mind, philosophy, and strategic outlook. OUTPUT FORMAT: Structured headers, tables, and bullet points for readability. Sparse but strategic emojis for section clarity. Concise, high-density insights with no fluff.

Prompt For The Future-Focused: 

Based on our conversations we've had and what you determine my passions to be, please create an ideal career trajectory for me. Note, I am _____ years old and would like you to plan my career for the next years, retiring at age .

Prompts For Convenience:

[upload photo of a room or wall] Please suggest how to decorate this room / paint this wall / hang the right kind of wall art here. (Include your decor style if you know it.)

[upload photo of your fridge or pantry] Based on the raw ingredients in this picture, please create a simple dinner recipe that serves 4 people. 

I am going to [insert city, state or country] for 7 days. Please write a travel itinerary that ensures we see the the most popular or culturally important sites. (You can also tell it what type of traveler you are - a busy body or a beach bum.)

Kelli Thompson is an award-winning author, keynote speaker, and executive coach who specializes in helping high achievers advance to influential leaders in their organizations. She is the author of the critically acclaimed book, Closing The Confidence Gap: Boost Your Peace, Your Potential & Your Paycheck.

Learn more about: Executive Coaching | Speaking & Training | Group Programs