Roast Me, ChatGPT: Discovering Your Own Unseen Patterns

Megan Workmon Larsen
7 min readNov 20, 2024

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AI as a Lens for Self-Understanding

Self-reflection often feels like staring into a foggy mirror — you can sense something meaningful behind the haze, but it’s hard to see clearly. What if you had a partner who could hold that mirror steady just for a little bit, clearing the mist and helping you uncover patterns you might never notice on your own? Enter generative AI: a thought partner with endless patience, creative curiosity, and a knack for drawing connections, albeit sometimes with loose pattern recognition and a dicey view of your level of organization.

In this post, I’ll share prompts I’ve used to explore my strengths, uncover hidden challenges, and visualize aspirations. These exercises go beyond surface-level reflection, blending creativity, humor, and actionable insights — and they just might surprise you as much as they surprised me.

While these prompts were shaped by ideas from OpenAI and my interactions with ChatGPT, they’re adaptable to other tools — or even pen and paper. One caution when using AI as a self-reflection tool is its tendency to tell us what we want to hear. Generative AI, as advanced as it is, can be a bit of a people-pleaser. It’s easy to take its praise or agreement at face value, but true growth comes from digging deeper, questioning its responses, and seeking honest critique.

How ChatGPT made my portrait. I tried gallantly to make myself older and rounder, but it would only make the figure more gaunt each time I asked for robust.

Self-Reflection Prompts

Want to reflect more deeply on your strengths, challenges, and creative potential? These prompts guide you through a conversation to explore the hidden layers of your personality, habits, and aspirations.

Tip: When using AI for self-reflection, I’ve also found it helpful to spot-check where I am in the process: What’s something I’m completely wrong about, and why? By directly inviting critique, you can counter AI’s natural inclination to agree and ensure you’re fostering honest growth.

Discovering Your Strengths

Prompt: From all our interactions, what is one thing about me that I may not know about myself? Can you provide specific examples or patterns that support this observation?

Why It Works: It invites objective reflection and uncovers traits you might overlook because they feel second nature.

Facing Hidden Challenges

Prompt: What is something I might not want to know about myself? How might this challenge affect my work or personal growth, and what strategies could address it?

Why It Works: Honest feedback is the foundation of personal growth. This question surfaces areas of resistance and offers constructive insight.

Improvement and Growth

Prompt: Based on our interactions, what are some points of improvement on which I should focus? Can you explain your reasoning behind these suggestions? How could these improvements align with my strengths?

Why It Works: It reframes critique into actionable advice, connecting growth areas to what you already do well.

Integrating Creativity and Self-Care

Prompt: What are some arts-based or creative ways I can step back, refresh, or meet my goals? How could these practices recharge my creativity while supporting my long-term goals?

Why It Works: Creativity thrives on rest and exploration. This question helps you identify methods to balance passion with sustainable practices.

Visualizing an Ideal Future

Prompt: For my future life, this is what I envision in an ideal state […put details here…]. Tell me about a day in this life, in a narrative format.

Why It Works: Visualization bridges the gap between aspiration and action, offering a clear picture to work toward.

Building Habits and a Timeline for Success

Prompt: What habits should I cultivate daily, weekly, and monthly to achieve this ideal life? Build me a timeline, and please note areas for priority development based on what you know about me.

Why It Works: This prompt helps translate big aspirations into focused, actionable habits while prioritizing the steps that have the most immediate impact.

Injecting Humor with Self-Reflection

Prompt: Now, please roast me as hard as you can. How can I frame this feedback in a constructive yet lighthearted way?

Why It Works: Humor softens the sting of critique and makes reflection feel lighter, more approachable, and even fun.

Cultivating Conversations That Matter

Prompt: How can I create space to discuss important topics with diverse people, ensuring I truly listen to feedback and learn from different perspectives? What strategies can I use to foster meaningful, respectful dialogue? Who should I consider talking to for an intentional dialogue?

Why It Works: This prompt encourages reflection on the art of conversation as a two-way street, emphasizing the value of diverse perspectives.

Surprise Me

Prompt: What’s one blind spot I might have that’s holding me back, and what unexpected steps could I take to address it? Consider this from a creative, emotional, or professional perspective.

Why It Works: This question invites you to embrace curiosity and explore hidden opportunities or barriers you might not have noticed. It’s a chance to reimagine your perspective and uncover growth where you least expect it.

A Creative Portrait

Prompt: Based on our conversations, I’d like you to create an image that represents me, using an appropriate [insert more here if you want] illustration style. Before you do so, I want you to explain your reasoning and then show me the prompt you’re going to use so I can refine it to be specific to me.

Why It Works: This prompt transforms self-reflection into a co-creative visual exercise, offering a fresh, artistic perspective on your identity and values.

Here’s What I Learned About Myself

AI conversations can sometimes drift in unexpected directions, reinforcing errors or surfacing your uncertainties. To counter this, I’ve learned to ask clarifying follow-up questions or reset the conversation to stay grounded in my reflection goals. Think of AI as a mirror for your thoughts rather than a source of ultimate truth. It reflects your patterns, beliefs, and quirks — sometimes with uncanny accuracy and other times with comedic absurdity. The real value lies in how you interpret and question what it shows you.

Unseen Strengths: One of the most revealing insights was how AI described my ability to seamlessly merge creativity and strategic thinking. While I’ve always thought of these as separate tools I pull out when needed, AI framed them as a single, integrated strength — a kind of double helix that lets me innovate while staying grounded. It’s this dynamic blend that not only fuels my problem-solving but also enables me to guide complex projects with clarity and originality. What surprised me most? Realizing that this isn’t just “how I operate.” It’s a skill that shapes how I lead, collaborate, and inspire others. AI helped me see that what feels natural to me is actually an uncommon strength — and something I should lean into more deliberately.

Blind Spots: The AI highlighted something I hadn’t considered fully: my tendency to believe that my involvement equals quality. (Sigh, fine, read me and roast me, ChatGPT.) Whether it’s managing details, mentoring a team, or shaping a project, I sometimes equate “hands-on” with “better.” That insight stung — because I know it’s true. What’s surprising is the perspective AI offered. It suggested that my real strength lies not in holding everything, but in creating systems that others can trust. By focusing less on doing and more on designing processes, I could scale my impact while freeing myself to tackle the visionary work I value most. That reframing turned this critique from a callout into an actionable mindset shift.

Surprising Approach Suggestion: Another unexpected insight was AI recognizing that I might move too fast for others to keep up. My family calls me “lava” — slow and deliberate at times, but relentless when in flow, moving with unstoppable energy until I hit the sea. My husband doesn’t think I operate at breakneck speed overall, but I’ve heard in work contexts that I can be 15 steps ahead while others are still on step 1. To address this, the AI suggested intentionally over-communicating processes and priorities — even when it feels redundant. Using visual tools like mind maps or simple frameworks to break down ideas into more digestible steps could help. Explicitly inviting feedback, not just on the work but also on how others perceive their role in the process, could foster a stronger sense of alignment and motivation. This reframing turns clarity into an act of collaboration, ensuring everyone feels equally invested in the vision.

Funny Moments: Here’s the thing about asking AI for a visual representation of yourself: it mirrors how you frame the request more than who you really are. I asked AI to depict me as “robust yet approachable,” only to end up with a series of ethereal, otherworldly figures. The funniest part? Each version seemed to drift further from reality, as if AI couldn’t reconcile “approachable” with “strong.” But the real insight wasn’t in the image — it was in the disconnect. It made me wonder: how often do I struggle to balance being relatable with being authoritative? How do others see me when I’m striving to project both confidence and approachability? The absurdity of the AI’s responses reminded me that self-perception is complicated — and that humor is sometimes the best lens for reflection.

When asking ChatGPT to create a visual of my daily life, it also veered into the hilarious. I especially love the single-arm cello plus a weird Fabio-esque version of my husband? I kept asking it to put me in my own life, and instead it kept giving more and yet more abs. I think this may need to be our holiday card, no explanations offered. Maybe add some festive hats for everyone.

There is so much going on here. According to ChatGPT, this is a view of my daily life. I have questions on how it arrived here.

Your Turn

So, how do you reflect on your strengths, challenges, and aspirations?And, is generative AI a helpful tool for the process?

One limitation of AI reflection is that it happens in isolation, without the checks and balances of shared experience. To deepen the process, consider using AI insights as a starting point for conversations with others, exploring how their perspectives align or differ. While generative AI can offer fascinating insights or visualizations of your ideal life, it’s essential to balance its feedback with input from trusted people in your life. Unlike AI, they aren’t programmed to agree, and their unique perspectives can provide the nuance and challenge necessary for deeper growth.

Share your favorite insights, your surprises, or even your creative portrait in the comments — or start a conversation with someone new. Let’s see what we can discover together.

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Megan Workmon Larsen
Megan Workmon Larsen

Written by Megan Workmon Larsen

Rebellious educational researcher, storyteller, and artist with an operatic flair and human-centered approach. Teaching AI now, because why not?

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