I asked ChatGPT to roast me based on my prompt history—and it didn’t hold back. What started as a simple request for humor quickly turned into an unexpected therapy session. ChatGPT has been my go-to tool for everything from brainstorming business ideas to generating new Medium article topics. Despite its endless patience and lack of judgment, I decided to give it explicit permission to criticize me based on our extensive and varied conversation history. The result was both brutally honest and uncannily accurate. My prompt history reads like a digital identity crisis. If you were to judge me solely by the questions I've asked on ChatGPT, you might think I'm a multitasking dreamer-in-distress, desperately trying to become a millionaire with no capital, three hobbies, and no sleep. Here’s a sampling of my inquiries: Business Ideas: "Can you help me come up with a business plan that uses AR and VR to create immersive educational experiences?" Hobbies: "How can I turn my love for pottery into a side gig?" Sleep Deprivation: "What are some tips to stay productive even when I'm exhausted?" Each question reflects different facets of my multifaceted, yet often chaotic, interests and goals. Curious about what ChatGPT had to say, I presented it with the challenge. ChatGPT’s Roast: "You seem to have a grand ambition to change the world, but your approach is scattered and unrealistic. Your business ideas, while creative, are often overly ambitious and lack practical planning. For instance, creating immersive educational experiences with AR and VR sounds innovative, but it requires significant investment and technical expertise, which you haven’t demonstrated. Your hobbies are numerous, each one a potential side project, but you struggle to commit to any single endeavor. Pottery, for example, could be a rewarding side gig, but only if you invest the time and resources to hone your skills and build a market for your products. Furthermore, your constant state of sleep deprivation is concerning. While it’s admirable to work hard, ignoring your physical and mental well-being will ultimately hinder your progress. It’s crucial to find a balance between ambition and self-care." The roast was a mix of harsh truth and constructive criticism. It highlighted the flaws in my approach but also offered actionable advice. While it stung to read, especially the part about my lack of commitment, the feedback was invaluable. Reflecting on ChatGPT’s critique, I realized that my digital footprint indeed reveals a pattern of jumping from one idea to another without fully developing any of them. This scattered approach has been a significant barrier to achieving my goals. The experience also made me consider how I use AI tools like ChatGPT. These platforms can offer valuable insights and support, but they should not replace critical self-reflection and disciplined planning. It’s important to integrate the advice given by AI with a broader strategic framework and personal development plan. In conclusion, while ChatGPT’s roasting session may have felt like an unwelcome therapy session, it provided a much-needed reality check. By acknowledging the gaps in my strategy and the importance of self-care, I can work towards a more focused and sustainable path to achieving my ambitions.