Let’s stop asking AI for answers and start asking it for questions.

Much of today’s popular discussions on AI seem to center on dystopian fears caused by job displacement or even humanity’s existential threat caused by rise of AI. But what about Generative AI’s potential for personal growth? How might AI enable greater self-awareness? How might AI, if positioned to empower agency and reflection, transform us for the better?

While many position and use AI as a solution for automation and answers, I continue to see profound opportunities using ChatGPT to generate and give me questions. If I could suggest one tip to anyone who regularly uses ChatGPT or similar LLM technologies, try asking it for questions rather than answers.

ChatGPT has changed in profound ways how I learn, think and write. For example, I regularly leverage ChatGPT or Bard to ask me questions to think before I act, reflect before I decide or explore before I narrow on a single idea. For writing , creativity, and personal development, I got a have an AI companion for journaling, a sidekick to get me out of a creative rut and a socratic mental health guide. Professionally, ChatGPT can and does serve on my deliverables in coding, marketing, meetings, and strategy but it’s even better as a powerful engine of creative exploration for my product ideas, technology and even fiction.

With rise of Generative AI services like ChatGPT, the obvious question (at least for me) is: How might AI tools enable us to be better and different humans (including such higher cognitive functions like decision-making, self-reflection and even creativity)?

I’ve long harbored a belief in the role that technology might play for self-improvement and personal development. For years this has centered on my self-tracking writings and code and products for quantified self. My core vision is about using self-tracking and personal data for greater self-understanding. For example, QS Ledger and more recently Quantified ChatGPT are two open source projects I created that enable you to aggregate your data from health and productivity services in order visualize trends and see yourself through data. Personally I use this mindset in my time tracking and my data-driven weekly goal reviews.

THESIS: The advent of Generative AI tools and the accessibility of vast personal data are revolutionizing the landscape of personal development. They enhance our capacity for self-awareness, deepen our self-reflection practices, and expand the horizons of self-expression in unprecedented ways.

AI can and should be an enabler of self-reflection. Over the coming years, I believe there is a huge opportunity for companies, education and society to position GenerativeAI beyond automation and productivity and towards empowering new forms of self-awareness. For example, I have personally modified my health and sleep using data from wearables and biomarker tests and a regular data-driven journaling and reflection practice. My productivity and time usage has change through time tracking and regular data-driven check-in’s and goal setting.

In the emerging field of what we might call “AI-enhanced personal development,” there is a significant opportunity to shift our approach from solely being introspective to one that is fundamentally iterative. This approach might materialize through the design of “Soft Feedback Loops” within our products and personal experiences. In the language of behaviorial economics, they are “soft” because we have a choice to enage or skip. They are complex systems for thinking and creativity. In the vocabulary of cybernetics, they enable the output of the system (or our input) to be routed back into the system as input, creating what are called feedback loops. These loops would not merely act as mirrors reflecting our current state and self but would actively engage us in an ongoing dialogue.

Let’s envision a scenario where an individual engages with an AI-powered journaling or reflection platform. The process begins with the user responding to thought-provoking prompts or freely journaling their thoughts and experiences. Then our “Generative Reflection Agent” (GRA) comes in to play, interact and reflect iteratively with us. GRA could parses through your entries (text, voice or even photos) and can offer advice and feedback but it might also be able enaging you to think and reflect in novel, sophisticated and empathetic ways. For example, by drawing on a reservoir of your historical data, past interactions, and a set of AI-generated intentions, GRA can generate insights and pose follow-up questions designed to provoke deeper reflection.

As users, we should never be just a passive recipient of these insights. We should automate out humanity. Instead, for AI-empowered reflective experience, we become active participants, selecting which threads of thought to pursue, which feedback resonates, and how to delve deeper into the self-reflection process. You get to make choices. As you iterate and interact reflectively, your responses feed back into the AI, creating a symbiotic and caring relationship where each interaction is a step towards greater self-understanding and potentially greater personal alignment, identity and self-worth.

The beauty of such a Generative Feedback Loop lies in its capacity to enable agency, choice and evolution. As you change and grow, so does the AI’s understanding of you, leading to ever-more personalized and authentic reflections. This iterative cycle is ‘generative’ because it produces new patterns of understanding and behavior, facilitating continuous personal growth and learning. Such an instantiation of AI is not about automation or loss of humanity but the transformative potential of human and AI agent together. The user always matters, and their meaning and sense-making are central. AI is a co-creator towards your personal growth.

As scary as it sometimes feels, the advent of accessible generative AI tools offers a new era where each of us are being challenged by what it means to be human, to be authentic and to be yourself. We all have become product designers and AI technologists in what comes next.

The potential of AI extends beyond automation and should be positioned in terms of transforming our ability to make informed decisions, empower authentic human experiences and enable greater self-awareness. The challenge—and opportunity—before us is to craft user experiences that harness the power of AI to guide us towards more valuable choices for individuals and for our collective organizations. I predict this will take many forms but believe Generative Feedback Loops offer one such approach that can already enhance our behavior, health, creativity, and career trajectories.

What do you want your customers to become with AI? Are you interested in using AI and data to empower your personal development and self-reflection? Is your product or organization considering how to design and implement AI to better your users, employees, students, etc.?

I am currently piloting a AI-empowered self-reflection POC I built with an educational organization. Will generative reflection change how students learn and employees grow their skills and career? I’m looking to connect, talk and/or partner with more folks (educators, coaches, etc.) who wish to improve our engagements in education and life.

I also actively designing and building a “Quantified Self 2.0” journaling and goal setting app. It currently offers a library of prompts to help you get started journaling, simple goal setting and goal tracking, and optional AI feedback moments towards greater self-reflection over time.

Both of these are currently in closed beta but you can find a few early ideas and a signup page at StayReflective.com.

I’m also writing a series of articles on the intersection of authenticity and AI with this post meant to herald an open-ended conversational start.

If any of this resonates with you, let’s connect and create a future where AI empowers us all to reflect, grow, and transcend.

AIDA (AI Disclosure Acknowledgement): The following written content was generated by me with the assistance of an AI-based system (ChatGPT). Specifically I used it to help me in pre-writing phase, copyediting and drafting a few individual points. The main cover was generated using an AI-based system (Midjourney).