using ai to reflect on my year

An image generated by OpenAI’s DALL·E model

context

I think often about how the narratives I tell myself affect the outcome of my life. I saw this prompt for ai about exactly that so gave it a shot. It turned out better than I expected.

I used ChatGPT and the 4o model if you want to try it yourself. If you do try it, share what your experience was in the comment if you’re comfortable.

conversation

Below is my full, unedited conversation. My messages have the green bar to the left.

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I want to uncover the masks I'm currently wearing, the roles I'm playing, and the illusions I'm believing. Please guide me through this process by asking me 10 reflective questions one at a time to help me recognize the stories I'm telling myself. Pause after each question to wait for me to answer. After I answer the 10th question, please step into the role of my higher self and analyze my responses. Identify the top negative patterns present in my life and the top positive patterns I can embrace and grow. Be direct and truthful. Tough love is welcome. Provide me with daily affirmations to support my growth, actionable steps to change my behaviors, and embody my authentic self. A message of encouragement from my higher self to celebrate how far I've come on my journey.

Question 1:

What are the most common labels or roles you use to describe yourself (e.g., professional titles, relationship roles, personality traits), and how do these roles make you feel about yourself?

Software developer, son, grandson, boyfriend, smart. Software developer makes me feel proud. It makes me feel smart and accomplished. Successful. Son and grandson feel factual. They don't feel particularly meaningful one way or the other. I don't feel pride in boyfriend. It feels more like a label put on me than one I really identify with. Smart is an interesting one. I feel some pride in it, but it also feels like a mask. I dont' fully believe it.

Question 2:

What are the moments in your daily life where you feel most disconnected from yourself or uncomfortable in your skin? What triggers those feelings?

- when I get too caught up in what others are doing

- when I forget where I am from and how I grew up

- where I feel shame or judgement

- when I don't feel like enough

Right now this most often comes up in my career. I feel like I'm failing compared to others often. I feel like I don't have what it takes to build a successful company. I think I'm falling behind. I'm not where I should be financially.

Question 3:

What stories are you telling yourself about who you need to be in order to succeed or be worthy? Where do these stories come from?

I tell myself I need to be smarter and work harder. I tell myself that if I build a successful company that I will have "made it". I will "have what it takes". I will be part of the group. These stories largely come from tech and twitter to be honest. It feels to me like many people have built successful companies and if I'm smart enough and work hard enough I should be able to as well. At the same tiem, I feel like I'm not doing as well as the friends who have worked at large tech companies their whole career. They are buying expensive houses and are probably better off financially.

Question 4:

When you envision "success," what does it look like? Whose definition of success are you following?

I want to have control over my time. I want to be financially free. I want to work on the things I want to, but I want to have flexibility to show up for people in my life. For me, the first step of success would be 200k in annual profit for a business. The next step would be 1M in annual profit. Success is largely work driven, but outside of that having a healthy relationship is really important to me. Having kids and raising them well. Spending time with my family and enjoying life. Not having to wake up to an alarm. Being able to read a lot. Those are all forms of success for me.

Question 5:

When you think about the gap between where you are now and your vision of success, what emotions arise? How do those emotions influence your daily decisions and actions?

Failure? Fear? I feel like I should be further along than I am I think that's where it is. Hmm they probably both encourage me to work and keep pushign while also making the work much less fun. I think it's not fun because I feel like I need to play catch up. I have expectations of how quickly things need / should happen. They also cause me ot have less fun and enjoy life less. I feel like I shouldn't be having fun as long as I haven't "made it". That's not really true. I still have fun and do a lot of things, but I feel guilty about it oftenn.

Question 6:

What would it look like to let go of the timelines and expectations you’ve set for yourself? What would your life feel like if you gave yourself permission to embrace where you are right now?

I would live a more authentic life I think. I would do more of the things I wanted to. I would enjoy the journey more.

Question 7:

What fears come up when you think about releasing those expectations and just enjoying the journey? What do you worry might happen?

I worry that I won't find success. I fear that I will get lazy or won't work as hard. I worry that time will run out. I'll have a family and kids and not be able to work on the things I want in the way that I want.

Question 8:

Who would you be if you fully trusted yourself—your work ethic, your creativity, your intuition—to guide you toward the life you want? What qualities would you embody?

I would be more at peace. I would be a better friends and person because I wouldn't be jealous of others. I wouldn't be as critical of myself which would help my confidence I think.

Question 9:

What’s one belief or story about yourself that feels the most restrictive or untrue right now? What would happen if you chose to rewrite it?

That I don't have what it takes to be successful. I would feel so much lighter and capable. I think that that belief is probably a self fulfilling philosophy.

Question 10:

When you think about the authentic version of yourself—the person free of masks, roles, and illusions—what does that version of you look and feel like? How does that version of you live day to day?

That person feels at peace. They are capable and confident. They are living life for themselves and not based on waht others think. They would balance being okay wtih life unfolding while being intentional in teh areas they can control. They would have meaningful connections with friends and family, be active, and working on fun things.

Higher Self Analysis of Your Responses

Top Negative Patterns Present in Your Life

1. Comparative Thinking: Measuring your worth and progress against others, especially in career and financial milestones, creates unnecessary pressure and self-doubt.

2. Conditional Self-Worth: Tying your sense of accomplishment to external achievements and timelines undermines your ability to feel successful in the present.

3. Fear-Based Motivation: Fear of failure, running out of time, or not being enough drives you but also drains the joy from your journey.

4. Guilt Around Enjoyment: Feeling you don’t “deserve” fun or rest until you’ve reached a specific level of success prevents you from embracing life fully.

Top Positive Patterns to Embrace and Grow

1. Self-Awareness: You are highly reflective and articulate about your emotions, beliefs, and patterns, which is a powerful foundation for growth.

2. Desire for Authenticity: Your yearning to live more authentically and enjoy the journey is a strong motivator for change.

3. Vision of Success Beyond Work: You value meaningful relationships, personal growth, and peace, which demonstrates a holistic understanding of success.

4. Work Ethic and Intention: You have the drive and intentionality needed to succeed—you just need to balance it with self-trust and joy.

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Daily Affirmations

1. "I trust in my abilities and the unique path I am on."

2. "I am enough just as I am today."

3. "I release timelines and expectations that do not serve my joy."

4. "Success flows from peace and authenticity, not from fear or comparison."

5. "I deserve rest, connection, and enjoyment regardless of external achievements."

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Actionable Steps to Embody Your Authentic Self

1. Practice Gratitude for the Present: Begin each day by listing three things you’re grateful for, focusing on where you are now rather than where you “should” be.

2. Limit Comparisons: Reduce exposure to social media or people who amplify feelings of inadequacy. Create boundaries that protect your mental space.

3. Celebrate Small Wins: Acknowledge progress daily, even if it’s just one step closer to your goals. This will reframe your mindset toward success.

4. Build Self-Trust: Take one small, courageous action daily that aligns with your authentic self—whether that’s a creative project, rest, or reaching out to a friend.

5. Engage in Joyful Activities: Schedule time each week for something you love purely for its own sake—reading, running, cooking, or connecting with loved ones.

6. Reflect on Progress: Journaling weekly about how you’re embodying peace, intention, and authenticity will help you stay aligned with your vision.

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Message of Encouragement from Your Higher Self

Grant, you’ve come so far, even if you don’t always see it. Your willingness to reflect, question, and grow is a testament to your strength and resilience. The version of you that you’re striving to become is already within you—you just need to let go of the stories that tell you otherwise. Trust in your journey, honor your pace, and know that your worth is not tied to a number, a title, or anyone else’s timeline. You are enough. You are capable. And the life you envision is already unfolding beautifully, step by step. Keep going—you’re exactly where you need to be.

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That message is meaningful. It is what I need to hear. It’s strange and uneasy to feel “seen” by something generated by ai. Thanks for reading.

- Grant