Putting my career on the hands of AI

Two years ago I survived and promise I would lead a life of purpose. I couldn't change it on my own so I asked Chat GTP to tell me what to do.

For almost two years now, I’ve been wrestling with the idea of quitting my job — a job that I genuinely love. After a major health incident, my perspective shifted. “I thought you’d quit and become a monk,” someone said to me when I finally returned to the office. But I didn’t quit, and I didn’t become a monk. Instead, I let the question simmer in my mind: If I were to quit, what would I do instead? And tonight, I decided to take a step forward — I hired ChatGPT as my career coach and you as my accountability partner for this journey.

May will mark two years since what feels like a second chance at life. And I can’t bear the thought of reaching that milestone feeling like I’ve done nothing different.

(Though, to be fair, that’s not entirely true. I have changed how I live: I make it a point to carve out time for my loved ones — but somehow, it still doesn’t feel like enough. I send random messages to people who cross my mind, expecting nothing in return, just wanting them to know I’m thankful for them. I say yes more often now — to new adventures, new memories, new people.)

But fundamentally, most weekdays, I’ve taken the same route to the same building. Most evenings, I’ve missed the sunset. And most of the time, I find myself grappling with deep questions: Am I spending my time, my energy, and my capacity on the right things?

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Chat GTP enters the conversation

I thought to myself: It’s now. It’s time. I need to start moving and find some answers. I decided I’d hire a career coach. But then the questions followed: Where do I even find one? How do I make it fit into my schedule? You already know where I landed: ChatGPT.

Here’s what I learned tonight during my career coaching session. My situation:

• You’re bored at work but still find it challenging.

• There’s no clear next step because you're not interested in climbing the corporate ladder.

• Your health incident made you rethink what you want from life.

• You want more freedom (location & time) but don’t have a business idea yet.

• You have financial security but feel hesitant to leave because of your high salary.

• You don’t like aggressive selling, which affects how you’d approach entrepreneurship.

• You’re afraid of losing steady income, which is a valid concern.

From here, we moved into journaling prompts for reflection — fairly obvious ones, but ones I’d never taken the time to actually write down. So, that’s exactly what I did. And here’s what I learned from interpreting my it:

• You’re a natural coach and strategist: You thrive on helping others grow, solving complex problems, and creating meaningful change.

• You value human connections and meaningful work: Your dream career and impact focus are deeply tied to empowering others and leaving a legacy of positive change.

• You crave freedom, creativity, and balance: A location-independent lifestyle with flexibility to combine deep work, exploration, and social interaction is essential.

• You’re grappling with two key concerns:

  • Whether a creative/writing career aligns with your desire for connection and purpose.

  • The fear of losing stability and taking a leap into the unknown.

Okay, I knew all of this already, but there’s something about seeing it written out in words that aren’t your own — it makes you pause and reflect. It’s like holding up a mirror. So now that we’ve laid it all out, ChatGPT, where do we go from here?

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Phase 1 Progress Plan

1. Narrow Your Options
   Let’s focus on two career directions that align with your reflections:

   • Option 1: Transitioning into a location-independent coaching/consulting role where you help others through strategy, leadership, or financial literacy (leveraging your strengths and desire to connect).

   • Option 2: Building a part-time creative career (writing, interviewing, storytelling) that explores human behavior or societal questions, without the pressure of aggressive selling or full-time commitment.

   These options can co-exist and evolve over time.

So far, so good. I’ve tried coaching before, and I enjoy it — but only if I’m doing 1 to 2 sessions per day. Anything more than that starts to feel draining. As for Option 2, I’ve considered it before but have always set it aside. It just doesn’t seem like a viable business model. (To be honest, the same feels true for Option 1.)

2. Actionable Steps for Exploration

Step 1: Start Small Experiments

• Coaching: Offer leadership or career coaching sessions to 2–3 people (e.g., through your network or LinkedIn). Use this to test if coaching feels right for you as a business.

• Writing: Start a blog or small project exploring a big human question that fascinates you (e.g., financial literacy, human resilience). No need to commit to full-time—just start exploring.

So now you know why we’re here. ChatGPT made me do it — this is my little blog project of exploration. And hey, if you know anyone looking for leadership coaching… send them my way.