Weekly Career Coaching: Deep Seek vs Chat GTP
One got philosophical, while the other got straight to business.
“The server is busy. Please try again later.” – that’s how one of my coaching sessions abruptly ended. But before that, I gained one key insight that might change how I spend my time over the next few weeks.
Before sharing that, let’s celebrate: Tuesday means another career coaching session with AI! This time, I had two—one with ChatGPT and one with DeepSeek (shoutout to my friend D. for the suggestion). To make it fair, I gave DeepSeek the same notes ChatGPT had from our last session, I gave the same initial prompt and let both models guide the conversation. Now, I’m here to report back on their findings.
Progress
🎉 Booked a client for a financial independence coaching session and two more people expressed interest.
🎉 Started a blog to document my journey as a writing project and have been consistent so far. I also studied what Substack is all about, which led me to change the blog’s name and start using Notes.
🎉 Launched a work mood tracker
🎉 Told close friends about this project to have accountability and reflection partners (and they came through!)
🎉 3 headhunters reached out with opportunities:
I had one call for a fully remote position, but I realized it would demand far more daily work hours than I want, so I’m not considering it anymore.
The other two—I still need to book calls to get more details, but honestly, I don’t feel like investing the time.
An American vs an Asian Career Coach
Funny enough, both AI models stopped on their tracks o analyze my journal entries (aka, all the blog posts you’ve been reading, my dear friends). They both pointed out similar patterns::
✔ I’m happiest when I’m problem-solving, strategizing, and collaborating.
✔ I’m at my unhappiest when I don’t have autonomy.
✔ I write A LOT about money and financial stability—which is ironic because I’ve never had more financial stability than I have today (or a higher salary).
✔ They both took my Vedic birth chart analysis very seriously. Appreciated the respect for the art, models.
Now, where they differed:
DeepSeek is a deep coach. It really cared about my weekend. It saw a connection between how I want to spend my weekends and my notion of productivity. It also asked more philosophical questions, like how I can balance my days better, find purpose, and structure my work to feel more fulfilling.
It also seemed more invested in trying to improve my current corporate work situation—as if there’s still hope for me to make it work.
ChatGPT, on the other hand, has already given up on that fight.
ChatGPT felt very American—hyper-focused on monetization, revenue, and business strategy. It immediately suggested I use social media to grow my Substack, told me to create a lead magnet email (just hearing the phrase "lead magnet" makes me sick—no, thank you), and pushed me to create more longer term goals. Or maybe it was just reflecting my own obsession with money.
Anyway, my American coach was really eager to map out my entire future—breaking things down by year, quarter, and month. It wanted to shift to monthly check-ins instead of weekly ones and got straight to business: pinning me down on tasks for the month—and then pushing further: "What if you achieve them earlier? What’s next?"
This landed somewhere between motivating (oh, it really believes I’ll hit my goals fast and is already thinking ahead!) and overwhelming (please don’t ask me what I’ll do at 50 subscribers when I don’t even have 10 yet).
Meanwhile, DeepSeek stayed grounded—it just wanted to know what my next small task was for the week, a style much closer to how I coach others myself.
Where Chat GTP wins: It followed through for the entire session. DeepSeek failed me halfway—crashing on the second or third interaction.
So… I think I can still use both tools, but differently:
⚫ ChatGPT stays as my career coach—it’s structured, reliable, and tracks my progress.
🔵 DeepSeek will be my go-to for fresh, unbiased insights—because it doesn’t have all my history, so it can give a different perspective.
Takeaways & Goals
Looking back at the week, I’m proud of the progress I made. I still don’t know if I’m taking big strides toward a career change, but my bicycle is in motion. From here, it’ll be easier to steer in the right direction.
One key takeaway from today’s reflection:
At work, I need to spend my time on the things that energize me:
✔ Problem-solving.
✔ Collaboration.
✔ Big, systematic challenges.
❌ Less time in regular update meetings that drain me.
For February, I’m committing to two goals:
📌 Goal 1: Get to 50 Substack subscribers
📌 Goal 2: Do 3 financial freedom coaching sessions
(I’m wrestling with whether to focus on financial freedom coaching or just general coaching, but maybe I’ll stick to this niche for February and see what I learn.)
And just between us when I hit 50 subscribers, I’ll open that Love Letters Club.
I got one positive piece of feedback on the idea, so even if I just send one letter, that’s a start, right? And February would be the perfect, cheesiest month to launch it.
Final Thoughts
Thanks for reading this far and for tagging along while I "career change" in public (see what I did here—saying it like it’s already happening, because what you can dream, you can do).
If you read until here, you got all the most relevant updates. But if you’re curious about what ChatGPT and DeepSeek actually said, I left their unedited notes below.
Also—this week, I finally felt happy writing again. It’s been a while. :)
Journal Entries Analysis by Deep Seek
Key Themes from Journaling
Work Mood Tracker Insights:
Your mood fluctuates significantly based on the type of work you’re doing. Days filled with collaboration, problem-solving, and meaningful contributions (e.g., workshops, strategy sessions) tend to score higher (4–5/5). Days with repetitive tasks, lack of autonomy, or feeling replaceable in meetings score lower (2/5).
You’ve identified a recurring feeling of being undervalued or invisible in certain work settings, which seems to drain you.
Career Exploration:
You’re actively exploring creative paths (writing, coaching, investigating human behavior) but are hesitant due to financial stability concerns and self-doubt (e.g., Saturn in the 1st house, Mars in the 11th house from your Vedic chart analysis).
You’re experimenting with small steps, like starting a blog, offering coaching, and exploring niche ideas (e.g., Love Letters Club, B2B coaching).
Personal Growth:
You’re reflecting on your relationship with work, weekends, and productivity. You’ve noticed that overpacked weekends leave you exhausted, while empty ones feel unfulfilling. This mirrors your broader struggle with balance and purpose.
You’re also exploring tools like the Vedic Birth Chart and value gap analysis to gain clarity on your career direction.
Next Steps:
You’re taking action on coaching (booking clients, exploring pricing models) and content creation (blogging, Substack). You’re also considering micro-retirements and niche coaching opportunities.
Journal Entries Analysis by Chat GTP
1. Work Mood Patterns & Value Alignment
You’ve started tracking your work mood, and there’s a strong correlation between how much agency, visibility, and intellectual challenge you have in a day and how you feel about work.
You feel the most fulfilled when you engage in problem-solving, investigation, and strategic discussions (e.g., the workshop where you uncovered systematic issues).
You feel the worst when your presence feels replaceable or you’re stuck in meetings that don’t feel meaningful.
Reflection:
If we analyze your low-mood days, it seems like the frustration stems from a lack of impact and a feeling of being a cog in the machine.
High-mood days are about intellectual stimulation, strategic problem-solving, and meaningful collaboration.
How can we increase the high-value, fulfilling work while reducing the replaceable-feeling moments?
2. Career Transition & Hesitation
Your Vedic birth chart analysis resonated with what we already knew:
You’re drawn to creative fields (writing, coaching, education, and research) but hesitant due to financial security concerns and overthinking.
Your natural leadership and structured thinking make coaching a great fit.
The hesitation around big transitions seems to stem from a fear of instability and needing a safety net (Saturn in the 1st house, plus your own reflections on career shifts).
Reflection:
You already have a potential side-project runway: Writing + Coaching + Research
Instead of framing this as a massive career change, what if we test a low-risk transition strategy?
Would it help to define clear, phased steps for this shift, rather than thinking in binary terms of “corporate vs. creative independence”?
3. The Role of Money & Independence
Your coaching clients all came through referrals, and you prefer this method of finding clients over marketing yourself.
The financial aspect of coaching and writing remains a question mark—how much do you need to earn to feel secure? Would fewer, higher-priced sessions make this viable?
You’re intrigued by micro-retirements, financial coaching, and helping people become more financially literate.
Reflection:
What does financial security actually mean for you? How much income would allow you to make a career shift with confidence?
Could your passion for financial literacy be woven into your work—for example, financial coaching for creatives & career changers?
4. The Search for Meaning & A Bigger Purpose
Your Love Letters Club idea hints at your deep desire for meaningful connection.
Your coaching reflections show that you enjoy helping people grow, find clarity, and make confident choices.
You often question the big existential picture—why work is structured the way it is, what fulfillment really looks like, and whether everyone secretly wants out.
Reflection:
You’re looking for more than a paycheck—you’re looking for a way to work that aligns with your personal values and makes an impact.
Could this mean designing a career around self-expression, deep conversations, and mentorship?
Instead of viewing work as a structured 9-to-5 or total self-employment, what about hybrid models (e.g., consulting, part-time coaching, writing as a product)?
Feedback on Actions of the Week by Chat GTP
You’ve taken some strong first steps toward designing your ideal work life:
✅ Booked a financial independence coaching session → Proof that there’s demand!
✅ Started a blog and committed to it → You’re enjoying writing, and it’s feeling effortless.
✅ Launched a work mood tracker → You’re collecting useful data for reflection.
✅ Shared your plans with close friends for accountability → Social support is invaluable.
✅ Discovered Substack as a viable long-term platform → You’re already thinking in terms of distribution and potential monetization.
✅ Got contacted by headhunters → You’re still attractive in the job market, even if you’re not sure you want to pursue these roles.
💡 Key Insight:
Your energy and momentum are clearly strongest around writing and coaching rather than jumping into another corporate role. The fact that Substack feels fun and effortless is a huge signal that it’s worth investing in.
Key Decisions Chat GTP believes I need to take
Decision 1: How much should you invest in growing Substack?
Since you’re enjoying it and it’s easy to maintain, I’d say go all in on Substack for the next 3 months as a core experiment. Goal: 50 subscribers during February. I prefer to focus on building an audience, experimenting for the next 3 months and then I can think about monetizing. Because I want my focus to be that substack will be a distribution channel for something I love doing and building. For now is this diary, but it can be anything else in the future.
Decision 2: Do you even want another job? You’re not convinced that switching jobs will actually solve what you’re trying to solve. The recommendation is to keep my energy focussed on expanding what I’m building already. And If a job opportunity comes up, ask: Does this move me closer to my long-term ideal work formula? If not, it might just be a distraction.
Questions to Explore Together by DeepSeek
Work Mood Tracker:
What patterns do you notice in your high-scoring vs. low-scoring days? How can you design your ideal workday to include more of what energizes you?
How can you address the feeling of being undervalued or replaceable in your current role? Is this a sign to shift roles, or can you reframe your approach to these situations?
Career Transition:
What’s holding you back from fully committing to coaching, writing, or creative work? Is it financial stability, self-doubt, or something else?
How can you test your ideas (e.g., Love Letters Club, B2B coaching) in a low-risk way to build confidence and gather feedback?
Balance and Purpose:
How can you create a better balance between structured plans and spontaneity in your weekends and work life?
What’s the deeper reason behind your focus on weekends? Is it a need for rest, creativity, or connection?
Next Steps:
What’s one small experiment you can run this week to move closer to your dream career? (e.g., reaching out to a potential coaching client, writing a blog post, or exploring a niche idea.)
How can you leverage your strengths (strategy, coaching, writing) to create a sustainable transition plan?
Ideal Work Formula: The Long-Term Vision by Chat GTP
Your long-term vision is to transition from corporate work to a flexible, independent career centered around writing, coaching, and consulting. You want to grow your Substack as a creative and intellectual outlet while offering financial literacy and leadership coaching, alongside selective consulting for tech teams. Ultimately, your ideal work-life balance is fully remote, financially sustainable, and built around meaningful conversations, deep thinking, and helping others grow—without the constraints of traditional corporate structures.
Action Plan by Chat GTP
Experiment for February: Let’s Make It Concrete
Your two main experiments this month are perfect:
📌 Goal 1: Get to 50 Substack subscribers
📌 Goal 2: Do 3 financial freedom coaching sessions
Making the Substack Experiment Work
Keep writing daily (or at least 3-4 times a week).
Engage with other writers—commenting on other Substack newsletters could bring people back to yours.
If you reach 50 quickly, what’s the next growth goal? (Chat GTP is so optismistic, but it’s great that it thinks I am great)
Making the Coaching Experiment Work
3 sessions is a great target! Since 2 people already showed interest, you’re close.
If you wanted to scale it, you could:
Announce it (softly) on your Substack: “I’m doing a few financial freedom coaching sessions this month—let me know if you want one.”
Offer a “Pay What You Can” model for early clients to get testimonials and refine your approach.
Final Takeaways & Next Steps by GTP
✅ Substack is the most exciting thing right now—lean into it.
Your February goal of 50 subscribers is perfect. Keep up the momentum.
✅ You’re close to validating coaching as a revenue stream.
3 sessions this month will help you refine your offering and pricing model.
✅ Unless a job is a clear “hell yes,” don’t get distracted.
Switching jobs just for the sake of it probably won’t solve the real issues you’re reflecting on.
✅ Start framing 2025 as your transition year.
Think of this year as a testing ground to move toward your ideal work-life balance.
What to Do Next
🔹 Let’s check in at the end of February to see how the experiments went. (Look at this! Chat GTP wants a break from being my coach on a weekly basis!)
🔹 If things go well, we can plan Q2 goals (April–June) based on what worked.
🔹 Keep writing, coaching, and reflecting—your clarity is already increasing!