Weekly Coaching: Financial Freedom Is Starting to Look Real
Week 4: day 18 of Letting AI Manage My Career (And It’s Weirdly Working?)
Can’t believe it’s been a whole week since ChatGPT channeled Viktor Frankl in our last session. Time flies when AI is shaping your career choices.
This time, I did something different: I gave my coach (aka AI) total freedom to design the session. I walked in with an open mind, and here’s what it came up with:
February Goals Reminder
📌 Goal 1: Reach 50 Substack subscribers
📌 Goal 2: Complete 3 financial coaching sessions
📌 Goal 3: Countdown to leaving corporate life
No spoilers yet, but there’s one goal I’m abandoning, but we’ll get to that later. First, let’s talk about what ChatGPT, my loyal career coach, had in store for me this week.
🧑🏫 The Coaching Session Structure
Here’s how AI structured my session:
✔ Check-in: How are you feeling about your career/life this week?
✔ Progress Review: Wins, insights, and lessons.
✔ Challenges & Blocks: What’s slowing you down?
✔ Deep Dive Topic: (Audience growth, time management, financial runway, creative fears?)
→ I picked financial runway. Would you have picked something else? Maybe I’ll take your advice next week.
✔ Next Steps: Clear actions before our next session.
Funny enough, ChatGPT decided to name this “Slow Ink Career Coaching.” I didn’t correct it—because, well… that’s the concept. A slow life. A lot of writing. That’s the dream.
💰 Deep Dive: Financial Runway
I’ve been procrastinating taking a hard look at my financial runway—but this is the one thing I want absolute clarity on. I want a plan, so it stops living in the back of my mind as a quiet source of stress.
So, I finally crunched the numbers. Here's the result (assuming I keep my job and my current savings rate until December this year):
Outcome? Seeing years (plural!) of runway is a massive relief.
For the past few years, I’ve been optimizing for salary—which meant more work, more dedication, and even relocating. And now? That work is paying off. I actually have the ability to take a risk. Stepping away from my job won’t be a reckless decision—it’s a well-earned option.
It’s funny… when I write this, it sounds like I’ve been working for 30 years. In reality, 80% of my savings and investments happened in the last three years.
🏆 Progress Review: The Goals Check-In
1️⃣ Financial Coaching Goal – Abandoned (With Peace of Mind)
🎉 I did my second financial coaching session! It was fun—I love helping people feel more in control of their money. But a few things became clear:
There were 1 or 2 questions I couldn’t answer.
I didn’t feel the urge to research and follow up.
I enjoy helping people set up financial systems, but I’m not interested in going deeper into technical financial coaching.
So, I’m stopping here. I can help people analyze their finances, set goals, and create systems—but beyond that, I’m out. And that’s okay.
2️⃣ Substack Growth – 22/50 Subscribers
🎉 We’re growing! We’re at 22 subscribers.
If you know anyone who dreams of leaving the 9-to-5, feel free to share this.
It means the world to have you here on this journey.
3️⃣ Countdown to Leaving Corporate Life – 344 Days to Go
🎉 The number is shrinking! 344 days until freedom.
And my favorite part of the past week? Writing these articles.
Not just the writing itself—but the conversations it sparks afterward.
The comments, the emails, the texts—your thoughts help me refine my own thinking and writing.
🔜 Next Steps: Planning the Exit Strategy
What’s the plan? A roadmap for leaving my job, hitting financial freedom, and transitioning into the next phase without panic. That’s the dream, anyway. Dreams are free.
✅ Target Financial Cushion: Accelerated savings plan to hit my new financial goal by June.
✅ Exit Timeline: Dec 2025 - Feb 2026 (but only after validating some income streams).
✅ Growth First, Monetization Second: Full focus on growing this substack (and any other passion projects like Slow Ink) first—then monetization once I hit 500 subscribers (goal: Summer 2025).
✅ Experiments Before Quitting: If I reach 500 subscribers before my planned exit, I’ll start testing monetization. But either way, I’ll quit with a solid financial cushion.
💬 A Note
You might notice I’m not disclosing exact monthly figures—and that’s intentional.
💡 Why? I don’t want anyone to compare their situation to mine. Everyone’s financial journey is different. Instead, I want to share principles you can apply to your own case.
But if there’s a specific area where more transparency would help, let me know. I’m open to your feedback.
Final Thoughts
This was a big clarity week. Some things clicked into place (financial runway!), and some things got left behind (financial coaching). I guess this exactly what this process should look like —refining what’s worth keeping and what isn’t.
Now, out of curiosity: if you had to pick a deep dive for next week, what would it be?