The 12 Stages of Becoming a Corporate Dropout
Ever feel like you’re living someone else’s life between Monday and Friday, but then on Sunday night, a knot in your stomach reminds you there’s more to the story? If so, you’re not alone.
This guide is for anyone who’s wondered what it’d be like to break out of the 9-to-5 bubble and actually, finally, bet on themselves.
Each stage peels back a layer, revealing more of who you really are - and who you’re bound to become.
1. Comfortably Uncomfortable
You’re comfortably uncomfortable. You're stuck in this place where everything looks fine on paper, but deep down, there's this voice that won't shut up. It's telling you there's more out there.
Signs you're here:
That knot in your stomach every Sunday night isn't just about Monday – it's about the next 40 years of Mondays
You find yourself zoning out in meetings, dreaming about what else you could be doing
Your most creative moments are spent imagining ways to escape this routine
You've mastered the art of looking busy while actually planning your exit
2. Restless
This is where it gets real. You start having these conversations with yourself – usually late at night or during your commute. You know you could do something else, something more, but the "what ifs" are loud. Really loud.
Signs you’re here:
You catch yourself watching entrepreneur videos during your lunch break
Your search history is full of "how to make money online" and "digital nomad lifestyle"
You start seeing your salary differently – not as security, but as seed funding for your dreams
3. The Call to Freedom
Something clicks. Maybe it's a video someone sends you, or a conversation that hits different, or just that moment where you realize your inner identity and your outer shell don't match anymore. You can't unsee it now – the gap between who you are and who you're pretending to be at work.
Signs you’re here:
You start feeling almost physically uncomfortable playing the corporate game
That desire to "just live and create" becomes more than just a daydream
You begin seeing opportunities everywhere, especially outside the 9-to-5
4. The Fear of Letting Go
Here's where it gets messy. You're dancing between your dreams and your doubts, and some days the doubts are leading. The fear isn't just about money – it's about identity. Who are you if you're not your job title?
Signs you’re here:
You find yourself doing late-night calculations about how long your savings could last
Every conversation about "career growth" at work starts feeling hollow
You're torn between feeling crazy and feeling like you're finally waking up
Your family's reactions become both a concern and a motivation
5. The Secret Planning Phase
This is where you start building in secret. You're still showing up to work, but your real work happens in the margins – early mornings, lunch breaks, late nights. You're creating your escape pod while maintaining your cover.
How it shows up::
Your "sick days" mysteriously align with side project deadlines
Your personal laptop has more business plans than Netflix shows
You start seeing your job as funding for your future freedom
Every free moment becomes a mini-workshop for your dreams
6. The Leap of Faith
It hits you: staying is now more painful than leaving. That knot in your stomach when you go to work? It's worse than any fear about what's on the other side. You make the call. Send the email. Have the conversation. You're out.
How it shows up:
The moment you decide, everything feels both terrifying and absolutely right
You alternate between feeling invincible and wondering if you've lost your mind
Time does this weird thing where it both speeds up and slows down
You have this unexplainable sense of peace, even amid the chaos
7. The Freefall
Freedom hits different when it's actually yours. Remember how you dreamed about working from home? Now you're learning that freedom requires structure – just a different kind than what you had before.
Time shifts. Relationships shift. Nothing is what it was.
How it shows up:
You realize Netflix isn't as fun when you're "supposed" to be working
Your relationship with time completely transforms
You discover that pants are optional but systems are essential
The coffee consumption reaches new heights (seriously)
8. The Hustle and Experimentation
This is where theory meets practice. You're testing ideas, failing fast, and learning faster. Every mistake is a lesson, every small win fuel for the journey. Those corporate skills you thought you'd never use again? They're coming in handy in the wildest ways.
Signs you're here:
You become fluent in tools you didn't know existed six months ago
Your definition of "work hours" becomes beautifully fluid
You start seeing results that validate your crazy decision
Your problem-solving abilities evolve exponentially
9. The Identity Shift
The old you is dead. The Corporate Dropout is reborn as a full time business minded creative. From this vantage point your business is poised to scale.
Something profound happens here. You stop introducing yourself with your old title. The corporate armor falls away completely. You're not an ex-[whatever your job was] anymore. You're a creator, a builder, an entrepreneur.
Signs you're here:
You catch yourself giving advice to other corporate dropouts
Your LinkedIn profile finally reflects who you really are
The impostor syndrome starts fading (slowly but surely)
You realize you're not just changing what you do – you're changing who you are
10. The Moment of Clarity
The fog lifts. You're not just throwing stuff at the wall anymore – you know what you're building and why it matters. Your purpose crystallizes, your audience emerges, and your direction becomes clear.
Signs you're here:
Your business model refines itself through real-world feedback
Systems and processes emerge organically
You understand your unique value proposition
Decision-making becomes faster and more confident
11. The Freedom Phase
This is it – the moment you realize you've built something real. Your income isn't tied to your time anymore. You wake up excited about the day ahead. You're living that "just live and create" life you dreamed about.
Signs you're here:
Money flows whether you're at your desk or at the beach
Your schedule adapts to your life, not the other way around
Mondays feel like Fridays (in a good way)
Your work energizes rather than depletes you
12. The Legacy Era
Now comes the full circle moment. You find yourself naturally stepping into the role of guide, helping others navigate their own escape. You're not just sharing tactics – you're sharing transformation.
Signs you're here:
You feel called to share your journey with others
Your story becomes fuel for someone else's courage
You find joy in supporting other corporate dropouts
You realize your struggles weren't just about you – they were preparation for this
That’s why I wrote this memoir.
So even if you don’t have it all figured out. Or you’re ashamed of where you are. You know that there’s a way through and a way out.
It started with honoring your story, because at the end of the day, it’s your greatest asset.
Get your copy now 👇🏽
Where Are You in Your Story?
Tell me where you’re at!
The Corporate Dropout’s journey isn’t a straight line - it’s a helix.
Each stage comes with its own challenges, but every step brings you closer to freedom.
So, where are you right now? Are you still in the Comfort Zone, dreaming of escape? Or are you deep in the Hustle, figuring out your next move? Wherever you are, know that the next step is waiting for you.
