Quitting a job, especially one you’ve dedicated years, perhaps even decades to, isn’t just a career move; it’s a profound life event, particularly if you do not have another job to go to. For me it was the culmination of countless hours of contemplation, a cocktail of excitement and trepidation, and the first concrete step towards a new vision for life. If you’re reading this, you might be on the cusp of this decision too, or perhaps you’ve already taken the plunge. Either way, you’re not alone.

It’s June 13th 2025. I’ve logged on to my work laptop and my first task for the day is to contact my manager to break the news that I’m going to be leaving my job. My heart hammered against my ribs like a trapped bird. This was it. The culmination of months, no, years of quiet contemplation, late-night spreadsheet sessions, and hushed conversations with my wife. Today was the day I was actually resigning from a career I’d built up over about 25 years – a job I worked immensely hard to get and maintain, a job that had defined a significant portion of my adult life and provided a security I’d grown so accustomed to.

The Emotional Rollercoaster: Hopes vs. Fears

The Morning Of: A Cocktail of Nerves and Anticipation

The moment you decide to escape the grind, or even just seriously entertain the thought, your mind becomes a battleground for competing emotions. This isn’t like resigning from one job to start another! This is much, much bigger!

I woke up this morning feeling strangely calm, yet with an undercurrent of electric anticipation. It was like the calm before a storm, or perhaps, the quiet after a storm I’d been weathering internally for so long. The decision was made. The “what ifs” had been analyzed to death.

The Fears:

  • Financial Insecurity: This was the loudest voice. “What if I can’t make ends meet?”, “What if things don’t work as planned?”, “What if all my calculations are wrong?” Decades of reliable income create a strong sense of security that’s terrifying to relinquish.
  • Loss of Identity: For many, our jobs become intertwined with who we are. “If I’m not a Senior Platform Engineer, then who am I?”
  • Fear of the Unknown: The structured path is familiar. The unstructured, self-defined path ahead can feel like stepping into a thick fog.
  • Regret: “What if I’m making a huge mistake?” “What if I miss my colleagues, the routine, or even the challenges I’m trying to escape?”
  • Letting People Down: Whether it’s family, mentors, or colleagues, there is a perceived pressure, maybe even a genuine concern about how the decision impacts others.
  • The Great Unknown: The corporate ladder, for all its faults, is a known quantity. This new path? It’s a route that doesn’t even have a map!

The Hopes:

  • Freedom and Autonomy: The allure of setting my own schedule. Not answering to an alarm and not spending endless hours staring at a computer screen.
  • Purpose and Passion: The chance to align my life with what truly excites me and gives me a sense of meaning. I want to feel alive, not to just be living!
  • Authenticity: The opportunity to build a life that feels more true to myself, rather than one dictated by external expectations.
  • The Sweet Taste of Freedom: The idea of owning my time, choosing my projects, and building something on my own terms was intoxicating.
  • Chasing Purpose: I yearned to do work that felt deeply meaningful, something that aligned with my core values, not just a company’s bottom line.
  • A Life Reclaimed: More time for wife and family, for health, for simply being rather than constantly doing.

It’s crucial to acknowledge both sets of emotions. They are all valid. The fears don’t necessarily negate the hopes; they simply highlight the stakes involved.

The Conversation: “I’m Resigning.”

Letting Go of the Golden Handcuffs

The company I work for is deeply impersonal. A global monster of the tech sector where resigning is as simple as pressing a ‘start separation’ button on web app. Neverless, I wanted to speak with my manager first, not because I had a close relationship with him or anything like that, I’ve probably only spoken to him half a dozen times in the last two and half years, but because I felt it was the right thing to do.

I’d rehearsed the conversation with my manager a dozen times in my head. I wanted to be professional, grateful for the opportunities, but firm in my decision. I wanted to make it clear this was a lifestyle choice and nothing against the company. Subconsciously I probably wanted to ensure the door was open should things go wrong and that no bridges were burnt.

I sent a message on Slack to see if my manager was available for a chat and waited in anticipation. When the answer came, it was not what I expected! ‘Sorry but no’ and with that my resignation plan was wrecked! I replied and said ‘No problem, I’d like to resign’ then headed off to the portal, hit the ‘Start Separation’ button then completed my days work before heading off for a pre-arranged vacation. I’ll be back in 10 days to see the response!

That reliable income stream has just been firmly cut off. The income stream that has paid the mortgage, funded holidays, and built a comfortable life will soon be gone. The golden handcuffs have been unlocked. It was secure and predictable, but it also kept me tethered to a situation that no longer serves my well-being or happiness.

Giving this up has required a significant mindset shift:

  • Redefining Security: Is security solely about a consistent pay packet, or can it also be found in your skills, your adaptability, your network, and your ability to create value in new ways?
  • Understanding Your True Financial Needs: Often, we overestimate what we need versus what we’ve become accustomed to spending. A period of financial planning and honest budgeting is eye opening.
  • Building a safety net: Having savings or a plan for initial income (even if smaller) can significantly reduce the financial anxiety of the transition.

This isn’t about being reckless; it’s about making a calculated decision that prioritises long-term mental and physical well-being over financial gain and material possessions.

And now it’s done. A palpable weight has lifted off my shoulders. It isn’t just relief; it’s a surge of exhilaration mixed with a healthy dose of “Oh my god, what have I just done?!”

Advice for Fellow Leapers

Reflections on That Day & Advice for Your Own “Leap Day”

If you’re contemplating or navigating your own resignation from the daily grind, here are a few thoughts that might help:

  1. Plan, Don’t Panic:

    • Build a safety net: As mentioned, save as much as you can. Know your numbers. Create a lean budget for the transition period.
    • Skill Audit: What skills do you have that are transferable? What new skills might you need, and how can you start acquiring them?
    • Network: Talk to people who have made similar transitions. Build connections in your community or the field or lifestyle you’re moving towards.

  2. Define Your “Why”:

    • What is driving this change? What kind of life are you trying to build? When the inevitable doubts creep in, a strong “why” will be your anchor. Write it down. Revisit it often.

  3. Prepare for the Conversation (and the Paperwork):

    • Know what you want to say to your manager. Keep it professional and concise.
    • Have your resignation letter drafted. A simple, formal statement of your intent to leave and your last working day is sufficient.
    • Don’t burn bridges, you never know when you may need them!

  4. Embrace Imperfection:

    • Your first step into the new unknown doesn’t have to be perfect. You don’t need to have all the answers. It’s okay to iterate, to learn as you go, and even to “fail”. We all learn more from failure than we do from success.

  5. Acknowledge the Emotions:

    • It’s okay to feel scared, excited, sad, and relieved all at once. It’s a big deal! I certainly felt a strange mix of grief for the chapter I was closing and pure giddiness for the one I was opening.

  6. The Act of Resigning:

    • Be Professional: Resign gracefully. Give adequate notice, offer to help with the transition, and leave on good terms if possible. You never know when paths might cross again.
    • The Conversation: Be prepared for various reactions. Stay calm and stick to your decision.

  7. Plan Your “What Next” (Even if it’s just for the rest of the day):

    • After the news is delivered, what will you do? I simply carried on with my day and let the reality sink in later. Maybe you’d prefer to take a long walk or celebrate with a quiet dinner with your partner/family.

  8. Manage Your Mindset:

    • Celebrate Small Wins: Acknowledge your courage and every step forward, no matter how small.
    • Seek Support: Lean on friends, family, mentors, and others who understand and support your journey.
    • Ignore the Critics: Some people will inevitably feel what you are doing is wrong and may even criticise heavily. Try to remember, no statue has ever been erected for a critic!
    • Be Patient with Yourself: There will be good days and bad days. This is a marathon, not a sprint.

  9. Remember, It’s a Beginning, Not Just an End:

    • While you’re closing one door, you’re standing on the threshold of something new. The fear of giving up that “secure and reliable income” is immense, especially after decades. But the hope for a life designed on your own terms can be an even more powerful force.

  10. Look After Yourself:

    • The transition can be stressful. Prioritize your physical and mental health. Ensure you’re getting enough sleep, eating well, and exercising.

The First Day of the Rest of Your Life

The Other Side

The day I quit wasn’t just about leaving a job; it was about choosing a different way to live and work. It was about betting on myself. The path ahead is still unfolding, with its own set of challenges and triumphs, but the feeling of taking that first, decisive step? Unforgettable.

Resigning from a secure job is undeniably daunting. It means trading the known for the unknown, the predictable for the potentially chaotic. But it also means opening the door to immense possibility – the possibility of a life lived more intentionally, more aligned with your values, and filled with a different kind of richness.

The fear is real, but so is the potential for incredible growth and fulfillment. If you’re on this path, trust your preparation, believe in your “why,” and take that brave step forward. The view from the other side might just be everything you’ve hoped for. If you’re standing at a similar crossroads, know that the fear is normal. The uncertainty is part of the adventure. But the potential for a life more aligned with your deepest aspirations is worth exploring.