Anatomy of a Resignation

Introduction

I’m starting to lose track of how many people have left my team in the two years I’ve been here.

When my first and second manager at PayNet recently stepped down, I wasn’t as distraught as I thought I’d be.

Perhaps that’s what happens when you’ve witnessed too many goodbyes, planned too many parting gifts and thrown enough farewell luncheons. After witnessing so many resignations over the years, I had slowly become desensitised to them.

To some extent, this shouldn’t come as a shocker. Life, after all, is a revolving door. People walk into our lives, leave their mark, and then continue on their own paths.

Some departures arrive suddenly; others are anticipated long before they happen. Yet each one serves as a reminder that nothing can ever resist the tides of change.

As I sat in the usual NPE traffic on my way to work today, I did what I assume many of us do to cope with the Monday blues: I opened Instagram and started doom-scrolling.

That’s when I stumbled upon a reel that piqued my interest and curiosity:

The reel got me thinking so deeply that when I finally arrived at the office, I stayed in my parked car for several minutes just to sit with my thoughts.

By the time I walked into the office, I already knew I wanted to write about it. Not to rehash what he had said, but to build upon it with my own observations and reflections after spending the last few years watching colleagues, friends, managers, and mentors come and go.

My First Resignation

The first of anything is almost always memorable. I still remember my first resignation from Dell with somewhat vivid clarity.

Long before I submitted my notice, I had already spent more than a year wrestling with the decision in my head. When I finally shared my intentions with those closest to me, the reactions were predictably varied.

Some (especially my family members) responded with cautious neutrality. They weren’t necessarily against the idea, but they wanted to make sure I had thought everything through and wasn’t making a decision I’d later regret.

Others were more discouraging, pointing out that I would be walking away from two hard-earned years of building my reputation, credibility, and social capital within the company. Perhaps if I voiced out my struggles to my manager and sprinkle a bit more hope that things would improve, I’d be rewarded for my loyalty and perseverance.

Interestingly, my close friends at the time took the opposite stance. They were the most supportive of the move, arguing that I was underpaid, underutilised, and underappreciated for the effort and talent I brought to the table. In their eyes, leaving wasn’t a loss. It was long overdue.

Looking back, what strikes me most is how none of these perspectives were entirely right or entirely wrong. They were simply different lenses through which people viewed the same decision.

Like most resignations, the journey rarely follows a straight or obvious path. It is often filled with uncertainty, self-doubt, second-guessing, and countless internal debates. A process of weighing who you are today against who you want to become.

Over time however, certain patterns begin to emerge to make it easier to recognize when it may be time to move on.

Removing Pathos from the Equation

The decision — or even the mere thought — of resigning comes with a great deal of emotional baggage.

I’ll admit that the idea has crossed my mind countless times, especially after particularly stressful periods at work.

If you asked my closest colleagues, they’d probably tell you they’ve lost count of how many times I’ve declared that I wanted to quit, only to show up the next day carrying on as usual… well, at least, not yet.

The reason is simple: Emotions are often at their loudest when we’re exhausted, frustrated, or disappointed. A difficult project, a conflict with a colleague, an unfair outcome, or a prolonged period of stress can make resignation feel like the most obvious solution in the moment.

But decisions made in the heat of emotion are not always decisions made with clarity. That’s why it’s important to separate the feeling from the fact.

As Raymond rightly pointed out, we should approach the question of resignation rationally and focus on identifying patterns rather than reacting to isolated incidents.

Just like the old adage “one bad day is not a bad life”, one bad week does not necessarily mean it’s high time to leave. Neither does a difficult project or an unpleasant conversation.

The more useful question is whether these experiences are recurring themes rather than one-off exceptions.

Are you occasionally stressed, or are you chronically burnt out?
Are you facing a temporary setback, or are you repeatedly encountering the same obstacles with no meaningful improvement in sight?
Are you dissatisfied because of a recent event, or because the role no longer aligns with what you want from your career?

The answers often reveal far more than the emotions themselves.

Retreating into the Shadows

One of the clearest signs that it may be time to take a leap of faith is when your personality begins to change.

You go from being vocal and proactive to quiet and withdrawn. You stop raising your hand. You stop speaking up. You stop making yourself visible.

A useful exercise is to compare how you behaved when you first joined the team versus how you behave today.

If you no longer recognise that version of yourself, then it is worth asking a difficult question:

Are you choosing this silence strategically?

For me, the answer was an unequivocal yes.

During my second year at Dell, I withdrew so much that some colleagues genuinely thought I had already resigned for good.

I went from volunteering as an emcee and committee member for various company events to barely showing up in the office unless absolutely necessary. I stopped putting myself forward. I stopped participating. I simply focused on completing my work and going home.

I stopped going out of my way to do more than what was expected from my role because, frankly, I no longer saw the point of it.

Looking back, the transition was admittedly abrupt and borderline unforgiving. Perhaps I could have handled it with more grace. But I cannot deny that it was intentional.

What I was experiencing was, in many ways, quiet quitting before I even knew the term existed.

The danger of prolonged frustration is that it risks no longer being contained within the workplace. Left unaddressed, burnout has a way of reshaping your whole identity. The enthusiasm, curiosity, and confidence that once defined you begin to erode.

As a staunch believer in self-compartmentalisation, that’s a huge violation of separation of concerns for me. What happens at work should not have a spill-over effect into my personal life.

Perhaps even more concerning is the impact on your professional reputation. Every time you choose to retreat into the bare minimum, you diminish your visibility, your influence, and your leadership presence.

When people stop hearing your voice, seeing your presence, or feeling your impact, they naturally stop associating you with opportunities, influence, and leadership. Not because you have become less capable, but because you have become less seen.

In other words, the less people hear from you, the less they think of you when opportunities arise. And that, more than anything, is why this particular sign should never be ignored.

When Rest Stops Working

This next pattern begs an important question:

What is the nature of your tiredness after work?

Most of us work five days a week and spend the remaining two days resting, pursuing personal interests, or spending time with the people we care about.

Under normal circumstances, the fatigue we accumulate throughout the week gradually fades over the weekend. We may not return on Monday feeling completely rejuvenated (I mean… who does?), but we are rested enough to begin another week and repeat the cycle once more.

But what happens when the exhaustion never really leaves?

For instance, have you ever taken an extended break or gone on a holiday, only to find that the dread returns the moment the end of your leave approaches?

You spend days resting, recovering, and enjoying yourself. Yet come Sunday evening, the mere thought of Monday triggers an immediate reaction.

Your chest tightens. Your breathing becomes shallow. Your mood plummets to near rock bottom. Suddenly, all the peace and joy you’ve spent the past week cultivating seem to evaporate into thin air.

This is what Raymond refers to as environmental damage.

At this stage, it is no longer ordinary fatigue that can be solved with just a good night’s sleep or a short vacation. It becomes psychological resistance — a sustained response to an environment that your mind and body have gradually learned to associate with stress, anxiety, or discomfort.

The troubling part is how normalised this experience has become. Yet many of us convince ourselves that these feelings are simply part and parcel of being an adult.

Think about it. Most of us will spend decades working until either when we retire or when we die — whichever comes first. There are 52 weeks in a year, and many people will remain in the workforce until their sixties.

If work occupies such a significant portion of our lives, can we honestly call it normal to spend all those years operating in a constant state of tension and emotional survival?

The longer we spend surviving internally, the harder it becomes to show up confidently externally. What begins as exhaustion gradually becomes disengagement. What begins as self-preservation slowly turns into self-withdrawal.

So it’s either you let that environment change you, or you change the environment. It’s your call.

The Complacency Trap

Career growth is one of the biggest reasons people choose to stay or leave. That is why discussions about promotions, compensation, and responsibilities inevitably surface in almost every productive 1-on-1.

Beneath all of those conversations lies a much simpler concern:

Am I still moving forward?

I don’t know about you, but stagnation scares the living hell out of me. It brews mediocrity and complacency in the long run.

You see, comfort on its own is not the problem. The problem begins when comfort stops being a by-product of growth and starts replacing growth altogether.

Raymond described complacency of career momentum using five simple indicators:

1. No new learnings
2. No sharper thinking
3. No stronger contribution
4. No bigger exposure
5. No increase in confidence

What I like about this framework is that it focuses on momentum rather than titles. Something I talked about in my old blog post.

Many people equate growth with promotions, managerial responsibilities, or larger paychecks. Those things obviously do matter, but they are often lagging indicators. Real growth happens much earlier through the accumulation of skills, experience, perspective, and confidence.

A useful question to ask yourself is:

Are you significantly more valuable in the market today than you were twelve months ago?

Not whether you’ve worked hard. Not whether you’ve remained loyal. But whether your capabilities have meaningfully improved.

Can you solve harder problems?
Can you operate at a larger scale?
Can you navigate more ambiguity?
Can you contribute in ways you couldn’t a year ago?

My answer to that question was far more complicated when I was contemplating my own resignation.

On one hand, I had undoubtedly grown. I became more confident communicating with people, navigating difficult conversations, managing expectations, and operating within the realities and framework of a large organisation.

In many ways, my soft skills improved dramatically. Yet it was my hard skills that kept me awake at night.

While some of my peers were building platforms and applications used by thousands or even millions of people within mature engineering environments, I found myself working on internal systems with limited reach, unclear requirements, and little opportunity to learn from experienced engineers.

Whether that perception was entirely fair deserves a separate discussion altogether. But perception matters. The longer I stayed, the more I found myself wondering if I was falling behind.

It goes without saying that today’s job market is far less forgiving than it once was. Skills that were highly sought after a few years ago can become table stakes almost overnight.

And perhaps that is why career growth remains one of the strongest predictors of resignation. People can tolerate long hours, difficult projects, and even occasional frustrations when they feel they are becoming better versions of themselves. But the moment they believe their growth has plateaued, the psychological contract begins to weaken.

Conclusion

The anatomy of a resignation is rarely dramatic.

More often, it is a collection of small fractures that accumulate over time: a growing sense of stagnation, a gradual withdrawal from the things that once excited you, persistent environmental stress, and an increasingly difficult time imagining a future version of yourself in the same place.

Individually, each sign is easy to dismiss. Together, they tell a broader unmistakable narrative.

To be clear, none of this automatically means you should resign. It would be foolish for Raymond or me to pretend we have discovered the holy grail of career decisions.

Sometimes the answer is a difficult conversation. Sometimes it is a change in team, scope, leadership, or expectations. Sometimes the problem can be fixed.

And sometimes, it all boils down to one’s gut feeling.

But by the time most people submit their resignation letter, that story has usually been written long before the document itself. So before deciding whether to stay or leave, it is worth paying attention to and cross-checking the patterns.

I was fortunate that my first resignation was met with understanding rather than resistance. My manager at the time accepted the news with a level of grace and kindness that I still remember years later.

I’ll never forget what he told me during our 1-on-1.

“You’re a nomad, Ray. You’re someone who leaves.”