How to Leave a High-Paying Job Without Regret: Break Free from Golden Handcuffs
Stuck in a six-figure job that looks perfect on paper but feels empty inside? Discover how to leave a high-paying job without guilt, and build a career that feels meaningful and aligned.
Feeling Stuck in a High-Paying Job? You’re Not Alone
We don’t talk enough about the quiet crisis that so many high-achievers in Singapore face — being in a job that’s “too good to leave,” yet somehow still feeling stuck.
Golden handcuffs don’t look like chains. They look like six-figure salaries, prestige, business-class flights, annual bonuses, and glowing LinkedIn titles. From the outside, it's success. On the inside, it can feel like a slow burn of disconnection from who you really are, what you care about, and the life you imagined for yourself.
If you're wondering how to leave a high-paying job that no longer fulfills you, this article will walk you through how to:
Recognize the emotional traps keeping you stuck
Reframe guilt into growth
Create a realistic transition plan
Get expert career coaching support from a trusted career coach in Singapore
Here’s how to begin your high achiever career switch— and finally create a path that’s truly yours.
What Are Golden Handcuffs?
Why High-Paying Jobs Are So Hard to Leave
Golden handcuffs refer to the financial and psychological incentives that make it difficult to leave a high-paying job. Think:
A high salary that covers your lifestyle needs (and wants)
A prestigious company name or job title
Years of effort and status you've built in your current role
The fear of disappointing your family or seeming ungrateful
These handcuffs keep you stuck not just financially, but emotionally. And that’s why breaking free isn’t just about money. It’s about mindset.
The Guilt That Keeps You Trapped in a Job You Don’t Love
Common Guilt Triggers for High Achievers in Singapore
One of the biggest blocks I see in clients — especially those attempting a career change without regret — is guilt.
Not fear of failure — but fear of being seen as a failure for wanting something else.
Many of my career coaching clients in Singapore come to me feeling this exact guilt — torn between external success and internal dissatisfaction.
When I work with clients, I often hear:
“So many people would kill for this job. Who am I to walk away?”
“My parents worked so hard to get me here. I can’t just throw it away.”
“I spent years building this career. If I leave now, it was all for nothing.”
I know these words well and it’s not just because my clients say them, but because I used to carry that same weight. The guilt that if I left, I’d be disappointing everyone: my parents, and my younger self who fought so hard to get here.
Why Guilt Isn’t a Good Enough Reason to Stay
But here’s the truth: staying out of guilt is also a form of self-abandonment.
You need to realize that these aren’t just passing thoughts. They’re deeply rooted beliefs that shape our sense of self and responsibility. And if we’re not careful, they become the reason we stay even when we know we’re meant for more.
My Story: The Six-Figures Life That Wasn’t Mine
Six years ago, I was earning six figures in my 20s, working in New York and Hong Kong, climbing the ladder in finance, living the “dream” that many of my peers admired.
But I was quietly unhappy. Is this it? I kept gaslighting myself.
“You should be grateful. You’re lucky. Why can’t you just be happy?”
The truth was, I wasn’t living my life. I was living a life that looked good on paper, but felt hollow inside.
So I left. I built Ctrl Alt Career to help high-achievers in Singapore to redefine success, reclaim joy, and build careers they’re proud of.
✅ Feeling the quiet nudge that you're meant for something more? Book a free clarity call with a career coach in Singapore who gets it.
Don’t Let Guilt Be the Reason You Stay
How Internalised Beliefs Keep High Performers Stuck
The guilt is not a weakness but it’s rather a signal whereas a reflection of internalized beliefs shaped by society, family, and our own unspoken fears.
In Singapore, we grow up learning that success means security. That work is supposed to be hard. That prestige is proof we’ve made it. But just because no one challenges these ideas doesn’t mean they’re true.
We internalize the idea that suffering is noble, that quitting is shameful, that leaving means failure. But what if we flipped that narrative?
Why Career Coaching Can Help You See Things Differently
This is where career coaching becomes more than just guidance — it becomes a mirror, reflecting back what truly matters to you beyond titles and paychecks.
Reframe the Guilt: From Shame to Growth
Mindset Shifts to Help You Let Go Without Regret
One of the most powerful tools I use for a high achiever career switch is reframing. This means looking at the same situation with a different, more empowering lens.
Try these mindset shifts:
“I’m not ungrateful ▶ I’m honoring my truth.”
“I’m not quitting ▶ I’m choosing growth.”
“My parents want me to be happy ▶ not stuck.”
“Walking away isn’t failure ▶ it’s a conscious redirection.”
Mindset is everything. You can be in the same situation as someone else, but your perspective changes everything about how you act.
I see it all the time. Two people, both in high-paying roles they no longer enjoy. One sees it as a trap they can’t escape. The other sees it as a launchpad into something more aligned. Same circumstances, different mindset and it changes everything.
Career Change in Singapore Without Regret: Real-Life Success Stories
From HR to Journalism: Izza’s Story
Izza, Tan Tock Seng Hospital
“I successfully pivoted from HR to my dream job as a journalist in Channel News Asia without going back to school. I even managed to get a pay raise in the process! Thank you so much Jen, I would not have been able to do this without you.”
From Corporate Law to Career Clarity: K’s Journey
K, lawyer
"Before I signed up with Jen, as a 6th year corporate M&A lawyer, I realised this wasn’t the job I wanted in 10 years time but did not know what the next step was.
Working with Jen, I was able to identify my passion, how I derive job satisfaction, transferrable skill sets I’ve gained as a lawyer and plan out my career exit.
I found most helpful her approach of breaking down tough questions such as finances or how to test my business ideas into smaller, more manageable steps, which has made my career transition less daunting and more realistic.
I’ve been feeling more inspired and confident in my decision to leave corporate with Jen’s support.”
it’s not just a lofty ideal, it’s possible.
How to Leave a Six-Figure Job Without Regret
5 Practical Steps to Start Your Career Transition
You don’t need to quit your job tomorrow. But if you’re wondering how to quit a job that pays well but makes you miserable, here’s where to begin:
Identify your limiting beliefs. What stories are keeping you stuck? Write them down. Challenge them.
Redefine success. What does your version of success look like (beyond money or titles?)
Have honest conversations. Especially with loved ones. You may be surprised by how much they support your happiness.
Get support. Whether it’s personalised career coaching, mentor, or community — don’t do it alone. (If you're ready, Ctrl Alt Career is here for you.)
Make a transition plan. Practicality matters. Think through your financial runway, emotional needs, and next steps.
Redefine What Success Looks Like (On Your Own Terms)
You’re Allowed to Change Your Career Story
You may have spent 10 years in law, finance, or marketing. That doesn't mean you owe the next 30 years to the same story.
Just because something has been your path so far doesn't mean it's your forever path.
You’re allowed to change. To switch. To pursue what lights you up.
All it takes is one decision: to no longer let guilt write your story.
Ready to Pivot from “Perfect on Paper” to “Perfect for You”?
Book a Free Clarity Call with Ctrl Alt Career
🌟 Book a free clarity call with a career coach in Singapore who understands high-achiever burnout, six-figure job regret, and how to transition without blowing up your life.
Let’s talk about what’s next — on your terms.