How to Leave a High-Paying Job in Singapore (Without Regret or Starting Over)

Outgrowing a Dream Doesn’t Make You Ungrateful

Why High Achievers in Singapore Struggle to Leave High-Paying Jobs

In high-performance cultures like Singapore, there's often an unspoken pressure to stick with the career you worked so hard to build. You’re told to be grateful, to stay the course, to never waste opportunities.

But here’s the truth: you’re allowed to change your mind. You’re allowed to want something more. And that doesn’t make you ungrateful — it makes you human.

As a career coach in Singapore, I often hear things like:

“I worked so hard to get here. Why do I still feel empty?”
“I used to love this job. Now I dread Mondays. What’s wrong with me?”
“Am I just being ungrateful?”

If you’ve ever felt guilty for wanting more and for dreaming of something else, even when your LinkedIn looks perfect — you’re not broken. You’re evolving.

Why It’s So Hard to Quit a High-Paying Job in Singapore

When I was working at BlackRock, that was my dream.
Make good money, build credibility, feel my parents’ pride when they told relatives, “Jennifer’s working on Wall Street.”

For years, that goal lit me up.
Until it didn’t.

I craved creativity, human connection, purpose. But walking away from a six-figure job felt like betraying my past self — the one who worked so hard to get here.

But letting go of a dream that once defined you is heavy. It’s grieving a past self. It’s confronting your ego, which tells you walking away means failure. It’s living in that awkward limbo where you haven’t quite shed your old skin, but you’re not fully living in the new one yet either.

That’s why so many people stay stuck in high-paying jobs they secretly hate — because playing it safe feels easier.

Why Changing Careers Isn’t Failure — It’s a Sign of Growth

There’s a belief that once you choose a path, you have to stick with it forever. Especially if you’ve invested years or gotten a Master’s degree.

This is a classic example of the sunk cost fallacy — staying in something just because you’ve already spent so much on it. But just because your old dream was right for you at 25 doesn’t mean it’s right for you at 35.

Through career coaching, many of our clients discover that changing careers isn’t about quitting. It’s about choosing alignment.

How to Leave a Six-Figure Job in Singapore Without Burning Bridges

Here’s what most people don’t realize: you can be grateful for your old job and still choose something new.

You don’t have to resent or regret your past. They brought you here. They taught you things. They gave you wins, lessons, networks, memories.

You can appreciate the past while still choosing differently for your future.

When I left BlackRock to join a tiny fashion startup, it felt like starting over. Truthfully, a lot of people thought I was nuts. But that step brought me closer to the kind of life and work I wanted — more creative, nimble, purpose-driven. Eventually, that leap led me to found Ctrl Alt Career, where I now help other high performers pivot with purpose — especially in high-pressure markets like Singapore.

If I’d stayed just because I’d already come so far, I’d still be living someone else’s version of success.

Read more: How to Tell If It’s Time to Leave Your Corporate Job

Career Change Success Story: From Healthcare to Journalism in Singapore

One of my clients spent years climbing the ladder in healthcare administration. It was stable, respected — exactly what her younger self wanted. But somewhere along the way, she lost that spark.

Through career coaching, we uncovered her long-held fascination with storytelling and current affairs. She completely pivoted and is now a journalist with Channel News Asia. And you know what? She didn’t just keep her old salary — she got a raise.

She told me:

“I wouldn’t have been able to do this without you. Thank you for helping me figure out what I really wanted, even when I couldn’t admit it to myself.”

Career Coaching Questions to Help You Redefine What Fulfillment Looks Like Now

If you’re a high achiever wondering if you’ve outgrown your current path, here are a few questions I use with my career coaching clients:

❔ What did your old dream give you?
❔ What does it no longer give you?
❔ Who are you becoming — and what does that version of you crave?
❔ If you weren’t afraid of “wasting” the past, what would you explore next?

Remember: what you do is simple — you change careers.
How you do it (with clarity, confidence, and a clear story) is where it gets tricky. That’s the part we help clients with every day.

How to Change Careers Without Regret: 7-Step Framework for High Achievers in Singapore

If you’ve been nodding along to those career coaching questions earlier, you might be wondering: “Okay, so what now? How do I actually go about changing my career?”

The good news?
The what is simple — you make the change.
The how is where it gets tricky.

Here’s a roadmap we walk our clients through to make sure their next move isn’t just a panic quit, but a purposeful pivot.

1. Start With a Deep Self-Assessment

Before you run off to rewrite your LinkedIn or scroll job ads, take stock of where you are.

• What drains you in your current role?

• What lights you up?

• What values feel non-negotiable to you now that maybe didn’t matter ten years ago?

Try tracking your energy for two weeks — jot down the tasks or moments that feel energizing vs. depleting. This might sound basic, but it’s often the first time many high-achievers pause to see what actually feels good now, instead of what just looks good on paper.

2. Rewrite the Stories Holding You Back

Mindset matters more than people like to admit.
Because if you’re telling yourself:

• “It’s too late.”

• “I’ll waste everything I’ve built.”

• “Who am I to even try this?”

…you’ll stay stuck.

Career coaching often starts here — unearthing those stories and gently challenging them so we can replace fear with curiosity. What if this next move is exactly what everything before was preparing you for?

3. Craft a Clear Vision & Set Some Anchors

What does an ideal day look like 12 months from now?
Who are you working with? What kinds of problems are you solving? How does your work fit into your life (not the other way around)?

Get specific. Then translate that vision into practical, bite-sized goals.
(Think: complete a mini-course, conduct three informational interviews, apply to five carefully chosen roles — not “change my whole life overnight.”)

4. Test Before You Leap

Before you quit your job to start all over, test drive your interests.

• Start a side project.

• Volunteer on a committee.

• Offer to help a friend’s small business with marketing if that’s the space you’re curious about.

Real-world experience builds confidence — and gives you stories you can later use to reposition your CV or LinkedIn.

5. Rebrand Your Professional Narrative

This is where many people jump too soon. They update their resume without first getting clear on who they are now.

Once you’ve done that inner work, reframe your LinkedIn, your elevator pitch, and your CV around the direction you’re going, not just where you’ve been. Highlight your transferable strengths and why this pivot makes perfect sense.

6. Build Your Circle of Support

The truth?

Big changes rarely stick in isolation. Whether it’s a coach, a peer accountability group, or even a supportive friend, find people who’ll keep you anchored when imposter syndrome inevitably kicks up.

Sometimes just saying out loud, “I’m exploring this new direction” makes it real — and opens doors you never expected.

7. Iterate, Adjust, and Stay Kind to Yourself

This isn’t a one-and-done process. Career pivots often unfold in loops, not straight lines. Check in with yourself regularly. Celebrate the small wins. Tweak your plan. Stay flexible.

Because ultimately, changing careers isn’t just about landing a new job.
It’s about growing into the person you’re becoming — and building a life that fits them.

That kind of growth doesn’t happen overnight — and you don’t have to figure it all out alone.

Whether you’re feeling stuck, quietly exploring a career pivot, or ready to take bold action, having the right support makes all the difference.

Frequently Asked Questions About Leaving a High-Paying Job in Singapore

Q: Is it normal to want to leave a six-figure job in Singapore?
Yes. Many high achievers feel misaligned with their careers as they evolve. Wanting change doesn’t mean you’re ungrateful — it means you’re growing.

Q: Can I change careers without starting over?
Absolutely. With the right strategy, most professionals can pivot without losing income or having to retrain completely.

Q: How can a career coach in Singapore help me?
We help clarify your goals, rebrand your experience, and support you through a structured career pivot plan.

Q: How do I know if I’m ready to change jobs?
If you feel consistently drained, bored, or stuck, it may be time to explore what else is possible.

Ready to Work With a Career Coach in Singapore?

Whether you’re planning a career switch in Singapore, feeling misaligned in your current role, or unsure where to start — you don’t have to figure it out alone.

Book a free clarity call with the Ctrl Alt Career team and get expert guidance from our career coaches in Singapore. We’ll help you get clear, get confident, and take the next right step.