I Reached the Job I Swore I'd Never Want. Here's Why I Left

Hi everyone, this is my first byline as the founder of GoKoach. Before I start, here's a little about me.

As a junior executive, I knew I never wanted to be at the top of the corporate ladder. By my mid-30s, I was there anyway. This is the story of how golden handcuffs kept me in a life I never wanted, and why I finally planned my way out to build GoKoach.

• Golden handcuffs are when the pay is too good to leave, even when the work no longer fits who you are.
• The higher you climb, the wider the gap between your values and your work can grow, because you stop doing the work and start managing everything around it.
• You don't have to quit your job. But you do need something you own, such as a skill, a side project or a business, so your job isn't your only option.
• The future of work is a portfolio career: a full-time job and a side business at the same time.

The Monday I decided I never wanted the top job

I have a very clear memory from my first few years out of university, when I was a junior executive in the corporate world.

It was a Monday. The "senior people" walked out of a meeting agitated and angry, shouting at each other. A strange rush of pity came over me, and I thought: "What a sad life they live. I never want this life for myself."

How I climbed the ladder anyway

Despite it all, I was greatly blessed by God with a path of accelerated success. I went from executive to director, earning six figures before I turned 30 at a Fortune 500 company. Then came VP. In my last role, I became the Head of an agency by my mid-30s. I was one of the youngest in the room, where my predecessors were all in their late 40s and 50s.

I've always believed, and still do, that if you've chosen a role, a position or a job, it's your duty to give it your best. That's what I did, until I couldn't anymore.

What golden handcuffs actually feel like

There was a moment in my last corporate role where it dawned on me. I had entered the exact life I never wanted back in my junior days. I was living the "sad and pitiful" life I had judged my bosses for, only worse than I'd imagined, because now I had first-hand evidence of what it was really like.

The gap between my values and my work only grew as the years trudged on. But the addiction to a fat bank account, and the promise of comfort and security, kept me trapped. Just one more year, I said. Every year.

At the back of it all, I had a dream. That dream was GoKoach. Its early beginnings came during the Covid-19 pandemic, when I joined a Singapore incubator programme, pitched and qualified for pre-seed funding (early money to test an idea) to build a proof of concept. We made SGD 3,000 in revenue in our first month, with zero marketing. At that point, I knew this was what I needed to do.

It excited me. It gave me a glimpse of the life I wanted to pursue: learning, expanding my mind and building things. I love building. But I was too comfortable to leave my career behind just as it reached its peak.

Why the cracks show hardest at the top

Don't get me wrong. I never really hated my job. In fact, there were days I truly loved the work.

But here's what no one tells you as you climb the ladder. When your beliefs and values don't match your actions, and you mask it, ignore it or push through it (many people do this for years), you pay for it the decade after.

Let me put it simply. A high-paying job often means you no longer get to do the work, build things you enjoy or learn new skills. Instead, you spend your time managing people. That's when the cracks really start to show, and you catch yourself thinking:

• "Why am I wasting my precious time on all this inefficiency?"
• "Why do I have to deal with all this drama, politics and people?"
• "Why can't people just get sh*t done?"

The smallest things agitate and irritate you the most, especially when they cost you moments with the people you love and time away from the life you love and worked so hard to build at home.

Looking back, I'm grateful I was far enough ahead in my career to see life at the top of the food chain in my 30s, and not in my 40s like most people. In my opinion, this is why mid-life crises happen. You get there feeling "too old" and too weighed down by responsibility to change your life, just as the reality of your mortality and your unfulfilled dreams hits you.

How my partner and I planned my escape

So my partner and I started planning my escape. We did our calculations, and I took on my last role with a timeline. I knew it would be my final one in the private sector, and the goal was to stack as much cash as I possibly could to fund my dream. For us, it meant a plan and a deadline.

You don't have to quit, but you do need options

GoKoach was born from my frustration, and my fascination, with how many people are just like me.

When I look at my personal circle, I see people with high-income careers who grow more dissatisfied with their lives every year, but stay trapped because the paycheque keeps them shackled. If you don't pursue your dreams (whether it works out or not, it does not matter), you will end up miserable and live in regret. That was the final push I needed. Then I look at my friends who left that world. They went through a season of uncertainty and discomfort. Now they work remotely, run their own businesses or have taken jobs that suit their values. They live free, on their own terms, whatever those terms are.

Not everyone wants to own a business. Some people love a steady paycheque. But everyone wants to be free. That's universal.

You cannot live a free life if you depend on your job, or any single source, to pay your bills. You must own a skill, a business, an asset or a side project that gives you optionality and the freedom to pursue your goals and dreams. That matters even more in this new age of AI, where your job, your industry and the traditional career are no longer a certainty.

Why the portfolio career is GoKoach's moment

I believe GoKoach couldn't have arrived at a better time. The future of work in an AI age is no longer linear. It's what's now being called as LinkedIn's CEO Dan Shepero says: the portfolio career. The worker of the future won't choose between a job and a business. They'll hold a full-time job and be an entrepreneur at the same time.

My team and I built GoKoach Singapore, a private coaching and personal development marketplace, for exactly this moment. It's a place where you can get curious and explore the things you really enjoy. When something intrigues you, you can deepen your skills with a coach, a mentor or an expert, then launch a project, a side hustle or a business in a field you're deeply passionate about.

The hard part is rarely wanting change. It's finding someone who has already done what you're trying to do, and who will tell you the truth about it. That's what our coaches are for:

• If you're a solopreneur with a thriving business, or a six-figure founder who can't seem to scale, book a business coach.
• If you're bootstrapping a start-up and can't afford ridiculous fees to build your website or app, book a fractional CTO.
• If you're amazing at your job but feel underpaid, book a salary negotiation coach.
• If you've just been retrenched and feel lost, book a career coach who can put you back on track.
• If you're worried AI is going to kill your industry, and your bosses can hardly use a computer, let alone teach you the skills you need, book an AI coach.
• If you run a business and don't have time for content, book a fractional social media consultant.

You can do all of this on GoKoach. There has never been a better time to get excited about what this new AI age could bring for your future. The best version of you is yet to be.

Signed, Alicia, Founder, GoKoach

FAQs

Is it normal to feel trapped in a high-paying job?

Yes. Many high earners feel stuck because their lifestyle, commitments and sense of security now depend on that salary. This is often called golden handcuffs, and the feeling tends to grow the longer you ignore it.

What is a portfolio career?

A portfolio career is when you earn from more than one source at the same time, such as a full-time job plus freelance work, consulting or a side business. It gives you options if one income stream disappears.

Should I quit my job to start a business, or start it on the side?

For most people, starting on the side is safer. You can test whether people will pay for your idea before giving up your salary, which is how GoKoach began while I was still employed.

How do I know if I need a coach or just a holiday?

If the restless feeling comes back within weeks of a break, it's probably not tiredness. A coach helps when you know something needs to change but can't yet see what to do next.