12 years, 7 jobs: What’s next?
I’ve been working for 12 years. In that time I’ve had seven full-time jobs, taken a pay cut I shouldn’t have, chased careers that sounded cooler than they were, and slowly worked my way from $3,200 to $10,000 a month.
This isn’t a success story. It’s just my story. And I’m writing it down because I think the messy, non-linear version of a career is more useful to read than the highlight reel.
The dream I didn’t chase
Before any of this, there was a version of me that wanted to be in the sports field. I dreamt of being a professional footballer, but sadly I didn’t have the talent. I contemplated sports science, but I talked myself out of it. There was no market in Singapore and so I took the safe path instead.
I then landed with Engineering. Because I thought it was about cars and fixing things.
Except it wasn’t really about cars and fixing things.
I don’t spend much time regretting that decision. But I mention it because it sets the tone for a lot of what followed: a career built more on what seemed sensible than on what I actually wanted.
Job 1 — Engineering
Starting salary: $3,200 · Exit salary: $4,320 · Duration: 4 years
First job out of uni. I tried to negotiate the offer and got nowhere. In hindsight I should have pushed harder. $3,200 felt low even then. But I didn’t have the confidence or the leverage, so I took it.
The first year brought a bump to $3,600. A promotion in year three got me to $4,600. Then the company cut my allowances and I ended my time there at $4,320. Just like that, I spent four years across engineering, supply chain and operations.
What I got was broad early exposure across different functions, which turned out to be useful later. At the time I just knew I wanted more: more pay, more growth, more of something I couldn’t quite name.
Job 2 — Finance
Starting salary: $3,550 · Exit salary: $3,850 · Duration: ~2 years
I decided finance was where the money was. So I made the leap.
And I took a pay cut to do it. From $4,320 down to $3,550. That was a mistake I should never have made. You should never accept less than your current pay when switching jobs, full stop. But I was trying to change careers and didn’t know how to value myself in a new field.
Finance sounded exciting, except that it wasn’t. Two years of feeling like I was going nowhere. At one point I asked my manager what I needed to do to double my income. He couldn’t answer. That’s when I got fed up and left. I should have left much earlier.
The lesson: a job title that sounds impressive doesn’t mean the role will actually teach you anything.
Job 3 — Consulting
Starting salary: $4,800 · Exit salary: $5,200 · Duration: ~1 year
Consultants sounded knowledgeable and cool. So I became one.
The pay bump was real. But the job wasn’t what I imagined. It was slides and endless slides. Remake this one, reformat that one. I realised pretty quickly that looking like you know things and actually knowing things are very different skill sets.
I stayed about a year. Long enough to know it wasn’t right, short enough that I don’t regret leaving.
Job 4 — Investment
Starting salary: $6,000 · Exit salary: $6,000 · Duration: ~8 months
This was the one I thought I’d been building toward. After years of engineering, finance, consulting. Finally, the thing I actually wanted to do. Again, it wasn’t what I expected.
The person I worked under wasn’t someone I could learn from. Decisions were made on gut feel with no real process or framework behind them. I had imagined rigorous investment analysis. What I got was organised chaos.
Eight months. Good salary jump. But you can’t stay somewhere just for the money if you’re not growing.
Job 5 — Corporate
Starting salary: $7,000 · Exit salary: $7,350 · Duration: ~18 months
The pay jumped to $7,000, which felt meaningful. And for the first time, I felt like I was in a sector worth building expertise in.
The leadership, though, was a different story. My boss was young, inexperienced, and next in line to inherit the business. This was not someone I could genuinely learn from and the ceiling was visible very early.
Job 6 — Consulting
Starting salary: $8,250 · Exit salary: $8,650 · Duration: ~2 years
I joined for the brand name. I thought with it came structure and proper processes.
The reality was messier. Leadership without clear direction. Meetings that made people feel productive without producing much. At some point I realised I couldn’t follow the leaders because our values were simply different, and that’s not something you can work around indefinitely.
But I did learn things. The brand name opened doors. The exposure to large projects was genuinely useful. I left with more than I came in with, which is the minimum you should be able to say about any job.
Now — Corporate
Current salary: ~$10,000
This feels less like a deliberate choice and more like where I’ve ended up, and where I’ve built the most relevant experience. Whether that’s the right place to double down or a comfortable rut, I’m still working out.
The path upward from here isn’t clear to me. What I have is a sector that I’m familiar with, skills built across a winding path, and a clearer sense than I’ve ever had of what I actually want, which is not to be dependent on any single salary forever.
That last part is why this site exists.
The arc, in one chart
Year-end salary progression from 2014 to 2026
| Year | Role | Year-end salary | Change | Note |
|---|
What I would have told my past self
Never take a pay cut to switch careers. If the role isn’t worth at least your current salary, it isn’t worth it. You can always negotiate. The worst they can say is no.
The job title matters less than who you’re learning from. I took roles that sounded impressive and ended up working under people I couldn’t learn from. The most valuable thing in any job is a manager or environment that actually develops you. Chase that, not the title.
Sector matters more than function. I spent years changing functions — engineering, finance, consulting, analysis — when the more useful move was finding a sector I could build deep expertise in. It found me eventually. I wish I had been more deliberate about it sooner. That early few years would have built serious capabilities.
- $3,200 to $10,000 over 12 years — a 3x increase, but not a straight line
- Took a pay cut once. Should never have done it. Don’t do it.
- Chased job titles and industry prestige more than actual learning opportunities
- Found the right sector late — but finding it at all matters
- The ceiling from here isn’t clear. That uncertainty forces me to write down my thoughts here.
Next: What will success actually look like for me? — now that I know where I’ve been, I’m trying to work out where I’m going.