Was having coffee with a friend, 40ish years old, and makes 220-250k SGD a year.

His life at the moment

2 days work-from-home , stay-at-home wife and 3 kids. Stays in Ang Mo Kio condo (1.5M? not paid off but not tight). Japan ski holiday every December and a short regional trip (bali, dang na) every June.

Not content. Bordering on unhappy. (I'm not surprised because I wont be incredibly happy with the situation either.)

My analysis

He probably wants and desires more. He's probably yearning for actual true wealth and true freedom for example: freedom to wake up anytime he pleases.

Let's be completely honest. He has it better than 95% of people. He should probably just stay where he is until retirement. The job is good and very comfortable (perhaps even meaningful) but you will have to keep working till you retire. golden handcuffs are real. There's zero chance of building substantial wealth if you're only socking away 40-70k a year. (No judgement here: car payments, mortgage, kids enrichment, ski holidays and regional trips adds up to 180-200k a year easy).

Then why is he unhappy? Probably because he's ambitious. He is sure he can do more, and better, and be in control.

My advice

Have a long and hard conversation with yourself (and a coach perhaps) to seek deeper clarity on what you are looking to get out of life, and get an honest assessment of whether you can stomach the uncertainty, and put in the long hours, of getting a business off the ground.