I believe that if you’re in a well-paying, low-stress job, it’s not the time to impulsively start a business. I don’t know how your work environment is so I’m not going to judge but,diving into a startup without a solid plan is risky and can hinder your ability to dream and strategize effectively. It’s often better to utilize the stability and resources of your current job to plan your entrepreneurial journey. Rushing into a startup, especially without a clear vision, can lead to unnecessary stress and challenges. In essence, a stable job can be a valuable platform for carefully planning a successful transition to entrepreneurship.

For me, it was when I could absolutely no longer stand working at any job, even my very well paid job, anymore.

Honestly, I’d try to see if you can move to the U.S. You will increase your comp and your odds of a highly asymmetric positive outcome.

There is no right time, there is only a wrong time.

The best time to start a startup is today. The second best time is tomorrow. You want to spend your life on the steepest learning curve you can, and there is no steeper learning curve than your first startup. You will be far more valuable and have a better perspective whether you succeed or fail. But if at all possible, succeed, because your life will change significantly - more freedom, more ability to do hard things, better likelihood of staying in a maximum learning environment.

When you have two years salary saved up and healthcare through your parents or spouse

You have to believe in the idea more than anything.

You need skin in the game or a good ESOP deal.

You need to be prepared to work more hours than are healthy

You need to be prepared for the idea to fail or for the company to pivot

You have to trust your co-founders

You need to understand the revenue model and understand the path to growth

You need to have very thick skin

You need to balance foolish optimism and catastrophe preventing pragmatism

You need to make decisions quickly, a lot of them.

You need to find pockets to sleep and refresh your body

Building a startup is rejecting the status quo. It is hard because economic, political, cultural and social forces are set up to force you down safer paths.

Startups are ugly thrashing caterpillars struggling to weave protective cocoons to transform them into beautiful butterflies that attract bloated beasts to eat them.

Believe in the change you want to create

Always

Starting a business because it is convenient and suits your schedule is probably not a great reason to do it.

Starting a business because you have an idea that you strongly believe solves a problem in a industry that you know well is usually the best reason.

The best time is when you stop thinking you’ll fail. You have the resources, why not do it? Here’s one article that will help you with common startup mistakes you should watch out for. https://www.cuppa.so/post/the-top-10-startup-pitfalls-to-watch-out-for

The right time to quit is when your start up is making more than your current job. You should start now and likely not quit unless you are making good money from your business. I did the whole save and quit to work on a startup but basically spent all my money, only worked on coding, and didn’t develop the sales skills needed to get it done. Startups are sales games, so don’t quit your job until you have proof you can win at sales (which likely won’t have a strong dependency on the quality of your product)

Build enough to validate that there is a market and you have so much demand you can’t do both jobs. That’s the time to jump.

The right time is now. Before you have a wife, kids and a mortgage and really can’t take a cut in pay.

Just ask for a lot of equity. Worst case scenario is you learn a whole lot of the thing fails.

Risk-taking at its finest!

I agree with the sell-before-build comments. Your idea should be validated before you even think about a resignation letter. I’m also of the view that it should be possible to transition into a startup. If you’re valuable to your employer then they will accept you on a part-time or consulting hours basis, and you can finally let the safety line go when your business is flying.