Ask HN: Do you have the courage to abandon your high paying job?

I am 38 yo now and I made 3 career decisions in my life that significantly reduced my income. I never regretted them, quite the contrary.

I was never as wealthy as you, but proportionally, it is a similar situation. My reserve wouldn't allow me to live for 3 years with no income, but I had the benefit (in my last move) of my wife being able (and willing) to pay the bills on a stable job she likes.

My decision process for those radical moves is: will I be able to endure the realistic worst case scenario?

In your case, I imagine this scenario would be something like this: failing miserably at your idea, not only financially, but not even enjoying working on it as you predict you will. During this period your family would be living in a significantly lower standard of living. A lot less luxury that 500k/year can afford. After 4 years and having consumed 1/3 or 1/2 of your reserves, you have to go back to the job market. You will find a job that will pay you 250k/year and you will hate less than your current one (this is the realistic part, I really doubt the skills that took you to a 500k job will not get you choices, even after a 4 year gap, if you are willing to earn half that).

Do you think you would be ok facing this worst case scenario? If you think it might lead you to desperation, depression and hurt your family relationships, don't do it. If you think it is not the end of the world and all your family is on the same page, do it.

I don't see how it takes "courage" or how it's a risk. If you're a software developer with in demand skills and have one of the FANG companies on your resume, it shouldn't take long to get a job if your startup fails. I don't have but one company that anyone has ever heard of on my resume, and I historically I can get a job in less than two or three weeks.

If you have $1 million in cash you have plenty of runway to find a job.

If you try, and your company fails, at least you tried. Studies show that people have a lot more regret about things they didn't try to do than things they tried and failed.

Life is short, go for it.

It's not about age discrimination. I'm only 6 years younger than you and while I'm not going to be working at the next cool hipster startup, I've been aggressive about learning the latest technology and moving around jobs to keep my skills current. It's never taken me more than two or three weeks from the time I started looking until I got an offer - and that's with me being relatively picky.

I would have no "security" being at the mercy of one company knowing that if they let me go, it would be hard to find another job. I felt a lot less secure between the time I was 28-34 when I had let my skills atrophy than I do now in my mid 40s and I look at job requirements in my market when I know I meet the qualifications.

As far as title, who cares? I left a job as a "senior architect" because I knew the road map wasn't going to allow me to stay current and took a job as a "senior developer" (making more money) at a company that would let me level up in my technical skills.

You can get decent insurance without a full time job - the ACA is still a thing. It costs a lot, but if you have savings or can generate enough income from your business - it's just another expense.

The 4% rule is a good one as it's (as you mention) much more likely. Also, if your withdrawal rate is 4%, the likelihood of you seeing that income until you die is much, much higher.

As stated elsewhere, getting yourself down to spending 37k a year is going to be the hardest part, no matter where you live.

The problem I see, time and time again as a bystander to the financial industry is that people simple aren't saving enough, or what they have saved is overspent at a rate that's unsustainable. If one needs to live off of 24k/80k/200k a year in retirement; then their investments should reflect that.

It's some protection, and there are niches that none of those tech companies have touched yet. I don't see why people don't see them. If it's a thought that should normally occur in your work day because it could related to your job description or company's products that you could reasonably have an impact on then you're not protected. If it's completely out of left field relative to the previous items then there's no way they could lay claim to it. How could they? Tech is much broader that a lot of people generally think about. Let's say you're doing front end work and your company is some social network but at night you have a brilliant idea for automating biological sample isolation using some robotic system you conjured up during a cup of hot cocoa on the weekend? How is the company going to even attempt to sue you for it when you used none of their resources, the idea was worked on during non-standard hours, and it has nothing to do with them?

If by tech you mean "along the same lines of what I'm doing at work" then you're gonna have a rough time. I do hope that your mind has the ability to wander a bit further from the train of thought you have you typically have while doing what you're paid for.

This goes for the other two replies above as well. If you have an original idea then you're safe. The hard part is having an original idea or even an idea that is several steps removed from a previous idea but still useful.