1. The first thing you do should be discussing this with your wife, not HN. If she's not on board with it, that's probably the first thing you're going to want

1. The first thing you do should be discussing this with your wife, not HN. If she's not on board with it, that's probably the first thing you're going to want to work on. If it doesn't seem like she's ever going to be on board, you have an uphill battle that you are going to lose in all likelihood. 2. Have you done market research? Needed startup capital? Have enough connections that in the case of failure you can just go back to a similar job in the industry? > Im not sure how to pay my bills while looking for product-market-fit. Yeah, you're going to want to test this before quitting your job. I think realistically if you can't get at least 2-3 paying customers for your product without quitting your day job, your chances of making it are pretty slim. > Are all startups at my age generally side hustles that become profitable enough to quit my day job? For someone like you, most likely yes. For someone who's a serial entrepreneur, probably not, because they can rely on their prior businesses to test out new ideas.