Ask HN: Decision paralysis looking for a job for the first time in 10 years

That said, I find myself on the market looking for a job as a senior engineer and have been completely stuck since I started job hunting a few months ago. I qualify for and am interested in a good number of the postings I have come across, but I feel completely disadvantaged by how little information the job postings confer.

I am especially overwhelmed by how all the big names have you apply for a particular position with a particular team, and worry about getting rejected applying for one team at company ABC when I should have applied for and might have had better success with a different position with another team at the same company. I'm also leery of silo culture and getting stuck in a team I don't mesh as well with at a company where switching teams isn't so easy.

Part of my problem is that I have an extremely diverse engineering background and a fairly expansive portfolio of projects and technologies. While there are techs and industries I would prefer not to work with, I see openings for osdev, web backend, distributed systems, cloud infra, various niche core engineering, etc. all of which speak to me at some level making it hard to choose.

As background, I'm in the USA and I've run my own successful tech business for the past 10 years, contributed continuously to various open source projects, and kept up to date with most of the latest tech. Due to recent changes in profitability and with my hand forced by familial issues that have incurred high and ongoing medical costs, I've made the decision to shut down the business and seek full-time (at least partially remote) employment instead.

I'm completely unsure of how to apply for multiple positions with multiple companies at the same time, but I don't see a better alternative than doing just that. I've held off applying anywhere because I don't know what's considered acceptable with regards to how long I can keep a company waiting before I give a commitment, while I want to make sure that I end up with a job that's if not pareto-optimal, I can at least stick to for a couple of years without much regret.

In summary, I have too many options and don't know how to proceed. Per-team positions make me leery even after I've found what qualifies as a good company to work for. I'm not sure what's the right strategy when it comes to applying to companies that says you can only apply to one or two teams in a six month period but have dozens of openings across as many teams available. I don't have a great network of peers at different companies that I can just ask about a position. My conscience would eat me alive if I left a job shortly after landing it. And as much as I hate for it to be a top concern, pay is, as explained, an important factor and job postings just don't give you any/a real idea of what the take-home would be, or how much room for negotiation there would be.