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> This is exactly why I've concluded trying to go my own way is the best long-term plan for me. Before learning about YC and HN and such, the thought never really occurred to me.

Interesting. It also didn't really occur to me that being an employee might just not be for me, until I read this comment on HN over a year ago https://news.ycombinator.com/item?id=22520709. Although the reasoning is a somewhat different from yours. Excerpt:

> The reality is that if you care about your craft a tiny bit more than average, you will most likely end up feeling that you are overpaid for trivial work, that you could do so much more for the company, that your coworkers and hierarchy are apathetic to things that do not directly affect them (and will seek to avoid any change as much as possible). The more you stay in this situation, the likelier you are to burn out.

> If you are that kind of person, then you need to GTFO and start your own thing - have your own skin in the game

I'd love to do that, but health insurance in the US makes it a nonstarter.

Cash is still king and joining something like kaiser is like $230/month for sub 30 yo.

Unfortunately, not nearly as affordable for a sole breadwinner supporting a family.

Indeed. I'm fortunate (or not, depending on one's perspective) in that I'm single and have no dependents. I pretty much only spend money on rent and food, and I'm more than happy living in a very tiny place with just a bed and a bathroom. (As long as it's a quiet place I'm not sharing and has a decent internet connection.)

This really isn't as true as it's made out to be. I've done it, and with four dependents in tow as well.

If you currently work for a big company (or really any company with >50 employees if I recall) you can qualify to take COBRA when you leave. Doing so is expensive, sure, but it's really usually about the same price as private insurance but much better (because it's a group plan). You can elect COBRA for up to 18 months, or 24 in some cases.

When COBRA runs out and you aren't yet in a position where you can have the organization you've founded pay for it, you can either look at joining a PEO or you can simply buy private insurance. Yep, it's definitely not great, but it is coverage. Additionally, if you are doing your own thing, look into setting up an HRA for yourself/your company--it lets the company pay for your medical costs without even when you're buying private insurance.

Not sure how to pay for it out of the gate when you might be pre-revenue for a while? You still have a couple of options. First, saving specifically for this use case makes a lot of sense. Even better, if you are currently in an HSA-compatible plan at work, max out the account for the year because you can use HSA savings to pay for premiums. Or if you have a spouse or SO and can hop on their plan for a while, good call too.

In general, and speaking from the position of someone who has spent far more time than I wish to admit building models and forecasting health expenses for when I was on private insurance and doing my own thing, it can be done. The freedom was definitely worth the price.

This is really helpful info. I've been looking at this stuff a lot and I learned these things from you:

- COBRA and private health insurance are comparable in cost (I always assumed it was way more expensive)

- HSAs can be used to pay premiums

These are important pieces of information for figuring this out for me. I don't have four dependents, but I have two and don't have the option of jumping to a spouse's plan, so thanks for the additional context.

Glad to be helpful. As noted in the other comment and with all things, YMMV, but there's definitely reasonable options out there.

> you can use HSA savings to pay for premiums.

This is not true, as far as I know. I'd consult a CPA for an authoritative answer, but from https://www.healthcare.gov/glossary/health-savings-account-h...

> HSA funds generally may not be used to pay premiums.

Good to note, this may have changed then. It was okay last time I did it.

HRAs on the other hand are a good vehicle for this.

EDIT: Ah, there is indeed an exception for continuation of coverage under COBRA which makes it acceptable to do so: https://dpath.com/hsa-and-cobra/

Awesome, thanks for digging that up! My bad.

I think you're correctly responding to incentives. If your hard work created a new product line for the company you work for, that made them millions, how much of that would you get? Close to 0%. So why should you work full-out for someone else?

This is me, but maybe to a lesser extent.

I tried doing my own thing but couldn’t keep at it after about 8 months.

I think the key is to at least have your expenses covered by your business. I couldn’t stand seeing my savings and retirement-fodder continue to dwindle even though I had plenty left in the bank.

Found a part-time job and now my days are less fun but also less stressed

> Regarding the author's username: yes, it's that one.

Curious to know who the author is or what he is famous for? I searched his posts, it looks like there were no post for a decade before last year.

Roko, of "Roko's basilisk".

He himself isn't really famous, but due to the infamous reaction his post on the subject received, his username will probably be etched into the history books for centuries. (Or at least a few fiction and non-fiction books here and there.)