There are also issues around your employer offering you specific tax/legal advice. It opens them up to liability. They can say "here are how options work in gen

There are also issues around your employer offering you specific tax/legal advice. It opens them up to liability. They can say "here are how options work in general" but they'll always follow it with "but for your situation, you should talk to a CPA/attorney." I also made the mistake of not working through the implications until a year or so in. Luckily, I joined early enough that my strike price (and valuation) was still low enough that I could exercise pretty easily. Disclosure: It appears that my former employer has filed their S-1 in the last couple weeks.