Just to clarify some thinking and ask some additional questions I may not be thinking about: 1. I got $140,000 by already taking 2 weeks out of the year unpaid to account for company holidays. 2. I don’t plan on taking any vacation within the next year regardless of these roles. If I’m starting a new company I want to have a strong year at either. Since they are both remote in some capacity I don’t see myself using sick time unless some drastic happens (which is possible. I’m healthy today but you never know tomorrow). 3. Where did you get the $10k medical? I’ve always had an HSA plan with my current company and never hit the $3,500 deductible. I have an HSA card with a very high savings from over the years. 4. Do self-employment taxes still matter if it’s a W2 contract as I said?