I read the Bogleheads version of this post, which was highly entertaining.
1. What should I do with my 401k and $1.4M in cash after selling the stock if I decide to pull the trigger? What funds?I'd do a blend of Total Stock and Total Bond (Vanguard, Fidelity, take your pick). Probably 80-20, but your risk tolerance is up to you. But whatever you do: pull the trigger! I am in complete agreement with all the Bogleheads, and with
@Laura33 below: from Bogleheads post history seems like most of your wealth is not only in one stock, it is in
Tesla stock. Do
not retire and plan to never work again while that is the case. Sounds like Tesla got you rich. Great! Good for you. Now sell it and buy a diversified portfolio and stay rich.
2. Does it look like we have enough?Eh. Maybe? You've got young kids, and hopefully a long life ahead of you. With full appreciation of the irony: unexpected expenses are bound to come up. Here's the thing: I totally understand all-or-nothing thinking, but the decision to quit doesn't have to mean that you then retire forevermore. Take a long break, and see how things go, and if they don't go well (monetarily, mentally, whatever), then go back to work. You have human capital to backstop your money, which puts you in a far better position than a 70-year old retiree if things go south.
And you might find that after a decompression period there are other things you want to do that people will pay you for. Full disclosure: I was not working most of last year. My circumstances were much different -- I was out on disability and did a whole lot of nothing because, you know, disability -- but I am back to work now and much more aware of the benefits of having tough by semi-solvable problems to occupy my mind and my days. Your work situation seems super toxic, and you have the money saved up to get out of it, so do that. Once that fire is put out, figure out next steps.
3. Should I start roll overs ASAP? or try to wait until next year when I should have lower income. I don't have enough for 5 years of expenses in my after tax.I would wait until next year. $270k (in taxable)/$60k (draw per year) = 4.5, so you have almost 5 years. Plus your wife earns some on the side. Plus if you need to you can always do something to bring in a bit of money yourself. Plus you might get severance. However, if you're planning to get healthcare through the ACA, game out whether Roth conversions will put you above the income cap you need.