[slaymaker1907]

Doing (2) has some extra risk that people don't talk about very often. If you, like most people, have to work a day job, it is actually less risky to invest outside of the area you work in (using a diversified portfolio). If you work in the tech industry and there is a tech downturn, it is not ideal if your investments are also doing poorly at the same time. By nature of working in that industry, your finances are already heavily dependent on that industry and it might be a good idea to take that into account while investing. You don't want to be both investing in a bunch of AI companies and working at an AI company if we end up in a second AI winter.

[whimsicalism]

Yeah, you shouldn't go long in an industry you work in.

[01100011]

This is a tough one to follow through on. I've got a ton of vested RSUs that I'm sitting on because I see my company as a growth stock. I really should sell it and buy a low ER S&P500 index. We're an S&P500 stock, so I'd still retain exposure to my companies performance, but the risk would reasonable I think. Unfortunately I'm irrationally fixated on the potential gains. It's doubly stupid because I have more RSUs vesting soon, so even if I sell, I'm still invested in my company.

[sobani]

One thing you can consider is: What if your company is Enron 2.0 and goes bust next month. Do you have enough savings to last until you find your next job and are your other investments on track for what you need for retirement?

If you answered yes to both questions, then you can consider not selling your RSUs. If you answered no to either or both those questions, I would strongly consider selling enough of your vested RSUs to turn those into yesses.

If you need to sell a significant chunk of your RSUs to reach those targets I would suggest you to take a good look at your current budget to figure out why your savings and investments are not on target.

Also, do you have any experience with dealing with a large drop in value and do you _know_ based on that experience that you'll be able to sit tight when such a drop inevitably will happen? Because if you don't have such experience (or worse: you know you're unable to sit tight), chances are you will be part of the stampede in times of panic. In that case consider selling 'more'.

Lastly, what would you suggest your best friend do in your situation?

[bartvk]

I started working at Oracle in 2001. There were two kinds of senior people there. The ones who sold their stock, and the ones who didn't. The first group would sometimes have a sold-off house or similar, the second group would sometimes have bitter people in it.

[whimsicalism]

I sell vested RSUs & ESPP stock immediately. That's even worse than investing in the same sector.

I agree that it can be hard psychologically in a high-growth industry like tech.

[CameronNemo]

Oh my goodness, sell at least half!