Sell new shares, those with losses, and those with small gains. Don't reinvest dividends. Make sure new shares get sold before the tax tail wags the dog again.5.Are there any views on selling vested company shares to maximize tax efficiency? The stock has appreciated between 2–5× since vesting (across multiple batches).
If you donate to charity, setup a DAF and liquidate via that, rather than donating cash. Donating $10k of VTI versus $10k of employer stock is no different as far as the charitable purpose is concerned, but it lets you bleed off some of the position.
I would get out of the rental. VTI/VXUS won't call in the middle of the night, and you've remarked that the day job already has long hours.6.Are there opportunities to simplify or better rebalance my portfolio structure?
How much are you saving in taxable? Saving 45-50% of "high 6 figures" gross (did you mean net?) doesn't leave a lot for taxes and 220-240k/yr of spending.7. Is there anything else I might be overlooking or should consider based on my current situation and goals?
Statistics: Posted by OODALoop — Mon Nov 10, 2025 10:57 pm — Replies 4 — Views 844