I’ve been very interested in a simplified portfolio and have taken actions to apply the Boglehead philosophy to both my 401k and Roth IRA accounts, and I think I’m going well there.
The problem I’ve been afraid to tackle is my brokerage account which has gotten out of hand. After a few years of doing stupid/naive things with investing, I’ve finally consolidated numerous accounts/services I was using into Fidelity (originally had roboadvisors, was doing things without thought in Acorns, etc).
It’s now been a year since I’ve moved all those funds into Fidelity, which is nice to have everything in one view, but now I have several problems.
1) Overlap
2) Too many different things in my portfolio (15 currently excluding SPAXX)
3) A large portion of my portfolio (almost 90%) is stock from my own tech company (ESPP and RSUs granted over the years).
Though ideally I’d like to address all three, I feel that #3 is my biggest issue as depending on which way my company goes (which has luckily been up for the most part), things can go south out of no where and cause a fairly devastating loss.
Is the only move here to start slowly selling RSUs + qualified ESPP shares and setting aside money to pay for taxes, then putting the remainder towards re investing (as I’m in California and at the 24% tax bracket, I’d ideally like to use VTI, VXUS, and VTEB, unless there is a better suggestion ) ?
My original thought for keeping my company’s stock was “I think it’ll go up, I should hold all these shares for the future” and while yes that has worked out well so far, I’ve realized that I’ve now created a bit of a problem for myself, which I’d like to start correcting.