Wednesday, October 20, 2021

About to pull the trigger. How ready am I?

Hi all, first things first, I've been so insanely grateful to be able to see everybody's perspectives here for so many years, from both below and well above my position. Having read this sub for years, I should know that I'm ready. I promise this isn't some sort of flex; in fact, I feel sort of small next to a lot of folks in here. I'm insanely keen on what you have to say about my scenario, and have been holding this until the very moment of imminent retirement to avoid abusing the community's generosity.

I'm 35 and single, and for now, my living expenses are just $60,000 per year. That's decidedly not fat, but I'm planning on bumping up to $130k or higher when life events call for it. Today, I think I'd have to majorly reshuffle some things to make $130k+ safe, but I'm hoping my low-spending years in the beginning will help things accumulate before I end up needing to draw that much. I'm comfortable taking a little more initial risk than would maybe typically be prudent. But, what's to come may be stupid!

The goods total up to $5.8M:

  • $2.6M of VTI in a taxable, right at its cost basis (no big gains yet)

  • $950K of stock in my employer (too much of this, but the capital gains to sell will hurt so bad! This company is a large one.) Cost basis is about 40% of this value.

  • $640K in Bitcoin (this is the “little bit” that’s left, after diversifying!) Cost basis is negligible.

  • $550K equity in primary residence worth $1.1M. Most of it is rented. It costs me net $600/mo while I also live in it. Mortgage balance is $550k at 2.625%.

  • $520K in a 401(k) soon to be rolled over into a traditional IRA so I can pick the investments.

  • $300K equity in a rental home worth $760K. It cash flows $2100/mo. Mortgage balance is $460k at 3%.

  • $150K cash which I should've invested months ago but, math be damned, sort of feels good to have sitting around.

  • $65K in other small cryptos

  • $65K in QQQ a Roth IRA. I wish I would have learned earlier about Mega Backdoor rollovers, and done more of this!

I don't have much in the way of tax sheltered accounts, since I've only been working full time for 10 years. There are definitely some things I should do:

  • Sell most of the bitcoin and company stock, to start. I think unwinding it by selling it first for living expenses will save on tax, but is it worth the risk?

  • I own an amount of BND not worth mentioning, and otherwise, no bonds whatsoever; I can't stomach the idea of bonds today, but maybe I should?

  • International exposure???

My $150k cash pad should allow me to slow down (not stop) portfolio withdrawals for quite some time in the event of a market crash, but certainly not forever. Regardless, this portfolio reeks of someone who just sort of haphazardly earned and saved a bunch of money, but I'm not sure how to clean it up without paying exorbitant LTCG taxes.

I'm thinking CAPE is so high right now that a SWR of just 2.7% is justified, per ERN's CAPE-adjusted SWR study. I'm well under that... for now.

Am I crazy to throw away a low-stress, mostly-wonderful $400K-gross job I'm so burned out on and depressed about that I fear I'm shortchanging my coworkers by staying in it? I need to live and breathe... and frankly I've been underperforming so terribly at work that I don't think I can get away with a sabbatical. If all goes according to plan, I'll be giving my resignation on Friday or Monday, and once I leave tech, I may never come back.

Thank any and all of you for your insights!


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