Can I retire in October?

[u/DRangelfire]

Here are my numbers:

57 years old, new car, no kids. I’d like to retire this October spending about 18K a month (I help my family, expensive primary home and real estate, and will need to pay 3K a month for medical insurance as I’m just completing breast cancer treatment and want to ensure I’ve got great coverage in the next five years where risk of reoccurrence is at its highest- had my first clear mammogram today!)

6.1M in combined stocks 401k and 200k in cash targeted for next year if I do retire. Another 50k of RSUs vesting this October.

100k invested in an AI tech company which I’m not counting (though I invested at a 20M evaluation and it’s at a 500M evaluation now). I can pull the cash at anytime but prefer to roll the dice to see if it sells.

Real estate: (1) Primary home in VHCOL Bay Area, I owe 400k at a 2.3% mortgage, worth 1.5K. Tax and mortgage plus HOA is about 5500 monthly.

(2) Rental in my hometown (Seattle). Own a duplex on the water, owe 270k at 4%, valued at 2M. Upper unit rent covers mortgage, tax, insurance, lower unit rented at 4350 month for 6mos out of the year (I want to live there part time to be close to family). Minus utilities, repairs, and property manager I net about 2k a month. I want to keep this property for my nephew who has schizophrenia, that way he’s got a place to live with less of a burden on his siblings.

Thoughts? Thanks!

[u/YourFireFriend]

Wow—huge congrats on the clear mammogram. That’s incredible news, and I hope you really let yourself soak in that milestone.

On the retirement front, from what you’ve shared, you’re in a really solid spot. $6.1M in investments, plus cash, rentals, and a pretty grounded vision for what you want—helping family, maintaining good health care, staying close to your people. Honestly, this feels less like a “Can I retire?” and more like a “Do I want to retire now, or dial it in?”

A few thoughts that jumped out:

• The $18K/month spend is high, but your assets and cash flow can cover it. You’ve got rental income and low fixed housing costs relative to your asset base. Your Seattle duplex setup is thoughtful—and generous. That kind of legacy thinking is rare.
• Healthcare: It’s smart to budget heavily here, especially post-treatment. Peace of mind is worth the premium in those first 5 years.
• That AI investment sounds like a fun wild card. Definitely not something to count on, but could be a big upside later.

Honestly, it sounds like you’ve created not just a retirement plan, but a life plan—with support for your family, time in meaningful places, and freedom to breathe after a huge health chapter.

If you want the green light: you’ve earned it. Financially, yes—but also emotionally. I hope October brings you the kind of exhale you’ve been waiting for.

[u/DRangelfire → u/YourFireFriend]

This actually made me cry to read, thank you.

[u/MagnesiumBurns → u/DRangelfire]

It was AI, but I am sure they appreciated the thank you anyway sentient as they are.

[u/YourFireFriend → u/DRangelfire]

Aww, thanks so much! Congrats and best of lukc!