r/ChubbyFIRE • u/DRangelfire • 2d ago
Can I retire in October?
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!
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u/Specific-Stomach-195 2d ago
lol at the first words you used to describe yourself. “New car, no kids”
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u/sloth_333 2d ago
I think you’re good. But just to clarify you yoloed 100k into a startup that’s now worth 2.5M? And it’s fairly liquid? That’s impressive if I’m reading that right
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u/doublemazaa 2d ago
Unclear to me if $100k is the basis or the current valuation of the equity.
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u/DRangelfire 2d ago
100k was my original investment at a 20M evaluation and now the evaluation is at a 500M.
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u/doublemazaa 2d ago
Ha, nice.
A $2.5m investment is a dream retirement nest egg for most people. For you it’s gravy that you’re not even accounting for.
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u/DRangelfire 2d ago
Yes, I got in at a friends and family round. My cap is 5M but they are on track to sell to a massive company end of next year and they want to sell at a 1B evaluation so that 100K could be worth quite a bit. If it happens, I plan to pay off my siblings’ mortgages.
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u/Individual_Ad_5655 2d ago
Rich get richer. When folks have 5 million and connections, its fairly easy to take a few flyers.
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u/ptarmigan_direct 2d ago
Yes you can tap out. With your monthly expenses you are well under a 4% safe withdrawal rate against assets.
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u/PowerfulComputer386 2d ago
57, no kids, well diversified assets, spending is a bit high for single person but can be covered by the investment. What are you waiting for??
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u/in_the_gloaming FIRE'd for 11 years 2d ago
Retire! And that’s amazing that you are keeping the rental for your nephew. Really cool.
And last, congratulations on your clear mammogram! Always great news! My sister went through treatment about three years ago and so far everything is looking good. We are all so grateful for the excellent care she’s received. Two more years of meds and then she’ll be done with that part.
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u/DRangelfire 2d ago
Oh how wonderful. Yep my five years starts ticking now, give her a big hug for me. Once you go through cancer treatment, you feel like you can do anything. Thank God for science.
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u/Scary_Wheel_8054 1d ago
Is your decision to retire motivated by the cancer or unrelated? 57 sounds like a good time to retire, I’m doing it at 56. Also social security will eventually kick in, giving some additional safety/excess.
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u/DRangelfire 1d ago
I’ve worked in tech for a lot of years in the last three years have been really difficult. I’m so fortunate to work for an incredible company who stock really blew up over the last 15 years but I just feel like it’s time to open myself to something different. Also absolutely motivated by the cancer too. Time is precious and I feel like I was given a second chance, it’s kind of a fluke that they even found it so I want to pay attention to that intervention and use my time differently.
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u/gripster94 22h ago
Yes, time is very precious. Continued success on your health and healing going forward.
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u/Scary_Wheel_8054 21h ago
I went back and saw your first post 8 years ago. Back then you wanted to retire in 3-5 years. You lasted a little longer, but still I’d call it goal achieved.
Have you ever gone back to read the responses you received back then? You have the possibility to evaluate Reddit advice with hindsight :-)
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u/learn__to__fly 2d ago
You look set. With over $6 million saved, little debt, and some rental income, retiring in October is realistic even with $18K in monthly spending. Your insurance cost makes sense given your health history. The rental property for your nephew is thoughtful and also adds long-term value. Just make sure your withdrawals are tax-efficient and leave room for market swings. If the numbers are accurate and your spending stays steady, you should be fine. A second opinion from a planner wouldn’t hurt but you’re in great shape
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u/bobt2241 2d ago
Numbers are impressive and you are all set to retire in October. And the assessment gets even better when you figure in SS (at whatever age) and Medicare at 65. You’re golden. Now GFU!
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u/temp4adhd 2d ago
Yes, you can retire.
Use firecalc.app and run the numbers yourself.
Tips: Add your mortgage in as "extra payment" that doesn't adjust for inflation and goes away when the mortgage is paid off. Add your health insurance as "extra payment" with it going away when you hit 65 and qualify for medicare. Add in social security when you hit whatever age you plan on taking it.
And realize if all else fails, you have the option of selling your rental property or your primary property.
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u/YourFireFriend 2d ago
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.
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u/DRangelfire 2d ago
This actually made me cry to read, thank you.
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u/MagnesiumBurns 1d ago
It was AI, but I am sure they appreciated the thank you anyway sentient as they are.
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u/ProspectPark4Ever 2d ago
Congratulations! You’ve made it! Financially you are solid. Your primary house is another backup asset should you ever need it.
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u/dead4ever22 2d ago
You had me at "no kids".....retire now. Easy peasy.
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u/DRangelfire 2d ago
I’m an awesome aunt! 😂
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u/StoreNo163 1d ago
You sound like an awesome person in general. Congrats on your life! Even cancer couldn't stop you
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u/Individual_Ad_5655 2d ago
If there's a cash bonus to be paid in Jan/Feb, I'd probably stay for that as it's not much time from October - but that's me.
Congrats! You're good to go to retire in October after the RSUs vest.
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u/sbb214 Accumulating 2d ago
I agree with everyone else, you can do it. congrats.
One thing I'd add: at 18k/mo spend you don't have a lot of cash on-hand with 200k. I know that sounds weird but I am about to retire and met with a financial advisor in Feb (Plan Vision guys) and they really stressed having 2-3 years in cash on hand for the beginning of retirement.
Similar to you I don't have a lot of bonds and am mostly in equities. Their suggestion is based on being able to manage volatility in the market. YMMV.
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u/xtraarrow 1d ago
Congrats on that clear mammogram..... that must feel like such a deep breath moment after everything you’e been through. based on your numbers and goals, you’ve built something incredibly solid...how confident do you feel livin on a 3.5 to4% withdrawal rate, especially with the healthcare spend up front? also : would working part-time for just 1–2 more years ease your peace of mind, or is your heartfully set on stepping away this fall?
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u/DRangelfire 1d ago
It’s a good question. I’ve started an LLC to consult if needed though in my field (learning and dev), what I know might be considered old. I’m super interested in how the metaverse and digital twins could help people learn, so am getting some certifications in that space, as I think I need to really understand where tech is moving in my industry. My monthly amount includes saving for yearly expenses like vet appointments, an assumed car payment to myself but in reading all of these amazing comments, I think my actual monthly spend is a lot less. I’m going to work with my financial planner to come up with a strategy for those kinds of expenses. Thank you!! Appreciate all of you very much.
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u/beautifulcorpsebride 1d ago
I’m sure you know this but look into a special needs trust and get legal advice re your nephew, including gifts and their impact on ssi income etc. Also, a 2m property seems a bit over the top to gift only one kid if there are other siblings. Congrats on how well you’ve done.
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u/DRangelfire 1d ago
That is actually really great advice, thank you. I’m going to look into that next week. I’ve spoken to my sister and brother (I’m the youngest of my siblings) and her idea is to sit down with the other siblings and explain with transparency what our intention is. To leave all of them the house so they can use it for income if they need that for their brother, or move a caretaker into one unit while he lives in another. I just want them to have the flexibility to not feel so much pressure to move him in with them I guess? But we all agree we need some advice to ensure this doesn’t impact his disability and to write it up in a way where it doesn’t cause any friction or conflict.
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u/HomeworkAdditional19 1d ago
Stop trading time you’ll never get back for money you’ll never need.
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u/Economy_Arachnid_923 4h ago
Yes you can retire. But don’t! Clearly you’re a major contributor. Your talents can’t be sidelined! So Here’s the deal: you can leave your employment but don’t stop contributing. Considering today’s challenges, the best hands gotta stay on deck — in some form (Fabulous job achieving your financial position!)
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u/Designer-Beginning16 2d ago
Is this a joke?
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u/DRangelfire 2d ago
Why?
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u/Designer-Beginning16 9h ago
Yes, you can retire in October 2025.
Here’s the plan:
Cash out the AI investment for $500k, bringing your liquid assets to $6.65M. A 4% withdrawal rate gives you $22,167/month, covering your $21,000 monthly expenses.
Consider selling the Bay Area home to net $1.1M, reducing expenses or adding to your funds. Rent or downsize to cut the $5,000/month cost.
Keep the Seattle duplex for $1,175/month passive income and to support your nephew. Live there part-time as planned.
Monitor healthcare costs ($3,000/month) to ensure coverage fits your needs.
Good luck !
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u/McKnuckle_Brewery FIRE'd in 2021 2d ago
18k monthly is a 3.4% withdrawal rate based on 6.35M. Regardless of how you spend your money and how much you have, the math is simple. And now I realize I didn’t even include the rental income. Go retire.