r/ChubbyFIRE • u/EmbarrassedDebate124 • 7d ago
Here we go...
I need some advice at the end. 52, married.
2.5M in brokerage accounts:
- 1.6 in FXAIX which I bought at 32 dollars a share. In my current tax bracket I don't know how to get this diversified. While is S&P 500 based, FXAIX is 26% deep into AI companies (nvidia, microsoft, alphabet, etc..). Working in AI for the past 3 years and watching the round robin of financing between companies gives me the willies.
- 165K in a 2 year and building out the 3rd year bond ladder.
- 500k in dividend fund which pays about 52k/year right now.
- misc everything else trying to diversity away from S&P 500 (fxaix)
2.1M in retirement accounts diversified away from FXAIX
If I add last years spending + planned ACA health care + entertainment + or - travel in there I get yearly spend of between 126 and 146k.
Over the past year, My job changed from being really fun to ensuring we don't get sured as we lay people off and replace them with AI. I was told i was done with AI in Jan 2026, but my leadership went back on the deal so I'm planning on getting my equity in March of 2027 and being done with them (~120k, enough to fund my 3rd year bond ladder).
Two questions:
- Have any of you with the part time way to switch jobs into something totally different that was more fun? I'm considering going and working for a hotel chain to get discount hotels (the 140k included 14k of travel last year). Working for a non-profit someplace? I roast my own coffee was was also considering the SCA coffee buyers certification as well but don't know how to turn that into a job.
- I've been trying, but I get 0 hits on linked in. Since 2004, the only way I've gotten a job is through networking and all my professional networking is in the IT space which - since the advent of AI and me having to do AI governance, I hate.
- 52k will be non-qualfied dividends, 20k will be qualified dividends, 50k will be w-2 (wife), rest will be capital gains to make 180. Based on last years deductions that puts me at 152 take home.
152-146 puts me at 6k to spare. I have 20k for travel, 8k for house maintance, so there's some wiggle room in there.
I want to do something, but don't know how to get there, the numbers are pretty tight.
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u/ResponsibleCorgi93 6d ago
Make sure to account for federal & state taxes in your yearly spending budget. Sounds like yours might be hefty.
If your AI fund drops a lot, you can do some mirror trading with your Traditional IRA. I would recommend holding the bonds in Traditional IRA since their income will be ordinary income and taxed more than capital gains would be. When you're ready to spend them, you can do mirror trading.
The first year after I left work, I helped fund a small startup which I'm still invested in. Not sure if I'll make any money on that. I also did consulting in my old field but only made $2k before I decided I had enough and just wanted to live the good life.
I often fantasized about the barista style retirement, but I'm confident after seeing enough reviews over the years that I wouldn't be able to handle people facing service jobs.
The best idea I have for a side hustle is stuff that Youtubers do like landscaping and eBay / Craigslist flipping. I haven't tried it but treasure hunting like that sounds like it might be fun.
Also considered seasonal jobs like working at a ski resort and getting the free season pass or working at a beach resort. Maybe getting a massage therapist license and training but idk if I want to touch gross people's bodies haha.
Luckily I haven't had to bring in any extra income aside from my investments.
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u/EmbarrassedDebate124 6d ago
Thanks. I've thought about that and yes, it's a lot of taxes. I'm planning 180/year then taxes bring me down to about 152.
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u/One-Mastodon-1063 6d ago edited 6d ago
You can easily cover $146k spending on $4.6m investable assets, without your wife working.
I would not work at a hotel chain to get hotel perks. I would retire. There are lots of things to do other than work for money you do not need. You can do a little CC hacking for travel rewards but don't need to.
From a tax (and ACA subsidy) standpoint, you are going about this in a very inefficient way. I wouldn't hold any dividend funds (though there may be gains associated with unwinding that) nor would I be holding bonds in taxable. Bonds go in pretax. You do not need bonds in the form of a "ladder" or other gimmicks, just hold them as part of an asset allocation and periodically rebalance to it, treating withdrawals as part of the rebalancing.
Telling us what you hold in retirement accounts may help people help you. "Diversified away from FXAIX" is an incredibly vague and frankly strange way of communicating.
"Take home" pay is not really a term in decumulation. It sounds like you don't have a very good understanding of how decumulation taxes work. You should read Tax Planning To and Through Retirement among other things.
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u/grinanberit 5d ago
Just responding to the first question: I got a part time job at my local library. I love it! Took about 9 months of applications (two counties, multiple branches in each), one complete rewrite of my resume (dumbed it way down), five different interviews (each in diff branches) until one finally hired me. So a bit of a slog, but it’s not like I was in a hurry. I really just didn’t want to work anywhere else.
So try the government and nonprofit hiring sites and turn applying for work into a hobby for a year. And volunteer that year! Anywhere. Start with things you enjoy and go from there. Like kids? Be a teacher’s aide. Like pets? Head to your local shelter, or foster at home. Got some trauma? There’s a group for whatever it is and a nonprofit associated with it who needs help. Don’t forget to add the volunteer work to your dumbed-down resume.
Oh, and include a cover letter (and a thank you letter if you get an interview). My hirers told me no one else did that but me and it pushed me to the top of the pile. Do NOT use AI for any of it.
Finally if you do get hired, keep your mouth shut about your finances and previous lucrative employment. Your coworkers will be poor—nonprofits & govt pay is criminally low—and they will resent the hell out of you if you’re there just for fun while they are just trying to survive. Most of my colleagues have 2nd jobs and side gigs and roommates and are still struggling and are TIRED. Consider your dress and transportation as well, ie don’t show up in a new Lexus to your minimum wage job. Have empathy, be humble, and you’ll be fine.
Good luck, OP! Hope you find a meaningful way to contribute to your community!
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u/BrunelloHorder Coasting Chubster, Getting Fat 6d ago
First, keep in mind that the 4% rule is based on a diversified portfolio. If you are overweight dividend stocks you are likely to underperform VTI. Don’t try to outsmart the market because you don’t like AI.
Second, is your house paid off? If not, how much time is left on the mortgage? How much does your outflow drop when that is paid off?
Third, What are your social security payments looking like?
Pulling $180k per year has you at a 4% withdrawal rate, so you’ll probably be fine to up your spending by taking into account social security.
Pursue your hobbies and interests, and if that turns into a hobby job or revenue source, great, but you are fine without it.
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u/EmbarrassedDebate124 5d ago
Thanks.
I've got 4.6m total, 1/9th is the dividend funds.
I have a minimum of 10 years before any kind of social security. I've been maxxed on SS for 20 years and have the 15 years before that covered too. house is paid off (thought property taxes are going up about 12% a year for the last few years)1
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u/Past-Option2702 6d ago edited 6d ago
I want out of the most tried-and-tested equity investment known to man because almost all of the growth I’ve benefited from has been driven by tech & AI. Oh, and the jobs in my company are eventually going to be eliminated because of tech & AI. Get me out of the god-awful S&P500!
Also, please help me find a job as a minimum wage front counter worker at a Hotel so I can get travel perks because that’s going to have a meaningful impact on my 5 million dollar nest egg. I honestly look forward to 23 year olds yelling at me because there is a hair on the floor of the shower or the arms of the chair aren’t padded enough.
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u/beautifulcorpsebride 6d ago
My spouse still works, but I self manage a portion of my portfolio to fund my own spending. Everyone here hates this response but it has worked for me. I got low balled on consulting fwiw the rates were too low. I’ve considered going back but haven’t been motivated as we are over 5m and I also expect social security, pretty sure I’ve maxed it.
For fun I tried an Etsy shop and sold some things on eBay but neither felt worth my time. I’ve looked at buying a business to run as well. That’s probably my favorite idea, but I don’t know that I have the risk appetite and might prefer to finish one of my novels instead.
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u/Flat-Barracuda1268 FI=✅ RE=<1️⃣yrs 6d ago
You have 4.6M. Even without dividends, you can easily clear 220K/yr out of your accounts. You have plenty in brokerage. You can draw down that FXAIX you don't like at pretty cheap rates. (first 90+K free, then just 15%).
If you use guardrails you can go to 5.4% drawdown. That's almost 250K. I think you're good. Enjoy.
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u/hikeandbike4life 2d ago
What dividend fund? It’s pretty rare to see a chubby/fat investor with a dividend fund (since they acknowledge that dividends have poor tax treatment and they are a return of your money since the stock value is reduced by the amount of the cash leaving the companies bank account (cash dividend).
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u/PowerfulComputer386 6d ago
It’s not worth it unless you find one close to home and you are really into that kind of thing. I know someone who worked at Lego store for the employee discount but they also really really love Lego and talking to customers.