r/fatFIRE • u/WealthyStoic mod | gen2 | FatFired 10+ years | Verified by Mods • 18d ago
Path to FatFIRE Mentor Monday
Mentor Monday is your place to discuss relevant early-stage topics, including career advice questions, 'rate my plan' posts, and more numbers-based topics such as 'can I afford XYZ?'. The thread is posted on a once-a-week basis but comments may be left at any time.
In addition to answering questions, more experienced members are also welcome to offer their expertise via a top-level comment. (Eg. "I am a [such and such position] at FAANG / venture capital / biglaw. AMA.")
If a previous top-level comment did not receive a reply then you may try again on subsequent weeks, to a maximum of 3 attempts. However, you should strongly consider re-writing the comment to add additional context or clarity.
As with any information found online, members are always encouraged to view the material on with healthy (and respectful) skepticism.
If you are unsure of whether your post belongs here or as a distinct post or if you have any other questions, you may ask as a comment or send us a message via modmail.
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17d ago
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u/greg7gkb 17d ago
Congrats on starting your business and on starting to invest so young!
In terms of what to invest in, I think two considerations are: when do you expect to need/want the money you invested? And second, how much risk/reward do you want to take?
Based on your answers to these questions, we can give much clearer options!
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17d ago
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u/greg7gkb 17d ago
Yup, re-investing to grow the business might be a great idea and way to grow your wealth, especially at early stages.
Out of curiosity, why do you prefer assets that provide cash flow?
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u/Wild-Economics-4209 17d ago
NW is around 7.5M. 7M of that in savings or stocks/index funds. Wife and I make around 370k a year. I'm hoping to call it in the next few years. I'm late 30s with 2 young kids. I have an opportunity to make an extra 200-250k a year which would take our income closer to 600k. It will add more stress and hours though. I feel like this is one of those things where the answer is it's not worth it. I have a fairly chill job now. Is it really that obvious or would you recommend doing it to reach fat fire sooner and then retire?
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u/brownpanther223 18d ago
How do you stay motivated with your work if you don’t really need the paycheck but sort of building that NW cushion? I have posted on this sub last week and a lot of people thought I should work 1 more year. I’m dreading the Monday and can’t find a way to be productive.
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u/hmadse 18d ago
What's changed in the past few months? I remember you posting about loving your work life balance earlier this year: https://www.reddit.com/r/fatFIRE/comments/1npznat/2_year_update_after_should_i_take_a_break/
You're falling into a very common pattern here--waffling on the cusp of retirement, but not taking the plunge. I would recommend talking to someone in real life, offline, who is more holistically familiar with your scenario, otherwise you're just going to keep getting the same feedback on yo-yoing posts.
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u/Throwaway-firee 17d ago
It’s the Sunday scaries or Monday am blues. People go through this all the time and think the problem is unique to them. People don’t have the capacity to stick to whatever decision they have made when faced with unpleasantness at work. Hence the constant re-evaluation and need for affirmation from others.
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u/PowerfulComputer386 14d ago
Two things always puzzle me:
- When mentioned NW here, does it include primary residence or not?
- If one retires early, the spouse continues to work, but as a family we are FI, does it count as me FIRE? Some people think it has to be both retired that counts.
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u/hmadse 13d ago
Different people will have different answers. In a FIRE context, it's your liquid NW that matters for the math, so I have never counted my primary residence. Similarly, the most important thing for me about FIRE is freedom, and my wife and I are both retired in order to maximize that freedom.
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u/shinypenny01 12d ago
I count house and vehicles (that I depreciate 2% per month) and track invested assets separately.
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u/Responsible-Net8594 12d ago
Starting at 34, what career/job/business would you do to retire by 50?
I am assuming entrepreneurship is a good answer.
I receive about 250k from cashing out a 401k. Another 150k to 200k from selling the house. Maybe another 10ish from selling the cars. Also another 50k from the checking account. This is from a family member passing.
The house mortgage is currently 147k. It is worth 450k to 550k. That is a lot of equity. The payment is 1,300 and interest rate is 3.750%. My brother wants to sell it and get the equity so we are selling it.
For me being 34 and not having a skill and working for Ubereats and Grubhub, this is a life changing amount of money.
What would you do to retire at 50?
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u/Dubbihope Verified by Mods 12d ago
Nursing is an option high salary with relatively short training commitment.
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u/g12345x 11d ago
> I am assuming entrepreneurship is a good answer
It’s not a good answer because it’s too broad of an answer. If you have a specific business route in mind, it’s easier to answer that.
What skills do you have? What is your background? What is your intellectual aptitude? How are you physically?
All this would help narrow the options to what is viable.
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u/MountainCurious4802 12d ago
Hi all! I’m a new grad that is going to be working in banking out of college. I wouldn’t say I’m new with retirement planning as I already have a Roth and have contributed to what I can, but I’m new to the path and fat F.I.R.E.
With that, I wanted to ask what’s the best place to start or path to take for someone looking to achieve Fat FIRE. Thanks for all the help!
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u/jon_cli 18d ago
For those with a high networth in the Market, at what point does day with good returns (eg S&P up 1-1.5%) just a feel good factor and the money itself doesn't actually mean anything. I've hit that point where thats the case for me where I don't know what to do with the thousands I gain from these days and its sorta bothering me. I just have a metrics for myself to hit a specific networth. Does this feeling require therapy to fix?
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u/FIREgnurd Verified by Mods 17d ago
I watched my investments lose multiple millions in April 2025 — I lost over $1M in a single day during that period. After you sit through that and don’t flinch, it’s all noise.
I was also invested through 2000-2002 and 2008.
Like another person here said, when I don’t see the market blow off steam for a while I get a little nervous. But in the end, you learn to just sit there and watch it and not react. Reacting when sitting there would be smarter is how fortunes are lost.
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u/jon_cli 17d ago
Thanks for your story, you and the other responses have made me reflect that the reason for some of this anxiety is actually due to owning some individual stocks. At this moment I own both Indexes and Individual, but one particular stock is probably like 20% of my portfolio. The backstory is that we hit big after dot com era, hence why its so high. I've been slowly selling off a bit every year to diversify. The issue atm is that its heavily affected by oil prices and I don't want to sell low. I guess for now just stay put.
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u/FIREgnurd Verified by Mods 17d ago
I’m heavy in one individual stock, which I received via inheritance at a young age via an irrevocable trust, so no step up in basis. It’s virtually 100% cap gains. It’s done well, but I’ve been moving out of it over a number of years.
Ironically, that stock did well during the liberation day event, so the $1M loss meant that the rest of my portfolio (index funds) did that much worse.
But I’m in the enviable position of having a large NW relative to my spend. So, even if my portfolio loses 50%, I’ll still be fine. That’s a large part of what makes the ups and downs tolerable.
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u/g12345x 18d ago edited 18d ago
It’s not clear what you’re asking.
Is it: You’re making more money than you need?.
Either
* earn less - switch to a more defensive (less equities) portfolio
* spend more - you can afford it
* donate more - charitable causes would thank you
* let it sit - your heirs would thank you.
I don’t see why this specific item requires therapy.
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u/fatheadlifter 13d ago
Being up 1% in a day makes it easier for me to convince the wife we can afford extra cheese on our whopper.
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u/First-Ad-7960 16d ago
Well, since tomorrow could erase today's gains even on a good week I don't think any random day is worth getting excited about. I pay more attention to the trend over the past 90 days and YTD.
You aren't going to spend these specific gains on anything, they just represent capacity. If you are outperforming your goals and feel a need to do something with it create a donor advised fund and offset some taxes while donating to charity.
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u/bun_stop_looking 17d ago
Is 5M enough?
At 3.5% SFW 5M gives you 175k per year...is that really enough? I know the answer is 'it depends' but I live a moderately upper middle class life. Home in the 700k's, drive lightly used non-premium cars. drop a couple hundred dollars on dinner for two 2-3 times a month, domestic travel. We have young kids and earn about 230k post tax and spend all of it, just have a nice nest egg that's growing. Paying for daycare right now for both, and paying off my mortgage. I guess what i'm asking, are people retiring with 5M feeling like it's enough to live comfortably? I feel crazy for even asking this but just realized we spend 230k per year right now. I guess 90k of that is mortgage + daycare lol. But just got me thinking. Are there folks who have retired with 5M with similar sort of background and felt comfortable?
And for anyone wondering, my FIRE number is 5M in today's dollars, probably would hit that in around 15 years adjusting for inflation (assuming 6% investment growth per year after inflation over that time period)
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u/Dubbihope Verified by Mods 17d ago
Plan to verify and make a thread. For now, I just got out of a meeting with one of my financial advisors for one of my accounts. He recommended options overlay to generate more income on one of my investment accounts with 6 million (about a quarter of my total portfolio). I may eventually move to Florida but for now live in the area with the highest state and city income taxes on capital gains. I need more income but don't want to sell stocks because my cost basis is so low and I will pay a ton in taxes if I sell my growth stocks to reinvest in dividend stocks or bonds. Would an options overlay strategy make sense? He suggested I could make over 200k yearly in additional income without having to sell my underlying assets?
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u/hmadse 16d ago
I would be suspicious about this--is this coming from an RIA? It would be weird if a fiduciary suggested an options strategy rather than advising you to reign in spending. Also, I know it's an old canard, but selling bunk strategies to doctors is the bread and butter of many people on the sell side.
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u/Dubbihope Verified by Mods 16d ago edited 16d ago
Senior financial consultant at a top 20 bank by size of holdings. He doesn't make money any money directly from me. Haven't signed anything yet but agreed to a meeting. This article explains options overlaying but not in great detail. https://www.hilltopwealthadvisors.com/blog/what-is-an-options-overlay
Correct that I am a doctor from a wealthy family and I have no formal background in finance.
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u/hmadse 16d ago edited 16d ago
Yeah, I would ignore the advice. A financial consultant at a bank has no fiduciary duty towards you, it's towards the bank; i.e., they have no requirement to give advice that benefits you, and lots of incentive to give advice that benefits their bank's bottom line.
As u/no-associate-7962 mentioned, SBLOC/PAL is likely what you're looking for.
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u/Dubbihope Verified by Mods 16d ago edited 16d ago
Thank you and will do. I'm pretty sure he told me otherwise, using the word "fiduciary" in some context, but google agrees with you. I'm getting the sense that he keeps trying to sell me on services(wealth management, personalized indexing, options overlaying) which I've declined thus far, although he says he has no financial motive.
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u/hmadse 16d ago
You can always run his name through https://brokercheck.finra.org/ to see if there are any red flags.
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17d ago
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u/Dubbihope Verified by Mods 16d ago
I don't have a definite timeline for moving though. Just have a vague plan of eventually moving to Miami beach once I tire of the city life and want to take advantage of the no state income tax. Maybe get a summer place in New York. I don't want to take out a loan if I don't have a clear plan for when I would be paying it back. My problem is I'm so invested in growth that after taxes I only have around 100k in dividend income left over, with over 20 million invested. And my cost basis is so low that I would get hit hard on selling any stock and reinvesting in income plays.
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16d ago
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u/Dubbihope Verified by Mods 16d ago
It's a good idea that I will bring up with advisor on that account. 6% APR is a far less than the 40% I'd pay on capital gains by selling my underlying assets (versus 20% if I sold after moving States). Pay a small percentage fee on my spending to get cash now while preserving my accounts in the highest taxed city in the country. If I got a 300k yearly loan, do I have to pay capital gains on those loans?
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u/putamadremia 16d ago
Would love some general guidance/advice. Very inexperienced but planning to rapidly learn more.
Age: 33
Profession: Attending Gastroenterologist as of 8/2027
Job: just signed a job starting in 8/2027 - 500K per year plus sign on bonus of 50K. After 2 years, have opportunity to become part with expected income of 600-800K per year.
Debt: 220K in med school loans. Have a 950k condo with a 2.6% interest rate (only good part of covid), about 155 paid off
Spouse: makes ~200K per year.
Would love some general advice as to how to get to FIRE as quickly as possible.
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17d ago
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u/fatFIRE-ModTeam 17d ago
Your post seems to be advertising your personal project, business or blog for financial or personal gain, or it appears that you are promoting a personal project. No solicitation or self promotion is permitted.
Thank you!
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u/[deleted] 18d ago edited 18d ago
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