<prompt> Human: edit 2: Thanks! I wrote him back honestly basically summarizing everything you guys said - that he didnt give me enough numbers on expenses or anything to help with an actual decision but that it sounds like enough to get by, and if all else fails I make enough money that they can live with me which seemed a funnier way of saying, Dont worry about me, which some of you suggested he was checking on in subtext. And that he cant rely on a bull market forever. it was a much longer email, but thats the gist. Thanks for the advice!!In his Money magazines that he gets, they said that past the age of 60, parents should ask their kids about money matters so they dont make bad decisions... but, well, I dont really know that much. He was originally going to retire May 2016, he then pushed that to 2017, but hes perpetually worried about having enough money, and now its February 2018. But he just sent me an email asking for my advice on whether he should stay on until 2019... I am not qualified to advise on this . Please help!Here is the info in the email I got: I have been reviewing my spreadsheet projections for next year, after I retire, thru Oct 2019. Quite an income drop not sure I am ready for that yet, even though I can make it up from investments. Going from monthly take home of 6,600 after Roth IRA investments to 1,350 after health ins costs. But gets better in Sept 2018 when your mother goes on Medicare. And improves even more when I reach Medicare and take social security Oct 2019, to 5,450. A short term hit on my investments of about 60,000 before I have extra money again. But I am definitely tired of working, and as long as the stock market stays strong for another 2 years, I should not notice the impact; guess I could always work till 2019. I know that isnt enough information, so here is everything else I know from searching emails hes sent me the past few years:- Theyre solidly upper middle class, living in CT. - Hes stated that when he retires, hell likely have to pick up a part time job to afford the taxes of CT and theyre never moving, because they built their house on family land and have never lived anywhere else. However - he cant figure out what he wants to do, so Im not actually sure the part time job is going to happen. Id put that at 40 likely.- We also have like 27 acres of land, which this September hes going to get a forester to come out and classify as forestry land, which I think drops the taxes on the land to somewhere between 3-5K. But then there are still taxes on our house.- I know he has a pension and a traditional 401k through his job, and hes been putting 13K or whatever its allowed for a married couple in the Roth IRAs every year.- He goes off the to save enough to spin off a benefit of 50K a year; using the 4 rule, one would need 1,250,000 in a 401K at age 65 to get that each year. I dont know if he has that, but hes told me that should be my goal. And I think he has at least 1m in assets, but idk if that counts the house.- Its very difficult for me to imagine that theyre short on money because my mom always talks about how much Im going to inherit, so I imagine my dad is playing safe rather than sorry. Plus, I make enough that if I live somewhere cheap like the Carolinas or Maine or something, they can come stay with me my boyfriend probably wont like that though, haha.- I know my mom has a lot of medical bills; she has thyroid problems and IBSThats everything I know. So... what questions should I ask? Or say? Or... ?!?! : Thanks!edit - Thanks! Im writing down the questions that you guys ask to pass on to him, and reading the rest, but I cant go on reddit a lot at work, so sorry if something requires a reply and a lot of time passes by. Im trying to check in the bathroom :. Also, I highly, highly doubt theyre leaving CT... they were talking about it, but then they just 5 more acres of land when a farm next door went on sale, so I think the probability of this is at like 0.  <response>: Too hard to know based on information provided. How much are current retirement savings IRA401kpension? What other investments exist brokerage account? What are currently monthly expenses and debt load if any? What lifestyle are they trying to live in retirement?The 4 rule allows for a gradual draw-down of your nest egg. You should have the expectation that your investment will shrink over time. It is not a rule that allows for principal preservation. If that is his expectation he needs to revise his approach.Also, 5450mo post-tax in retirement income is substantial. Thats over 60kyear. Spending every dime every month living paycheck-to-paycheck doesnt matter anymore because you are retired with a million dollar plus emergency fund in the form of your nest egg, which is spread around your various retirement accounts, brokerage accounts, cash in hand, and cash flow from SS. 