OurNextLife.com // Pre-Retirement To Do List, Things to do before we retire, pre-retirement checklistgearing up

Our Pre-Retirement To Do List

As we get closer and closer to our retirement date, the idea that we are actually going to retire early is becoming real. Not that we ever thought we wouldn’t do it, but saving up to never have to work again is such a big goal, one that takes such a long time to accomplish, that for most of the time we’ve been saving, the goal itself has been a bit abstract. It’s like trying to imagine crossing the finish line of a marathon before you’ve learned how to run a mile yet. (That was also my experience training to run a marathon, by the way, as a non-runner. I know when I first started, I couldn’t actually picture myself going that distance. I could barely picture running a mile without stopping.)

But month by month, we watch that ticker count down and our account balances go up (lately a lot faster than planned). And it’s slowly dawned on us that this is really happening. We’re really doing what we set out to do, and we’re close to earning our freedom for good.

As that realization sinks in, we’re slowly shifting into what we’re calling tactical mode. For years, we’ve been planning our investment strategy (short version: index funds and a rental property), putting contingency plans into place, and pondering the big questions like what kind of people we want to be now and in retirement.

But now that we’re getting closer, we’re creating a different kind of to do list, mapping out everything we need to do before we pull the plug on our careers sometime next year.

OurNextLife.com // Pre-Retirement To Do List, Things to do before we retire, pre-retirement checklist

We’ve got lofty aspirations for our early retirement, but to get around to writing novels and climbing big walls in remote places, we have to have the basic elements of our life and health in order. And that means taking care of some checklist tasks before we leave our work. Here’s what our pre-retirement to do list looks like. Let us know in the comments if you think we’re missing anything!

Must-Do Tasks

Switch our health insurance — We’re currently insured through our employers, and will need to switch over to health insurance on the Affordable Care Act exchange (or at least that’s what we plan to do, assuming there are still insurers left on it by the time we enroll). We’re hoping to keep our post-retirement income under key thresholds to keep our health care costs affordable and predictable, and have been doing research to get a sense of what that coverage might look like. But given how much plans have been jumping in price each year, and how many major insurers are dropping out of the exchanges, it’s hard to know what our options will be next year.

Take care of preventive health care — Even though we anticipate having good health coverage in retirement, we’re not wasting time using our preventive benefits now. We just got a whole bunch of vision stuff taken care of (full work-ups at the ophthalmologist, not just optometrist, plus new contacts/glasses/sunglasses), and we have dental care scheduled so we can get as many fully-covered cleanings and exams as possible before that coverage ends. (Not expecting dental coverage in retirement.) And though we’ve fessed up to being cheapskates about doctor visits, we’re committing to getting all of our preventive medical check-ups and labs done before we quit.

Determine our withdrawal strategy — We expect our finances to continue evolving in retirement. We’re going to have to learn how to budget at least a little bit, and also expect to evolve on how much we end up spending. But we’ll need at least a starting strategy for how and when we’ll sell shares, in addition to cashing out the dividends that we currently reinvest. We plan to have a few years’ expenses in cash at the time we quit, so we don’t have to have this completely figured out the day we leave our careers, but the intent behind the cash cushion is to buffer against market dips, not to buy time while we decide our withdrawal plan. So we have some homework to do. (Input welcome if you’ve read something that makes a strong case for one approach over another!)

Pick a cell phone plan — I have a work-paid iPhone, and I’ll be honest… I get a little twitchy whenever I think about having to give it up. I know people love Republic Wireless, but I’m not totally there yet on having only a couple of phone choices. Fortunately, the budget-friendly wireless market seems to be exploding right now, so we wouldn’t be surprised if there are more options out there next year. I don’t know that we’d be willing to pay full price for a new iPhone, but if work let me buy mine for cheap (it will be over a year old by the time we quit), then that might sway us to consider a plan with a carrier that lets you bring your own phone.

Buy computers — On the subject of technology, we’re actually totally work-reliant when it comes to computers. Mr. ONL has an iPad Mini and I have a Kindle Fire, but neither of those can serve as full-time computers, and our laptops are both work-provided. We’ve started exploring options, and are still at the very early stages. Mac or PC? Full-powered laptops or netbooks? Laptop-tablet hybrids? (That’s probably not even what those Surface things are called, but that’s how little research we’ve done.) I suspect we’ll probably get one full-featured laptop so we can do things like edit video (foreshadowing!), and one much cheaper option since Mr. ONL does less RAM-heavy stuff than I do.

Determine impacts of our quit date — We’ve been in our jobs so long and policies have changed so many times in the meantime that we aren’t actually sure of our companies’ 401(k) vesting policies, COBRA rules, sick leave pay-out policies, etc. We need to do some stealth research to figure out if any of those things should affect what we call our last day.

Should-Do Tasks

Pay off the house — This is definitely happening, so it’s only on the should-do list because it’s not technically mandatory for us. But we want to keep our retirement incomes low for health insurance purposes, and that would be tough to do if we were taking out enough value from our investments to make mortgage payments. With as ahead of schedule as we are currently, we’re thinking we could pay off the house this year even, depending on how year-end bonuses shake out, but Mr. ONL finally admitted that he doesn’t want to do that because then, every week in 2017, I’ll ask, “Why can’t we retire yet?” Ha!

Move our 401(k)s — We can’t wait to get our true retirement accounts out of the expensive hands of Fidelity and Merrill Lynch. We can’t technically do this before we retire, but will do it as soon as we possibly can afterward. Stay tuned for a full post on this!

Cancel home phone service — Because we both work from home, we have the fastest cable internet and two cable phone lines. We’ll be cutting the phone service and re-evaluating our internet bandwidth needs shortly before we quit. Though, because we cut the cord and rely on internet for TV, we’re not eager to slow the pipe. We do plan, though, to keep our Google Voice numbers that we currently use for work, so that we’re still reachable beyond our cell phones — that’s a free service, after all.

Wish List Tasks

Buy an RV — We have big terrestrial travel plans, especially our endless winter idea, and that would be so much more comfortable in a vehicle with walls (and an indoor toilet) than in a tent. The last time we wrote about it, we were leaning toward a small travel trailer, but now we’re leaning toward a micro class C RV. That could change again, of course, but we’d love if the stars aligned to bring us a lightly used, low mileage RV in the model we like best for a super low price. ;-)

Take an expensive trip or two — My mileage account should top 1 million miles this year, and Mr. ONL has another half million more, so we’ll be able to travel in retirement even if we mismanage all of our money and have a lot less to spend than we plan. But there are lots of places on the planet that are terrible for budget travelers — Iceland, Australia and Japan come to mind. We’d love to visit one or more of them while we still have big cashflow coming in each month.

Already Checked Off the List

Review our insurance policies — Earlier this year we did a full insurance review and added umbrella liability insurance. (If you’ve saved a lot, you should consider doing this too! Because contrary to what Rihanna sings, you can’t stand under my um-ber-ella. You need your own.) But we’re glad we took the time to make sure we had the right levels of coverage on our home, rental property and cars.

Crowd-Sourcing Time

What did we miss? What is on your pre-retirement to do list, if you’re in the planning stages? For those who’ve already retired, what else should we add to our list? We’re all ears!

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78 replies »

  1. So smart to get that preventive health care in! I did the same thing before my last set of benefits ran out! I’ve used a number of different MNVO’s for cell service over the last few years and I have been happy with all of them. It isn’t a big jump once you make it :) We are starting to look for travel trailers too to begin our journey’s next fall! We’ll have to compare notes on that one. My husband is against the RV idea – but we are early stage researching now. We have friends going to Iceland in September! Crazy expensive but they are FI and retired – and they are normally frugal travelers too. A great list!

    • That’s great you got your health care taken care of before you lost benefits! It’s so, so important. And good to know re: phones. I’ve just had a work phone for almost a decade, and so haven’t had to learn any of that stuff. The idea of looking at a cell phone bill even feels foreign. Haha! And how exciting that you guys are looking at trailers! In a perfect world, we’d already have an RV, just because it will give us so much more flexibility to just take off for a short or long trip on a whim (which we could really use now, to be honest!). If you want more info, message me on Twitter — I pretty much have learned every pro and con of every type and model out there. ;-)

  2. Wow that feels overwhelming just reading the list of things to do.. but on the other hand it is insanely exciting, I cannot even imagine being that close to the end goal – that close to the FIRE that has been planned for years upon years. It gives me those excited butterflies for you guys just reading your countdown (16 months to go..!).

    Taking that final plunge is probably the hardest part, even after such careful planning.. Are you guys having any pre-retirement jitters or cold feet?


    • Thanks for sharing our butterflies! :-) Ask us the cold feet question again next year… right now I’d say no, but that could change as we get closer. I’m definitely an over-planner/over-thinker, so I’d say jitters are quite possible. :-)

  3. Looks like you guys have a pretty good checklist going. I can’t imagine why you would need it, but now’s the time to get any financing for anything you might need (car?) while you still have W2 income.

    I like the joke about the healthcare insurers, although it’s unfortunately not that laughable anymore. I’m sure that you’re watching that area closely just like a lot of us are right now. Pretty scary stuff!

    — Jim

    • It’s a good point about financing if someone was going to take out a new mortgage or buy a business or something like that. Though we hope to never need financing for anything ever again, and even if we did, we expect to be able to show enough cash to where our income would be irrelevant. (But I think you know we are way more conservative about debt than others are!) And honestly I didn’t mean that insurer stuff as a joke — I’m serious! It’s pretty tough to plan right now with the landscape shifting so much!

  4. This is so fun to read, made me giddy for you. The only thing I would add (but what do I know, I am not retired lol so take that with a grain of salt) is determine post tax vs pre tax amount to ensure you can have your roth conversion or other strategy ready for withdrawal before the regular retirement age (and tax implications). Lastly that your 401k plans don’t have true ups – that is that if you maxed out early the match does not come until early NEXT year.

    I will say, I am drooling over your mileage account lol. Way to go!! (if you have not tried Singapore air first class cabins or Cathay Pacific Business yet…I just wrote about our trip to Hong Kong, Singapore and Malaysia – btw in Hong Kong hiking in Sai Kung is AMAZING).

    I cannot wait for your travels so that I can follow along and get even MORE motivated about retiring.


    • Aw, thanks! It makes us giddy too! Haha. That Roth reminder is a good one for most folks, so thanks for adding it. We aren’t planning to convert any of our true retirement funds over (here’s why: https://ournextlife.com/2016/04/20/later), but we know we’re outliers on this. ;-) And don’t be too jealous of that mileage balance. We’ve earned those miles the hard way! Haha.

  5. I hear you on it getting real. I said to Mr. PIE just the other day “in January we’ll be able to say it’s just next year!”
    Your to do list is similar to ours, and I really must write some of it down soon to stop it from swirling around my head. The extra part for us is selling our current home, along with many furnishing and possessions. There are several projects that need doing to get our house ready for sale.
    The most confusing thing to us at the moment is timing. In an ideal world we would put the house on the market, quit work as soon as the sale was pending and move to our new home all in time for the new school year. The worst case scenario is quitting work and not having the house sold. The to do list will also contain some contingency plans!

    • So exciting how close it’s all getting! I would imagine that your to do list must feel much longer given that you have a home sale on your list and a downsize of your possessions. We had that a few years back when we sold our city home and committed full-time to mountain living… I’m so excited for you guys that you’re on the same path! I bet you won’t miss the city at all. :-) And I can see the challenges of trying to time it all out, though I will say that I moved mid-school year a few times as a kid, and it was never actually that big a deal. It’s admirable you don’t want to put your kids through that, but it’s really not the end of the world if you have to uproot them at an unideal time. Kids are so resilient!

  6. I love the big trip idea. Do it now..and do it again later?! :) My parents are kicking around the idea of buying an RV once my mom actually retires and stays retired this time (?). I will say that the thing that makes me the most nervous for anyone who is retiring is the cost of being sick. It’s been on my mind so much lately. I’m loving the fact that you’re focusing on health care before you retire! Also, if you could figure out a phone option and write a detailed process review before next April, that’d be perfect. Ha! Our contracts will FINALLY be up!

    • Oh yeah, there will be MANY trips in our future! I just don’t know how much we’ll want to stomach Iceland prices, for example, once we’re on a teensy budget. (Not really that teensy, just teensy compared to those spendy countries!) And yeah, we’re pretty much obsessed with health and health care. I didn’t say it here, because we’ve said it so many times before, but it’s why we don’t constrain ourselves to a tiny grocery budget, because we always want to be able to buy the healthiest food. And it’s why we’re super focused on staying active, too. So yeah, we have some extra preventive care to check off before we quit. And I’ll add that phone option post to the queue! ;-)

  7. This is the most exciting to-do list ever! Glad you’re ready to tackle this stuff–it means you’re so close. On the computer front, we bought a used business-model HP laptop (eBay) last year and really like it.

  8. The healthcare plan part seems like the biggest issue, mostly due to unknowns. I am sure you two will figure it out and keep us posted though. I did read on another blog that full time RVers have a hard time getting health insurance through the affordable care act because they don’t live in 1 state for the majority of the year. I know you are planning on keeping your home base so it shouldn’t affect you.

    Other than that I think you have everything checked off, good luck stealth researching your works policies!

    • Yeah, so many unknowns on health care, and the presidential election will affect that, too. We’ll for sure keep talking about that here! :-) And yeah, keeping the home base will for sure help with health coverage!

  9. The to-do list can seem endless! Like you, we still need to figure out health insurance, though we’ll probably Cobra at least for the first year. For us, it’s a lot of preparation of the Airstream for full-time life. Like, solar panels (will be installed in November), a Honda 2000 generator, bikes, fixing a leak, etc. Lots of stuff, but we’re glad to do them because of what it all means – early retirement from full-time work.

    Paying off the house is an excellent one. If we hadn’t sold both of ours, we definitely would have looked at paying at least one of them off too. I’ve grown to hate mortgage interest…and owing the bank *anything*, really. No mortgage = flexibility!

    • Take a look at ACA coverage before you go with COBRA — the latter is SO expensive, I bet you could save a bunch with ACA, plus given that you won’t have a permanent address in the future, getting established on a plan while you’re stationary could help a lot. And yeah, I can definitely see how the project list on the Airstream could seem endless! I’ve heard that that stuff never ends, but I think it’s smart to get as many things done as possible before you hit the road full-time. And yeah, we’re as anti-mortgage as you are! We just want that home base, so that means getting the mortgage monkey off our backs ASAP! ;-)

      • I bet you’re right, Mr. ONL. I just keep remembering back to the good ol’ days when you weren’t required to have health insurance. I voluntarily went several years without it, and I saved a BUNCH of money – and then proceeded to spend it, of course, on stupid stuff that I didn’t need. ;)

      • Haha, yeah, we had those days of the stupid spending too. :-) And yeah, before the ACA, plenty of people who retired early just got catastrophic coverage, but since that’s not an option anymore, you might as well find the best deal for yourself within the current system!

    • Have you looked into COBRA at all? For me, it would cost about $500/month. It would be worthwhile if I’ve say already hit my deductible for the plan year possibly to finish out the plan year on it, but otherwise, not necessarily.

      • We haven’t done a lot of looking yet. We hit the healthcare.gov web site several months ago just to get a feel for our options, and it actually wasn’t bad. Cheaper than we had thought, actually.

      • Based on the budgets you guys have talked about, if anything it seems like your challenge will be staying ABOVE the Medicaid threshold. You should be able to get a big subsidy, though.

  10. Our timing is still getting worked out, but barring a disaster of a year for Prof SSC, the new plan will look like me quitting while she is still working. I’ll just go to SAHD mode, and probably 2 months alter wonder why I thought work was so hard and I wanted to leave in the first place, hahahahaha…. Actually, that really freaks me out more than the “retirement/money” side of it anymore. :)

    BUT, we have similar plans in place as the date gets closer. I had to replace the abtteries in my retirement countdown clock this weekend and bumped it back to Aug 2018 from where it was set at July 2017. That was predicated on Mrs. SSC still working the corporate life, sigh…

    I also realized this over the weekend. I’ll take our new “relaxed” schedules over hitting FI a year sooner any day! That in itself is a pretty powerful statement.

    Our biggest post retirement change is cashing out our pensions from our old company. I elected not to when I left, but as soon as we’re not in a top tax bracket, I trust us with that $$ way more than those guys still having it in another 20 years. We’d get hit pretty hard with taxes if we took it now, so we wait.

    I also want to do some traveling, and almost have Prof SSC on board with a pop up. Some things could happen that might change that, but that’s my current thought for some summer time road tripping family vacations.

    • It makes me happy every time I see Prof SSC. ;-) I’m so intrigued by this, that you’re concerned about getting cold feet and missing work! I sometimes wonder if I will miss feeling relevant and useful to the world, but I feel pretty sure I will not miss the work part. :-) And yeah, it does speak volumes that you guys are willing to slip a year on your timeline to have a more relaxed life in the meantime. I think we’d make the same trade, too, if that was an option, but we can’t figure out any change that would have us slip ONLY a year… more likely a job change would mean either an equally stressful situation or a way bigger paycut. Oh well… Poor us, retiring next year. :-p

      Your pension strategy makes total sense. We can’t wait to be in a lower tax bracket for a bunch of other reasons, too, like actually having positive cashflow from our rental. Right now it’s all taxed at our high rate, so it’s a net negative, but that will flip.

      Re: the popup, take a look at small travel trailers. Popups tend to be heavy and expensive for what they offer, as well as not super durable. This is something we’ve learned in our exhaustive research! :-)

      • I think with the work aspect – it’s more of the fact that I currently really like my job, people I work with, and corporate culture. However, they are slowly going down a path to “bureaucratize” themselves like one of the majors and that is sad, because currently it’s great. 2 years from now – who knows I may be running out the door happy as a clam to be able to leave. :)

        Also, they just keep giving me more financial incentives to stay. 2019 I’d be up to a mid-year bonus of almost $40k on top of the “regular bonus” from April…. It’s mind boggling really. Not that, that reason alone is worth it but, if life is easy and there are no outside of Houston teaching gigs, it does serve the purpose of “Long Term Incentive” and could possibly keep me here long enough to get it cashed out.

        Thanks for the tip on the popup and small trailer! I’ll definitely look into it. That has been my alternative to road tripping with only camping or hotels/motels. I think Prof SSC is on baord with the idea of it, we’d just have to find the right deal. That’s for Future Mr. SSC to worry about though as it could be a while, lol.

      • I want that mid-year bonus! My retention bonus is a lot smaller that that, if it makes you feel extra special. Haha. Apparently I’m way less valuable than you are! ;-)

        Also, loved your ref to Prof SSC in Monday’s post! Just haven’t had a chance to comment yet, but it’s coming. :-)

  11. House maintenance projects – perhaps worth looking hard at potential big ticket items like roof, windows and heating system. I suspect its easier to suck up a $10,000 bill when cash is coming in on a biweekly basis. Yet this sort of stuff will not go away in FIRE. Deal with now or later? It’s a mental game to do now or defer to later. Its all money.

    Regarding withdrawal strategies, Darrow over at Can I Retire Yet has a great series of posts on this very topic. It is a critical aspect of FIRE, arguably THE most important. Here is link to the latest.


    I have to say I really like the concept he is advocating on the CAPE Median strategy — choosing to liquidate stocks or bonds based on Robert Shiller’s Cyclically Adjusted Price-to-Earnings ratio (CAPE). Of course if you are all in on 100% equities (we don’t have that appetite- others may well do!) or have blended index funds (mixing bonds and equities like VWIAX) this strategy won’t work. And the big questions on bonds are always out there. Is the bubble about to burst? Have bonds been in the sun too long? A minefield of endless debate…..

    Go take a look at his approach and other withdrawal strategies he discusses on his blog. I can imagine there will be more posts to come as he refines his methodology further. Certainly worth considering at least.

    Finally Wade Pfau also has some great technical articles. A podcast he did with the Financial Mentor (Todd Tressider) may be a great place for you to start by listening to his philosophies.

    Hope this helps.

    • Good point on house maintenance projects! If we hadn’t had every appliance and major component of our house fail right after we moved in, we’d be thinking about this! But we already have pretty much new everything. :-) And thanks for the links on withdrawal! We’re definitely not 100% equities. :-)

  12. Have you guys written about the paying off mortgage vs investing that money debate? To me, it seems totally logical to pay off the house and lower expenses (vs the income in retirement needed to keep paying the mortgage), but I know there’s been a lot of analysis about how investing the money could be more financially beneficial.

  13. Great list! It’s exhilarating just thinking about early retirement. Seeing you get closer and closer gets me jazzed up again about my own exit from working life, something I can still take for granted now that it’s been nearly two years. A few things you might add: get your prescriptions filled on the company plan out as far as you can go. If they do the super cheap mail order prescriptions, try to get renewal dates so you can get another ninety days on the old plan. ACA prescription plans are not as generous as employer paid plans, and don’t offer as much leeway as far as medications, so refill as many prescriptions as you can ahead of time. When you’re checking into ACA plans, be sure you ask about any medications. My migraine medication, which I take infrequently but when needed, actually works, is not on the $945.12 Blue Shield plan. Even though I received a good supply last March, I am very low now and the cost to purchase the medication is $370 out of pocket. Additionally, my physician here isn’t familiar with the medicine, so it’s a battle even obtaining a script for it. Something worth checking into sooner rather than later. For cell phones, we switched from ATT at nearly $180 per month to Consumer Cellular at $52 per month. Same phone (iPhone for me, Android for Mr. AR), chips sent free of charge, and same connectivity (they use ATT towers up here). No difference, just much cheaper! We also returned everything Comcast, including the router (I never even knew we were paying a monthly rental fee for it). We purchased one from Amazon, and after going internet only for ninety days we were able to go online and snag a year of the highest speed for less than $60 per month as a “new” customer. Review your bank statements for any recurring monthly charges (Hulu, Netflix, post office box, etc.). It’s easy to get nickeled and dimed to death in retirement. We still have our trusty Apple desktop, but we use our tablets and phones almost exclusively so I’m not certain I would replace it if the time came. Transfer everything personal from work devices to some other storage method sooner rather than later, and take the time to review all the data on your work devices. I rushed through this process and occasionally still recall something I didn’t move from my work desktop to a memory stick. No big deal (I got all the photos), but if you have the time I’d start the purging process soon. Lastly, if you have and certifications, licenses, or anything else that is work related but belongs to you personally (like a real estate license or an HR certification), take the renewal courses and renew while still employed if your employer offers any financial break on doing so. You may not ever need that stuff once retired, but it won’t hurt to have it.

    • So many good suggestions here! I didn’t think about prescription meds because we don’t have any that we take regularly, but there could be some that we’d want to have around that we should load up on, especially for future travel to less developed countries. (Hmm… I wonder how long Cipro keeps…) And maybe we should look into getting travel shots while we’re still on our current insurance. You’re getting my wheels turning! :-) That’s GREAT to know about your new cell plan. I didn’t know that there were any plans that cheap that I could use with an iPhone!

      • Go to google and search MVNO with your carrier. It’s a rather fun rabbit hole to go down. :)

        It’s my understanding hat quite a lot of people aren’t so fund Republic…it just happens to have a lucrative affiliate program.

      • Okay, I’ll schedule that rabbit hole for next spring sometime, when I plan to have five seconds. :-) And that’s super good to know about Republic! I’ve wondered if the whole wifi-first thing is really that seamless. But yeah, it’s exactly that kind of thing that underscores why we don’t do affiliate links here. The promise of profit could color our view and make us recommend something that’s not actually that great. We’ll pass. :-)

    • That’s a good suggestion! We’ll add this to the list! (We’ve also thought we would get dental cleanings and exams abroad when we travel, which we hear is much cheaper and just as good of quality.)

  14. So excited for you guys. Great to-do list that you shared. Figuring out your health insurance is going to be very important. I’m glad that here in Canada we’re covered by universal health insurance. The only thing that I need to do is to pay for my coverage (work pays for it right now). We also get extended health coverage for things like dental, physio, massage, and etc through work. Won’t get that if I leave work once we reach FI… but there are similar insurance you can get. Overall, I think Canadian health insurance is better set up for FIRE ppl than Americans. :)

    On computers… it depends on what you plan to do. If you plan to be on the road quite a bit, a laptop makes sense. I’m a Mac guy so I like MacBooks. If you need something with higher horsepower, definitely get the MacBook Pro. At home we have an iMac because I use it for photo editing and it’s nice to have a bigger screen. When we reach FIRE eventually and decide to travel around the world, we’ll probably go with a smallish laptop.

    • Thanks, buddy! Yeah, you guys have it so much easier when it comes to health care! Our system is better than it was, but still such a mess, especially the patchwork from state to state.

      The MacBooks are definitely in contention, but I think a light weight and small size will be super important because of how much travel we plan to do (and I’m a diehard carry-on-only purist). :-) I have a big monitor at home, at least, so I can make even a small laptop feel like a big screen when we’re home!

      • For work I used to have a 15″ laptop, now have a super lightweight 12″. I don’t think I can ever go back to a large laptop. Hooking up to a monitor when you’re at home is a good way to get more screen real estate.

        I’ve seen a few ppl using Surface and iPad as a travel laptop but I think MacBooks are better since it’s based on OSX.

      • Is it weird that my biggest concern is actually the keyboard? I don’t like that the tablet keyboards or surface keyboards don’t type like a real one. I feel like a lot of machines have plenty of power these days, so the keyboard is inordinately important to me. ;-)

      • Not weird at all. I type pretty fast so a good keyboard is very important to me. I find MacBook and Lenovo keyboards are pretty good. Another thing to consider is the track pad.

  15. It is so good that you guys are totally on top of things and what you need to get done :) I never would have thought of utilizing all the medical/dental/optometry things before leaving, but that’s brilliant!

    • Health is super important to us, so maybe we should remind people of that one more often! We should all be using our health care benefits all the time, but especially if your cadillac insurance is going away at some point, it’s important to get all that preventive stuff taken care of! And Accidental Retirees pointed out earlier to fill up on prescriptions as needed — I’m now thinking about what meds we might want to have when we spend months in countries with travelers’ diarrhea, and whether we can get those antibiotics in advance. ;-)

  16. What about decluttering? I continue to find it cathartic. :) We keep surprising ourselves with just how much stuff we don’t really use. I think a good decluttering sesh will be one of the ways we use the space in between work and what we do next.

    • Good one for the list! We declutter on a rolling basis, but maybe we will crave one more big wave before we quit… though I could also see a big downsize being one of our first tasks after we actually quit!

  17. I just went through this and I think you have it pretty well covered. I quit mid-year so I could max out my 401k but keep our income below the Obama care cliff after HSA and 401k contributions. You’ll want to use up your flex contributions (at my company the expenses had to be incurred before the end of the month in which I termed). I was given my laptop in exchange for being available to support my successor (I knew she wouldn’t need any). No one wants a used laptop so you may find it pretty easy to take it with you. I could have negotiated a pro-rated bonus based on the portion of the year I worked but I didn’t. I stockpiled my PTO so I ended up with about a month paid out.

    Jim Collins recommends changing your investment accounts to pay out dividends and capital gains. Since you’re already taxed on these, it seems like a painless way to pull some cash out.

    • One more thing–think about how you want to communicate your resignation. I told my boss and asked that he let me tell my team and key colleagues before the message went company-wide.

      • If anything, we probably OVERthink this one, because we dream every day of the resignation moment. Haha. But yeah, good for people to add to their list! The timing, the actual “how” of doing it, etc.

    • That’s so awesome that you managed to engineer everything so well! We know we won’t qualify for any Obamacare subsidy next year even if we only work a little bit, so that could be an X factor — but we still expect to work most of the year if not all of it, so we’ll probably do a short stint on COBRA and then transition to full ACA coverage at the start of 2018. Our companies rent our laptops, so we probably won’t be able to swing that arrangement you worked out (awesome!). And yeah, we’re absolutely going to follow Jim Collins’ advice and have the dividends pay out, for exactly the reason you said. If we’re paying tax on ’em, we want to use ’em as cashflow!

  18. Love the cloud pic! This is a constant battle for us… when to do what. When and how do we ramp up a self-employment project for the future but not give up our time freedom we enjoy now? How do we give the kids the travel experiences we want them to have before we leave work? Will Mr. T go for his boss’s job when she retires in a couple years or do we take that time to high tail? When you don’t have a solid plan, making a pre-plan to-do list is tricky. :)

    • Thanks! The clouds have been magical lately, both here and from the plane all over the country. I saw the craziest thunderheads last week over Kansas! Awesome. And I know what you mean about making the to do list when the rest of the plan is still coming together, but give it time. I know it will all get clearer for you guys. :-)

  19. I tried to take care of all my health care stuff too.
    Have you looked into life insurance? I had life insurance with my employer and had to get a new policy. We have a kid so it’s a big deal for us. It may not be necessary for you.
    Also, if you are thinking about refinancing, you should do it while you have a job. It sounds like you’re planning to pay off the house, though. That’s good too.
    Don’t forget to make the “I Quit” soundtrack. It’ll be great when you walk out for the last time. Good luck!

    • That’s great you took care of your health stuff before pulling the plug! And yeah, we definitely have life insurance. We’ll lose a big chunk of our employer-provided insurance when we quit, but we have separate term life policies that won’t go away. (We don’t have kids so it’s debatable whether we even need these, but they’re cheap and we think of them as “grief money” for the surviving spouse.) ;-) And what a good idea to do the soundtrack! We definitely have to do that!

  20. Have the cash buffer as a true buffer and not as a learning vehicle for figuring out how you’ll stagger your withdrawals will be a great boon. Personally, as a horrible sleeper, I would want to use my excellent cash flow to buy the best bed I could before retiring. Would be so much harder to justify the expense later, but I know that my body sleeps poorly and that I have pain management issues. Doing that for myself would do a lot for my feeling good during retirement.

    • Totally agree! I don’t want the cash buffer to be there just because we haven’t done our homework and then have it not serve its intended purpose. And good call on investing in a good bed! I’m a big believer in good mattresses, good office chairs and good shoes — life is too short to put ourselves through pain from bad foundations. :-)

    • That’s great to know! We’re on PCs for work, but are definitely contemplating going back to Macs once we get to choose our own technology. If it wasn’t more expensive, it would be a no-brainer, but the price difference is at least enough to give us pause. :-)

  21. I love that mileage balance but I can’t be jealous because I know what you’ve gone through (at least a sliver of it) to earn those dang things! Thanks, Twitter.

    Not that I’m on the cusp of ER but I know I’ll miss the fringe benefits of work (fully funded computers, FSA accounts, subsidized health care premiums, etc) when we do finally exit the workforce ;)

    You mentioned that you will have good healthcare when you leave but would you mind elaborating? That’s definitely a key factor to be addressed in our retirement planning – I know if I want to keep our currently-good coverage, it’s going to cost us!

    • Thank you for knowing that we’ve earned our miles the hard way. :-) Lots of folks have commented over time things like, “Wow, nice travel hacking!” and I’m like, “Uh, no, that’s time in the seat. Hundreds of trips through airport security. Hundreds of delays.” ;-)

      And yeah, losing those work fringe benefits will hurt! I know! I’m still a year out and already mourning the loss of my iPhone. Hahaha.

      Okay, so healthcare. We’re planning to keep our income low enough in retirement that we’ll qualify for a subsidized ACA plan, assuming the ACA is still a thing. In some situations, there are silver plans that, at certain income levels, actually have better benefits than the gold plans, and at a lower cost, and that’s what we’re aiming for. The out-of-pocket maximums are really what we’re focused on, but at least based on what’s available now, we should be able to get very solid insurance without risking a huge outlay each year, which is good for long-term planning, at least theoretically.

  22. Wow, you are so close. I am so happy for you. Also, selfishly, I thank you. By posting such things you help keep me motivated:) We are saving. . . I’ve not been a long time reader – just found you a week or so ago, but am loving it. Something to think about is the little stuff. Perhaps you already have and I’ve missed it, but taking stock of anything that might die or need repairs within the next year. It wouldn’t be much fun if you “retire” (Woohoo!) and 2 weeks later the refrigerator dies or the water heater conks out. Does that make sense? Whatever those things are in your life that keep it working smoothly, making sure they are all in good repair might be a tedious but valuable task. Not sure why as we are a ways out yet, but those things have been on my mind “in preparation.”

    • Thanks, LL! So glad you’re enjoying the blog. :-) It’s a good point about taking stock of things that could die — we had the good fortune (*sarcasm) of having every appliance in our house die pretty much simultaneously after we moved in, so we know everything is new and in good shape. But that doesn’t apply to everyone, and it’s a great reminder!

  23. Wow, what an awesome list! I’m still many years from retirement so I’m not sure I can add anything. Maybe look into getting a HELOC opened up on the house while you still have income so you can access the extra money in case you end up needing it for some reason?

    That’s all I got! Best of luck and I’ll be following your updates on the site!

    • Thanks, Jon! I think for folks who embrace debt as leverage, opening a HELOC before losing W-2 income is potentially a good call… though I’ll confess that that idea makes me a bit nauseous, as I am super anti-debt. Haha. But another reminder that personal finance is personal! And thanks for reading and following along. :-)

  24. New to your blog but digging it! Looks like there’s a lot more to retirement than just stopping work. Thanks for providing this list!

    You’re so close to the finish line. Look forward to reading more!

    • Welcome! Thanks for reading and commenting! There’s definitely TONS more to retirement than just leaving work behind, and we’re doing our best to plan well and get our heads in the right places before we leave our careers for good. :-)

  25. Just a couple of thoughts on your list…

    I know your iPhone is close to your heart, but with so many international destinations, have you looked at Google Fi? It is also wifi-first, but the international rates are amazing. (even if you aren’t on wifi!)

    Also, regarding the 401k:
    You say you can’t move them. Are you sure? It is up to the plan, but often you can move your contributions whenever you want. It would at least let you get the destination IRA started, and make the big rollover easy to do. (My company is with Fidelity, and I can do so…even online!)

    Also, surprised to hear Fidelity lumped in with Merrill Lynch. One reason I stay in my 401k is the very cheap index funds they have. (institutional pricing) But, of course, you could have a bad / expensive mix.

    • We’ve definitely looked in Google Fi, Republic, Cricket, etc. I am willing to give up the iPhone if I must, and will be curious to see what options exist in a year… I’d bet there are some new ones that pop up between now and then.

      We’ve checked, and we can’t easily move our 401k funds, but we’re so close to being able to fully roll them over that it doesn’t bother us too much. On Fidelity, we do have the Spartan S&P index fund option, but that’s the only index fund — the other choices are much more expensive in terms of fees. Merrill is much, much worse with its options.