What We’ll Lose When We Stop Working // The Lament of Aspiring Early Retirees

another weekend gone, another week begun. we’re both the type of people who were never eager to grow up, who always wished time would slow down. one of us remembers turning eleven, and saying aloud to the assembled celebrants, “okay, i’m good now. i don’t need to get any older.” so it’s especially weird for us, now, to love the feeling of time flying by. because every day that passes means we’re another day closer to our dream of early retirement. one thing is for sure: it makes the thought of mondays a lot less daunting, because it’s still another day closer to early retirement. (try reminding yourself of that when you’re having the sunday blues.)

this feeling of wanting time to hurry up and pass is one thing we definitely hope to lose when we quit working. but even though we hope that early retirement will be all sunshine and roses, there’s actually a lot that we’ll lose when we quit our jobs. of course, it’s still 100 percent worth it, and a trade-off we’d make any day of the week. but it’s worth noting the many ways we currently benefit from our jobs that will go bye bye when we earn our freedom.

here’s the rundown:

income — this one earns a big “duh.” of course we’ll miss the paycheck, though that’s why we’re socking away most of each paycheck now. will we also miss feeling like useful providers? only time will tell.

health insurance — we can buy new insurance on the exchange, but we’ll lose the generous coverage we’ve enjoyed for years through work.

swanky hotels — “swanky” is probably overstating it, but we stay in medium-nice hotels when we travel for work, which is virtually every week. when we travel on our dime, we stay in much more modest establishments, so quitting our jobs will mean saying goodbye to the marriott marquis and hello to the fairfield inn. (or loads more camping, which we’re completely okay with.)

elite airline status — right now, with weekly travel, we each have elite status with our chosen airline, and that means free access to seats with more legroom, occasional upgrades, early boarding, a shorter security line, a dedicated reservations line, better customer service at the airport if there’s some problem, better access to award seats, free checked bags (though we always carry on), and faster mileage accrual for the miles we fly. flying with status is, quite honestly, better than flying without it, and we’ll miss it once it’s gone.

dining out — following the pattern here, if we’re paying for our own meals, we’ll almost always eat at home, or if we go out, we’ll go somewhere super reasonable. but not so when traveling for work. work travel gives us the fully reimbursed ability to try new and trendy restaurants, to dine out in different cities, and to get that whole city experience despite living in a small mountain town. we even valet park at restaurants when it’s for work, without batting an eyelash. losing this could be tough for us — we love trying different foods, but once it’s on our dime, it’s a very different calculus.

take-out coffee — a related corollary to dining out is take-out coffee. we don’t buy it on our own. we almost always make our own coffee, but we’ll buy it out if we’re meeting someone and will drink the coffee at the coffee shop. when it’s reimburseable work travel, though? bring on the starbucks!

social connections — we already work at home, so our adjustment to retirement won’t be as pronounced as for someone who’s worked in an office for a long time. but we’ve each been in our job for more than 13 years. that’s a long time that we’ve been shooting the s&%t with the same colleagues, some of whom we count among our closest friends. even the ones we aren’t close to still count as social time, and we’ll miss that, especially because we know that social interaction is so important to avoid getting old too quickly.

fancy titles — just as there’s inflation in the price of goods and in clothing sizes, there’s clearly inflation in job titles. proof: we both have way too powerful sounding titles, relative to the responsibility of our jobs. but, man, nothing beats the feeling of whipping out a business card on a plane, and watching someone’s jaw drop as they read said inflated title. maybe we’ll make ourselves pretend business cards in the future with some equally highfalutin and made-up titles, just for fun. ;-)

free technology — right now we get our home internet paid for, laptops provided, printers provided, and cell phone plans covered. one of us even gets a new iphone every two years. for free. all in the name of work. that will all go ::poof:: the second we quit, which we will sorely miss. fingers crossed that we had the good sense to hang onto one of our old flip phones… (kidding.)

what will you lose when you quit your job? does any of it give you any twinges of regret? we admit it — we’re super bummed we won’t make it to million miler status on our chosen airline before we quit, because then we’d have gold status for life. but we aren’t willing to work a few more years to get there. life is too short!

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40 thoughts on “What We’ll Lose When We Stop Working // The Lament of Aspiring Early Retirees

  1. We had a conversation about an earlier post you have about a change in identity after retirement, which is related to what we’ll miss. When I asked Garrett what he’d like to become after retirement, he said “entrepreneur,” and then I asked him if he’d miss being an engineer, and he couldn’t say for sure. I think whatever we do in early retirement will involve some engineering project/gig so that he maintains that part of his identity.

    Overall, I think this is the same list we would put together. Garrett says we’ll be fine (forever an optimist), but I think initially I will miss job security. I don’t mean my job necessarily, just any job–the ability to procure work that someone pays you to do. Having not grown up in a financially-secure home has really made me value a good-paying job and employer-subsidized health insurance.

    1. Good for you guys for having this conversation now, instead of realizing that you have this void to fill after you’ve quit your jobs! And it seems like the job security piece is something that you can fill with any number of freelance or temporary positions. And thank goodness for Obamacare — subsidized health care can be had outside of employment now!

  2. Interesting to think about. I think the only thing that I will miss with my job is the paycheck. I’ve only worked for this company for about a year, so I don’t have that social interaction built up at this point. In fact, since I work from home and on the complete other side of the country from where the majority of my company is, I will never have quite the same level of social interaction with my co-workers. But honestly, that’s okay.

    I suppose that I will miss the occasional meal on the company, but I don’t travel all that much so those opportunities are fairly rare. Heck, even my last job with an impressive title (I was the “Director of Information Technology”) that I quit so I could work from home, I didn’t travel much.

    The more that I’m thinking about this, the more evident it is that I’m not going to miss much at all about my job or the work that I do. I suppose that’s kinda sad on one hand, but easier to finally make that decision to call it quits once the time comes.

    1. So that’s the upside of fewer perks — easier to cut the cord when it’s time! We’ve been at this plan for so long now that even this long list of perks won’t stop us from pulling the trigger when we hit the magic date (or the magic number, if we manage to do that sooner). But like always, we think it’s better to go into ER with eyes wide open, so knowing what we’ll be losing is part of the process. :-)

  3. What I’ll miss after quitting. Income, check, health insurance, check, social connections, sorta. We live in Houston which means everyone I get along with at work is about an hr away on the weekends, and 2 toddlers in a car for that long, no thanks! I don’t travel enough to benefit from that, and hotels will still be mid-range or as you said, loads more camping, but I see that as an upgrade!
    We do coffee at home minus an occasional Friday coffee date and we don’t eat out much anyway. Although we may do that more when the kids get back into the “well behaved realm” and out of the 2 and 4 yr old “crack monkey kingdom” they currently reside in. :) We’ll see.
    I agree with Steve though, I won’t miss this specific job much, but I would do consulting in this field if it somehow landed in my lap and I didn’t have to hustle more than I do now to make it happen. I love what I do, but it will still be easy to say, “Thanks job, I hope I don’t see you again.” haha!

    1. Especially given your kids, it seems like such a no-brainer to walk away as soon as you’re able! And in that way, maybe it’s better that you have fewer perks or don’t feel that connected to your current job — easier to walk away. We have more perks, which might make it a hair harder to say goodbye, but even then, we have a hard time imagining that we’ll hesitate when it’s time.

  4. The social connection is a biggie for me. There just aren’t enough people with flexible schedules to meet up with during the day. Volunteering and freelancing help, but there is just something I miss about going to a regular job with co-workers. That is why I wish part time work for professionals was more available. The rest on the list is not an issue for me. I go to coffee shops more regularly, now, just to get out of the house. Thank goodness for ObamaCare! That was literally a life saver for me, otherwise I would be at a job right now, stressing out, just to get health insurance coverage that allows for pre-existing conditions. I hate traveling for work. So, now, when I travel, it is purely for enjoyment.

    I never want a fancy title again. It was nice to work in a high powered position for awhile, but now, when I look for freelance and part time opportunities, I actively avoid any job that has a big title, because I know the stress and time commitment that comes with it. I recently backpacked in Australia and stayed in hostels. They were private rooms, not shared, but cheaper than hotels. After my trip to Australia, I met my family in Hawaii and stayed at a luxury resort that my parents paid for. I was bored out of my mind and wished that we stayed somewhere that was less luxury and more fun. I don’t care for the swanky hotels at all. They just don’t provide enough adventure for me. I don’t miss the smartphone one bit. I actually do still have an old flip phone…. they are also way more environmentally friendly.

    I guess I’m lucky that simple living actually brings me more joy than all the perks of a luxurious life. Although, the luxury of time, freedom and adventure is much, much better. :)

    1. Hooray for Obamacare — we feel the same way, and just hope the next president doesn’t get rid of it! That’s part of why we plan to work through 2017, so that we will know before we quit if any big changes are coming!

      On social interaction, it’s interesting how different each place is. Where we live now, very few people have standard M-F jobs, and nearly all of our friends want us to hang out during weekdays, and they aren’t free on weekends and in the evening when we are. So we look forward to joining them!

      Thanks, also, for your perspective on fancy titles. We for sure don’t need them, especially given how ridiculous they are — it’s just funny. :-)

      Glad you’ve found such a happy place with a simpler life!

    2. I share your perspective on the fancy titles. I have one now and, sure it’s fun to have for the pride of it, but the expectations, demands, and stress I will not miss someday.

  5. Wow! You’ll be giving up a lot more than we will! We will only be losing the income and the health insurance. Although the health insurance is amazing, and that’s going to be a huge deal. Especially in Alaska where docs can charge anything because there isn’t a whole lot of competition (or any competition for specialists). Here’s to all the gains in early retirement! Cheers!

    1. Another instance of “thank goodness for Obamacare!” — none of us have to rely any longer on employer-provided health insurance. And the other commenters have made a strong case that having fewer perks than we do makes it easy to say “sayonara!” when it’s time. Here’s to easy decisions! ;-)

  6. Never gave it a serious thought, yet. So, here we go

    Health insurance, company car, mobile phone and internet.
    Health insurance sounds to be the most expensive to replace. (We own a car now, in retirement, we can live with only one)

    Feeling to achieve something: will be the most hard to give up.

    Hence, the plan to use a step up approach. Ideally, I go freelance first, then reduce the numbers of day I work per year. Let’s see how it goes

  7. You definitely both have a great set-up for compensation & perks through your work! The flipping out the fancy business card, I can completely relate. That’s something I dreamed about as a kid, and with all the conversation I like to create via airplanes (if the person is interested, of course) has generated many networking opportunities with just the exchange of that card. Although, all of the trips have been covered via work you now will get intentional traveling of where you would really desire to go, which may make it a whole new experience!

    1. We think about that every day — we travel a ton now, but only a small percentage of it is the travel we choose. Not too long from now we’ll get to choose where we go, and for how long. No more multi-city trips packed into a week because we’re short on vacation time!

  8. It is so important to think about the little perks of working when considering alternate options. I would definitely miss the technology that comes along with my job. Having an IT department there to fix my computer or phone is so helpful. Having to manage (and pay for!) all that on my own would be a challenge.

    1. We’ll miss that too! Even though we work from home, we get full remote IT support for free, and at the snap of our fingers. Someday we’ll be having IT troubles, and think, “ah, memories…” ;-)

  9. You have pretty sweet work perks! No wonder you can save so much money! With all that provided, how do you find time to spend!?

    When I quit, the biggest loss will be the social connections. I’m really horrible about maintaining friendship connections. I don’t want to go grab dinner, or drinks, or coffee dammit! Can’t we just go for a walk? Oh, the struggle. Thank God for the internet.

    New title suggestions: Passion Master, Lady and Lord of Freetime, “Trust me, I’m awesome,”

    1. Ha — Oh, believe me! It’s still easy to spend if we want to! But we do suspect that our already high grocery budget will go up once we’re not getting several meals a week covered during work travel. Of course we don’t eat remotely the same as we do while traveling, but still.
      Signed, Lady of (Future) Freetime

  10. We would miss the paycheck and healthcare obviously, but on the softer side, I think people get a lot of their adult interaction at work. It would probably take a bit of time to rebuild that with other people with your weird and open schedule during early retirement.

    1. The missing social interaction is definitely on our radar, and something we’ve written about several times — so good call! In our case, we think we have a slight leg up because we haven’t worked in an office with our colleagues in years, so the adjustment won’t be nearly as steep. But still, not talking to people, even on the phone, every day will be an adjustment for sure!

  11. Haha I agree with all of these. I sure as hell am not paying for the Ritz with my own money and no corporate discount! Also no such things as layovers when I fly for work, which isn’t true when flying for leisure. I think you’ll get over everything fast. The one that will hurt the most is the paycheck :(

  12. I work in government so the benefits like health insurance/pension are the biggest things I would have to give up. Actually, the pension is a big one and a bit of a golden handcuff. If I leave early, there is a big penalty and I’m leaving a lot of money on the table!

    1. That would be tough to wrestle with, for sure — losing a pension. Golden handcuffs come in all forms, though… our employers both do big year-end bonuses to try to lure people into staying at least until the end of the year, and then “one more year…”

  13. I’ve been thinking a lot about this very question, since I’ve just quit my job!

    My biggest loss will definitely be the people. The people I work with are GREAT. I’ll probably keep in touch with many of them, at least through FB and LinkedIn, but it won’t be the same.

    1. BIG NEWS! Need to head over to your blog to catch up on the latest info. People are definitely a huge part of most jobs — glad you’ve been working with great ones, and hope you can find a way to keep in touch with some of them!

  14. I’m about to lose that paid for internet, cell phone bill and new cell phone every 2 years…. I, of course, put that into my new retirement monthly budget but I have to admit, I’m going to miss my iDevice just a little (moving over to Project FI shortly). I don’t have baller status on the airlines, but going to miss the rare occasion upgrade I get with my silver medallion. Finally, I have been running all my work expenses through my personal CC for the past 15 years, and I’m going to miss all those extra travel miles I accumulated doing that though before last fall, I basically spent or gifted my miles as I accumulated them.

    1. I am 100% going to miss my iPhone. In the second half of this year, I’ll start trying to figure out if I could buy an unlocked one and use it on a budget plan. I did recently buy a personal laptop, though, and completely love having that. (Typing to you on it right now!) And I’m with you on missing all the miles accumulation from work travel expenses. Those miles are going to fund our travel for many years to come!

      1. Nice! My IT guy surprised me last week and said, “Just keep your laptop, I’ll get it all wiped clean when you are here in June.” Kind of stoked about that… but gave me an idea – how are you planning purchases like this once you get close? Like are you trying to push some larger purchases into the next 7 months? I had a situation recently where I just went ahead and pulled the trigger on some orthodontic work for the kiddo – ortho has been pushing me to do it for a year, I sort of wanted to hold off another year but then with the ER looming, decided to go for it, get whatever small discount she was offering to pay all at once. Sort of obsessed with adhering to my 3-3.25% rule in a short 34 days. :) And I didn’t expect you to answer all of these comments. You are a conscientious one!

        1. Ha — just trying to clear through the backlog on comments and email today! ;-) And yeah, we’re thinking along similar lines. Anything pricey we know we’ll need we’re trying to buy this year. Same for bingeing on medical care before our insurance gets worse! So definitely will buy whatever my new phone is before we quit. Glad I bought my own laptop, though — it’s way nicer than my current work laptop. ;-)

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