Don't Let Life Get Too Easy in Early Retirement // Work Optional author Tanja Hesterpost-retirement process

Don’t Let Life Get Too Easy in Early Retirement

When you retire early, you suddenly get to subtract a whole lot of annoying stuff from your life: your commute, conference calls, year-end reviews, whatever annoying paperwork your particular job entailed, ever visiting the dry cleaner again, the need to be connected at all times, and on and on.

But in addition to that, you also have more time and mental energy that you can put toward removing other pain points from your life. You can plan off-peak travel so you’re dealing with fewer crowds and the annoyances that accompany them. You can study when the grocery store is the least crowded and do your shopping then. If there are little things that bug you in daily life, you can figure out how to fix them. You can optimize every line item and tweak every knob, if you’re into that sort of thing.

Related post: The Downsides of Off-Peak Travel

All of those things undoubtedly sound good, and to a point, they are. We did not evolve to sit in traffic, check email at all hours and take criminally little free time away from work to recharge. Removing some of those unhealthy things is 100 percent good for us.

But the key words there are some and to a point.

Removing too many pain points from our lives risks actually doing ourselves harm in a different way: a life with no pain points makes us soft. And is that what you want for your early retirement, to go through it as a person who’s growing less and less resilient, who is so used to everything being easy that you become intolerant of dealing with challenges? Because that’s what we’re talking about.

Don't Let Life Get Too Easy in Early Retirement // Work Optional author Tanja Hester

I’ve noticed an interesting (to me) trend in the last few years: whether it’s on Twitter or in real life, I’ve heard some early retirees talk more about the indignities of various forms of travel. Of course, complaining about travel is the Official American Pastime these days, particularly complaining about air travel, but in several instances, I’ve witnessed certain retired people whose lives have become extremely easy and minimally stressful these days complaining at length about basic things like, “My flight was delayed and I missed my connection and got in later in the day than I planned and now I’m NEVER FLYLING THAT AIRLINE AGAIN!”

So sure, flight delays are annoying. Missing a connection is annoying. And maybe a customer service person was also rude to you in the process of getting all of it sorted out. But flight delays happen. They happen all the freaking time! If you can afford to travel by air and you still got in the same day you intended to arrive somewhere, I am of the opinion that whatever transpired in the meantime is not real hardship. (Unless you flew Frontier. In that case, I’m sorry.)

My point isn’t that it’s annoying for me to see or hear someone complain about such things. I have been through some truly gnarly things while traveling (as have most who’ve flown a million lifetime miles like I have), and people complaining about delays and misconnects mostly just get a friendly eye roll from me. And I’m using the air travel example because that’s so widely relatable, but I’ve heard quite a range of other complaints, too, from how virtually everywhere is too crowded to visit ever now, to it being an absolute necessity to have a duplicate of some gadget in your house because you use it in more than one place and hate having to walk a few steps to retrieve it each time.

Related post: A Million Mile Flyer’s Tips for Maximum Efficiency Travel (Part 1)

Related post: A Million Mile Flyer’s Tips for Carry-On Travel, Including For Business (Part 2)

My point is that, in these instances, these particular folks complain about routine travel happenings as though they are real hardship, which means that those things feel like hardship to them. And if things that aren’t hardship feel like hardship, that means your internal barometer for such things has gotten way off in its calibration. It probably also means that, if you’re in that situation, you’re probably feeling way more stressed about a routine happening than you should, which isn’t good for you either.

But most importantly of all, it kinda means that you can’t handle routine things anymore, or at least not in all categories. And isn’t the point of early retirement, for a lot of us anyway, to make time to experience more things, not to box ourselves into a smaller and smaller set of things that we can handle, as we gradually get more and more intolerant of even normal levels of stress?

Replacing the Soft Thoughts

I’ve noticed a little bit of this softening happening for me, too, in one particular area of my life: I don’t like hanging out at the beaches on Lake Tahoe or going to the more touristy areas when it’s even a little bit hard to park or to find an uncrowded spot to hang out. In the past, “too crowded” meant mostly just the July 4 and Labor Day holiday weekends. Then, the longer we lived in Tahoe, it started to mean “most weekends.” This year, I’ve noticed myself avoiding the busier areas virtually all days and at all times, even though there would still be plenty of space to have a good time. Maybe it’s because it would take a few extra minutes to drive there, or if we biked, there’d be more inconsiderate dog owners on the trail with off-leash dogs in the way. Are those things annoying? Sure. But are they hardship? Not even a little bit.

Fortunately, I’ve noticed this thinking, and I’m working now to fight back against it. Whenever I notice myself having the thought, “Ugh, it’ll be crowded,” I try to replace it with something like, “I’m super lucky to live somewhere so beautiful that so many people want to hang out here, and spending a few extra minutes in traffic is a small price to pay for the privilege.”

So far, it’s helping. And that wouldn’t be true if I couldn’t see the soft thoughts for what they are. Instead, I’d just be staying home more, and getting more intolerant of the normal conditions in the area where I chose to live because I love it so much.

It’s important to replace those soft thoughts, but first we must recognize when we’re growing softer.

What To Do Instead: Toughening Up

Of course, an even better course of action than just trying to spot soft thoughts is to work actively to toughen ourselves up a bit.

Thought the standard working life script is annoying in some ways, it also softens us in other ways. Even the frugal among us now have many conveniences in life that people didn’t have as an option a generation or two ago. I still a remember a time when none of us had phones in our pockets, and the internet wasn’t a thing. (Not for civilians, anyway.) And then, even when we got the World Wide Web, as you were legally required to call it in the olden days, you had to 1.) make sure no one in the house was on the phone, 2.) dial in to the internet using a thing called a modem, that was like a phone inside the computer, 3.) sit through a long period of digital monster sounds to signal you were possibly connecting, and only then, 4.) “surf” around graphic-free sites at a snail’s pace, only to get kicked offline and have to start the whole process over again just as you were about to get the info you actually wanted.

None of us would put up with that now. We expect to have fast internet at all times, with no lag while we connect. In matters of online-ness, we’ve all gotten soft.

So what to do about it? In the internet example, you could make the deliberate choice not to use it occasionally. Sometimes, when Mark and I are trying to think of the answer to some question that we feel like we should know, we’ll force ourselves not to consult our phones or Google. I’ve started to leave the house without my phone more and more. (Honestly, I mostly just miss the camera when I do that.) I’m sure there are better ways to wean yourself off the constant internet reliance, and if you have great suggestions, please share them in the comments.

But fighting against our reliance on the internet is probably a losing battle at this point, so it’s best to focus on the areas of your life that are particular to you. Only you know what ways in life you’re susceptible to softness, and that means tailoring your own toughening program.

My Toughening Program: Harder Travel

Though I traveled a ton while working, most of that travel was made easy by necessity. I had so little time to get from place to place that I had to fly the most direct flights, stay at well-located hotels with all the amenities even if they cost a lot more and take the most convenient transit options. I virtually never took mass transit if a cab was an option, and for the most part, stayed at hotels with 24-hour room service and concierge lounges. The travel was still taxing because of the volume and frequency, but it was easy.

And we’re creatures of habit, so I got used to the easy. Not to the point that I complained about flight delays and misconnects, because the best way to deal with that stuff is to laugh at it, but I started to find myself preferring certain kinds of hotels when I booked travel for me and Mark outside of work, or I’d find myself reaching for Lyft when I’d arrive in a city for a fun visit instead of figuring out how to get downtown on a train or bus.

Related post: Structure Your Life to Avoid Overspending

So in retirement, I’ve forced myself to get out of that easy travel pattern. Not on every single trip, and not with every single lodging choice, but most of the time. (If it’s a “work” trip like FinCon, I allow myself some easy choices because those trips are much more taxing.) The biggest symbol of that is shifting to staying in hostels instead of hotels, which have the nice benefit of being a lot cheaper, too.

This year alone, I’ve stayed in four hostels, in Portland, San Francisco, New York and Philadelphia, and there will be several more. If you haven’t stayed in a hostel or it’s been a while, the main thing that’s “hard” about hostel stays is you’re sharing much more space with strangers than you do with hotel lodging. You’re probably sleeping on a bunk bed, shared with someone you don’t know, as well as sharing bathrooms, kitchen space, etc. If you cook (which you can always do at a hostel!), you’re doing your own dishes. You’ve very likely making your own bed, through the linens are always provided these days. It’s not “hard” in any real sense of the word, but it requires an adjustment if you’re used to having all your own space and everything done for you when on the road.


But that adjustment is totally worth it. Just as being “selectively hardcore” about something is totally worth it, like we are about keeping our house cold. When you force yourself to get out of your comfort zone a little bit, you can actually watch yourself becoming tougher, which really just means able to handle a wider range of situations. The first time I shared a bunk bed with someone who kicked the bed frame during the night, waking me up, I fumed about it the whole next day. Now, I barely register the “offense” before going back to sleep.

Of course, hostel travel is not actually difficult, it’s just a few degrees less convenient than hotel travel. You are more likely to have convenient places to plug in your electronics in a hostel than in even the fanciest hotel, for example, and the wifi is always free.

But you will get woken up sometimes by someone on a different schedule, and you might find it weird to brush your teeth next to a stranger doing the same. For someone like me who enjoys my own personal space but also wants to travel to places in the world where personal space is not to valued (or possible), hostel travel forces me to get accustomed to having other people around more than I might prefer, while hotel travel would keep me isolated in my own little bubble, becoming increasingly less able to tolerate crowds and crowded places.

And sometimes making life a little “harder” than it could be results in wonderful surprises. Case in point: Right now, as I type this from my last night in my current hostel before returning home, I’m listening to a fellow hosteller practicing Debussy on the piano in the common room. And he’s good, so I’m basically getting a free concert. That’s never happened at a hotel. Before that, I talked to a traveler from Australia about her favorite beach in Borneo, and got several other ideas for some of our upcoming trips.

Tomorrow, I’ll ride a bus to the train station, and take the train to the airport, completing this trip without ever getting in a car, which is certainly a bit more onerous than calling an Uber, but doing so will remind me that I’m still capable of navigating public transit in places where I don’t live, an important life skill for someone who values travel as much as I do. And when I arrive home, I’ll do so knowing that I can travel anywhere, not just to places with cushy hotels, easy-to-hail cabs with English-speaking drivers and ample personal space. (We wouldn’t have done well in Taiwan if we couldn’t figure out how to deal with places where no one spoke English, and we’d have hated Japan is we couldn’t handle crowded trains.)

I encourage you to look at your own situation and your own priorities and to ask yourself questions about how you could see yourself getting soft or how you’ve already gotten soft. Explore whether you find yourself wanting to avoid the very things you want to do most. And when (not if) you find those areas, make a plan to toughen up. Because the whole point of writing your story is to expand your options, and you can’t do that if you let your comfort zone shrink ever smaller.

Don't miss a thing! Sign up for the eNewsletter.

Subscribe to get extra content 3 or 4 times a year, with tons of behind-the-scenes info that never appears on the blog.

No spam ever. Unsubscribe any time. Powered by ConvertKit

38 replies »

  1. W glamped for two nights in North Tahoe last week. The beaches shrunk and the water was cold!

  2. Wow! Great post. I’m a regularly-aged retired person, and I’m shocked at how much my cohorts can complain. And we are all among the luckiest people in the world.
    But I have to look at my own life and see what I can do differently too. Thanks for the inspiration!

  3. Ok, NEVER even considered a Hostel, but I go on WordPress to see what other early retirees who travel (and other interests of course) are up to and how they make it work. So while I dont have any plans at the time, I will put this in the file for the future on considers, so thanks for the inspiration.

  4. Yep! This one of the reasons I like camping. It’s not as comfortable as my bed at home so when I go home I appreciate it more, there are no walls between you and your neighbors so you hear people and activity a lot more than at home and you’re awakened by birdsong at 4am. All things I would have found annoying at home, but instead recalibrate to, which allows me to cherish home even more and flex my toughening muscles.

  5. Great post. I have always thought that people have their own internal stress barometer. Some people will always find something’s stressful even when their lives to an outsider look idyllic and stress free. You just adopt new things to worry about to give your stress barometer something to do.

  6. ‪Good article Tanja. As French we tend to be the one that are complaining a lot so I’m surprised to see that Americans are too :-) Another pro for living with less convenience is that we can use our brain again and especially keep them healthy. For instance we tried to stop using Maps for navigation and we had a pretty hard time finding our way around first. But after consistent practice now able to orient ourselves without some tech at our fingerprints. It’s amazing what our brain can’t do if we use it everyday isn’t it? :-)

  7. Hostel in NYC? Next time you and/or Mark need a place to crash, let us know. Not being from NYC, we have family and friends staying w/ us all the time and have a separate room.

    Side note: For Lent, even though I’m not Catholic, I gave up reading anything FIRE related. It went so well that I kept it going until last week and dropped all other FIRE blogs/articles besides yours. This is my second article back and your last article about guilty spending was spot on, hilarious and I loved it. I’d be spending money on back-country skiing as well!

    – Mark

  8. I have a feeling I’m going to see this all over the place now that you’ve pointed it out. The work I complain about because it’s just a bit harder than my last role. The takeout I get regularly because cooking seems hard after a long day. The bike that I won’t ride now that it’s always over 100 degrees. (Okay, maybe the last one is okay for a while.)

    As for a way to break away from the internet for a while, I did stumble across something that works for me, at least:

  9. I was wondering why we seemed to be getting more cranky and intolerant the older we have become. We’ve been living the “financially cushy” retired life for too long!

    When we have “travel issues”, I try to be patient and think, “in time this will be just another funny travel story we will look back on and laugh about.”

    Here’s our background information for context:

    My hubby retired in 2005 due to health issues about 5 weeks before his 50th birthday. He did have to wait a couple years before being eligible for the modest ongoing pension payment he still receives today. Plus, he’s reached the age for early Social Security, so he’s collecting that also.

    I retired “early” in 2013 after turning 55, also due to health issues. Although I retired with a moderately sized 401k balance, I also received a monster sized five year period certain payout from my employer’s contributory pension plan, the majority of which ended up in a Rollover IRA that now provides the passive income stream (via dividends and annual capital gains) needed to fund our lavish “not quite Fat Fire, but certainly not Lean Fire” lifestyle.

    Since we both have health issues, we’ve decided to start collecting Social Security sooner rather than later.

  10. Wow, you’ve articulated a worry I’ve had in the back of my mind since I early retired 14 months ago. I’m definitely concerned about losing some of my resiliency in my new lifestyle. For example, the prospect of facing I-80 traffic between the Sierra Foothills and Sacramento has dissuaded me from attending meetups and cultural events in Sac. We moved out of the Bay Area to escape hassles such as freeway congestion. Living in a quiet bedroom community is starting to make me soft. Thanks for raising a novel and important topic for FIRE walkers to ponder.

  11. Enjoyed reading this i think we are all too spoiled with too many Convienens life is to be enjoyed even if its not always a box of chocolate!

  12. Tomorrow I am going to start my day by showering with cold water while standing on my head, eating my cereal without milk and removing the seat on my bicycle. Next week, I am going to….

    • Watch out – remember this cautionary tale from CXGF:

      Imagine your kids taking a shower before they go to school
      They douse their skin with ice cold water
      A huge shock to their little systems
      At first it’s downright unpleasant, but then
      It gets them wired in a way they’ve never felt
      And they think to themselves:
      “That shower felt great, maybe I’ll try cocaine!”

      So your son’s on coke, your daughter’s pregnant
      And your husband’s probably having an affair
      Just like the movie I Am Legend
      But not like that at all

      No hot water
      Which means cold showers
      Next thing you know
      Your kids will be on crack

  13. Being tragically neurotic, I’m jealous of your self-awareness and capacity for change. If only we could all just change our nature. This is why self-help philosophies have dedicated followers and those who don’t understand. Changing our nature only goes so far. But, I do admire those who have the lifestyle and natural ability to do these things. As always, everyone is different.

  14. Financial Independence is the detachment from other people money – their money can no longer enslave you.

    Financial Freedom is the freedom from money itself – money plays no role in the true meaning of your life.

    Financial Independence is the first mile maker! Most of us are conditioned into chasing the number for
    so long that less than 1% of the population ever gets to the next mile marker – Financial Freedom.

    Financial Freedom is the mile marker after FIRE. It is where life will blossom to the fullest with passion and purpose!

  15. My favorite quote, which seems appropriate here:

    “To enjoy bodily warmth, some small part of you must be cold, for there is no quality in this world that is not what it is merely by contrast. Nothing exists in itself. If you flatter yourself that you are all over comfortable, and have been so a long time, then you cannot be said to be comfortable any more.”

    From Moby Dick

  16. If I run out of milk for my coffee, tough. I will not make a separate trip to buy it. Next time, I’ll remember. I stayed in hostels in the past. I had difficulties with trusting strangers however, so I showered will my wallet and passport. Otherwise, sleeping with strangers in the room was ok. And the cellphone. Believe it or not, I turn it on just a couple times a month and charge the battery. 99% of the time, it just sits on my table. I refer to it as my emergency phone. Fortunately, I have extremely few emergencies. I’ve been working just one day a week for 8 years already. I refuse to get soft.

  17. Truth!

    I’ve become incredibly spoiled by my work situation which allows me to avoid people 90% of the time, I realize whenever I have to talk to them, but it leaves me with so much more energy to do the things I need to do at home. If and when retirement is on the boards, I’ll likely put myself in more situations where I have to interact with people. Not so much that I undo all the good that not working brings!

  18. After retiring last year (after a corporate layoff), I sold my apartment and just about everything I owned and moved to Mexico. I think starting a new life in a new country, and having to make all new friends (and in a different language) will likely keep me from getting soft for a while.

  19. Nope. No way. No thanks. I’ve worked hard and I deserve a soft and cushy life. I don’t feel the need to prove to anyone I’m tough or need toughening up. I’m rich!

    Yes, that felt good. Really good. 👍

    • I’m with you, Dave. 100%. I worked very hard for my retirement and I intend to enjoy every cushy minute of it. I’m rich with time, to spend as I want and as I see fit. So far, so good. WAY good!

  20. This can apply in all areas of life. In today’s world, it’s easy to cultivate an environment specific to your tastes and viewpoints, which fosters ever increasing levels of discomfort whenever we encounter anything that falls outside. Regularly exposing yourself to new challenges and perspectives keeps your flexibility and curiosity intact.

  21. Oh thank goodness! I thought you were about to say we should all go back to work. Whew, glad I don’t have to run from the screen screaming! Seriously, great post! I retired (at age 53) about 4 months ago, joining my husband who retired about 4 years ago. I’m in that early phase of totally enjoying having no commitments in terms of “show up here at a certain time on a regular basis”. We moved cross country the day after my last official day at work, so right now my mind is occupied pretty well with making new friends and trying to get back in some semblance of physical shape/eating well that work stress and commuting had forced to the back burner. But once I get over my commitment phobia, this very good food for thought.

  22. Sorry, I completely disagree with the concept of getting out way early for many reasons. There is a great article called “The FIRE Movement is Morally Wrong” at that will make you think twice. Not a FIRE hater, just think most people don’t think it completely through before jumping.

    • Just read the article and it was not well written. You can always argue both sides of the movement, but most critics miss the fact that those in the fire movement will earn money once again if the need arises. I am not in the very early retire movement, but I will leave corporate America as soon as I hit my comfortable number.

      • Oops I meant to say not Tanja’s Article but the one from MrWallStreet was the one I thought was not well written. Tanja always writes great thought provoking content.

  23. I love the idea of not letting life get too easy in early retirement and finding a balance between keeping some of the hardships and drive that gets one to early retirement in the first place with enjoying the benefits. As a longtime reader whose favorite part of each Monday and Wednesday used to be reading a new our next life post but who doesn’t take the easy route of social media or email newsletters to get information, I’d really like to see a post about what you plan for the blog’s future, and how you feel about its and your evolution.

  24. Your article is so relevant to where I find myself in retirement. It is so easy to persuade myself to not do an activity due to traffic, amount of effort, or suboptimal weather. When I think back on some of my most memorable adventures, they have taken place in challenging circumstances. Toughening up serves to promote self confidence, learning, and fun.

  25. Hey Tanja, I am aiming to have early retirement as well, currently working hard to achieve my goal! Btw very inspirational, thanks for the great post!

  26. I appreciate blog posts such as this one. I will surely follow a few of them. Keep writing such detailed blogs.Thanks for an Informative article for my post retirement plans