Leaving the Cushy Job


I have a pretty decent job, all things considered.  And I’m going to quit it anyway.

But that’s all big man talk.  In reality, I’ve found this is easier said than done.

I’m not even talking about whether or not I feel financially ready to quit.  I am — I’ve covered this in great detail in other posts and I’m simply not worried about the money anymore. If anything, I’ve over-saved.

Nope, the real problem is that I no longer hate my job in Software/IT. There are even times when it provides some small bits of satisfaction, perhaps a couple of times a week, as I solve a tricky technical problem or automate an irritating task.

Other acceptable aspects:

a) The people are all right.

b) My manager, although sometimes a pain in the ass, is by no means an out-and-out dick.  Occasionally I’m almost fond of him.

c) Salary is good.  (Money good.  Money always good.  Mmmm, money.)

d) Hours and Commute are fine, i.e. I have as much work-life balance as it is possible to obtain while holding down a job in my industry.

So it makes sense that inertia has taken hold.  The easiest forward-looking option is to select the default:  Continue to report to work. Continue to grind through week after week. Continue to chase additional security, i.e. The Endless Pursuit of Happiness Through the Accumulation of Money.

I’ve come to believe that what I’m going through is normal for many people as they reach the last few miles of their Financial Independence / Retire Early marathon.  You know you’re going to finish the race, but at the same time, there is some powerful questioning going on behind the scenes:  You are closely examining, perhaps for the first time in several years, your real reasons for leaving the job.  This examination may lead to elements of doubt creeping in on the fringes of your consciousness.

Unless you have a powerful motivating force urging you to up and quit, it’s difficult to change the status quo.

Good, Evil, and N/A.

SuperHeroes usually need an event that turns them into what they are.  A traumatic experience occurs and suddenly there’s no going back.  Peter Parker could have been a lame-assed Spiderman who did nothing but wrestle for money except for the fact that his Uncle Ben died because of his irresponsibility. Spidey just couldn’t deal with that, and a Good Hero was born.

Batman may have decided:  Fuck Gotham.  But he couldn’t, because of intense internal wrangling with guilt and anger over the murder of his parents, which motivated him to try to save a city full of sin.  This idea holds true even for SuperVillians.  Uh… Jack Napier thrown into a vat of acid, anyone? Nicely done.  We’ve instantly created the Joker.

Geek Note: Yes, I know that Napier is a construct of Tim Burton’s 1989 Batman.  Please don’t send me emails explaining that I don’t understand Comic Book Batman versus Movie Batman.  It will make me sad.

At any rate, for people in the real world, that aforementioned happening might take the form of a health issue that makes you increasingly value the limited time you have left on this planet.  Or it might be a Horrible Boss.  Maybe you need to immediately switch to full-time child-rearing, because hey, your kids are only going to be young once.  You get the point.

Thing is, none of these scenarios apply to me.  I want to quit, sure, but that particular feeling doesn’t feel all that urgent most of the time.  Instead the path forward seems uncertain and obscured, as though it’s clouded in fog.  I could leave, or I could stay, either way.  Meh.  Whatever.  Does it matter?

There hasn’t been a single specific horrifying incident to prompt me to make the leap.  Lots and lots of things that bother me, yeah, but no particular event that’s made me say:  That there — that’s the final straw, ya see?  I’m outta here!

Bottom line: I’ve got that FI power, but I’m not yet doing all that much with it. I’m a completely inactive superhero, just sitting on the sidelines, watching shit go down around me.


Inability to take action is often based on emotional turmoil lurking beneath the surface of our inner worlds, so I think it’s time that I list out concerns that flicker in and out of my consciousness.  Then I will refute them.  And this is all going to be done in tabled format to make it more easily digestible.




I’ll lose skills in my industry and never be able to come back to a high earning job again, even if I need to.


You’ll always have a core skillset to which you can return, even if it means you have to take a crappier job.
If I do have to find another job, it’ll never be as good as the one I currently have.  I’d be a fool to give this up!


 There are a wide variety of jobs out there.  You can find decent something in the unlikely scenario that you need to, which you probably won’t. Statistically we’re talking about a couple of percentage points’ possibility of this happening.
I won’t know what to do with my time once I’m not working.


Are you kidding me? Exercise, sleep late, read, spend more time with friends and family — all while pursuing semi-retirement, i.e. finding something constructive to fill 10-20 hours a week.  My experiments with extended time off are among the happiest of my life.
My lifestyle requirements may unexpectedly go up in retirement i.e. I may regret limiting myself to a 20K annual spend rate.


Ridiculous.  I’ve been spending below this level for over a decade.
My manager and teammates will be disappointed I’m leaving.


Yeah.  They probably will, in the short term. But they’ll also forget about you in 6 months. And you’ll forget about them.

If a Net Worth of 750K is great, 1 million must be 33% better.  I should hold on.  Maybe I want to be rich!


We always want more than we have.  It’s human nature. Don’t confuse the pursuit of money with the pursuit of happiness.

Other people would be grateful to have the job I currently have.  I shouldn’t just give it up.


This is precisely why you should give it up.  Other people will be grateful that you’ve left your job — your employer must hire someone to fill your position and it will be a massive professional upgrade for them.

Maybe the quality of my relationship with my wife will go down due to this life change.


Doubtful.  We will finally have time to go adventuring together.  Right now all we do is “cope.” Suck.

I’ll get bored or depressed.


You’re bored at work already.  Work already places you two steps away from depression because you dislike so much about the grind.  If you’re not feeling any better without work, just go back to work, dummy.

Leaving work will change relationship dynamics with your friends and family — for the worse.


My friends are OK with what I’m doing.  My family will be told I’m “freelancing” so they think I’m still working. Relationship dynamics will be fundamentally unaltered.

It’s time that I recognize all of these thoughts for what they are:  Stalling tactics.

The primitive part of my brain is urging me to not change anything about my lifestyle because it has, to this point, kept me alive.  So there is an underlying survival mechanism that’s urging me to just keep on keepin’ on, because since we’ve been walking down this path we haven’t had any trouble finding food to eat or shelter to sleep under.  Hell, we even have a pretty good mate.  Why would we change things up?  From the standpoint of getting our physical needs met, we’re doing just fine.

Thing is, our primitive brain isn’t looking out for our emotional health.  It’s only concerned about our ability to feed ourselves and produce offspring.  It wasn’t evolved to care whether or not we’re “happy.”  To our ancient mind, staying alive and making babies is the same as happiness.  That’s why it creates all of these primordial feelings which are designed to make you stay the course.

But in the modern world, these things are not enough. Humans need more than just food, shelter, and an occasional toddler underfoot for mental well-being.  We need intellectual stimulation, variety in our day-to-day activities, numerous healthy friendships, continual learning and growth, and a feeling of connection to our communities.

I’ll be damned if I let my crusty old lizard brain define a future life of sub-par mental happiness because of a few stone-age concerns.

I will quit this job and start the next phase of my life.

The Next Episode


Uhh, not a good idea, Spidey.

We can boil the entirety of my internal debates down to one simple fact:  There’s no requirement to RE just because you’re FI.

Although I’ve done what I can to make sure I’m ready to quit my job, leave my industry, and, ultimately, move on, nothing is making me leave my job.

I should point out that, in the past, I’ve had no trouble whatsoever quitting. In fact, I’ve quit four, for various reasons.

  1. Left Job Number Uno after becoming fed up with the work and, unfortunately, not seeing any path out that might result in better professional satisfaction.
  2. The second I left because I couldn’t tolerate a particularly toxic manager, who I nicknamed The Cthulhu.
  3. Job Three I departed mostly because I was overworked, but also because I was bored with the underlying function.
  4. The fourth was simply a mistake — I took a job in Startup Hell, reporting to a psychopathic CEO.  I lasted just over six months and took great pleasure in leaving.

But the point I’m trying to make here is that I had a reason for leaving each of these jobs — survival, pure and simple.  Looking back at my past, I can see the pattern:  I quit after reaching a low point with an employer; the worm turned and things suddenly felt intolerable.  From there it seemed as though I had no choice but to leave.

On the other hand, I’ve never left a job before reaching that rock-bottom point. Sure, I have less than terrific days, but even then, the feelings of anger or dissatisfaction do not remotely resemble how I felt during similarly marked “bad days” at any of the jobs listed above.  Attributes I associate with Bad Days with my current employer (overwork, fatigue, conflicts with co-workers and management, boredom) are exactly the same as Average Days felt in Startup Hell.  There’s really no comparison.

My observation is that we tend to work until the point at which we can no longer stand it. Very few of us are able to leave prior to hitting that breaking point, and I haven’t yet reached it, hence, my mental waffling and the intense stalling tactics described above.

The challenge, then, is to actively and consciously choose a path which I believe will result in greater life satisfaction.  To choose to get the hell out before I’m feeding at the bottom of this lake.

It’s time to put the fears, reservations and hesitation behind.  Time to move toward something interesting and awesome.  Time to focus on a new future instead of a difficult and boring past.

It’s time to choose life, whatever that may be.

Digital Fusion TIFF File

Fact:  SuperVillains have more fun.

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16 Responses to Leaving the Cushy Job

  1. Moonwaves says:

    It sounds like you’re reaping the much-touted benefits of now having sufficient fuck-you-money on hand. That is, you can put up with a certain amount of crap at your job, concentrate on enjoying the good bits and refusing to really get drawn into the bad because in the back of your head you have the comfort of knowing that you can leave at any time.

    While I can understand feeling like you’re avoiding making the jump simply out of comfort/being in a rut/not wanting to rock the boat or however you might describe it, I do think it’s important to acknowledge what you mentioned above. Just because you’re FI doesn’t mean you have to RE. It sounds like you’ve made your decision but if you’re still not entirely convinced you could always dip a toe in the water, so to speak, by trying to arrange to go half-time, or three-quarters. Maybe try it out by arranging to just not work on Mondays anymore, for example. How great it is that you have the choice!

    • livafi says:

      Thanks for the thoughtful comment. While it’s true there’s really no harm in staying with my employer for a longer period of time, I’ve come to the conclusion that this (read: leaving) is something I need to do this year — I must allow myself to finally complete and achieve the goal that I set out to accomplish so long ago. That being said, I have thought about reviewing options for extended time off with my employer i.e. taking a leave or sabbatical, to keep that door cracked open just in case. And you are spot on that it’s wonderful to be in a position where the decision is completely up to me. I like your blog, btw. I make a lot of lists too.

  2. Doug Nordman says:

    I’m a new reader here from the MMM forums, and I’m enjoying your writing.

    In your situation (with no compelling reason to leave) this might be a good time to ask for at least 30 days of vacation (or unpaid leave or a sabbatical). The typical bureaucratic response is “We don’t do that”, but of course that becomes negotiable when they learn that your other choice would be to give yourself a permanent sabbatical by resigning. At that point people start remembering things like the Family & Medical Leave Act.

    With that 30 days off (or longer), you can practice both your FI and RE lifestyles. You don’t have to repaint the entire house or write the Great American Novel, although you could put those on the “what you’ll do all day” list. Instead just spend time with spouse & family, work out, catch up on sleep, and try to figure out your future plans. Maybe you’ll use Ernie Zelinski’s Get-A-Life Tree to jumpstart that thinking, or maybe you won’t need it.

    At the end of that time off, you’ll return to work. You’ll either be thrilled to catch up on everything you missed while you were gone, or you’ll realize that you were suffering from slow-boiled frog syndrome. You might also realize that you now have too many new RE plans & projects (that you want to get started on) to stay at work. Or you might have the epiphany that you actually kinda missed work and wouldn’t mind building up your net worth for another year or two.

    In the 1990s, Intel used to give their more senior employees a sabbatical of several months. When most of them returned to their old environment, they soon quit for either RE or part-time work.

    • livafi says:

      Nords, thanks for taking the time to offer suggestions. I enjoy your own writing quite a bit, even have a few links to your blog scattered around these parts. Much of your advice is relevant to all ER hopefuls, military involvement or no.

      Right, taking a sabbatical is something I’ve seriously considered, to the point that I recently asked MMM forum-goers for advice on how to frame the request, so I have a roadmap to follow if I end up going that route. There doesn’t appear to be much downside to it, as you’ve pointed out. Worst case, I get back to the office, despise it, and give notice.

      Loved your note about the Intel guys returning. That’s seriously inspiring. And it makes sense: high on my list of complaints about work is the regimented 40 hour a week schedule which does not allow for much flexibility or dynamism in life. I find it difficult to believe I’ll voluntarily return to that — but again, as you’ve pointed out, I just don’t know. A famous green muppet once said: Future, cloudy it is. Damn skippy.

      Ernie’s a funny guy, by the way. I recently read his book and, judging by his writing style, he’s got more enthusiasm for life than everyone in my office building, including me, combined.

  3. Jennifer says:

    I’m so glad you decided to keep writing. I am struggling with this list of thoughts as well and I look forward to following your journey and reading about the decisions you make. I recently switched to 80% at work (Fridays off) and it has made a huge impact to my happiness. Maybe you could request something like that to start off. Basically I’ve added 52 days of vacation per year. When combined with holidays and actual vacation, it really adds up!

    • livafi says:

      This period of transition (read: completing the journey to early retirement or semi retirement) has certainly been more challenging than I expected. Glad some of the sharing is useful. Re: abbreviated workweeks, it’s a good suggestion and one that periodically pops into my mind as an option — I just don’t see anyone else at my employer doing this, which makes me think that HR lacks the ability to grant these types of schedule requests. 52 extra days a year off sounds amazing though 🙂

  4. I’m two weeks away from notifying my employer of my leaving. I can’t call it retirement, but if everything works out as planned, it will be the end of my days as a paid employee. Or at least one paid by the Man.

    Most of what I “earn” in my new career as homeschooling homesteader is in the wonderful currency called “negabucks”.

    Good luck sorting out that transition for yourself.

    • livafi says:

      Two weeks? Holy hand-grenades, batman. You must be getting pretty excited about it, that’s terrific. My only negabucks producing hobby is cooking because I’d do it even if it didn’t save us money, but it does, so: awesome.

      Thanks for the encouragement.

      • David says:

        Yeah, definitely excited! 9 years of no weekends as a family has been long enough, I think 🙂

        I’ll be busier than ever in “retirement” as having weekends together will predominately mean time for me to tackle projects that have been laying around for years because they’re too hard to get done with kids underfoot. And time for us to get out on the bikes together. Lots of biking, hiking, and whatnot once the weather improves – unless there’s garden stuff to be done. Garden is going to make me its bitch this year – and I wouldn’t have it any other way 😉

  5. bilgepump100 says:

    You may find it best to fore go the sabbatical safety net and opt for the freelance safety net instead. Your current form of employment is in hot demand, so the risk is minimal. The up side is that you can give yourself more space to discover your purpose in life as well as some extra time to shake off the work cobwebs. 30 days off isn’t enough to figure it out. I was totally fried in May of 2013. The push that I needed was a couple of assignments that demanded that I work with the team until 4AM (common in your industry and mine). When I didn’t have the passion to stay for the expected duration, I quit. After that I wondered if I deserved early retirement when, clearly, very few people were doing it. My work muscle memory was still in performance mode (passion was at 5%) and job opportunities abound in San Francisco. So I freelanced and just stopped in August 2014, comfortable knowing that I finally go work out of my system. And I was able to throw a little more cash onto the pile. The time between gigs let me volunteer, take on chores, cook gourmet meals and focus on helping my wife get through her work stress (she insists on working, like your wife). Perhaps you too need the proper amount of time to flush your mind clean of the work habit so you can start anew? (Great blog, BTW. I’m so happy I found it through Brave New Life comments).

    • livafi says:

      Thanks for sharing some of your experiences making the jump. I’ve also wondered if I ‘deserve’ early retirement. (Answer: of course. But knowing the answer doesn’t stop the thought from popping in from time to time.) As you point out, there are a lot of ‘safety’ options available (sabbat, freelance, asking to work fewer days per week.) I’m still mulling things over. Congratulations on leaving, that’s absolutely terrific. Love to hear about people who have successfully cut the cord.

      • bilgepump100 says:

        Lacking Ambition found another safety option: “sniff out a position where I can get all my work done for the day in less than an hour, sometimes less than half an hour, and I’m free to spend the other ~7 hours/day doing most whatever I want, so long as I can do it at a desk.”(http://lackingambition.com/?p=1427) I think I would still feel like a prisoner in that situation. I wonder if for you it’s more about the journey than the destination? Perhaps you’ll need another large life goal to work toward in order to make you feel good about cutting the cord. I suspect it may be something like that and not just that you have a fetish for collecting money! Enough with the psychobabble. You’ll figure it out. Regards.

  6. Lisa says:

    2015 is my year too. 🙂 I alternate between frightened and exhilarated when I think of it.

    I love your chart analyzing what might be considered cognitive distortions. I have just been transferred (as of January 30) to a department of incompetent people. The only competent one has transferred to another location in order to finally rid herself of the resentment and rage that her department mates let her do the vast majority of the work. I was so happy for my friend until I found out I would be her replacement. I suspect that I will be in full “can’t take this shit one more moment” mode by the end of 2015. Just maxing out my benefits and saving a bit more.

    Love this site of yours and I’m selfishly happy you’ve decided to keep it. So, thank you!

    • livafi says:

      Yep, the silver lining on horrendous workplace BS for FI’ers striving to RE is that it can really motivate you to take action. I occasionally wish for something catastrophic to happen at work which would make my decision easier. Weird.

  7. Pingback: Leaving the Cushy Job – Retire In Progress

  8. Rhian says:

    First of all, I know I’m late to the party but congrats to you for pulling the plug on your cushy job. I can’t tell you how much I appreciated you for saying you retired FROM something, and not TO something.

    In the past year or so I’ve read endless blogs, articles, books and comments about saving and preparing for retirement. I’ve come across ‘case studies’ of people who have saved a few mil and own a couple of rental properties. Not me! I’ve struggled mightily with the fact that most people in my workplace manage to keep working for 20-40 years (local government). Why couldn’t that be me? Well it isn’t, and comparison is truly the thief of joy.

    I’d been thinking about quitting my job for a couple of years but always thought it was a frivolous pastime and then my mother passed away February 2020. Soon afterwards our department granted us, the employees, work from home ‘privileges’ and I thought my work angst would resolve. Don’t get me wrong I’m grateful that I have a job, that I’m able to pay my bills, but I simply don’t want to work at my job any longer.

    I’m considering leaving work to return to the UK to care for my 93-year old father. I took FMLA leave in November 2019 to care for both of my parents, so I (believe) I know the pitfalls and challenges that face me including double taxation! Nevertheless that’s my short-term goal.

    Since I’ve been thinking about my plan more seriously, I decided it was wise to think more realistically about caring for my dad. My father could change his mind and tell me he’d prefer to be alone, or he might need to go to a care home or he dies. Any of those outcomes would mean I’d return to the US, and then what?

    I’ve struggled with depression for the last ten years and often wondered ‘what if I’m not any happier after I quit my job?’ Once again you came to my rescue and stated the obvious “If you’re not feeling any better without work, just go back to work, dummy.” Or I could purse the medicated route.

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