Quitters Never Win, Except When They Do – 3/3

Leave if you must. But leave when you are strong, not weak. Leaving should be a choice and not the only option.

― Ram Mohan

The previous entry, if you need it.

Later on Wednesday, after things have quieted down around the office, I jump on the treadmill.  It’s around four o’clock in the afternoon and I need a boost of energy. Between the meetings and everything else, I’m drained.  Running usually fixes me.

Fifteen minutes in, and my body is hot, my mind relaxed and loose.  The belt hums below me, and my feet fall in rhythm.  I’m finally where I want to be.


When I’m in these states it’s as though I’m drifting through the database of my life, all experiences available, accessible, and accounted for.  This is where I go to think.  This is where my life lays open, end to end.

I query myself:  

Why are you still conflicted?  Do you really feel connected to this job?  Your function?  The people? 

The response comes through quickly.

I’ve made it through life by serving others.  It’s how I’ve achieved everything I have.  People tell me what to do, I do it, and then money appears.  It’s not that I care about them.  It’s that I’ve needed the means to live.  I associate approval from management with drawing breath.

But you don’t need the money anymore.  Why do you still feel connected?

The connection is my link to security.

You know you’re secure now, right?  You have more than anyone could possibly need.  Some people retire successfully on a third of what you have.  


So what’s the issue?  Why the hangups?


This time the response is slow in coming.  My arms pump, my legs move, and I wait for the blankness in my head to take some form.  Then, finally, there’s a shifting: a new viewpoint into my past.

I’m young again, seven or eight years old, and my family doesn’t have enough.  My parents are fighting about money.  I’m wearing my older brother’s hand-me-downs and they don’t fit.  At school, I am different. My so-called friends have limitless quantities of cool toys.  GI-Joes.  Transformers.  The Star Wars Endor Forest set — Ewoks and everything.  I, on the other hand, have a sock puppet of Kermit made by my mother.

Several years later, my parents are divorced.  When they do manage to speak, they’re still fighting about money.  Some nights we don’t have any food in the house and I jump on my bike to pedal through the darkness to the Stop N Shop to get spaghetti, paid for with earnings from my bakery job where I scrub sheet-pans over sinks full of boiling hot water. I arrive home breathless, cook and feed my younger sister, and do homework until I fall asleep.

I don’t have enough.  I will never have enough.

Because there’s a part of me that’s insecure.  Even after all of this, I still feel poor sometimes.

<<I’m shivering on the treadmill.  Goosebumps line my arms.  I’m barely conscious of the body moving somewhere beneath me.>>

But you know you’re rich, right?  What, do you want to die with the most toys?  Since when has that been your goal?  Are you still fucking six? 

No.  I’m a man who recognizes I have plenty.  More than enough.  I’m unbelievably fortunate.  I’m ready to stop working and pursue things that actually make me happy.  

Then why are you angling so desperately for a sabbatical?  How would you actually feel coming back?


I picture it.  September.  I’ve just spent an entire summer away from my desk job, doing whatever the hell I pleased.

But that’s over now.  I’m sliding a badge past an electronic reader, opening doors into a building that consists of sections partitioned off into offices and cubes.  The offices house insane overlords.  The cubes house the workers.  But the variations in quality and spaciousness of the specific work areas make no difference:  The employees are all slaves.

I find my own cube and sit down, logging into my workstation. Then I’m running reports against servers, staring at pie charts and alerts and emails and the blinking red light on my desk phone that indicates I have voicemail.  I am surrounded by synthetic, mass produced products that plug me into systems and applications.  My job is to create these abstractions, link them together, watch them grow, care for them.  They are my virtual babies.  My silicon children.

A manager’s voice becomes audible in my head, giving instructions for the day. This task is urgent. That stakeholder’s request is critical. It is imperative that we complete project X on time and under budget.

Nausea hits me first, then anger.

And it suddenly strikes me that it would be infinitely more difficult to come back to this place than it has been to leave it.   It’s impossible.

And with that, the sabbatical charade has come to a conclusion. I am not sure how I’ve been so blind to this truth.


You still there?  Repeat: How would you actually feel about actually coming back?

I’d feel like shit.  I’d feel like I failed.  Like I was nothing.  I’d rather die than return to this.

With that, there’s an instant lifting. The dull ache that had been following me since the beginning of the week disappears, and every trace of guilt, irrational loyalty, and inexplicable indecision departs with it.

And then I’m roaring forward on the treadmill, strong and weightless, another force powering this thing attached to me, this body.  The machine shakes underneath, unable to contain the energy.

I jump off, head out of the building and into the cold March air.

And I run.

It’s Friday.

I’ve made it through the remainder of a week that included additional meetings with higher-ups.  I met with my Chief Information Officer.  I met with the president of Information Technology Services.

Each time, the scene played out the same way.  Why am I leaving?  Family.  Where am I going?  Nowhere.  Don’t you need the money?  No.

I don’t vary the story because I know they’re all talking with one another and my responses should be consistent.

In the morning, I have a meeting with my manager and he asks me if anything has been clarified in my picture.  He wants to know if I will accept a sabbatical with a commitment to return on September 1st.

I tell him I can’t commit to anything.  That I cannot, in good faith, promise to return on September 1st.  I go further, saying that I know it’s in my own best interest to sign an agreement to come back, knowing that my job will still be available, even if I am not sure whether or not I can follow through.  Because there is no risk on my part; If I can’t return, nothing bad happens to me.  It’s the sort of agreement where the entirely of risk is shouldered by the employer.

But I will go against my own interests and not sign.  I say that we all need to move on.

My manager is confused.

Didn’t we agree that leaving the door open is the best approach?

Yes, but I’m not willing to commit to something I think will not happen, even if it’s clearly to my advantage.

How about a terminate-to-rehire clause?  It basically means that if your position isn’t filled and you’re looking for employment, you’ll be at the top of the list.

Okay, that sounds reasonable.  Thanks.

<<I don’t care.  I won’t be back.>>

If we do it this way, and you’re rehired, you won’t be eligible for the working arrangements we’d discussed before.  No 3-day workweeks or part time.  No work-from-home.

Yep, I completely understand.  I think this is the right way to handle things.

<<I don’t care. I won’t be back.>>

How about your leave date on April 3rd?  We could really use you around until the 10th because of <<final implementation of project X>>

I will be leaving on the 3rd.

What if we paid you through the entirety of April — through the 30th, including all benefits — if you work the one extra week?

That’s two weeks of free pay?


<<I decide on the spot to put the extra 3 weeks of post-tax salary into a charity founded by an old friend of mine.  It’ll come out to several thousand dollars and would make me feel terrific.>>

Okay.  Sounds like a deal.  Let’s put it in writing and sign the paperwork.

Half an hour later I’m in another meeting with my manager and an HR rep and we again go over the details.  There’s a multi-sheet printout in front of me, bound by a fat silver stapler.

I cast a glance at my manager, who is chatting with the HR rep as though I’m not there.

This time I barely recognize him.  He looks like a combination of people from different jobs I’ve held at various points in my life, the faces blurred together, features mixed. My CEO from a startup? My first superior at my very first software company? I see something around the eyes that strangely reminds me of me.

I sign the document, banishing them all to my past.

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28 Responses to Quitters Never Win, Except When They Do – 3/3

  1. G-dog says:

    Whoa! Sorry about your rough childhood, I hope this means you are finally free of those fears.
    Go, be free.

    Me, still struggling, set a date in my head. Haven’t had the discussions with my manager yet. I can just about guarantee that there will be no angst or extreme offer of ‘anything’ to keep me. She doesn’t believe in having anyone in my current role, but rather have attorneys do the work – so this will open up an opportunity for her to change the demographic to what she envisions.

    • livafi says:

      Hey G – Yeah, I’m totally fine. Better than fine. My childhood wasn’t that bad – despite the money issues, I always felt loved, which is the most important thing. The other stuff is just peripheral.
      Congratulations on setting a date. If your experience is anything like mine, you’ll be very happy and relieved to put it all behind you. And it’s a bonus, if anything, that you’re pretty sure that they won’t be putting you through the “let’s-try-to-keep-you” rigmarole. Looking forward to hearing your own story once you’re on the other side.

  2. It’s Sunday and I’m on my computer to do some work that “needs” to get done before tomorrow, assigned by my manager… Maybe my FI date of 40 is too far away…

    • livafi says:

      You don’t have to wait until your FI date to a) seek a better job or b) consider semi-retirement AKA part-time work of some kind. You also don’t need to hit the 4% WR rate if you are comfortable going back to work in the shit-hits-the-fan scenarios. Being more flexible regarding usage of safety nets can potentially shave years off of your full-time-employment lifespan.
      Good luck managing your manager.

  3. Tim says:

    Ah that problem. You know in your head you have enough, but you question it in your heart. Feeling it is different than knowing it. Glad you found a way through it all. Best of luck on the upcoming freedom.

  4. Excellent update. The attachment to job feelings fade over time. Takes about six months. I stay connected with some of the old cow-orkers. We get together for lunch a couple weeks after each quarter to let them celebrate bagging another one. For the most part, if management likes you, they get over you leaving and are happy to join for lunch without pressing you to come back. Life is good.

    • SU says:

      I really really hope that cow-orkers was deliberate. It’s perfect.

    • livafi says:

      I’ve read that 6-months figure over and over again, in forums as well as books about retirement, so I believe you. Incidentally, it also typically takes 6 months to get used to a new job. So there’s something magical about that figure when it comes to human adjustment to a new situation.

      I don’t think I’ll be hanging out with anyone from work in the future (although I do occasionally get together with a few people from previous jobs).

  5. Jon says:

    Boom goes Dr. Doom! Very nicely done…regrouping and executing. I too do my best thinking during some quality exercising. Good job gathering the courage to withstand the final bum’s rush from the various “suits” at work.

    • livafi says:

      It was much easier to meet with the last two. Just breezed through. Coming to a firm decision about not wanting to return was the key piece. And yes, exercise can be a terrific tool to improve clarity of thinking. I solve work problems while running all the time — helps me think creatively and attack issues from new directions. Good stuff.

  6. Frankies Girl says:

    Wow. I swear, I have had some of the exact same conversations in my head. I didn’t grow up worrying about food on the table, but was definitely led to believe that everything could disappear at any moment. It is still hard for me to really internalize that logically, things are going to be fine and work out based upon the basic plans made. Fear and uncertainty are what I was raised with, so it’s been a real battle to undo all of those years of programming. Sounds like you’ve been facing that same battle.

    Good for you for sticking to your guns on leaving. You deserve to be free!

    • livafi says:

      Thanks – now I don’t feel so looney tunes for writing about some of this. I also have a sense we’ve had some overarching similarities in our childhoods, even if some of the details were different.
      I’m really glad for you, too, btw, recently caught up on your story on the forums: Awesome. I’m looking forward to joining you shortly in not-going-to-work life.

  7. David says:

    I noticed that your day countdown changed when I first pulled up this article, and now I know why 🙂

  8. Wow, that post was incredible! It was like I was at a high-stakes poker table with you – offers and counter-offers; knowing the bluff while the opponent / the employer makes big, crazy gambits… Sounds like it worked out, but I’m still not sure, my head is still spinning. I’ll be thinking about it while I jog tonight!
    I quit a contract job (twice actually, it ‘backfired’ in 2006, and then permanently in 2007), which was really easy. But quitting my current job might be similar to what you describe, good to have a little heads up on how to go about it if it comes to that. I’ll definitely take a 1 year sabbatical though….

    • livafi says:

      For the record: Every other job I’ve ever left has been very easy to quit.
      But despite some of the challenges, this has been the most exhilarating of them all. Because: Not going to another one this time.
      Absolutely, please use my mistakes as a learning opportunity for how to handle your own exit. Some of my theories about how to handle the exit were put to the test and basically disproved.
      And you know what? I’m OK with being wrong — ‘s’all good. It’s over, after all.

      • Jared says:

        You should summarize what worked/didn’t work in a future post. I love the play-by-play posts, but it is a little tricky to distill them into specific lessons 🙂

  9. Clare says:

    You have much deeper (and coherent!) conversations with yourself on the treadmill than I do.

    • livafi says:

      Maybe not. I have to repackage the brain chatter into a form that makes it passably readable — Full disclosure: the real-time internal stuff feels a little less coherent than how it’s represented here.

  10. eamann888 says:

    I read all of the popular FIRE blogs, but I have to say that of all of them yours is my absolute favorite. It’s the most human, and the only one I’m aware of that is really willing to confront the darker and more uncomfortable thoughts surrounding FIRE. I think many more people have these feelings than all the super-optimistic-analytical-engineering-minded blogs would have you believe. Please keep writing in this open and honest way – you’re really helping people.

    • livafi says:

      >>I think many more people have these feelings than all the super-optimistic-analytical-engineering-minded blogs would have you believe.
      I completely agree. Thanks for the comment.

  11. Edward says:

    Geeze, Louise–talk about not letting an issue go! I’d go mental if I announced I was leaving and they kept on my back day-after-day like that. Sure, maybe a little flattered at first, but eventually annoyed beyond belief. I’m generally pretty calm but nothing can rise a bile-filled temper like incessant nagging.

  12. Thank you so much for sharing this story. I also grew up poor, and have identified the need for security as my reason for wanting FI. Good for you for sticking to your guns and your principles on Project: Quit. Congratulations on reaching the goal! Again, thank you very much for sharing this. It really resonated with me.

  13. Living in a Sun Dress says:

    Just found your blog recently. Thank you for posting your experiences and mental and emotional processing. I’m working through my own feelings. My working plan is to take a slightly early retirement in 2016. Before finding your blog, I felt embarrassed and guilty. I mean, who in their right mind would NOT be 100%, unequivocally at enthusiastic (or, at least at peace) with retiring when FI (unless the work was a passion). At the same time, what kind of nut would I be to leave work that others would love to have. What if……. I’m learning a lot about myself while reading your posts. While part of me wants to binge read (to see what happens next and, honestly, because I’m hard wired to make progress and “complete the project), because your words are so pertinent to my life situation I am pacing myself and trying to digest and reflect. This post, in particular, resonated on a deep, deep level. Reading it is helping me look in a mirror at my child self and my adult self. As you described, not a bad childhood, but one in which financial and social stress contributed to my choice to always wear the “cloak of responsibility” and to using that cloak to extend protection and provide a safety net for others. Over the years, quickly adding the “muffler of risk management”, “hat of planning for all possible outcomes” and layers and layers of other (all chosen by me, I will add) apparel and shielding. Ha! Perhaps subconsciously I thought that wearing all of that was my superpower!
    Reading this post was an emotional gut punch, but in a very good, very clarifying way. You have done a great service to your fellow humans. Your writing has been a great help to me. Thank you.
    With today’s insight, I will choose a forward looking name for myself:
    Living in a Sun Dress

  14. Xenaga says:

    I’ve binged read all of your job experience posts from year 1 out of college to this last series when you have given your final notice. It was very satisfying to read…the roller-coaster ups and downs from the various jobs and situations you have been in. I think we all can relate to it, as most people make this journey but never get out as early and well off as you have. Kudos to you! And I appreciate you sharing your journey. This has inspired me to start my own journey, although right now I am saving for FU money which could eventually be the seeds for retirement.

    Thank you very much for sharing yourself with complete strangers.

  15. Stephen says:

    I stumbled upon your blog through a link in the MMM forums, and have really been enjoying reading it over the past couple weeks! MMM was my introduction to frugality and it’s changed my way of thinking about almost everything. I love how you tackle the subject in a different way and cover subjects that he doesn’t. Especially enjoy the stories of you wrestling with fears and doubts that all people encounter, this seems to be a neglected topic on a lot of these types of blogs. Your account of your career has also been really insightful and interesting, as I’m in a similar field.
    Hope you find the time to post more in the future!

  16. Hey Dr Doom, haven’t seen a new update from you in a while, just wanted to let you know since our initial contact back in 2014 / 2015 that I’ve exercised the option to F.I.R.E and left my banking job.

    I’m now in the wilderness exploring life, and boy does it make me feel alive. Hehe. Anyhow I’m very grateful to have chanced upon your blog and writings and it was one of the blogs that sustained my inspiration along this journey.

    I hope you are doing fine whereever you are. If you are ever heading to Singapore let me know and I’ll be happy to buy some beers. Cheers.

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