How to Live in Corporate Prison


Working for The Man pretty much sucks.

I suspect this feeling holds true for most people who hold down stressful jobs in corporate America.  But if you achieve financial independence (FI) then you can escape the standard working life and everything that comes along with it, allowing you to pursue things that truly make you happy.

Before you get to FI, you’ll likely be slaving away in a job that you don’t particularly care for.  In most cases this will be for an extended period of time.  For the most dedicated, intelligent, and fortunate, this may be as little as six or seven years.  For others, it may last a couple of decades.

No matter how you slice it, this is a long goddamn time to be doing something that you don’t love.

The question, then, is how to manage the years without going insane.  I figured I’d share a few techniques that have helped me ride out my own sentence.

First, I dedicated myself to my profession.  This sounds counter-intuitive.  Don’t you want to run from your job?  Get away from it?  Isn’t that why you’re learning how to save and invest so aggressively?   Yes to all of those things.  But at the same time you have to recognize that you’re currently in the slammer and until that door opens to let you out, it’s best to accept the current state of affairs.

Humans function better when they’re dedicated to something.  You’ll feel better giving it your best.  So work at being interested in whatever you do.  Pretend you’re going to be there forever and make decisions accordingly.  There are tons of benefits to this approach.  You’ll get better annual reviews, which will probably translate into bonuses and salary increases.   Increased respect and likability.  It’ll be more pleasant to socialize with peers or managers because, as a high performer, you’ll be confident and smooth.  Most importantly, study after study proves that people enjoy doing stuff that they’re good at.  So the better you get at your job, the more you’ll like it — or, at least, the less you’ll hate it.  This approach will go a long way toward helping you ride the years out until you hit your FI goal and the bars unlock.

Don’t tell other people about your real plans.  Ever.  This is a set-in-stone rule and there can be no exceptions at the workplace.  Telling co-workers that you want to retire early will result in pain and suffering at best, stunted career opportunities and broken relationships at worst.  Nobody likes the inmate who thinks they’re better than everyone else.  How would you feel if your cellmate “Butchie” kept telling you that she wasn’t like you, and in fact she had plans to escape the slammer in a couple of years while you continue to waste the rest of your sorry existence stuck in the joint?  Not good, I bet.  In fact, I suspect you’d substitute a different vowel for the u in her name and start calling her that, instead — at least with your inside voice.

And keep in mind that gossip like this is so juicy that no one can keep it a secret.   “So and so thinks that he or she is going to retire!  At age thirty!”   It’ll make the rounds quicker than news of someone’s impending divorce.   When I find myself tempted, I remind myself that the cool personality trait of FI will be perceived as a disease by everyone else.  You wouldn’t tell anyone at the office you had gonorrhea, would you?

One of the cool things about keeping your cards close to your chest is that you’ll always have this incredible secret that nobody knows about.  It feels like a superpower.  You’ll look around every day and watch people behave the way that they do, shopping for Amazon garbage on company time, bitching about meetings or work-life balance or their inability to make ends meet and so-on, and it won’t bother you nearly as much.  Your secret protects you from being crazy upset about work, because you know that this whole working-for-the-man thing is only a phase, and you’ll grow out of it and into yourself.  But chances are, everyone else in your workplace will not.  Your secret makes you as bulletproof as your co-workers are vulnerable.  Somewhat paradoxically, knowing that you are going to leave your position within a couple of years makes you a better worker and also improves on-the-job happiness.


Your secret will power you like an arc reactor.

Your secret will power you like an arc reactor.


Then there are annual reviews, where you must go over objectives with management.  Questions will be asked.  Where do you see yourself in five years?  What are your big goals here at the Company?  My advice is to figure out what they expect you to say, and say it.  I treat these meetings like athletes treat interviews after the game.   They just say the standard vanilla stuff, like “Couldn’t have done it without my teammates.  I focus on the things I can control and try not to worry about the rest of it.  I put everything out there on the field.”  So I say the business equivalent. The closer you stick to the script, the faster you are out of that meeting and back to doing something less unpleasant.

Now I’m not saying that you should look for a promotion if you’re not ready for one.  A few times my own manager has tried to assimilate me into his group, but I’ve always declined. (I could fill a separate blog post with reasons I don’t want to go into management, but let’s just say I’m not interested.  That hypothetical blog post would have a lot of swearing.)   After telling my manager that I’m not interested, I’m quick to moving back to the standard script, to get his consciousness back on a pleasant, familiar track.  So complete nonsense like this will be coming out of my mouth:  “I’m really happy doing what I’m doing and want to keep doing it.  So my goal is to, a year from now, be better, faster, and more efficient at everything I currently do.  I’m striving for continual excellence and it is only once I’ve achieved perfection that I’ll be looking for the next rung on the ladder. ”  What you don’t want to say is anything that might upset your boss, like “I’d kill myself if I had to do what you do.”  Just keep that tidbit to yourself.

Personal Story Time

Sometimes things get really bad at work.  When I was still pretty young, in my mid 20s, I went through a horrific stretch that nearly broke me.  I’d just gotten a position at a financial company that I won’t name where all I did was crank.  Days, nights, weekends. They expected you to devote your entire life to the institution because they paid pretty well and provided opportunities to become downright wealthy if you were willing to devote yourself completely — body, soul, and shit-covered nose — to the job.  The work was endless, and instead of being rewarded for getting things done, individual contributors got the opposite:  nonconstructive criticism.

Why wasn’t this done yesterday?  How could you fail to prevent this problem before it happened?   Why aren’t you working on more visible projects?   I expect you in the office at 8AM, regardless of how late you were up last night working on other required tasks.  And on it went.


At this point, I found it useful to remind myself that although I was stuck in prison with these complete assholes, they were also stuck with me. So I started pushing back.  In my second year at said company I had built a proper stash of security in the form of F-You money — over five years of living expenses.   My spine was growing in proportion to my assets.  That’s when I realized that the rules were changing.  I had the confidence to make my own (reasonable) voice heard, even when it was politically dicey.   I stopped fearing conflicts with management and trusted myself.

Rorschach is a bad-ass.  Read Watchmen if you haven't.

Rorschach is a bad-ass, aint’ he?

Being secure in my financial well-being allowed me to say no to weekend work, push back on that valueless project which existed only to put a feather in my manager’s cap, and stop demeaning myself by kissing up to people that I couldn’t stand.  I put my time and energy into the most important projects, worked with the smartest and best people, and was able to shut out most of the rest of the white noise.

Ultimately, it also allowed me to leave when the time was right.  I left and took a job at a different prison, where the wardens were a lot nicer.  I doubt I’d have made the transition if I’d been living paycheck to paycheck because I would have been paralyzed by fear, too scared and discouraged to look for anything else.

While you’re on this journey, no matter how things are going at work, you can always remind yourself that you’re in a better position than most.  After all, you have options.  You’re financially stable, and eventually you’ll be completely free.  And if things get too intolerable to bear– well, simply ask your F-You money to fulfill its true purpose and say the magic words to your employer.  After all, that’s what it’s for.

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5 Responses to How to Live in Corporate Prison

  1. Moooooser says:

    Excellent use of my favorite Rorschach scene! It fit into your post quite nicely 🙂

    • livingafi says:

      Watchmen is one of the best graphic novels I’ve read. Will have to try to include V somewhere in a post at some point, too. That Alan Moore is one talented guy.

  2. RB35 says:


    Came across your blog from a link sent by BnL from Twitter and I have to say this blog is buzzing with awesomeness written all over it.

    By way of introduction, I’m a late 20s dude working in Singapore, doing prison time in the investment banking world with the exact same mindset as yours.

    I’m grateful for the guidance and relevant articles that you’ve written. Pretty helpful and your humour is infectious.

    Hope all is well now that you’re done with work. Would love to see more of your articles post retirement.

    • livafi says:

      Thanks for stopping by – always great to have new readers. I’ll keep writing as long as I have content. And I’ll add that blogging has, so far, been immensely enjoyable and rewarding. Highly recommended… oh wait, you already do it.
      >>doing prison time in the investment banking world
      You’ll make it. The nice thing about coming to the conclusion that you’re just not that into the office-type existence early in life is that it really focuses your thoughts and energy on saving/investing/ER, which will allow you to make a quick escape, by normal human standards.
      Good luck.

  3. Aperture says:

    Hello – I just wandered in from the cold to enjoy a few warm moments at your FIRE. October 1, 2018 is my parole date. I enjoyed this article because it is advice for exactly where I am right now. The closer I get to my financial goals, the harder, more intolerable I find work. I suspect it is because I have stopped dedicating myself to doing the best work I can and instead have drifted into daydreaming about everywhere else I would like to be. I appreciate the practical advice. I will put it to use in my next 1:1 with my manager. Cheers, Ap.

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