My Five Year Prison Sentence

Today was another day spent in the office.  Another day surrounded by people who are working hard for status and to buy expensive stuff that they don’t need.  I couldn’t feel more disconnected from my coworkers.  And when you don’t feel challenged or engaged by your work, it can become extremely tedious and depressing.  There is no satisfaction from a job well done anymore.  You suffer from the “Sunday-Night Blues” every seven days when the realization that the weekend, your short furlough from the office, has expired.  But, I’m here to tell you that there’s hope, if you can just learn to adopt the right perspective about work.



I may be pretty unhappy while contained by the four beige walls of my office, missing my husband and children.  I would love to spend my time on so many different, more personally-meaningful activities.  Even though it seems like my path is controlled by debt and student loans, I still have a choice to make.  The choice is between dwelling on my lack of current options or adjusting my thoughts about time.  Time is the key.  We only have about five years left of this phase of life.  At the end of 2021, I will be finalizing my escape plan from full-time employment.  The next few years are just a temporary punishment for being irresponsible with money for so long.  I have a five year prison sentence for my crime of taking on too much debt.


There are two antagonistic messages that seem to be everywhere these days.  First, you should work hard for success.  But, secondly, remember that you only have one life to live, so be impulsive and follow your dreams right now.  I’m not saying it’s impossible to do both, but the ability to do so is very rare.  I still have a lot of student loans, and we racked up quite a bit of credit card debt over the years.  My current job pays well and provides a good amount of flexibility, which helps me have some semblance of work-life balance and time to side hustle.  As much as I dislike my job right now, it really is the best hope we have for achieving our goals.


I agree with, and try to apply, the knowledge that life is what we make of it.  Perspective plays a huge role in our happiness.  I can choose to be miserable about this “prison sentence” or I try to focus on the positives that can come out of the experience.


If I were really sent to jail (obviously wrongly convicted), I like to think that I would make the most of my time behind bars.  There wouldn’t be any excuse for not reading or writing.  I would have tons of time to partake in those activities.  I would try to get in really good shape with regular exercise.  Some correctional institutions provide educational opportunities, so perhaps I could learn a new skill or language.  It would even be nice to do volunteer work, like training guide dogs.

***Disclaimer: I know very little about what it’s like to actually be in jail (besides watching some Orange Is The New Black).  These thoughts on how I would spend my time are based on big assumptions and the fact that Piper was always reading a new book.


I would never choose to be incarcerated.  Just thinking about being away from my family other than visitations is downright painful.  My point is rather, that if there were no other option, I would hope to possess the grace to make the best from a horrible situation.  I don’t want to wish away time, because it is such a finite resource.  Even if I do have to spend large portion of my days and energy on work, I can still make most of next five years.  There is still time for family, friends, bettering myself, and enjoying hobbies.


It’s also not fair to fault those on the outside, enjoying their freedom, although I certainty deal with frequent pangs of jealousy.  There are many female bloggers who achieved financial independence in time to raise their children from home.  It would have been amazing to be there for my kids from the beginning, never dropping them off to spend the day with paid caregivers.  But, these other models of frugality respected the laws of finance at an early age and deserve the rewards of their efforts.


As a society, we don’t like to take responsibility for our actions, always looking to blame someone else or some unforeseen circumstance.  I was careless with money and made financial mistakes.  There is a price to be paid for my transgressions.  I hereby plead guilty and am willing to serve my sentence.


It’s easier to endure less-than-pleasant experiences if you know that they will only be temporary.  For example, think about the doctor tells you the shot will just be a quick stick.  I’ve written before about adopting the mentality of a soldier when it comes to cutting way back on spending.   I suggested going extreme with your frugality, but only for a discrete period of time, like a six-month “mission.”  The exercise becomes instantly less challenging if you know it’s not going to last forever, or even the indefinite future.  I often remind myself that my life will be changing dramatically, and for the better, in just a few years.


The first day of the work week can be depressing.  That “case of the Mondays” can be pretty contagious.  I always hear complaints and see the memes.  They get to me for a moment, but then I remember something pretty awesome.  Unlike the vast majority of people, I am not facing a life sentence, twenty years, or even ten years in the prison of full-time work.  I will be done in just over five years . . . and maybe less, with good (financial) behavior.






  1. I hear ya on the prison sentence. I try to focus on the positives to help myself get through, and also knowing that many others unfortunately have it much worse. There’s a lot to be thankful for and once the “sentence” is over you’ll be in a much better place, I know I will be too. Thanks for the post.
    The Green Swan recently posted…The Frugal MillionaireMy Profile

    1. I wondered whether it was a little too dramatic to compare work with a prison sentence, but it’s a good analogy for my feelings about the present and the future. We really will be much better off in a relatively short amount of time.

  2. When we lived in New York the stress was horrible. We felt like a big old sink hole would open up and swallow us. But when we made the decision to leave and executed our 3-year plan, almost instantly, everything became bearable. Perhaps you can change your 5-year plan into 3-year plan followed by a 2-year plan. It’s these little games we play that keep ourselves sane.
    Mrs Groovy recently posted…My Cousin Joe was Delivered to My DoorstepMy Profile

    1. The stress certainly gets to me and is a big reason I vowed to not work like this for too much longer. This little 5-year game helps a lot on not feeling trapped in this situation forever.

  3. Best of luck with the next few years, and hopefully it will be even shorter than you think! It sounds like you have a good plan and will be successful with whatever you choose.

    Luckily, once your “prison sentence” is over, you’ll be able to enjoy true freedom without the stigma of being a felon and the restrictions on the jobs you can have, benefits you can receive, opportunity to vote, and sometimes on where you can live or travel while on parole.

    1. Thank you! I do hope we can find a way to decrease my sentence. Good point about all those post-release restrictions on your freedom – those are definitely some things I never want to deal with!

  4. Nicely done.

    It’s a bit like dealing with a big challenge in science. You have to break it down into smaller components to even begin to tackle it. And in science, nothing is gained without experimentation. Sometimes you have to try different ways and see what works. Some wil work, some won’t. Whatever happens with those experiments, don’t lose faith in trying another one. What we gain is always learning about ourselves and that is never a bad thing.

    If I could hand you a get out of jail card, I would! 😀
    Mr. PIE recently posted…A Letter To A FriendMy Profile

    1. Thank you my friend 🙂 I would gladly take that get out of jail card . . . too bad we can’t put Monopoly money to use either, I think we have three different versions of that game in our house.

      Great analogy about science experiments. I figure the worse thing we’re really doing right now is improving our finances, so that will be helpful no matter where we end up.

  5. Great post!
    An interesting perspective for sure. It’s like you said though. You have to focus on the positives. And 5 years is minimal compared to the 20-to-40 most will go through. My view on doing a job you hate is that it has to be leading to something better. There has to be skills being gained or it needs to be a stepping stone.

    1. Thanks for stopping by Graham! There are certainly skills being gained even though the job sucks. I hope to transition into a part-time, consulting role using this experience once we reach financial semi-independence.

  6. I think a prison sentence sums it up pretty nicely plus it is a catchy headline anyway you look at it.

    You’re stuck doing something you don’t want to have to do but are going to do to pay your “dues” if you will.

    I get the tedium of 4 beige walls as I’ve been in a windowless office for the last 3+ years. After a year and a half, I worked out a way to work remotely from home for 2 days of the week because I was going stir-crazy.

    I’ve set a 5-year plan for my wife and I as well but I’m working hard to try and have it done by 2.5 years.

    You’ve got a good attitude and approach to your debts. Just keeping looking forward as you grind them down to $0’s.

    1. Glad to hear that others can identify with the analogy. I too hope to decrease my sentence, but it’s motivating to know that there are no more than five years left before the next phase of our life. Thanks for stopping by, Adam!

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