An Elderly Convict’s Advice for Early Retirees

One of the best pieces of early retirement advice I ever got came from an elderly convict incarcerated in Angola Prison, AKA the Louisiana State Penitentiary.

Now: you may think you see the whole Joss Whedon/Firefly/”You can’t take the sky from me” AKA “You can’t cage my mind” angle coming, but that’s not it. Freedom is where you make it, but I wouldn’t waste your time with such an overdone cliche, however noble it might be.

Nah, this piece is about structure. 

Prison is a very structured place, I’m told, but that’s not entirely so. True, your movements are limited, and they tell you when to get up and eat and sleep and shower and hit the head and such, but after that your time is pretty much your own. Lot of empty hours to fill. And assuming you avoid prison and achieve FIRE instead–which you can, if you want it badly enough–you may find yourself in a predicament that’s much the same.

After turning in your so-called “final notice” and becoming a FIREee, it’s likely you’ll experience a decompression phase. You’ll probably be sleep-deprived, you’ll have tons of long-procrastinated chores to get caught up on, and…well, it’s not mine to judge, but there’ll be many hours for you to indulge in what let’s call “less productive” pastimes. Stuff a lot of people associate with leisure: reading, gaming, Netflix, swinging in your hammock in the back yard with a tiki drink in your hand and old Grateful Dead bootlegs blasting you through the afternoon…

And that’s as it should be. You’ve earned early retirement, man, through years of hard work and focus and sacrifice…all of which you’ve accomplished by virtue of the same self-discipline that empowered you to get up too early in the morning, dress yourself like a peacock at a funeral, endure a commute, work in an open office environment, and all the other grueling mundanities that nonetheless HAVE to be done. But now? You’re sitting on the couch in dazed disbelief. You made it. You’re out.

But you’re also sitting there in a great deal of danger; danger of squandering the rest of your life.

So here’s where the advice from the old con in Angola comes in. For those who aren’t familiar, Angola is a maximum-security ex-plantation work farm in eastern Louisiana that mainly holds black male lifers; a real hell on earth run by white overseers mounted on horseback, brandishing shotguns and truncheons and pepper spray and tasers, who watch intensely while the inmates hoe beans in the skull-roasting sun.

The con didn’t give me the advice personally, but indirectly through a documentary I can’t put my hands on just now. YouTube? At any rate, the documentary began with a young black drug dealer slash murderer as he rode the prison bus through Angola’s gates and saw the place for the first time. After going through the intake process–bend over and cough and lift your privates so we can make sure you’re not concealing a high-powered rifle under there–he got processed into general population and reunited with his long-incarcerated uncle; an elderly fellow who’d been estranged from the family for decades and had never met this nephew of his.

They sat down together at a little table in a conference room. The nephew gave the old man some family news the old man didn’t seem to care much about. Then the old man asked the kid what his plans were.

“I’m gonna learn the law and get outta here because my little man needs his daddy,” the kid replied. I think those were his exact words.

The old man shook his head in sadness at the kid’s naivete. He’d obviously heard it all before. “You need to accept that you’re gonna die here,” he told the kid. “Get your routine down and stay away from the wrong crowd and get your GED and don’t waste your time.”

The kid frowned and you could tell he was already blowing his uncle off. Another ancient geezer trying to tell him how things were. What did he know about life in the streets? He was obviously a dipshit or he wouldn’t still be locked up.

But the old man sat back in his chair and looked the kid straight in the eyes. “It’s good advice,” he said. And it was.

I don’t remember the kid’s name, but I could probably dig it up if I cared to, and I imagine that if I looked him up in the Louisiana department of corrections database he’d still be imprisoned. And I further imagine that his “little man” has grown up and rarely thinks of his daddy, if at all.

Or, and this is the real mind-screw, little man is now in Angola himself, and his daddy’s giving him the same advice as his daddy’s uncle did: accept that you’re gonna die here. Get your routine down and stay away from the wrong people and don’t waste your time. And little man is ignoring it to his daddy’s despair.

So there’s a bummer for you, eh? Bet you’ll remember it, though.

Sitting on my couch wasting time surfing YouTube and watching that scene play out, I realized that I needed structure too. Not the behind-bars kind, but for sure a daily routine centered around positive and productive goals.

In the FIRE movement we use a lot of hyperbolic prison metaphors for pre-FIRE life: “escape” and “breaking out of my cell” and “ankle monitor.” And sure, they express profound emotions: “My circumstances feel terrible and I need dramatic change.”

I for sure used them. One of the main reasons I wanted to FIRE so badly was that I’m not into structure. Hate it, especially structure that’s imposed on me by others. And these days there are only two people in the whole world who get to tell me what to do: 1) my wife and 2) my mom. But now, working on this post, I see that there are three. I’m a close third to numbers one and two.

So let me offer you my daily routine.

  • 7:00 — Up, coffee, journal, clearing the moderation queue of Reddit’s FIRE forum.
  • 7:45-ish — Five-mile run, usually my tough hill course.
  • 8:45 — Home to see my daughter off to school at 9. Wife may or may not have left for her volunteer work or hobby job at that point.
  • 9:00 — Shower/shave/make bed.1
  • 9:30 — noon: Write. Journal, blog, and/or fiction. I shoot for a 250-word journal entry and a thousand words of whatever else.
  • 11-30ish — Lunch of protein and fruit and nuts.
  • 1:00 to whenever: errands and/or household chores.
  • Whenever I get finished with what I start at 1:00, the rest of the day’s unstructured. Rum & hammocks, perhaps. Kid gets home at 4:45,2 we eat dinner, she does homework, and fun-time begins.

See? Structure. A daily routine. HIGHLY RECOMMENDED.

Welp…when I get done with this article I’m gonna throw a bag of clothing and a bit of camping gear and such into my mini-van and split for the Hulaween music festival in Live Oak, Florida. The String Cheese Incident is playing a few sets, and also in the lineup/schedule are several of my favorite electronic music bands including Odesza and Gramatik. I’ll be hanging with a couple of bros from my festival family–good dudes I haven’t seen in several months–and along the way I’ll be taking a trail with a fine FIREee who blogs under the pseudonym “The Millionaire Educator.”

During the festival I also don’t doubt that I’ll be tuning my brain up for the music with a certain controlled substance ex-Speaker of the House John Boehner is now whoring for. And if that makes me the wrong crowd to hang out with, then so be it. Boehner might be worse, but from all appearances he’s already inhabiting whatever circle of hell hypocrites inhabit. I, on the other hand, am free.

But, and this is what I want to leave you with, please believe me when I say it’s the self-discipline that opens the door to self-indulgence. I work damned hard, albeit enjoyably, to fill the hours of my day with things productive, and then when it’s time to slip the chain and chase the frisbee, I work damned hard at that too. Which much to my surprise makes my post-retirement life very similar to my pre-retirement life.

And also in a strange way similar to life in prison. So I’m guessing that the elderly Angola lifer from the documentary and I could sit down at that same conference table where he counseled his nephew, and despite the utter incongruity of our lives, we’d still share many values. But I’d listen more than I spoke, and I for sure wouldn’t blow him off.

And I hope when you reach FIRE that you won’t either.


  1. And let me point something out. How the hell are you gonna develop/maintain your self-discipline if you can’t muster up the willpower to make your bed in the morning and shave after a shower? Each takes only a couple of minutes, and yet they’re so important. And ladies, I understand that face-shaving isn’t your thing, but equivalents abound.
  2. She’s in the local STEM school, which keeps untraditional hours.

Author: ER Dude

Sick of your job? After a thirteen-year career, Early Retirement Dude fled corporate America for good. You can do it too! Visit or email

17 thoughts

  1. Outstanding, and a topic I don’t think I’ve seen addressed well – at least like this. Timely for me, as I’m 4 years in, and the laziness creep has grown a bit. I’ve added some new routines to keep me focused, but it’s amazing how quickly time can pass and then you wonder what you’ve done. Thanks for this, enjoy the festival and keep up the great writing.

      1. Meditation, journaling, a pretty consistent weekly exercise routine and more consistent eating times and habits. The kids’ schedules dictate some things too (mornings, sports). I’ve also been better about making the bed daily, but I think that’s a byproduct of some of these other habits. Other things seem to fall more into place as well (except shaving, I hate that). Funny thing is, some of the habits seem arbitrary, but the ritualistic nature creates more structure and makes me more productive.

  2. Dude,

    Waking up early and making your bed are signs of a disciplined life so essential to obtaining FIRE. Once FIRE is obtained, those same habits are need for a purposeful life.

    Thanks for posting.

    Semper FI,

  3. Only three months into early retirement, I haven’t yet developed a schedule/routine with any consistency but am starting to come down off the initial freedom high and realize I need to implement a bit more structure. Specifically, I need to exercise more consistently and dedicate time to doing all those chores I was putting off until retirement.

  4. Thanks for this post – I’ve been on the lookout for this type of information.
    Can you comment on other recurring activities that keep you involved socially? I think you’ve posted about being an emergency responder and your extended camping/travels.

    1. Hmm. It’s tricky to maintain an active social life in this lifestyle, or at least for me.

      I’ve had to keep switching things up. I’m not much involved in EMS anymore, and my extended trips tend to be solo, but I stay up late at night playing first-person shooters with my best friends and I’ve just started Brazilian jiu-jitsu at an academy with a family approach. Sucks that my social circles keep changing, but at least, as you say, I’m involved.

  5. Totally agree. Three years in to FI. Structure is key. I’m about like you. Productive from roughly 8 am till about 2 pm. Then do whatever–including being productive some more if I want–beyond that.

    I’m way way healthier after leaving a stressful (though rewarding) job, but also a lot more isolated.

    Keep up the writing!

    1. >I’m way way healthier after leaving a stressful (though rewarding) job, but also a lot more isolated.

      Yeah, the isolation can suck. Like I say, it’s the price of depending on your job for your social life. Golden handcuffs aren’t just made of gold.

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