Would You Go to Jail For a Year For a Million Dollars?

Have a GREAT imaginary proposal for y’all today ;)

I was talking to an old friend last night about all the random hustles he’s done over the years (eBay flipping, acting, design work) when out of the blue he told me he was once asked if he wanted to be a part of a heist.

“A heist??” I blurted out. “As in, robbing a bank? And get away cars and going to jail when you’re all caught??”

“Yes – that type of heist. Only it wasn’t a bank, and there’s no way we would have got caught.” – He cockily (word?) shot back.

Thankfully we’ll never know because he didn’t end up going for it, but it did lead us down that fun path of what we’d both be willing to do – and not do – in general for money. And particularly a LOT of it. This is when I put on my creative pants and asked if he’d be willing to go to jail *for an entire year* but at the end of it get rewarded with a million dollars in cold hard cash :)

His response was immediate with an “Of course!”

To which I followed with, “Um, HELL. NO.”

For one, I’d probably die on the first day out of sheer panic alone, but even if I survived and didn’t become someone’s bitch in the process (also a high level of certainty) I wouldn’t be able to leave my boys for a year and miss out on that thing called LIFE. The money could help make up for a lot of that of course, but as my wife chimed in when I presented the same question to her – “A million dollars wouldn’t change our quality of life much.”

Which is true in a weird way. If we were given a million dollars today it would literally all go into investments and not affect our lifestyle a bit. On the other hand, a large sum of money like that would shave off YEARS of work down the line, if not decades?, so technically you’d be saving a lot more time in the end when everything’s considered. And you may even be able to retire upon your release! You’d definitely be accustomed to living on less, that’s for sure! ;)

My friend, on the other hand, looked at it more like a research project and felt he was scrappy enough to make it out without a hitch. He also doesn’t have kids or a wife or anyone else to “report to” (nor even a full-time job), so in theory it wouldn’t affect anyone else but himself.

So to spice it up, I then asked if his answer would change if everyone in the jail KNEW he’d be receiving this money too? Because to me that just solidifies my answer even more because the risk levels at that point just shoot through the roof. I always assume the worst when taking on additional risk, however for my friend it only seemed to excite him more:

“I’d use it to get the biggest cell on the block, and then buy my own security while there so no one can mess with me. Everyone would love me! And it would probably only cost about $300,000, leaving me with $700k in the end. “

While he forgets the money doesn’t come until *after* he served his time, something tells me it still wouldn’t work out as smoothly.

At any rate, I couldn’t stop thinking about it all night, so I figured I’d release the question unto you and further help augment my fascination :)

So… Would you take a million bucks in return for one year of prison life? And would it change if everyone there knew you’d be getting this million upon release? For arguments sake, let’s assume a) it’s a million in cash – no strings or taxes attached, and b) you’d be sent off to a medium-secured prison. So not a minor crimes one, but also not a maximum security.

And if those questions are still too easy, try swapping in “solitary confinement” instead and see if that changes your mind :) I could probably deal with that a lot better, but how I’d be feeling upon release would be an entirely different situation, haha… You could literally go insane! And what good would a million dollars be then?

The crazy part is that thousands of people DO go to jail for a lot less money than that, and for a lot longer time than just a year too. So you can’t help but feel blessed just to have the freedom you and I already have regardless of our current financial situations!

Freedom of life trumps freedom of anything else!

PS: If you like questions like these, check out our whole “would you rather” series :)

[Photo by jariceiii]

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  1. Chris @ Flipping a Dollar February 12, 2016 at 5:40 AM

    No freaking way! Ignoring the fact that I’d be away from my family, I’d probably go nuts. Sure, I could work out and read a bunch of stuffs. Maybe get a sweet new tattoo, but to be degraded and treated like a non-human being would be so demoralizing. I’ll stick with my legitimate work for now, even though I sometimes joke that it feels like a golden prison cage. eBay changed my mind about what stuff was worth. When I first sold a few things in a month and made over $100 profit, I realized that if I did it full time, I could EASILY make more than any minimum wage job. Just blew my mind. And that’s the other thing, there’s so many avenues out there to get income now that it doesn’t make sense to try this.

    Now, if some catastrophic event hit my family, and I was all alone, would I go backpacking across the world to gain some mental clarity? Probably.

  2. Slackerjo February 12, 2016 at 5:48 AM

    Um, housing prices in Canada are So Out of Control I’d need 1.5 million (or 2.5 million if I want to live in Vancouver or Toronto after I get out). Then after my year in jail I could buy a modest house.

  3. Brian @DebtDiscipline February 12, 2016 at 5:54 AM

    What kind of jail? :) Sorry all kidding aside, no way! Having to live with the fact that you committed a crime to get this money would make me crazy. I’m with you it would be incredibly tough to be away from my family for one year. I still to building wealth with hard work.

  4. Thias @It Pays Dividends February 12, 2016 at 6:30 AM

    Not a chance – You can’t get back time but you can always get money. We never know how long we get to live so it is possible that 1 year of your life is worth way more than $1 million.

    Knowing my luck, I would piss off someone while I was in jail and then they would have someone take me out as soon as I got out!

  5. Mr. Tako @ Mr. Tako Escapes February 12, 2016 at 6:33 AM

    No way I would go for it. Butt-rape for a year just isn’t worth it.

    Once you get out, you are a convicted felon. Getting a good paying job again is probably pretty hard. With only $1m, there’s a good chance you might need to go back to work again.

    1. J. Money February 14, 2016 at 5:58 PM

      Oooh good point on the felon part… Although you can always easily explain that one *if* given the chance.

    2. Mike S February 19, 2016 at 12:43 PM

      The thing is, $1M plus what have saved would give me more than 25x my annual expenses (I assume that the $1M is after any potential taxes / illegal fees whatever).

      With an assumed 4% return on investment, that $1M would take me ~ 15 years to amass.

      So the question here is: Is one year in prison worth 15 years of work?

      If I didn’t have kids, my answer is that it probably depends on the prison. If safety and security could be guaranteed, the experience might even be an interesting exercise in stoicism. After living at a very low standard of living for a year, I bet I could learn to live a more frugal life than I currently do. I’d also probably be more willing to take risks in the future after living through a pretty bad “worst case scenario”.

      I think that the math above might refute J. Money’s argument about time. I also have young kids and trading one year of time missed time now for 15 years of more undivided time later might actually be tempting. In a way that’s what we’re all doing by working anyway. The trade off is just less extreme (and more socially acceptable).

      But, for me the answer is still no. Because even thought I think I’d be buying more time with my kids, I think I’d lose their respect. I’d also be setting a pretty terrible example to them.

      1. Mike S February 19, 2016 at 12:47 PM

        Getting ahead of myself. It’s actually 20 years, not 15. Makes prison look a bit better?

  6. whiskey February 12, 2016 at 6:53 AM

    I’d rather not spend a year in jail but if the money was enough, say 10+ mil, then yes. So what, now I’m labeled a thief. Not worried about getting a “career” when I got out. Money would be invested and with contacts made in prison, I’m sure you could turn it into more. How many of you have taken an hour at work and gotten paid for it? Hmm..
    Everyone has a price at some point…

  7. Roy Largo @ Band of Savers February 12, 2016 at 7:27 AM

    If I didn’t have my family to factor into the situation: Definitely, no doubt about it. But taking my family into consideration this is a much harder question, I would have to confer with my wife about it and see if she would agree to it but I would still be mighty tempted by the offer. This is also assuming that I don’t have to do anything illegal that would show up on my conscience or background check.

    1. J. Money February 14, 2016 at 5:58 PM

      Let me know what she thinks, and if she’s in I’ll start working on coming up w/ the cash ;)

  8. Mario February 12, 2016 at 7:34 AM

    I would say a definite no here. The end might seem worth it, but I don’t think losing a year of my life is worth it. Who knows what might happen in a year? Heck, maybe I’ll piss off the wrong people in prison and protection won’t matter. A million bucks is enticing but if you’re going to give up a life in prison, might as well just take a risky chance instead. Try it for a year, and see how that goes.

  9. Kalie @ Pretend to Be Poor February 12, 2016 at 7:40 AM

    I am so not cut out for jail! As I kid one of my worst fears was accidentally doing something wrong and having to go there. Yeah, if you want money for the purpose of freedom rather than consumerism, you probably wouldn’t want to give up your freedom for a year of lockdown. Your zany questions are very fun!

  10. COD February 12, 2016 at 7:51 AM

    If it was guaranteed to to be rich white guy country club jail I might consider it. Military personnel go away from their families for a year at a time for far, far less.

    1. Jack February 12, 2016 at 12:10 PM

      I had the same thought – our military serves stints in very rough, very dangerous conditions for longer, for much less.

      If it weren’t prison, but just “you’re going to be away from your family, friends, life” for a year, that changes the question dramatically. Prison risks aside, I’d not give up a year with my family just for money. Money comes and goes, but family is forever, and I value my family more than anything.

  11. Dee @ Color Me Frugal February 12, 2016 at 8:01 AM

    Not a chance. I don’t even exceed the speed limit, so committing crimes is pretty far out of my comfort zone! A million dollars seems like an awfully small sum to live with that on your conscience for the rest of your life. And we would also invest 100% of it, so it really wouldn’t change our lives at all either. Great food for thought, though!!

    1. J. Money February 14, 2016 at 6:01 PM

      It shouldn’t mess with your conscious much cuz you’re not committing a crime to go in there, more of a dare or challenge :) Not that that would probably change your mind much…

  12. Catina Marie February 12, 2016 at 8:27 AM

    Helllzzzzz no!
    Maybe my answer would have been different when I was in my 20’s and thought I was so bad ass. The 42 year old me knows better…I’d be like “MOMMY!”. LOLZZZZ

  13. Lisa O February 12, 2016 at 8:54 AM

    Not this chick! I cannot image being told what to do and when to do it for 365 days.

    I would rather live my budget life….hoping, dreaming and living free!

  14. Ann February 12, 2016 at 8:54 AM

    Put on your Martha Stewart hat (she was in prison a while ago) and grab your Andy Dufresne money knowledge, that place may be a lot better than you think. There’d be a big personal finance library, tax filing parties,….(Been a while since I’ve seen The Shawshank Redemption. Other things Andy did are escaping me right now.)

    Maybe they’d let you out on good behavior. It says you go to jail for a year, but doesn’t say anything about needing to stay if they release you for good behavior. ;)

    1. J. Money February 14, 2016 at 6:02 PM

      True! Although it also doesn’t say anything about *causing trouble* in there and getting an extension! What if it changes you and you snap one day and now get committed to life – ack!

  15. Laura February 12, 2016 at 9:39 AM

    At this stage of my life (retired early, home owned free and clear, money safely invested in reliable income streams) there is very, very little I’d consider doing for any amount of money. As you noted, it would have very little impact on my life. Definitely more spendable cash because I’d invest in tax free bonds, but even a million wouldn’t create such a hefty income stream that I’d make any major changes to my day to day life. I actually enjoy being frugal (go figure), and I need and like the discipline of a budget (it really is sexy), so I guess the million would basically create a more substantial inheritance for our children and grandchildren, which while nice, wouldn’t come close to being worth trading a year of my life in prison! Even ten million, or a hundred million, wouldn’t do that. Maybe if I were younger, or single, or childless, or broke, or homeless, or all of the above I’d consider it (but I doubt it). Money is not more important than freedom, and that’s why I retired early in the first place! If I thought answering to someone else ten or twelve hours a day was bad, how well would I do in shackles 24/7? No amount of money is worth that to me, but thank you for putting the proposal out there! I’ll look at my independence differently today. It’s great to gain some perspective every now and then.

  16. Jason B February 12, 2016 at 9:47 AM

    There is no way in hell that I’d spend a year in jail for a million bucks. I like women too much. I also like my freedom.

    1. J. Money February 14, 2016 at 6:09 PM

      HAH! Totally forgot about the sex part – d’oh.

  17. Laura February 12, 2016 at 9:48 AM

    I’m 25 and single, and I’m very tempted to take the money (and jail time). I’d have to keep working after I got out of jail, but as long as I didn’t touch that million, I probably wouldn’t have to worry about retirement savings any more — I could spend my money on experiences instead. Very, very tempting. The main thing that makes me reluctant is that I’d be missing out on everyone else’s life experience, e.g. my friends would be getting married while I was in jail and so forth.

    1. Cait Flanders February 13, 2016 at 12:13 AM

      I’m with Laura. I think I’d do it. (Didn’t see that one coming, J, did you? haha.) I think I could handle it and hold my own. Wow. That’s really weird to say out loud, haha.

      1. J. Money February 14, 2016 at 6:12 PM

        What??? YOU?? The sweetest person in the world?? You’d survive if they all died from your cuteness!

  18. Kyle February 12, 2016 at 9:50 AM

    Hmm I’m not sure what I would do. A million would be more than I need to retire, but my mental health is already on shaky ground, and I do have a few chronic illnesses. Prisons have been known to deny appropriate medical care, so it would be pretty miserable for me. I’d have to figure out how to launder that money too, it’s hard to pay rent with cash nowadays, and you can’t exactly just deposit it into your checking account, haha. Tricky! Not sure what I would do, but this was a good thought experiment!

  19. The Money Babe February 12, 2016 at 10:00 AM

    I would never do that. I’m so scared of prisons. I can’t even visit a prison because I’m scared they’d lock me up just for being scared! I seriously can’t even watch Orange is the New Black because I’m so scared. It’s not a good place. I need to be around people who aren’t criminals.

    1. J. Money February 14, 2016 at 6:17 PM

      Haha… such a great show though!

  20. RMF325 February 12, 2016 at 10:08 AM

    No, no, no, no. I’m female and child-free, but I’d still never consider it. Even the sort of place Martha Stewart ended up would be too horrible to consider.

  21. PhysicianOnFIRE February 12, 2016 at 10:33 AM

    Interesting proposition. I would say NO today, but I might have answered differently 20 years ago. I’ve got better ways to make that million, which would be closer to $500K to $600K after taxes.

    An entrepreneurial way to look at this would be to go all in for the year in jail, get to know your inmates and the ways of prison life well, document the experience, and write a book about it afterwards. Publicly donate the million to charity, talk about it on the Today Show, and make several million from the book and public appearances.

    1. J. Money February 14, 2016 at 6:19 PM

      BOOM! Like the way you think, sir!

  22. Abigail February 12, 2016 at 10:39 AM

    Nope! With my health problems, prison would be especially bad. Tim needs a bunch of help he couldn’t get without me around. Also, a million wouldn’t go all that far if I can’t get a job afterward! Especially since Tim can’t work. At best, we’d break even after about 10 years. And then what?!

  23. Matty B February 12, 2016 at 10:47 AM

    Too pretty for jail. But maybe if it was in Sweden or someplace like that… their jails are nicer than most of my apartments!

  24. maria@moneyprinciple February 12, 2016 at 11:08 AM

    J., I won’t accept to go to jail for a year for ONLY million dollars (everyone has their price and mine is a bit higher than that). I certainly won’t go to jail if everyone knew I’m there for the money – I reckon being seen as a fraud in jail is not the thing to happen and I may be paying with my life for this money.

  25. Jeffrey Kelly February 12, 2016 at 11:23 AM

    Yes if I can have it before I go in and have time to invest it. That way after a year with all the dividends getting reinvested it would be worth a lot more than a million. But only for a year when the stock market is going up not down.

  26. kg February 12, 2016 at 11:44 AM

    No. Freedom to do what I want and to be with family and friends is more important. Besides in this day and age if you have marketable skills and/or are a good entrepreneur you can probably earn that over a lifetime of work.

  27. BeachMama February 12, 2016 at 11:53 AM

    I actually had to spend some time in the city jail earlier this week – I wasn’t incarcerated, it was work related, I swear! The inmates were on lock-down while I worked in their indoor common areas. It was really creepy to see all these faces staring at me though the tiny little windows in their cell doors. I worked in the both the women’s and men’s areas – the women stayed at their windows and stared much longer than the men! I can’t imagine having to be there for an extended period of time – no thanks!!

    1. J. Money February 14, 2016 at 6:24 PM

      Ahhh!!! So fascinating!!! I hope you blog about all that craziness on your own site!

  28. Broke Millennial February 12, 2016 at 12:08 PM

    Valuing a full year of my life (which who knows how long it will even be) at only a million dollars seems like a really bad valuation. Perhaps Mr. Wonderful would disagree. Now a billion — eh, if it’s a Martha Steward style jail block, we might be able to do business. Plus, I could totally leverage that into a reality TV shows/book deal/money making machine afterwards.

  29. Michelle February 12, 2016 at 12:13 PM

    If everyone at the jail knew that you would be getting a million dollars, I think that would make for a very unpleasant stay HAHA

  30. Crystal February 12, 2016 at 12:27 PM

    Yes, I’d do it for a no strings attached million. But no, I wouldn’t do it if I had to keep it a secret forever…hard to launder and invest a million bucks if you don’t know the right people, which I don’t. And definitely not if everyone in jail knew I was getting it at the end of the year. People are jealous buttheads in general…no need to deal with jealousy from your prison mates.

  31. Crystal February 12, 2016 at 12:31 PM

    Oh, and definitely not in solitary. I’d be bonkers after a day. My husband says it would be different for a guy, he might consider it if it was solitary, but not a regular, medium security prison…he’s pretty sure he’d be someone’s bitch way too fast.

  32. Alyssa February 12, 2016 at 12:35 PM

    Hahahaha, no.


    I’m a huge baby.

  33. Yetisaurus February 12, 2016 at 12:44 PM

    OMG — J. Money, here’s your million dollar idea! Pitch this as a reality TV show to the networks! Some crazy so-and-so (ahem, your friend) could volunteer to serve a year in prison in exchange for $1 million, but he only gets the money if he lasts the whole time. He might get a lesser amount ($50,000 per month) if he taps out early. They could put hidden cameras in the guy’s cell, and we could watch him suffer through his prison sentence, including negotiating deals for his safety. What do you think? You know Fox would pick it up and run with it.

    1. Hannah February 12, 2016 at 12:59 PM

      I would for sure watch that… once it came out on Netflix, and if somebody reminded me (and also if there aren’t any new Marvel shows that I like more). So, it sounds like a strong pitch.

      1. J. Money February 14, 2016 at 6:30 PM

        Writing up the pitch now! :)

  34. Brittney @ Britt & the Benjamins February 12, 2016 at 12:46 PM

    No way. Give me 10 million, though, and it’s a whole different ball game. Is this negotiable? ;)

    1. rdherself February 13, 2016 at 9:02 PM

      There was a reality show called “Take the Money & Run” which involved a briefcase of $100,000 and an hour to hide it, followed by 2 days of interrogation and lockup. If the case stayed hidden the team kept the money. It was pretty interesting to see how people cracked under incarceration even though they had signed up for it and hadn’t done anything wrong! I guess it wasn’t popular but I thought it was interesting.


      1. J. Money February 14, 2016 at 6:31 PM

        Yeah! I remember that show! There were so many teases with it but I never got to actually watch any of them… I guess it went off air before I was able to :(

  35. Michelle February 12, 2016 at 12:55 PM

    That would be a whole lotta HELL NO! There is no way I’d go to jail for any sum of money. But then again, it begs the question, would you go to jail for a cause you believe in? Maybe fighting for financial education or financial freedom?

    1. J. Money February 14, 2016 at 6:32 PM

      Hah! I don’t like financial education that much :)

  36. Chuck February 12, 2016 at 1:01 PM

    Absolutely would for the year. That million would put us over the top to check out.
    I’d reconsider your statement about solitary though. I got put in solitary while at bootcamp. (Total, typical, misunderstanding. Honest.). spent Friday afternoon through Monday morning. (For some reason the guard really didn’t believe that it was a mistake until Monday Morning and they were like “why is he here?”)
    I’ll tell you – solitary will drive a person insane, quick. No way. I don’t believe anyone should be confined to it. Ever.

    1. J. Money February 14, 2016 at 6:33 PM

      Oh man, that’s crazy! And that was “only” a weekend!

  37. Stockbeard February 12, 2016 at 2:16 PM

    So… Would you take a million bucks in return for one year of prison life?

    –> Yes.
    I spend 12hours a day on “work related” things (commute, etc…). I’ve been disliking my job for about a year and a half now, and I’ll keep having to dislike it for a good two more years.
    All things considered, I’ll have spent the equivalent of 2 full years of my life in a Job I really don’t like. I can see myself exchanging that for a year in prison, I don’t feel I would “lose” that much more bonding opportunity with my kids. It’s one full year, but it’s not 4 years of semi-pain with a bad 9 to 5.

    A million dollars *is* a life changing amount. Considering that the max “happiness” level is reached out at an income of $75’000 a year, a million invested correctly puts you half way there. I’m sure for many readers of this blog who already have investments, 1 millions would push them through the finish line (Interestingly, I’ve discussed a similar topic with friends, although it was about winning the lottery, a much more typical discussion but with interesting outcomes: http://howtoretireearly.net/youll-never-get-a-better-return-than-1-5-if-you-keep-doing-things-this-way/ ).

    As such, for many readers of the blog, the question can be read as “would you spend 1 year in jail in exchange for financial independence?”

    And would it change if everyone there knew you’d be getting this million upon release?
    –> Yes. This would add significant risk and I would not take that risk. If the question is, “would you leave with a significant risk of dying for 365 days in exchange for 1 million”, then my answer would be no.

    1. J. Money February 14, 2016 at 6:37 PM

      Financial Independence def. makes it more enticing… I’d still opt out just cuz I don’t think i could last safety-wise, but if that part was a guarantee somehow I’d probably take it. I can last a long time doing boring/stupid stuff, but safety comes first!

  38. Joe February 12, 2016 at 3:02 PM

    I guess it depends on what kind of jail. I might consider a minimum security white collar prison when I was young and single. Now, there is no way I would lose my freedom for a year for a million bucks. It would cause a ton of problem with my family. It’s not worth it especially when we’re already pretty comfortable.

  39. Tonya@Budget and the Beach February 12, 2016 at 3:10 PM

    I’ve watched Orange is the new Black so no way!!! I’d rather live poor(er) and free! Funny the first thing I thought too is I’d end up someone’s bitch. I hate fighting so I’d cave in about 3 seconds!

  40. Latoya @ Femme Frugality February 12, 2016 at 3:40 PM

    Honestly, I can’t see how that would work out in anyone’s best interest. People usually seek extra money for freedom. Giving up freedom in exchange for cash…nope, that doesn’t sound good at all.

  41. BeSmartRich February 12, 2016 at 5:37 PM

    No way that I will be going to jail for a million dollar. Make it two then I may consider. What’s prison life like?

  42. Harmony @ CreatingMyKaleidoscope February 12, 2016 at 6:03 PM

    I started watching a few episodes of OITNB here and there, and found myself wondering about whether there were any side hustles you could do from prison.

    I wouldn’t be able to handle being away from my hubby and kids. If it were just me, with a ton of debt that was holding me back . . . the answer would still probably be no, but I’d think about it a little longer.

    1. J. Money February 14, 2016 at 6:38 PM

      TONS of hustles in jail! And most probably illegal! :)

    1. J. Money February 14, 2016 at 6:40 PM

      HAH! Awesome!!! You’re welcome back anytime, teacher friend :)

  43. Elizabeth February 13, 2016 at 12:33 PM

    What an interesting question! I think the answer depends largely on your stage of life. And maybe your gender and physical characteristics come into play. I’m a female and the idea of women’s prison doesn’t really scare me that much, but if I were a guy – especially a smaller guy, or part a certain ethnic group or religion that might be viewed as weak in that particular jail system – I might feel much differently.

    I think along the lines of your friends that it would be a fascinating research project. I’d probably plan to write a book on my experience and make it into an actual research project!

    However I’m 2 years into marriage and 32 years old, i.e. squarely inside the window of my child-bearing opportunity for this life. Going to prison NOW for a year might just be long enough to disrupt my relationship or possibly even dwindle my fertility to the point that I miss the chance to have kids. A year in jail might be worth $1M but it’s not worth losing the opportunity to create a family…but on the other hand I’m not even sure if I want kids, and $1M would be a lot of money I could use to take a few years off to have some babies guilt free! Plus the royalties from my “year in prison” book and I might just be set for life. :)

    1. J. Money February 14, 2016 at 6:41 PM

      I’ll let you know if Netflix buys the idea from me ;)

  44. Pengepungeren February 13, 2016 at 3:07 PM

    Well, a million bucks is a lot of money.

    I couldn’t do it if I had to commit an immoral crime. But if it was an open prison and I didn’t have to steal or hurt someone, I’d probably do it after conferring with my wife.

    It would be an interesting experience.

  45. Jayson @ Monster Piggy Bank February 14, 2016 at 3:14 AM

    It depends on the jail. But, most likely, I would never take this challenge as I have a great year not to waste. :D

  46. No Nonsense Landlord February 14, 2016 at 10:58 AM

    I went in the military for a LOT less than $1M, and it was 4 years! lol

    For one year, I just might do it. It’s not a bad gig for a single year. Especially if it’s a county jail, or a federal prison.

    1. J. Money February 14, 2016 at 6:41 PM

      And depending where you served it could be just as dangerous, if not more, too!

  47. Investment Hunting February 14, 2016 at 9:33 PM

    Sign me up, I’ll go to jail for a year if I am guaranteed $1 million dollars.

  48. superbien February 15, 2016 at 10:39 AM

    I have a friend who is into criminal ‘justice’ reform, so she shares a lot about how awful our American prison system is, so I find this question baffling in the extreme.

    Prison is awful – victimization by other prisoners, guards, the whole system. People actually, inexplicably, joke about being raped in prison as if it’s a natural and unpreventable feature of society punishing crimes – really??

    Then there’s how utterly stigmatized felons are – good luck *ever* getting a good job.

    $1 million is just not enough for that to be worth it.

    $1 billion though? Hmm, maybe I could brush up on my krav maga :)

    1. J. Money February 23, 2016 at 3:10 PM

      Just had to google what that is – sign me up too! I could use some self-defense skills up in here (I don’t think crying and running away fast really counts?)

      1. superbien March 3, 2016 at 12:32 PM

        Oh, yeah, if you’ll only do one martial art ever, make it krav maga, the Israeli martial art (actually, the founder Imi Lichtenfeld developed it in Eastern Europe, against anti-Semitic gangs trolling the Jewish quarters to beat or murder Jews, but he fled the Nazis to Israel and taught it in what became the military).

        Why do I love krav maga? First, no silly uniforms or belts to buy. Second, no bowing or elaborate choreographed routines that teach only in abstractions. Third, the people tend to be really high quality — my experience has been that krav students tend to be *serious*, but that even though it’s largely guy students, they don’t seem to be d*cks to women (which, as the chick who likes a lot of ‘dude’ activities, can be super rare). Fourth, krav helps you develop the situational awareness that makes it so you hopefully never have to fight. Fifth, krav is defensive – never ever start the fight, but by darn finish it however necessary, at least enough so you can run away safely.

        1. J. Money March 3, 2016 at 2:33 PM

          That is so interesting! Had never heard of that style before but sounds pretty incredible (and empowering). Thx for sharing the wealth :)

  49. Gerald February 15, 2016 at 11:27 PM

    Hey J$,
    I mentioned you in one of my blog posts. While all of us could use $1mil, I agree that it would not change many people’s lives. Pay some bills, drop it in your 401K, not going to change your life significantly.
    The bigger question is whether you would want someone to hand you $1mil or whether you would like to teach yourself how to make $1mil.
    You see, you can choose to believe in the lottery (someone handing you cash) or you can choose to believe in yourself.
    In my blog post, I brought it all back to fitness. We all get into bad habits. I know if my fitness gets off track, I know how to lose that last 10 pounds. I believe in my ability to reach my fitness goals
    The same can be said of our businesses. If you know how to make money, if you have systems in place, if you choose to believe in yourself, you can make your own money.
    Now, I have not made a dime with my business – yet. But I am learning all of the steps I need to make a great living from my solo-preneur business. It is taking time (it might take a year!) and I will be able to make money (and I’m sure lose money) over and over again.

    1. J. Money February 23, 2016 at 3:12 PM

      YES! My wife laughs at me whenever I mention that I wouldn’t be too upset losing the lottery cuz it would be MUCH more gratifying earning the money more myself, but of course if you already have the systems in place and you DO come across large amounts of money, even better :) I don’t think I’d keep any of my street cred if my net worth jumped by millions because i won the lottery though haha… i’d be shunned in the personal finance world!

  50. Mortimer February 23, 2016 at 12:20 AM

    I’m with you J$. Money is for freedom. A year is so much time, especially when you have young kids. I guess a bundle of cash at the end would be tempting, but what a crap way to get it. Not through your own ingenuity or hard work, but more as a lucky payoff. Reminds me of lottery winnings. Too much potential damage to the family, not nearly enough reward.

  51. just a thought March 18, 2016 at 10:31 AM

    Minimum security, midwest prison…happily! Hell, I would do it for 500k, shoot the more I think about it, 250k tax free would be fine.

    A friend of mine was a prison guard for a few years, aside from going home to sleep, he was basically in prison for about 35k a year for 10hrs a day.

    1. J. Money August 22, 2019 at 1:40 PM


  52. Mark August 22, 2019 at 1:32 PM

    Hell yeah I would go to jail for a year for million no way I would turn down that I could do it setting on the toilet wish it was true because I would in a heartbeat

    1. J. Money August 22, 2019 at 1:40 PM

      You’re braver than I!