Freedom May Not Be Priceless: Consider Going To Jail For Money

Since 2012, I've been arguing that freedom is priceless. After giving up a healthy income and my career for more freedom, how could it not be?

But maybe I've just been telling a lie to make myself feel better about not being richer! We lie to ourselves to help justify our decisions. Otherwise, we might feel like idiots for giving up so much.

In this article, I'd like to explore when freedom matters most. It seems all freedoms are not created equally and have different values at different ages. 

Jail Time For Money

For example, in a past newsletter I had erroneously calculated Elizabeth Holmes would only serve half her 11.25 years sentence with time off for good behavior. A part of me entertained whether I'd be willing to give up 5.625 years of my life for $4.5 billion if I could get away with what she did.

Hmmm. That's almost $1 billion per year served.

After sending out my newsletter, several of my law-enforcement readers corrected me and said there is no half time in the federal system. Instead, Holmes must serve at least 85% of her sentence, or at least 115 months in prison, before being eligible to be released on probation.

If I could get away with $4.5 billion, would I be willing to spend almost ten years in jail? Hell no! At my age, ten years may be about 25% of my remaining life. That's just way too steep a price to pay.

I know some of you would never for a millisecond think about doing something illegal and serving jail time for money. You've also never told a lie, had bad thoughts, or did something wrong in your entire life. And good for you! Your place in heaven is secure.

But for some of us, this exercise of thinking about jail time for money, may be a worthwhile exercise. People who move into the gray zone think about their downside risk. Then they rationally proceed if they believe the potential reward is greater than the potential risk.

Freedom Is Valued Differently At Different Ages

Given time is finite, the value of freedom tends to appreciate the older we get. Contrary to popular belief, there is no universal value of freedom. Let's discuss.

The Value Of Freedom From Ages 0 – 18

Freedom has the lowest value when we are kids. We listen to our parents, study hard, gain skills, and sometimes go to college. We are not free to do as we wish, especially if we are living with our parents.

But if our parents are loving and kind, that's OK! Not having freedom doesn't feel like jail because our young lives are all we know. As we grow older and interact with kids who have more freedom, we slowly begin to realize the potential of true freedom.

More freedom can also be dangerous. Without parental supervision, some kids go to the dark side. There are an endless number of temptations teenagers face, which can unduly influence them to do bad things.

Immaturity and temptation are a bad combination. Hence, you don't actually want too much freedom before you become an adult. You'd rather be nurtured by caring parents until you feel mature enough to decide between an optimal and suboptimal decision.

Given freedom is not worth much before the age of 18, I'd probably be willing to go to jail for at most a year for at least $1 million. How about you?

The Value Of Freedom In College

If you decide to go to college, the value of freedom skyrockets. Suddenly, there's no supervision, only the need to get good grades.

But maybe it's not the value of freedom that skyrockets, but the appreciation of freedom. Since we have total freedom, we tend to take our freedom for granted.

College can be a wild time of fun, growth, and enrichment. It's the juxtaposition of going from little freedom to maximum freedom that provides the most joy.

Once you experience what true freedom is, it's hard to go back. As a result, many wish they didn't have to graduate from college. Some end up taking five or six years to graduate. While others become “professional students” by pursuing their PhDs and then just hanging out after!

Entering the real world, in contrast, seems intimidating and less fun. The semester before you graduate may be the time when you really start to value your freedom the most.

There is no way I'd go to jail for money when I was in college. It was just too exhilarating a time.

Related: Achieving Financial Freedom One Income Slice At A Time

The Value Of Freedom When First Starting Work

If you're lucky, you'll land a fantastic job with a wonderful boss. Unfortunately, most people are not so lucky. Almost everyone starts at the bottom, does menial tasks, and gets paid the least amount for their first jobs.

It usually takes several job hops before you find a good fit. At the very beginning of our work careers, we will long for the freedom we had in college or before we had to make a living. Sooner or later, we stop daydreaming about better times and begin to focus on the importance of now.

During your first 10 years of work, the more motivated you are, the less you care about freedom. What you might care more about is gaining experience and making money.

As someone who didn't have any money growing up, I didn't care if I had to give up weekends for work. I'd gladly take a Sunday flight to see a client on a Monday morning. If weekend work could advance my career, I was in!

Originally, I told myself I would sacrifice most of my freedom until 2017 when I turned 40. I calculated 18 years was enough time to aggressively save and invest to be free forever.

However, at age 33, I started to despise going to work. Facing seven more years of grinding hell felt like a lifetime. So if you had offered me $3 million to serve one year in jail, I might have taken it.

Thankfully, I only had to sacrifice 13 years of freedom due to a lot of luck. When you're feeling like crap, you rationally find ways to get better!

The Value Of Freedom Once You Have Kids

If you decide to have kids, your desire for freedom will surge higher for two reasons.

Most parents love their children more than they love work. Therefore, most parents will logically desire to spend more time with their children and less time at work. I'm not talking about spending 100% of the time with your kid, as variety is needed for sanity. I'm talking about more time.

At the same time, once you have children, you lose a tremendous amount of freedom. All the time you had to hang out with your buddies, play sports, and work on your hobbies gets crunched.

Therefore, after having kids, you also value freedom more to do your own thing. There will be a constant battle between “me time” and childcare time. The struggle between career and parenthood is tough.

The first five years of a child's life is supposedly the most important for development according to every book and doctor I've ever read and spoken to. Therefore, the freedom to spend more time nurturing your child during their initial years is more valuable.

After two-and-a-half, most children are eligible to attend preschool. And usually by age five, a child can attend kindergarten full time. At this point, a parent frees up more time to pursue their careers.

The Value Of Freedom Once You Have Enough Money

Once you've achieved a minimum level of financial independence, where your passive income can cover your living expenses, the value of freedom skyrockets once more.

Since you have enough money, giving up your time to make more money becomes less appealing. Unless you're saving lives or truly doing what you love, you will no longer be willing to sacrifice time for money.

If you retired early, then only the most amazing job opportunity may cause you to consider giving up your freedom. Alternatively, you might be bored or have a toxic home life and just want to get out of the house!

Most early retirees will eventually find meaningful things to do to fill up their time. You could have the best job in the world, but if you still have to take orders and have a schedule, it just feels too jolting once you've retired.

The only job I'd take right now would be as a tennis coach to a top 50 player or as an NBA general manager. I'd love to do the job for a year and experience what it's like. If it's great, then I'd continue. If not, then I'd quit.

Related: How To Retire Early And Never Have To Work Again

The Value Of Freedom Living In America

After living abroad for 13 years and then spending another 13 years in international equities, I firmly believe we Americans take our freedom for granted. Life is too easy for most in our great country and we don't even know it!

Just look at what's going on in China. After almost three years since the pandemic began, China is STILL implementing a ZERO COVID policy. Various Chinese cities are locking down its citizens right now.

If you're rich in China, you better have a palatial compound and a VPN network to get around all the censorship. Chinese television is even blurring out the crowds at the World Cup in Qatar because they aren't wearing masks!

Even the richest Chinese don't have the freedom middle-class Americans do. Heck, even the poorest of Americans are able to roam freely without big brother getting in their way.

Is there any wonder why foreigners will continue to buy up American assets? Foreigners appreciate how good we've got it.

At least there are some wealthy Americans who know how to pretend to be middle class to fight envy. Once you know how good you got it, you tend to keep a lower profile.

No Jail Time For More Money At The Moment

The main reason why I'm unwilling to give up my freedom now is that our daughter is still only two. Given she will be our last child, we want to spend as much time with her as possible before she starts to attend school time full-time in 2025.

Time goes quicker when raising children because their physical changes and mental development are so noticeable. Yes, I will miss out on making maximum money. But I will regret missing out on more time with my kids.

Our son is 5.5 years old and in kindergarten all day. Yes, we can spend the mornings, evenings and weekends together. But it feels different compared to when we homeschooled him all day in 2020 and most of 2021.

I know Fall 2025 will arrive before we know it. As a result, the freedom I have to spend more time with our daughter is priceless. Even if you gave me $1 billion to give up one year of my life in jail, I wouldn't take it.

But if you gave me $10 billion, I'd strongly consider it!

Related posts:

The Not So Obvious Reasons Why People Want To Achieve Financial Freedom

The Minimum Amount Of Money You Need To Start Feeling Financially Free

Reasons To Strive For Financial Independence And What It Feels Like

Reader Questions About Freedom

Readers, do you think freedom is priceless? When is freedom most and least valuable to you? For older parents, how do you view freedom once your kids are adults?

For those over 60, how do you evaluate freedom? Do you ever take your freedom for granted as you become set in your ways? When does your appreciation of freedom begin to fade?

SBF finally got arrested on Dec 12, 2022. $80 million in political donations bought six weeks of freedom! He also posted $250 million bail to spend the holidays with his parents.

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About The Author

33 thoughts on “Freedom May Not Be Priceless: Consider Going To Jail For Money”

  1. I sometimes think about Hugh Hefner’s third wife, who spent 5 years in her twenties married to a guy 60 years older than her. She inherited $10 million (in real estate and other funds) at his death when she was still under the age of 30. No moral judgements here…I’m sure she did the risk/benefit analysis.

  2. I disagree with your valuation of freedom in childhood. The value of freedom from 0-18 is potentially huge! If you end up in jail in high school, that would set up an entirely different path of unintended but highly likely consequences that could negatively impact one’s entire life, eg abuse, criminal thinking, not finishing school, etc.

    Love your posts – they’ve helped me a lot!

  3. Frugal Bazooka

    I’m seeing a lot of new ads on your blog…that makes me feel like I’m in marketing purgatory which, as we all know is exactly like federal prison. It certainly inhibits my freedom to not have to click off 5 ads from weight watchers…and how did they know I was overweight in the first place???

    You’ve written a lot of great posts over the years and from what I can tell you may be the last great FIRE blogger from the glut of bloggers that existed just a few years ago. Most of them have burned out and have no passion for helping people create wealth – so kudos to you for keeping that going.

    However…(lol – you knew that was coming right?) this post is stretching the limits of ridiculous rhetorical pondering to the breaking point. The idea that a sane person would trade years or even 1 day of their life in jail for any amount of money is nonsense. I’m all for weed enhanced tangential rabbit hole dorm talk, but trying to figure out what phase of your life could be sacrificed for a billion dollars is a bridge too far, even for me – and my friends call me “The Terrible Tangentialist”.

    If you want to answer a question that is actually happening as we speak, post your theory on how many billions a billionaire should be willing to lose to be able to say crazy nonsense that completely nukes his formerly valuable brand.

    ; )

    1. I have no control over the type of ads that are served once conditions are placed. They are actually based on your search history, sites you visit, and areas of interest. It’s called “contextual ads.”

      I wish you good health.

      You may not think you don’t have a price, but you might surprise yourself! Many of us are only limited by the choices we have. Don’t take your freedom for granted.

  4. This is an interesting thought experiment. I that it is interesting to apply this income/social classes. Someone who is well off would be much less likely to accept this trade than one who isn’t. For instance, compare an MD in high finance to a hourly worker at the local Dollar General store. Compare that same MD to someone who is unhoused. Life and/or current situation can feel like a prison to some people, no way to break free or rise above what their baseline is.

    I like one your comments in here Sam saying that everyone has a price. I think that is true to the extent that the price might not be something tangible. It might not be for money, but it might be for an idea, principles, to make a change, etc.

  5. In my early twenties I’d probably spend a year in prison for a 100k. Hell, I was in and out of jail anyway. Now, in my fifties there is no amount of money I’d take to spend a year in prison.

    Thinking about this a different way though gives me a different answer. If I got into trouble and was facing a year in prison how much of my OWN money would I give up to escape going to prison? I don’t have a answer for this question but my guess is the number is far less than my net worth.

  6. Don't be a space Karen like Elon Trump

    I, for one, am glad that Holmes has been convicted and is headed for jail.

    At least this shows that no billionaire is above the law. I hope we will continue to clamp down on big tech with regulations to prevent egregious frauds like this one.


    1. I’m really glad her “sudden” and in my opinion very calculated decision to get pregnant didn’t sway the court in her favor. If anything, it should point out that she definitely has sociopathic tendencies for getting pregnant knowing she’d likely have jail time.

  7. I’m with you Sam, no amount of money could tempt me to miss any of my kids early years. The trauma of that could never be offset by financial reward.

    For those who would be tempted surely which prison is a big question, $1bn for a year in a Swedish prison doing pottery classes with a single ensuite cell is a very different kettle of fish to a year in a tough US prison banged up with psychopaths.

    Out of interest would $10bn really make you think differently to $1bn? Whats the difference in lifestyle? Surely $1bn is well into the realms of FU money, how would more money affect happiness at that level of wealth

  8. Happy to see that your priorities are in order Sam. No success in business, or public life can compensate for failure in the home. Keep up the good work and stay the course !! Freedom means many different things to different people.

    For me it always meant controlling my own destiny in my work and my business. It means always having plenty of cash on hand to handle any major crisis or emergency. Having little to no debt on major assets and keeping any credit card debt to a minimum.

    Being able to buy almost anything you want anytime you want. Being able to spend time solely with people who truly love and enjoy your company. Rarely having to worry about your wife and children because you have helped them to learn how to handle any situation in life.

    Perhaps most importantly, being at peace with your thoughts and station in life because you have made excellent choices with regard to your future and that of your family.

    In the end you ultimately want to be surrounded by those who love you, in a place you have chosen, on your own terms because no one is rich in the cemetery. This is freedom.


  9. That has to be one of the most “unique and unusual” articles I’ve ever read! But I love your outside the box thinking, along with your willingness to think about something that most of us would consider to be “unthinkable”.

    I would like to gently point out that you didn’t really take into the consideration the harm that was done to others so the individual in question could get to that level of wealth. I also think this omission was intentional and necessary to make your point, of course. On the basis of money alone, perhaps it would be worth it to go to prison, but when other factors are considered, “probably not”.

    Thanks for what you do.

    1. Oh, I have. Everybody has a price, which is one of the points of this article. So when we say, some thing is priceless, I actually now beg to differ. Because once you have the option of taking the money, suddenly, things might not be so priceless after all.

      Thanks for reading!

  10. This is an unusual article.. I think you need to make a distinction between operating in the “Grey Zone” where rules and law may not be fully established or tested versus crossing the line with willful or intentional fraud. The “Grey Zone” can be interesting especially in emerging markets or new industries… and crypto is a great example. It was and is a Wild West.

    Regarding Elizabeth Holmes and Theranos though, it was really a Medical Device company. The rules and regulations for Medical devices are well established in the US. However, they were able to exploit a weakness in the regulations specifically in lab-developed tests (LDT) which the FDA has less control over and allowed Theranos to run their “tests” through their single lab. But even so, their device and tests simply did not work and did not do what they claimed it would do and they knew this. So this was fraud. At an individual level committing fraud is never a good plan or idea, so not sure where you are going with that…

    I think the bigger question is when a Corporation decides to operate in the grey zone or knows that they may be sued or fined for a certain practice, but makes the assessment that the profit may be larger than the fees/fine and makes the business decision to continue that practice…

    1. This is consistent with past articles, like when he advised us to give false information to deceive Zillow etc. I’ve got all the evidence now to see the author has a far weaker moral compass than I’d like for my advisors.

      1. Thanks Adam. Merry Christmas to you.

        May I ask why you keep reading my site then? Feel free to share examples of your moral superiority. What are some things you are doing to help others.


      2. The Watcher

        Adam, are you the Adam Chase from Curriculum Associates who reportedly fudged your taxes and has a complaint against you by a colleague?

        You read for free. Sam doesn’t owe you anything. Go cheat on your taxes and harass your employees instead.

        You sad and pathetic man.

  11. You assume she’s still a billionaire? That was all paper wealth and private funded so private valuations. When she went under I would highly doubt she had 100 mill in cash siting liquid. The rest poof gone.

  12. Christine Minasian

    I just cannot figure out how ANYONE can blatantly LIE about such a big thing as claiming a product does something it does not, let alone knowing it would affect someone’s life!! Where is our moral compass as a basic human characteristic? I agree- we need to value our freedom here more. My husband’s grandmother escaped Armenian with nothing but a blanket.

    1. It’s one of those things where sinning is easier when the temptation is not in front of you. But if the temptation is right in front of you every day all day long, it is going to be harder to resist.

      In Elizabeth’s case, she had every single venture capitalist, throwing money at her. And she had the most powerful people on her board telling her she could do no wrong. That kind of constant messaging is hard not to believe after a while. You can make yourself believe and do anything if you got enough convincing.

      1. Christine Minasian

        That’s true! It was a self-fulfilling prophecy with all that smart money offered to her.

  13. Great post Sam! Yes, we as Americans take our freedom for granted, and it’s unfortunate. Sure we celebrate our Independence on July 4th or we thank Veterans one day a year, but in my eyes this is insignificant. I was watching scenes from the World Cup and saw many of the players completely balling their eyes out at the sound of their National Anthems. They know what ‘lack of’ freedom feels like, and the sound of their National Anthem makes them value the freedoms they do have, which are likely less than we have in the US.

  14. Great article Sam, I would definitely go to jail for a 1 year for $1 million dollars. Problem with the plan is that you can never be sure what happens in a trial. I would not go to jail for 5 years for a million dollars that is for sure. Your blog is always thought provoking and outstanding. I wish more Americans would invest and save for the future.

    American economic history is the history of bubbles and bursting bubbles. It would be better for Americans to save a large percentage of their income so that we could all take a more leisurely approach to life and our careers. Most Americans work too hard and never take time to enjoy their lives. It is sad really that people do not understand the overwhelming power of compound interest and how it can make us all rich over time.

    1. I like the honesty! Yes, compared to our friends in Europe, we Americans work way too hard. But then, compared to our friends in Asia, we might not work hard enough. So it depends on where we are in life.

      I think our children are going to have a huge amount of competition thanks to globalization. I wish them the best! But in the meantime, I am going to plan for an advance to make sure they don’t get eaten up and spit out by the system.

  15. If I was friendless with no career and no risk of stigma, I suppose maybe I would consider a white collar crime in my 20s for multi billions. But not really. There would just be too many unknowns and too much risk of screwing up my entire future.

    I can’t believe China is still zero Covid policy. And blurring out the crowds on tv who aren’t wearing masks – really?! Gosh their government controls are worse than I thought.

    I am so glad to have freedom and unfiltered content!

    1. China is incredibly backward in terms of their political rights and freedoms and that must change for them to truly become an economic and social superpower. I am always hopeful that the people of China will breakthrough the fog of lies that the leaders there have told them. China and it’s people deserve freedom and democracy that most of the world’s people now take for granted.

  16. Great article! The only logic I couldn’t follow was the last thought of 1 billion vs 10 billion. Maybe you were being a bit cheeky!

  17. Captian PJS

    HaHaHa, sadly, we all seem to have a our price. I would like to think that I don’t, I like to say that money is number three on my list.

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