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?

For more nuanced personal finance content, join 55,000+ others and sign up for the free Financial Samurai newsletter and posts via e-mail. Financial Samurai is one of the largest independently-owned personal finance sites that started in 2009.