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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 I 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.”

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 in high school. 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 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 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 away envy.

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.

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. 

Consider Going To Jail For Money is written by Financial Samurai for

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IRS Out For Blood More Than Doubling Penalty Interest

IRS taxes increase

In a blatant act of financial tyranny, the IRS is intensifying its assault on hardworking Americans by shamelessly jacking up the interest penalty on underpaid taxes from a pitiful 3% to an exorbitant 8%. This calculated move, recalibrated quarterly, serves as a stark reminder of the insatiable appetite of the IRS, an oppressive behemoth relentlessly extracting every last penny from citizens already shackled by burdensome taxation.

Specifically targeting non-corporate taxpayers, the IRS demands the federal short-term rate plus an additional three percentage points, a blatant money grab that directly targets struggling self-employed individuals, independent contractors, and gig economy workers. These individuals, already grappling to make ends meet, find themselves in the crosshairs of a government voraciously hungry for more of their hard-earned wages.

For those daring to resist this blatant financial coercion and falling short on their payments, brace for the punitive underpayment penalty. There’s a meager concession – if the amount due is under $1,000 after begrudgingly considering credits and other tax factors, citizens might receive a temporary reprieve from the claws of the taxman.

This audacious maneuver puts the self-employed and independent contractors in the IRS’s oppressive grip, coercing them to make quarterly estimated tax payments under the looming threat of severe financial retribution. The January 16, 2024 deadline for the fourth quarter of 2023 is fast approaching – a date that casts a dark shadow over those grappling with the suffocating weight of government overreach.

While the regular W-2 employees might momentarily sigh with relief as taxes are conveniently siphoned from each paycheck, tax experts issue a stern warning against such complacency. Joseph Doerrer, a CPA and financial planner from New Jersey, challenges individuals to scrutinize their tax situation, posing the provocative question, “Are you where you should be?” A question that echoes as a stark reminder of the government’s overreach into the pockets of hardworking Americans.

One taxpayer, Sameet Durg, found himself blindsided by an underpayment penalty reaching into the thousands – an unwelcome surprise that serves as a chilling testament to the relentless demands of the IRS. Durg, a marketing executive, now watches his finances with unwavering vigilance, refusing to endure a hefty hit come April.

As the IRS unabashedly cranks up the interest penalty, taxpayers are left grappling with the heavy-handed tactics of an agency that seems insatiable in its quest to confiscate more of their hard-earned money. This move underscores the urgent need for citizens to vehemently resist the oppressive tax regime, actively defy the IRS’s overreach, and reclaim sovereignty over their wages.

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GUILTY! Sam Bankman-Fried Faces Over 100 Years in Prison

GUILTY! Sam Bankman-Fried Faces Over 100 Years in Prison

( – Sam Bankman-Fried has been found guilty of all charges related to the collapse of his Bitcoin exchange, FTX.

“A New York jury in Manhattan federal court agreed with prosecutors that Bankman-Fried defrauded investors, customers and lenders in connection with the collapse of his crypto empire,” reported Fox Business.

“Prosecutors accused Bankman-Fried, who founded and controlled both FTX and sister hedge fund Alameda research, of misappropriating and embezzling billions of dollars in FTX customer deposits, scheming to mislead investors, and instructing other executives at his businesses to do the same,” it added.

Bankman-Fried was charged with five charges of conspiracy and two counts of wire fraud in the first two criminal trials.

The maximum sentence for each crime was 110 years in prison.

The hearing for Bankman-Fried’s sentence has been scheduled for March 28.

The Southern District of New York’s U.S. attorney, Damian Williams, commended the decision and said that Bankman-Fried “perpetrated one of the biggest financial frauds in American history.”

“The cryptocurrency industry might be new, the players like Bankman-Fried might be new,” Williams said. “But this kind of fraud, this kind of corruption, is as old as time.”

NBC News gave some background information and historical context before the decision:

“FTX and Alameda quickly collapsed in November 2022 after some of their financial liabilities were exposed.

The fact that Alameda had taken billions of dollars from FTX’s customers and that much of Alameda’s balance sheet was comprised of digital currency assets it had created was central to the case against Bankman-Fried.

Unnerved by disclosures about the firm’s financial position, many of FTX’s customers tried to get their money back. That set off the equivalent of a bank run.

The value of Alameda’s investments crashed, and FTX couldn’t return much of that money because it had been given to Alameda. Some went to the fund’s lenders, and billions were spent on sponsorships, commercials, and loans to top executives. That, too, was a major part of the case against Bankman-Fried.”

Following the collapse, more FTX and Alameda executives were prosecuted, including former CEO of Alameda Caroline Ellison, co-founder of FTX Gary Wang, and chief technology officer of FTX Nishad Singh.

All three pleaded guilty, agreed to cooperate, and testified against Bankman-Fried.

In exchange for their cooperation, they will receive less severe punishments.

In his defense, Bankman-Fried stated that he never intended to deceive anyone and that, following the failure of FTX and Alameda, the government had been searching for someone to blame.

“Mr. Bankman Fried maintains his innocence and will continue to vigorously fight the charges against him,” Mark S. Cohen, counsel to Bankman-Fried, said in response to the verdict.

Williams stated that he hoped the conviction would be an example for others.

“It’s a warning, this case, to every single fraudster out there who thinks that they’re untouchable, or that their crimes are too complex for us to catch, or that they’re too powerful for us to prosecute, or that they could try to talk their way out of it when they get caught,” Williams said. “Those folks should think again.”

Copyright 2023.

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Brutal ‘Bidenflation’ Has 1 in 6 Retirees UNRETIRING

Brutal 'Bidenflation' Has 1 in 6 Retirees UNRETIRING

( – According to an analyst, “Bidenflation” may be a long-term issue, leading one out of every six pensioners to contemplate retiring early.

It will undoubtedly persist if Biden wins re-election.

In the far-left USA Today, Patrice Onawunka laments the possibility that the “financial insecurity” brought on by inflation—which was brought on by “reckless federal spending”—will last forever.


“People have connected the dots between ill-advised government policies and harsh economic outcomes. Spending nearly $2 trillion on government transfers to almost every household during supply-chain disruptions and exacerbated labor shortages caused inflation to accelerate. Putin’s invasion of Ukraine and other production disruptions worsened it.

The Biden administration and congressional Democrats passed a climate change bill that they falsely labeled the Inflation Reduction Act in hopes of fooling Americans, especially seniors.

The bill never addressed rising food, housing, or energy prices — households’ most basic and critical needs. Any climate savings would take years to come to fruition and could be offset by new costs for families — tens of thousands of dollars — on new electric vehicles.

Meanwhile, the green subsidies cost more than three times what the law’s supporters claimed.”

What could be crueler than adopting a law that does the exact opposite and is titled the Inflation Reduction Act?

55 percent of those who have already had to un-retire claim it was because they needed more money.

The White House and corporate media continue to lie to us by promising that the inflation issue will pass quickly, yet nothing ever appears to change.

Everything’s cost is skyrocketing especially housing. Meanwhile, Joe Biden is exerting every effort to keep inflation high. The federal government spends like a drunken sailor, which cheapens money.

Even worse, Biden has permitted countless millions of illegal immigrants to enter our nation, which raises the price of housing by increasing demand for limited items like housing.

Housing is a necessity, Onwuka tells us, unlike other discretionary expenses. Rent costs in America are rising, disproportionately affecting older folks and those with low incomes, especially those on fixed budgets.

In addition, she states that “10 million households headed by people aged 65 or older spend more than a third of their income on housing, and half of these pay more than 50%.”

See what happens when you factor millions of illegal immigrants into the housing problem.

Biden punishes Americans who have lived by the book, paid their taxes, saved money, and worked hard. He is putting the interests of millions of illegal aliens—who raise demand for everything and drive up prices for everything—above the interests of those Americans.

“In a little over four years, I intend to retire. I’ll never be wealthy, but since I started my first 401K in 1994, I’ve been setting money aside for that moment. I enjoy both my job and my coworkers.”

That isn’t the problem. The dream is the problem… the desire to live out your third act with the freedom and resources to do whatever you want.

Similar actions are taken by many working Americans who save money and forgo immediate enjoyment to prepare for their elderly years. As a result, I find it difficult to understand what it must be like to enter a dream before having it destroyed.

The anguish of coming out of retirement, returning to the grind, and facing Monday mornings all over again escapes me.

The only idiots, child abusers, and masochists vote Democrat.

Copyright 2023,

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