Sin—actions deemed morally wrong or harmful—can be difficult to resist, especially when money is involved. A hefty paycheck or a prestigious title can make it easier to overlook the potential harm our work may cause society. Moreover, unless you’re working for free, there’s often a moral trade-off involved—someone or something usually has to bear a cost for you to prosper.
The debate between wealth and morality is deeply personal. We are all sinners in some way. Some people are more sensitive than others to what constitutes “the right way of making money.” That’s what makes this discussion so fascinating—it’s not one-size-fits-all.
This isn’t a post about determining who holds the moral high ground. After all, we live in a capitalist society that prizes profits and wealth. Capitalism is part of what makes America exceptional, gradually raising the standard of living for its citizens.
Instead, this post is for those who feel conflicted about building wealth from a product or service they believe doesn’t offer a positive net benefit to society. I want to help those wrestling with this dilemma find clarity and resolution, having experienced similar conflicts myself before making a change.
Dissatisfaction With Work Is Common
Work dissatisfaction is a widespread experience. Whether it’s due to unfulfilling tasks, limited growth opportunities, challenging colleagues, or misaligned values, many professionals find themselves asking: Is this all there is?
Often, dissatisfaction stems from a disconnect between what we want from our careers—purpose, recognition, or flexibility—and what our jobs actually offer. Long hours and insufficient work-life balance only make matters worse.
Perhaps the largest factor of work dissatisfaction is a lack of belief in a company’s product or mission. This dissonance triggers an internal morality clock that becomes harder to silence over time. Yet, the pursuit of wealth and status keeps many tethered to roles devoid of deeper meaning.
While playing pickleball, I met a college graduate who didn’t pursue her dream of working at a nonprofit addressing child malnutrition. When I asked why, she replied:
“Google came on campus recruiting, and I couldn’t say no. Everyone wanted to work there, but most couldn’t even get an interview. I felt foolish not to accept their offer.”
After our game, she admitted, “I don’t want to work at Google forever. I just want to make enough so I can leave. Maybe I should start planning my escape now? Let’s run it back.”
Her story highlights the societal pressure to “make it big” at the expense of pursuing something meaningful. It’s a struggle many of us face—balancing financial security with the desire to make a positive impact. Sadly, some never quit chasing the money.
When Building Wealth Started Feeling Empty In Finance
When I landed a banking job in 1999, I was thrilled. It was the only offer I received after graduating from William & Mary, and I was eager to work in a field I was passionate about: investing in the stock market. For a while, as a middle class kid with no money, it felt like a dream come true.
But the global financial crisis of 2008-2009 changed everything. Watching the industry be vilified—and rightfully so in many cases—made me question my purpose. My role in International Equities wasn’t connected to mortgages, but the entire financial sector was painted with the same brush. I was guilty for the collapse of the housing market by association.
Roughly 10 million U.S. homes were lost to foreclosure, short sales, or deed-in-lieu arrangements over a six-year period around the crisis. It no longer felt fulfilling to help institutional clients outperform or Asian companies raise capital to go public when so many families were suffering.
Burned out after a decade, I devised a way to leave the industry, negotiating a severance package in 2012. Since then, I’ve been helping others achieve financial freedom—which has felt like a far more meaningful endeavor. Though I left the pursuit of getting rich in finance, I feel my soul is richer for the pivot.
The Risk Of Sinning For Too Long
Unless we’re talking education or social work, I’m not sure if any industry is free from sin. The tragic assassination of UnitedHealthcare executive Brian Thompson on December 4, 2024, brought these thoughts to the forefront.
Thompson, who reportedly earned tens of millions during his tenure, was killed by a masked gunman using bullets engraved with words like “deny,” “defend,” and “depose.” The attack echoed grievances outlined in the book Delay, Deny, Defend: Why Insurance Companies Don’t Pay Claims and What You Can Do About It.
While violence is never the answer, it’s clear this incident stems from widespread frustration with the U.S. healthcare system. Given health care is so expensive in America, we need healthcare insurance to protect ourselves from medical catastrophe and potentially bankruptcy. But at what cost? And how much are the healthcare insurance companies part of the problem?
As a UnitedHealthcare customer at least since 2012, paying $2,500/month for an unsubsidized Silver plan, I’ve had my share of aggravations—fighting denied claims despite exorbitant premiums. For example, it took my wife 11 months of unnecessary stress to resolve issues with our daughter's surprise $3,500+ ambulance bills.
Healthcare industry executives understand that denying more claims often leads to higher company profits—and by extension, higher personal compensation. While checks and balances are essential, the question remains: where do we draw the line between profit and patient care?
Every Industry Can Be Considered A Sin Industry If Money Is Involved
Perhaps you work in an industry that feels inherently unethical and find yourself unfulfilled or conflicted, as I once did. Or maybe you wrestle with whether your company’s impact on society leans more toward harm than good.
As I reflected on various industries, including my own, I realized that almost every industry could fall somewhere on the “sin spectrum” when money is involved. At the same time, every industry can also argue they are doing good for humanity. Here are some examples along that spectrum:
Social Media Companies
While these platforms connect people, their primary way to earn profits is to hook users and sell more ads. Unfortunately, this business model has contributed significantly to the adolescent mental health crisis, with social media addiction often linked to anxiety, depression, and self-esteem issues. The “Wait Until 8th Grade” is a great movement to encourage parents to hold-off on giving their children mobile phones until later.
Buy-Now-Pay-Later Companies
These companies thrive on helping people buy things they can't comfortably afford. While convenient to meet instant gratification desires, this model often encourages unsustainable debt, leading to financial stress and hardship.
Credit Card Companies
Credit cards offer convenience, rewards, and 30-day interest-free loans. However, they also charge sky-high interest rates and rely on a percentage of users failing to pay their balances in full, creating a cycle of debt that may be hard to get out.
Cigarette and Vaping Companies
Smoking might calm the nerves temporarily, but it comes at a steep cost—causing cancer and significantly reducing life expectancy.
Processed Food Companies
Processed foods are often more affordable and accessible, helping to feed more people. However, the excessive use of additives and sugars is contributing to widespread health issues, placing a significant burden on the healthcare system.
Gambling Companies
While gambling in moderation can be entertaining, it can be highly addictive and lead to financial pain. I once played poker for 10 hours straight, only to be nudged awake by the pit boss at 4 a.m. when it was my turn to bet—not good! With the rise of legal sports betting, many gamblers are likely to face even greater financial risks.
Drug Companies
Developing a successful drug requires significant investment and risk, often spanning years of research and trials. Company's should be compensated. However, once a drug is developed, setting prices so high that they deny access to life-saving treatments or critical care feels unethical. Balancing innovation with affordability is a moral challenge.
Elite Universities
Educating young adults to become righteous, contributing members of society is commendable. But if elite universities truly aim to serve society, why not significantly increase the number of spots available? Additionally, prioritizing wealthy applicants through much higher acceptance rates feels unnecessary when endowments are already immense. True impact lies in expanding access and equity.
Criminal Defense Lawyers
Criminal defense lawyers have a professional and ethical obligation to ensure every individual receives a fair trial, regardless of guilt. This duty upholds the presumption of innocence, a cornerstone of the justice system. However, knowing a client is guilty—especially of a heinous crime—must be an incredibly uncomfortable reality, and winning such a case likely can't feel good.
If you feel stuck in an industry that conflicts with your values, it might be time to explore alternatives. Wealth isn’t just about money; it’s also about peace of mind and knowing your work positively impacts the world.
How To Reconcile Getting Rich Off Of Sin
As I mentioned earlier, how you feel about work will naturally tell you if you're in the wrong place. If you start feeling guilty about the money you're earning, hesitant to share where you work when others ask, or ashamed of the lifestyle your job supports, these are clear signs it’s time to make a change. Here are some steps to help you take action and heal your soul.
1) Work for sin until you reach the minimum investment threshold
If you are not already rich, then you must take work wherever you can get it. So long as your work is legal, then you should feel good enough knowing that you are getting paid for your valuable time. If your work wasn't valuable, you wouldn't have been hired or wouldn't still have a job.
Ultimately, however, you must break free from the job that is sucking your soul if you don't believe in its product or its mission. To do so, you need to save and invest aggressively to the point where you reach the Minimum Investment Threshold where money and status are no longer the focal point.
The minimum investment threshold where work starts to become optional is calculated by taking the inverse of the historical return of the asset class you want to own for retirement and multiplying it by your gross annual income. The formula visually looks like this below.
For instance, suppose you work at an “average sin company” and earn $100,000 annually. If the S&P 500 is your go-to investment, you might need to build a $1 million portfolio before being able to walk away for good.
However, if you're employed by a “highly sinful company” and feel drained every day, aim for a smaller target so you can leave sooner. Your goal could be as simple as covering your minimum fixed annual expenses divided by a safe investment rate of return. For example, if you can live on $20,000 a year, divide $20,000 by 5%-6%, resulting in a target of $333,000–$400,000.
Once you've got these investment amounts saved, it's time to leave your job and nurture your soul.
2) Negotiate a Severance Package for Greater Financial Security
Leaving a lucrative job is incredibly difficult, even if the work feels soul-crushing or harmful to others. However, for the sake of your well-being, it’s crucial to move on—and negotiating a severance package can be the catalyst to doing so. It absolutely was for my wife and me.
By proposing a separation agreement where you stay on temporarily to help find and train your replacement, you create a win-win scenario. This ensures a smooth transition for the company while giving you a financial runway to pursue something more fulfilling.
Many companies are open to paying severance to both top-performing and average employees if it helps avoid reputational damage and maintains business continuity. Plus, since you’re leaving the industry rather than joining a competitor, your chances of securing a package increase even further.
A severance package can eliminate the financial excuse for staying in a role you dread. Coupled with your pre-existing savings or Minimum Investment Threshold, a severance package becomes the ultimate catalyst for leaving a harmful industry behind and embracing a better future.
3) Make Up For Your Past Misdeeds Or Wasted Time
The level of harm your firm caused and how many years you spent supporting it will help determine what type of new role you should pursue and for how long. It's ultimately up to you to decide what feels right.
One simple guideline is to spend an equal amount of time working in a more ethical, socially responsible industry as you did in the “sin industry.” For instance, if you spent 15 years selling sugary drinks and cereals to children, consider getting certified to become a grade school teacher or personal trainer.
If you spent 10 years denying insurance claims to families in need, consider spending 10 years at a place like St. Jude Children's Research Hospital in any capacity. Families never receive a bill for treatment, travel, housing or food. If you spent five years getting customers hooked on online sports gambling, dedicate five years to working with Gamblers Anonymous to help others regain control of their lives and overcome their addiction.
Matching the time spent helping others to the time spent contributing to harm can significantly heal your soul and reduce any lingering guilt. After spending 15 years writing on Financial Samurai without a paywall, my 13 years in international finance now almost feels like another life.
4) Donate your time and money or create a platform to counteract the harm you helped create
Finally, you can take it a step further by donating your time and money to help reverse some of the harm you contributed to. The more guilty you feel, the more money in time you should donate.
Additionally, creating a platform to spread awareness and prevent others from falling victim to the same issues can be powerful. Just make sure your thoughts and actions remain consistent.
For example, the 1997 Asian Financial Crisis had a profound impact on me while I was in college. It highlighted the dangers of excessive debt, and as a result, I've become cautious about endorsing credit cards on Financial Samurai, fearing that some may not use them responsibly. One or two rewards credit cards is all you need.
My experience in the finance industry during the housing crash led me to create the 30/30/3 home buying rule. It felt horrible to see what so many people were going through, including ourselves, after taking on a huge mortgage in 2005 and another in 2007. This rule has helped protect thousands of homebuyers from overextending themselves and experiencing unnecessary financial strain.
5) Sell sin stocks and investment as responsibly as possible
If you’re looking to align your investments with your values, consider divesting from sin stocks as a step toward financial “repentance.” Holding onto such investments while opposing their ethics is akin to a vegan wearing leather shoes.
The S&P 500 may no longer align with your principles if it includes companies you oppose. In this case, you can build a custom portfolio featuring only companies that meet your criteria or opt for Direct Indexing. This service allows wealth managers to construct a personalized index tailored to your parameters.
Although achieving a 100% sin-free portfolio is challenging, taking these steps will bring you closer to aligning your financial goals with your values.
Get Rich Enough To Walk Away From An Uncomfortable Job
The wealth-versus-morality dilemma has no easy answers. Each of us has unique preferences for how much money we desire and varying thresholds for how much of our soul we're willing to sacrifice to achieve it.
Some of us couldn’t care less and happily use our sin money to buy mansions and luxury cars for all to see—stealth wealth be damned! Meanwhile, others stay so low-key and frugal that they might start questioning why they work for sin money if they’re not going to spend it.
Telling someone to focus solely on doing something meaningful for society is a luxury belief. In reality, we must strike a balance between earning enough to care for our families and pursuing work that feels fulfilling.
For many of us personal finance enthusiasts, there’s hope. After diligently saving and investing for 10–20 years, I'm confident most of us can build a financial foundation strong enough to make a career shift if our current work no longer aligns with our values.
Readers, do you think one of the main reasons for dissatisfaction at work is because employees deep down know their companies aren't doing much good for the world? How do you reconcile getting rich off a “sin” industry? If you’ve left one, how did you make the transition, and what are you doing now? How do you feel about the work you are doing now?
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Love the newsletter. And your insights are always solid, but I don’t think it’s acceptable to find any “reason to justify” or even try to understand the murder of the CEO. No matter ahat someone does for a living, murder of those we disagree with has no place in our society. It is immoral and a slippery slope. We have a legal system for disagreements and violence or taking actions into our own hands is not acceptable for any reason.
True, but nobody will miss someone making $10+ million a year by denying people healthcare services. That’s just obscene.
Sorry you feel that way. Your observations are that of an autoimmune disease; you are needlessly attacking yourself. ALL elements of serving society, the basis of capitalism, have a negative impact to some other value. When every you eat something, that something died to sustain you with nutrients, whether it be a plant, animal or single cell bacteria. Everything you/we do impacts our environment, so just chill and be proud of the problems you solve, package and sell to people that want your solution. Let the buyer decide if it is “evil”, not the supplier.
Morality changes with each generation and demographic so falling on your sword now may appear as virtuous to some but will look foolish to others, especially in the future and past.
Sounds good to me. What is it that you do?
United Health stock outperforms Google for the last 10 years, yet unlike Google that won 3 Nobel Prizes and literally started the current AI revolution, what does United Health do but to take money from the left hand and give it to the right hand?
Excellent blog to today ! You touched on morality, that’s what makes your thinking outstanding
Respectfully,
I would adjust one line..
“ Ultimately, if you’re not feeling good about the work you’re doing or people you work with, you’re wasting your life.
Thanks,
Andy
I guess blogging for a six figure living is sin too?
Probably. Depends on if the blogger has a paywall and how they earn their revenue. There is always some level of sin if money is involved.
What is it you do?
Hi Sam,
I typically enjoy your thoughtful writing, although this one a bit hits me as though the targeting of Thompson was justified. For that high claim denial rate circled in red. Could be higher because they do have difficult claims process. Could be theirs is higher because they take on people no one else will insure. Or …
I do agree that our current system needs work. But providing explanations on why it’s understandable to target one person for a perceived failing of a company I find short sighted. Which is really unusual for you.
Thanks for sharing your thoughts.
I don’t justify murder. But I understand why a lot of the population is angry with the healthcare system.
Perhaps you are lucky to not have to pay for healthcare, never had an important claim denied, or are rich enough to not feel the sting of a denied claim. If so, you are fortunate. Many are less so.
To resolve conflict and solve problems, the key is to have the empathy and emotional intelligence to better understand someone else’s point of view.
Feel free to share your background so we can understand where you are coming from. And what is it that you do for a living, per the topic of this post. Thanks
Hi Sam,
Have had difficulties, never bankrupted. Not connected to UHC.
You wrote, “Perhaps you are lucky to not have to pay for healthcare, never had an important claim denied, or are rich enough to not feel the sting of a denied claim.” Even if this young man had been denied a claim (was he a UHC customer?) why would I be empathetic of his action of gunning someone down on the street?
On the work front, I’m in the social work sector. So my work does feed purpose and meaning which is quite nice.
Thanks for sharing. I’m discussing being empathetic to the collective group of people who have had their claims denied and who do not have the money to pay for it. You don’t have to condone the actions of someone to understand why they did what they did.
Sam,
The United States is the evil empire now, we make our money by exploiting other nations around the world. We exploit the resources of Africa to make iPhones. We exploit the resources of Asia to get all of our low value goods, we exploit the economies of the tropics to get good tasting tropical fruits.
We are the World’s only Superpower now and we get rich here because of it. Sam, what you are saying is important, you are helping people understand the game if they are smart enough to read your blog. The main point of this article is make enough money you can choose to be less evil. That is where we are at as a nation. I started following the FIRE principles before I knew they had a following and a name. I wish I would have invested more money earlier, but live and learn.
The only way to truly escape the destructive career game and be your own boss is to invest early and create your own streams of income. Only then can people truly speak their mind about things that matter in our lives. If we are always slaves to our bosses or to corporations we are not truly free and we often have to make decisions that go against our true moral compass to appease someone else and meet their demands or needs instead of our own.
When I was in high tech in the 1980s, my company transferred me to a defense sector and I did not want to work at a job to improve the lethality of an F16. My boss didn’t agree with me, he felt like he was doing his patriotic duty, which was fine. But for me, it was not in tune with my moral code. However, in that short time working in that sector, I learned C and the Unix operating system, which was an invaluable asset in my career. I quickly buffed up my resume, got another software development job and ended up working in hospital and clinical trial software for the next 30 years, which at least tangentially were helping people. Later in my career, I once interviewed a developer who worked for a porn company, he was having a moral crisis and wanted to leave.
I work in the drug industry R&D and I find it very fulfilling to develop cures for rare diseases. That’s what motivates me when I’m working my tail off, and that everything is logical and based on science. I also have great appreciation for the government who regulates us because they really make sure the products are really, really, high quality, unlike many consumer products. I also feel a sense of community at work, and tend to like being at work then at home with my 3 screaming kids and not-doing-so-well wife.
I’ve had many battles with insurance companies. Years ago I even had a blog and eBook. I was bothered by unresponsive they were to obvious conflicts.
For your last statement, as soon as you embrace that nobody cares about you or what you are doing, it unlocks an incredible amount of freedom. It’s one reason how I keep going in terms of writing on Financial samurai since 2009.
I’m probably a relic: I found my most fulfiling jobs were in govn’t. If you simply ignore the occasional slack employee and work often with motivated and helpful employees to you and the public,it makes a huge service. Yes, I did believe in “serving the public” ultimately. I worked for a fire code enforcement and emergency planning agency, the courts/judges, legal aid and for municipality. In between, I did work for 4 different national and global firms in private sector (which included 1 of the big 4 accounting firms).
That is great and I am happy for you. We all serve the public. Capitalism holds the individual accountable to society as the individual is compelled to solve the problems of society, real or perceived, and in return the recipient of the solution gives a portion of their wealth to the problem solver. The US Constitution holds society accountable to the individual in order to preserve and defend their rights by government agency. These 2 reciprocating construct have done more to empower the individual than any others in human history, maybe to a fault as the individual becomes their own worst enemy.
Hi Sam, long time reader and owner of your book Buy This, Not That here.
I think one can even argue that engaging in any economic activity here in the US is sinful. Why? Because you use US dollars, the strength and stability of which is implicitly backed by the US military, which is a military force that has a questionable moral standing in the eyes of many countries outside the US.
Going one step even further, you can argue that using any product of human civilization is sinful, because morally wrong ingredients like war and slavery has been baked into the development of it.
After about a year or two of working, every employee deep down knows whether they are spending their time doing good or doing something unhelpful for society.
So it always amazes me how some people who have enough money are still working at jobs and at companies in industries that have extreme morality problems. Like dude, you already made tons of money, go do something that is more helpful to society ready.
I’ve wondered the same thing, but especially focused on real estate. I live in a place where the median priced home is quite unaffordable for those making typical salaries in the area. While I was lucky enough to get into a home, I know several enthusiastic real estate people who own multiple single-family homes. If a home were to come onto the market at a decent price, they would scoop it up as fast as they could. Meanwhile a family that could almost afford to buy the home, but is outbid, is now likely forced to rent the same home. Instead of giving this slightly less advantaged family a chance to build equity, they are instead forced to pay a higher cost for rent and without the chance to have long-term stability. One group is definitely profiting off the other, and without really providing any value that wouldn’t have existed if they weren’t involved. If real estate investors were less aggressive, more people would be able to afford homes as the demand drop would lead to lower prices.
As an alternative example, if someone builds a four-plex and then rents out the units, I have no objection: they first helped create construction jobs and then they provided some likely affordable rental options that didn’t exist before. I also have no objection to those who fix up houses that need a ton of work before anyone can live in them and then resell.
I know you are a huge fan of real estate investing, but I have thought long and hard about where the morality balance is when many decent people are forced out of the market due to investors. But I agree with you that nothing is perfect, including employment and stock investing – so it is not an easy question to grapple with.
What a great post, Sam! I’m not going to lie; I feel a tinge of remorse as we made our money creating a recyclable shipping envelope for Amazon. We sold the company because we couldn’t keep up with demand, and P.E. came and gave us a nice retirement check. But I do feel bad for the mom-and-pop stores that are being displaced. I’m justifying it by saying someone else would’ve created this earth-friendly package, so it might as well have been us! As humans, you justify anything and this article makes me feel better that all wealth-building requires a bit of sin. Thanks again for all you do!
Maybe when we move to Mars with Elon, we can earn and enjoy wealth free of sin. On planet Earth, here is no way to gain wealth without some sinning if sin is defined as earning money via something that causes harm.
For instance, we can thumb out noses at working for naughty companies, but if we invest in major stock indexes, all of which include sinful companies, we are still gaining wealth through sin. As you noted, money morality isn’t a one size fits all, so everyone has to find the sin size they can wear comfortably.
I definitely relate to your Google friend who just wanted to earn enough to leave. I was the same way at the company I worked for and I left with a severance package as soon as I hit your Minimum Investment Threshold. Although this now sounds especially cringy considering Thompson’s murder, some colleagues used to say, “Shoot me if I start enjoying my job, cuz I’ll be dead inside.” Many of them are still miserably grinding away and they think I’m the crazy one for hopping off the money train to invest my time with more joy, though not without sin.
Thanks for sharing. What is it that you did and what do you do now?
That’s great you made a change based on your own values.
I was a technology worker for a variety of large companies. Existential malaise is common in those institutions, as we hear frequently in the news. Of course, most big tech workers have the luxury of being able to afford self-pity for self-inflicted conflicts in seeking self-actualization.
For example, although I didn’t work at Google, I explored opportunities there and remember one of my long tenured manager interviewers telling me he no longer felt he was adding value and didn’t know why he still worked there, which was one of the stranger moments in an already odd interview loop (he left the company soon after).
I now manage our investment properties and do some technology consulting part-time. I miss the compensation that went with my life as a full time tech employee, but that’s the only thing I miss and it would be a cold day in hell before I’d return.
Will know how bad Brian Thompson felt making over $10 million a year at United healthcare by seeing how he lived.
If he lived flamboyantly, then we know he didn’t give a crap about denying claims and helping contribute to the deaths of tens of thousands of people in America.
The healthcare industry must change for the greater good.
I can relate to this a lot. I left my last job because it left me feeling hollow inside. I put in a lot of sweat, hard work, and tears into it, but I didn’t feel like I was making the world any better. Sure, I was helping other people help other people get richer, but they treated me like dirt. If my clients had treated me with respect, appreciation, and kindness instead of being aholes maybe I would have lasted longer. But it didn’t give me any sense of meaning or purpose. It made me feel angry and exploited. It took me awhile to quit, but I eventually did. I saved a lot, worked on building new skills while still collecting my paycheck, and found new purpose. I had to sacrifice on pay, but the decrease in my stress and increase in my self-worth and happiness made it all well worth it.
Thank you, Sam. This article is balanced, nuanced, fair and brave. You demonstrate courage, character, deep & honest thinking . . . wisdom earned and backed up by action.