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Self-Sabotage: The Biggest Risk Once You Have Money

Having money can change you, and not always in good ways. The risk is greatest for those who start out poor. For those lucky people, they have an additional challenge before them. If they fail they go all the way back into the swamp. Self-sabotage is an insidious demon.

Money doesn’t make you a better person; it makes the kind of person you are more pronounced. If you are a kind and generous person, money will tend to make you more kind and generous. And if you are a a-hole, money will make you a much larger one.

Today I will share with you three stories: two personal and the other from a client. My hope is that you, kind readers, will learn from these lessons rather experience them personally.

I work hard sharing ideas on building wealth and lowering taxes. These are worthy goals that make the world a better place. What I don’t talk about often is the risks people face once they make it. There is no greater thrill than to watch someone born in poverty finding their way to an abundant life. All too often this is the moment they destroy their lives. Usually it is temporary; sometimes not. These lessons can help you avoid the same fate.

Turning on the AC

Believe it or not, you need to give yourself permission to be successful. Most people get exactly what they think they deserve. When their net worth declines the mental thermostat is turned up to bring them right back where they think they belong. And when things start going well, all too often the thermostat is turned down until the AC kicks in and pulls you down to where you think you belong.

There were two times in my life where I kicked on the mental AC is a big way. Working with clients on a regular basis as a tax professional I should have known better. I should have seen it coming. Yet, I let my guard down and suffered financially in each case.

My background starts on a farm in the backwoods of Nowhere, Wisconsin. We were poor, yet happy. We didn’t know better. We milked cows, planted and harvested crops and enjoyed life to the fullest in our sheltered world.

By the time I reached high school I realized there was another world out there. I was driven. Coupled with the energy of youth I kicked tail and took names.

The family farm went through a wrenching bankruptcy in 1982, the year I graduated high school. I’m not certain, but I might have been the only one in the family with a positive net worth. Not bragging. Just had no debt so the nickels and dimes in my pocket was my edge.

Destructive financial habits are set at a young age. Learn to give yourself permission to have nice thing, a good life and financial success.

As hard as losing the farm was on me (I always thought I was going to be a farmer all my life) it was a blessing is disguise.

Rather than dig into a farming lifestyle I focused on blazing my own path. I started several businesses. We call them side hustles now. One of those businesses was preparing taxes for up to 50 people. It took seven years to realize that would be the course my life would take.

I started buying real estate. Most properties were single family homes and duplexes in the beginning. I bought larger and varied types of property as I gained my sea legs.

By 1990 I figured out I was going to be a tax guy. (What better way to keep your real estate profits than by learning the Tax Code inside and out?)

My dad and brother joined me in a real estate partnership called LuK Enterprises. No LLC. Nothing special. Just a family general partnership.

My tax practice that started as a side hustle preparing 48 returns per year jumped to 148 returns the first year full-time and 402 the second year. I never looked back.

A backwoods farm boy saw his net worth and income explode. My tax practice started earning real money by 1992-3. I was living the dream.

And my subconscious started to scream You don’t deserve this!

By all outward appearances I was handling the wealth rather well. Except for an early mid-life crisis.

I bought a Z-28. It was a sporty little number. Bought it from Fox Communities Credit Union (back when they sold their repos to the public rather than ship them to auction). Sold it a year later at a profit. (As much as the car made me look cool, it was small even for me back in those day. I could barely get in and out of the driver’s seat.)

This is the part of the story where I will refrain from an info-dump. Suffice it to say, I did not feel good about myself. I felt like an imposter. Farm boys don’t end up like this.

So I sabotaged myself. And boy did I do a number. Looking back it I was lucky to come out alive.

My income stagnated for a few years while my net worth kept growing. I had a good setup and it worked while I was flipping out. Fortunately.

The worst part is I saw it coming! When I couldn’t self-destruct, I upped the ante and made it known I was off the rails. I never hurt anyone or put anyone at risk. But I certainly loaded both barrels and pulled both triggers with the barrels pointed at my feet. Toes were flying everywhere. Now you know why I limp; self-inflicted financial wounds.

It took a long time to undo the damage and in some ways never did. The good news is my tax practice eventually started growing again. I sold most of my real estate 5-10 years later, converting equity into cash. I rebuilt my life and moved on. Lesson learned? I wish it were that simple.


You would think once a farm boy became seasoned he would not be so prone to industrial-strength stupid. Ah, but I’m going to make you proud.

You see, I have a strong drive to learn and try things. Drake Software developed a DIY program based on the professional version used by my firm. I thought this could be a real profit generator while providing a powerful tax preparation tool for those going it alone. I got half of it right.

The software worked just fine and Drake kept improving the product. I think it is the best product on the market. Unfortunately, it is hard to get people to try your tax software when the major players are dug in deep. Even price didn’t encourage people! They gladly pay more for TurboTax when I see many of these folks in the summer when they need issues fixed their software screwed up.

I needed a hook to get people to try the product. That is when I came across a blogger called Mr. Money Mustache (MMM).

I loved Pete’s (Mr. Money Mustache is Pete Adeney) work, especially the frugal ideas he espoused. His real claim to fame is early retirement. He dumped traditional work at age 30 and had a stint in real estate before rocketing to fame in the blogosphere.

Retirement never interested me. There are too many things I want to do. Mix in some OCD and I’ll probably twitch in my grave, to say nothing of my behavior while alive. But for Pete the message resonated. He worked hard building his blog and his IT background gave him a serious advantage. He likes to make it look easy. Blame it on social media and cherry picking daily activities to report.

Well, I packed my bags with a plan to meet MMM and sell him on the DIY tax software idea.

I attended a Camp Mustache outside Seattle that year. As long as I was there I figured I may as well give a presentation on some tax strategies. Pete took an instant like to me.

Pete made me his tax guy on the spot. It was time to spring my idea. He shot it down posthaste.

Little did I know how badly the wheels fell off! It was the worst possible outcome and I had no idea what was about to hit me.

Pete published a post about my presentation on his blog, a blog with the better part of 10 million page views per month. Do you have any idea what that does to a small tax office? It nearly destroyed my business. But that isn’t where I went off the rails.

And I had no partnership with Pete on the tax software.

While still at Camp Mustache people started asking me if I had a blog. Well, ah…

I purchased the URL for this blog a few years prior with plans for what eventually came to pass. My timetable was pushed forward is all. I now needed to have a blog up and running!

With a push from an A-list blogger I was on the map. Blog traffic jumped right out of the gate.

Traffic climbed and people took notice. People knew me! A farm boy! From the backwoods of Nowhere, Wisconsin! And my brain started to plot revenge. This isn’t right.

Fame (even if only modest in scope) brings out the less desirable people of the world. Some would email or call, trying to use me as a relay to contact Pete. (Me: Call Pete yourself. Them: He doesn’t answer. Me. Then he doesn’t want to talk to you.) Others wanted to pitch me. And 20,000 people wanted me as their tax preparer!

I was a popular dude, at least from what I ever experienced prior in my life. I was getting more uncomfortable by the day. I never connected well with the FIRE (financial independence/retire early) community. I found nothing familiar about them, except for the frugality.

Pete was the father of the FIRE movement. I felt obligated to attend more gatherings and conferences. I hated it with every fiber of my being. My brain was working hard now on a way to sabotage me.

Beat self-sabotage.

The best things in life are worth having. You are worth everything you have and more.

The zenith was at hand. This blog was nominated for a Plutus Award: The Best New Personal Finance Blog of the Year. And I won! I think a lot had to do with me being Pete’s tax guy.

But that is not where my brain loaded both barrels again.

The night before the awards ceremony I had three late visitors to my hotel room. Remember how I told you fame, even a small amount, attracts the least desirable people in the world? Well, three showed up at my door. The worst part is I knew who they were and liked them! Not so much now. The warts are too visible to me now. There goal was to hurt me and I fully cooperated!

Without going into too much detail, I found my way to get out of the trap I felt I was in. After the awards ceremony I wrote a blog post, and boy was it a blistering attack. I pulled it down a few hours later and eventually deleted it in my files. But the damage was done. It was a terrible post, a rambling attack on all I felt slighted by. I gave new meaning to the acronym FIRE.

Blog traffic slowly declined as the FIRE community kept their distance. (Who could blame them? Even I scare me sometimes!) Now I’m working on rebuilding this blog. No more awards, no more conferences and a lot fewer emails.

Without a doubt I could have done things differently. I did not have to be an ass about it. It is easy to point finger. The thing is, I can’t control them, but I can control my behavior.

If I wanted out I should have politely excused myself and left it at that. There was no reason to bring a blow torch into the picture. (Note: A large number of people in the FIRE community still communicate with me. They are good folks and forgave the wayward child.)

Of course, there is plenty more. Buy me a beer (or three) and I’ll tell you more than even I know.

My stories were only to warm you up. The real reason for today’s post involves a long-term client. Her risks are no less than what I faced. Hopefully I can help her navigate the swamp better than I did. I’ll let you be the judge.

Rags to Riches

The year is 1992. Brenda walks into my office for the first time. (Faces and names have been changed. Brenda is aware of this post and approves.) She said two words at best. I prepared her return. As soon as she was finished she turned with a snap and left.

As the years went by I discovered she had a story that breaks the heart. She was molested by her step-father from the time she five or maybe even younger. This had a profound and negative impact on her adult life.

Brenda had no self worth. She didn’t talk because she was so abused. As a young adult she got pregnant, married the man and later divorced him. She told me she was practically forced into the marriage when she got pregnant.

After the first failed marriage she jumped into an abusive relationship next. That marriage also failed.

The details are too sordid to include here. Suffice it to say, she was one suffering young lady.

Fifteen years ago, after she put her failed marriages behind her, Brenda finally met a decent man worthy of her love. Brenda took her time to get it right this time. She took years to make a commitment of marriage. She wanted a real marriage; one that lasted. (They have an awesome marriage I am proud to report.)

Brenda was still deep in debt and lived in a $500 mobile home. Life was not good. Financial problems were crushing her. All she had was a man that loved her. Her body and spirit broken from an abusive step-father and marriage to a man no less abusive had crushed her spirit.

Over the last 10 years she made every attempt possible to dig out of the financial hole she was in. She had a good man in her life. She now had a reason to live, to build a life worth living.

Somewhere around this time she started talking to her tax professional a bit more. Even before this blog I worked with clients on financial issues as well as tax. Brenda would be a special case, handled pro bono.

She listened hard. Much of the advice she refused to take. If it worked it would be too much too fast. I could see it on her face. Her AC kicked in below the freezing mark!

Slowly her finances improved. She got out of the mobile home and bought a “real” home. Her debt declined to a manageable level. Her retirement account was growing. She was starting to live the dream. Her credit score approached 800; it had been in the 500 range most of her life.

All the while this was happening I could see in her face she felt deep down she did not deserve a life as good as it had become. She was about to release a subconscious financial bomb, something I am all too familiar with.

The money grew; her lifestyle did as well. She now has more money than she ever had in her life. She has a good job. A good stock market meant her index funds (my advice) exploded! She was sitting on a nice stack of green.

Not an overwhelming amount, mind you. A nice stash of moolah, for sure, but not enough to go crazy.

All the pandemic craziness worked on Brenda’s mind. She wanted to get away.

Earlier this year she informed me she was checking out.

While my flare-outs were much more entertaining (ahem!), she is doing what she knows best: running away. It is a common trait among abuse victims. She has enough money for a gap year or so, but she also has some debt. There is a bit more financial work to do before she can punch her card.

When I talked to her recently she informed me she tendered her resignation at work. She has a good job! One she actually keeps instead of switching jobs every few years. And she likes the people there; the people there like her!

I asked her to reconsider before the two-week notice came due. She has stability in life now. She doesn’t have another job lined up and doesn’t know where she wants to go. She is scared because this kind of life is so alien to her.

I suggested she cut her hours instead because it will not take long for her finances to start screaming for help if she takes early retirement too early.

She can always quit later if that is her desire. My advice was to think before she leapt.

Her employer allowed Brenda to rescind her resignation. She will be taking a shorter workweek and more days off. That makes sense to me. No bridges in flames and more time with her family. Now if she can only convince herself she deserves such a rich life.

There is no magic answer. Sometimes, when you are too close, it is hard to see the forest from the trees. We are all guilty of it. It is also the worst time to make a decision…

…without input from a third-party interested in your well-being.

The story hasn’t ended. She could easily crash and burn. She is at a dangerous time. Things have never been better for her, but deep down she is still fighting the demons of a past that tells her she is worthless.

It is hard when you care for your clients. I hurt when they hurt. I can’t fix her or any client for that manner. She has to find her own way. All I can do is hold the lamp and hope she makes the right decision.

Advanced Self-Sabotage

Brenda’s and my stories have multiple lessons. But there is one more lesson.

Self-sabotage doesn’t always take place once you have had some success. Often, we have an idea that when fleshed out has real promise. Before we ever begin our brain envisions the successful outcome.

To prevent any overheating our brain tells us to sabotage the effort. Procrastination kills more wealth than all other dangers combined.

There are so many ways to burn your future. The goal is to short circuit the thermostat. Life when you were a child built many of these walls. They need to come down.

You do deserve a good life, filled with financial abundance and good friends and family. Break the thermostat. Let your dreams flourish.


There is no other line of work for me. I make a difference. Every morning I jump out of bed ready to serve. It gives my life meaning, helping others find meaning in theirs.

I made enough mistakes, some rather large as we just saw. Perhaps if the right person came along I would not have committed the slash and burn I did. I doubt anyone knew how deep the knife cut. I needed to open up and accept help.

Coming from the outside I can help people see the forest from the trees; provide a gentle guiding hand. I have plenty of experience, and the scars to prove it. I have no problem telling my stories, even the less flattering ones.

The story doesn’t end here. It never really ends. Each day is a challenge to live up to our potential and convince ourselves we are worth everything we have.

Have you ever self-sabotaged? Of course you have. Same as Brenda and me. How did you find your way back to the light? What lessons did you learn? How did you convince yourself it was okay to be wealthy, to have life good? Are you still picking up the pieces?

Many times the conversation ends up on Facebook. Consider adding the conversation to the comments here so others that come along later have a full guide on how to avoid the self-sabotage we all plan when things go better than we feel deep down we don’t deserve.


Sunday 15th of August 2021

I love your honesty and willingness to share your stories and experiences, Keith. Many try to tuck their past under a rug and put on a facade. I read a select few blogs these days but always find something to learn from yours. We all have plenty of good and bad memories and experiences from our pasts to learn from that hopefully help us to grow into better people throughout our lives.


Tuesday 10th of August 2021

Good topic but I feel the article loses some value because of the vagueness. In the past you went into more detail regarding your journey and it really helped with providing valuable life lessons. I understand that it requires vulnerability but it is the content that helps the most.

I would agree that FIRE is not where it’s at. It doesn’t really answer the “now what” question very well. Even Pete seems more and more directionless as time progresses. (At least in his writing)

Keith Taxguy

Tuesday 10th of August 2021

MB, I apologize for the vagueness. It really would have ended up an info dump 5,000 words or longer. At some point I will publish a book and will spend 100 pages explaining what might be the most interesting part of my life. The lessons learned is in the dozens. Some of those lessons took 2-3 years before I figured them out.

The FIRE community is composed of a group of good people. I love much of what they do, but find the rush to the endgame unsatisfying. It's me, not them.

Don't be too hard on Pete. He is a good guy with a good heart. He is living the dream; his dream. It is hard staying motivated once you reach 8 figures. Steve Jobs is one guy who found motivation even after he didn't have to do anything. His words, "Stay hungry, stay foolish" mean something to me. Steve found a way to stay relevant when the task of success has been checked off. He wanted and did change the world for the better. He stayed hungry and foolish. We are all better for it.

There is a YouTube video of Jobs talking about staying relevant. He said it's hard to keep pushing, to run a business and innovate. It often hurts. Sane people quit because that is what normal people do when in pain they don't have to take. I hope I can live up to one-tenth of one percent of what Steve Jobs did. I don't have to reach his financial heights, but it would be a fitting cap on my life if I stayed hungry, stayed foolish all the way to the finish line.

There is nothing wrong with Pete or the FIRE community. As Steve Jobs said, they are the sane ones. You guys will just have to live with the crazy accountant over here. I hope it is worth the journey, a trip well traveled.


Tuesday 10th of August 2021

Thank you for your blog. I really appreciate you mentioning that "all that glitters isn't gold", as far as the personal finance blog-o-sphere is concerned. I have had some cynicism about what I've read....but I've tried hard to separate the wheat from the chaff. I have wondered at times how much is for the profit/fame of the writer, rather than the good of the reader.

I appreciate so much what I've learned from your blog.

Keith Taxguy

Tuesday 10th of August 2021

Planedoc, my hope was to show how we self-sabotage in ways we are not aware of. I'm as guilty as the next person.

My intention was never to put down another blogger. Pete did what he thought was the right thing at the time. You can't argue with his success. I, on the other hand, could have been a smidge better in my response. Yes, I do show my warts more often than many bloggers. The warts need to be seen. Not to get you down, but to show you that we all fight the same battles with ourselves.

Writing and publishing is a fame game. I wish it were not true. (I could sit alone in a modestly lighted room as I punched out my stories without ever venturing out the door.) But it is better for the reader! When I get out I learn more and can share stories and lessons. Truth is, I work just as hard to be seen and that means modifying behavior. The alternative is crickets and then why bother.

Keep reading. Theirs and mine. That is how you discover wheat from chaff.

Donald T

Tuesday 10th of August 2021

A great post. I was a bit younger than you when we lost the family farm in 1986 and it dashed my dreams of being a farmer as well. Years later I became a physician so I suppose it all worked out.

I certainly identified with this topic because I have become an expert in self sabotage. Even in medical school I sabotaged myself. It wasn't until I came across the work of Carol Dweck that I realized what was going on. In her book 'Mindset' she explores the ideas of people having "fixed" mindsets or "growth" mindsets. I definitely fall into the camp of having a "fixed" mindset. The only thing I was praised on as a child and young adult was my intelligence. It became part of my identity. I didn't want anything to threaten that so I would sabotage myself in able to give myself plausible deniability. If one never goes to calculus class and doesn't ever lift a finger to study for a test, one can say "I didn't really study" when a bad grade is received. One can then preserve the identity of being a super smart person. The truth may be, as it was in my case, that I wasn't as gifted in math as I believed and I would have to have worked diligently at the subject to get an acceptable but not outstanding grade.

As the years have passed I have attempted to work on developing a growth mindset. With that change, I hope to see the self sabotage decrease.

Keith Taxguy

Tuesday 10th of August 2021

Donald, we have a lot in common. I'll check out Carol Dweck's book and insert a link in your comment.

Michael Crosby

Monday 9th of August 2021

Hey Keith, nice to see you're around. One thing is for sure, you've shared very personal stories for all to read. Hope all is well with you and your family.

As the years have gone by, I've noticed most bloggers don't post like they used to, if at all. It's understandable. Like anything else, blogging has a life of its own. I wonder how many who have had successful podcasts/blogs, think, what do I come up with now. Where before there was this spring welling up with ideas that had to get out.

Keith Taxguy

Monday 9th of August 2021

Michael, I have hundreds of blog idea in the queue. At some point I have to promote or slowly fall into oblivion. I will start publishing on Medium and a few other places to reach a wider audience. When appropriate I will share the links on The Wealthy Accountant social media pages.

To free more time I am also hiring people to manage some social media work for the blog. There just isn't time to be good at everything. I find I want to dig deeper into subjects now versus a few years back. That all takes more time per post.

I'm not going away. Life just sopped up a lot of my time (family medical issues). I write and love writing. My production will increase.