The Dangers of a Side Gig

Tax season is officially over and not a moment too soon. As much as I love the work, when months go by without a day off it begins to wear on me. The worst part is the sitting. Too many hours planted in a chair coupled with sleep deprivation and health is not getting the attention it needs.

Loving something as much as I love tax work is also a challenge for people around me. Mrs. Accountant is an angel, allowing me the opportunity every year to disappear for months to help complete strangers and semi-strangers with their tax, accounting and financial problems. My daughters have learned from an early age dad is a very intense man when it comes to his work.

Work has never been a four letter word for me. (Considering my profession you would think I could count to four better.) Growing up on a farm meant everything was work, but not work. Running to the creek to fish was something you did. Planting in spring was fun, not really work. Harvesting was an addiction; sleep was hard to achieve until the crops were off the field. I know of no greater pleasure than watching a barn filled with bales of hay, placed there by my own hands. There is no greater thrill than to see the milk cooler fill each day to the rim. A full bulk tank meant money, and therefore, life. It was a good life and I had no idea what the real world was like outside my vision horizon.




Formalized work is another story. Working on a farm is just doing stuff you feel like doing. Calling the cows for milking was more pleasure than work. Even the farm dog knew when it was time to sic’em. Our worldview was narrow, yet innocent. And there is something to be said for ignorant innocence.

But I was smarter than the rest of them. And restless. Never satisfied, I had to know what was on the other side of the hill. “Greener”, you say? Well, I gotta see that for myself.

Innocents Abroad

The family farm was reaching the end of its lifecycle and the world would open before my eyes. With an optimism only the ignorant can feel, I headed out into the world as the family farm took its last gasp in bankruptcy court. The cows were gone and some of the land. The homestead and most of the land (the core holdings, for sure) were preserved in the family name. I had different ideas.

On one hand I say work doesn’t bother me, but you may have noticed I have yet another hand. Neat, huh? With this extra hand I’m lazier than shit. I wanted nothing to do with the daily grind and obligations of milking cows. Working for the man would never cut it.

Well, of course, those lazy-ass business owners have it made. Hire a bunch of slaves, ah, I mean employees, aka team members, to do all the work while I did the one thing I really enjoyed: counting the money.

This whole early retirement thing is an alien concept to me. Retire early? From what? My plan was to never start! Take that Mr. Money Mustache. Work until you’re 30. Pftt!

Unfortunately the world is not always kind to idiots, ah, innocence. I had a plan and life had a few plans of her own for me.




The Best-Laid Plans of Mice and Men

The best part of living in the middle of nowhere is that you never develop the bad habits of the world at large. As a kid, my biggest expense in life was dropping money into the plate Sunday morning. My senior year of high school I think my entire spending for the year never broke $200 and most of that was enforced school spending which pissed me off to no end. Come to think of it, I still have a burr in my shorts over it.

By nature I was fiscally tighter than a rusted ring shank nail. Working at saving was like saying I have to work to keep my heart beating. The darn thing does what it does without any conscious input by me. Money, saving and investing worked on the same rules for me. And good thing. If the world had taught me the bad money habits most people have you would not be enjoying this wonderful story this very moment. (I am not conceited. But I am right.) It was thrift which gave me a fighting chance to pull the stunt I was planning.

I needed to find a business where I could work very part-time and screw around whenever I wanted. My preferred screwing around was books. I loved to read and still do. I read every day. That is one better than eating because I periodically fast.

Out of high school I was still working on the family farm. A few months later it was gone. With few options available in the Rust Belt during the early 1980s recession I went to work for my dad’s agricultural repair business. Talk about work. This was nothing like farming! Hundred hour work weeks for minimum wage or less (I worked for family) educated me about the “real” world damn fast.

Bookkeeping, taxes and payroll all looked mighty good. Sure beat crawling into another dirty silo. (My brother, on the other hand—remember, most of us have two hands—enjoyed the silo work and still does. To each their own.) My dad hated paperwork so the task fell to me. For a few years I had my side gig while busting tail another 80 hours a week turning a wrench. Don’t feel sorry for me though. The lessons learned from hard work are never lost.

I learned I needed to get that side gig going and going fast. Sick of the ag industry, I left the family business and moved into my own home. I was 22. For the first time in my life I could indulge my reading habits with reckless abandon. Lucky me. My side gig was 50 or so tax returns each spring. Investments rounded out the rest of my financial needs.

My first home wasn’t much to look at. Houses are cheap in the boondocks. I paid $12,000 and change. Don’t quote me; I don’t recall the exact number, but I am close. I had money; I had books; I was happy as a pig in shit.

Then I met Mrs. Accountant.

From the FIRE to the Frying Pan

I would never have amounted to anything if Mrs. Accountant hadn’t found me and shown me the way. A year after we met we were married. Now some folks would say I went from the frying pan to the fire, but it ain’t so. I was in the FIRE (financial independence, retire early) and Mrs. Accountant kicked me back to the frying pan. And good thing.

Frugality allows for some serious laziness. When needs are small and desires nonexistent, so are money needs. Without debt, the required money needs are rather small. Any side gig would do. But the one thing I love was unfulfilled.

As Mrs. Accountant and I prepared for married life, the minister marrying us required we take marriage counseling. Innocent enough. As the counseling reached its end the minister commented on my lack of employment. He offered me a job as janitor (that’s custodian to you!) for the parochial school attached to the church. What could I say? I accepted. As memory served, I fought back tears at the time. Once again I was working a dreaded job by the clock. I thought nasty things about God. In his house, of all places.

Don’t let the whelming tears in my eyes cause you any emotional trauma. The work of a janitor is honest work and I took to it like a duck to water. The main reason it took so well is I discovered a janitor can get his work done in a fraction of the time needed. This allowed plenty of time for reading on the clock. God was coughing up a hairball for your favorite accountant!

Regardless how honest the work and wonderful the people at the church and school, I had other plans. It was during this one year swilling toilets, picking up puke and mopping floors that I decided on my official side gig: tax preparation.

I had it all figured out. I’m a smart guy and I’ll tell ya about it if you ask. If you don’t ask I’ll tell ya anyway and wonder what the hell is the matter with you. Tax preparation was the perfect job for a guy that really wanted to spend all day reading. For two and a half months I worked reasonably hard (don’t take on too many clients now) and for nine and a half months I do . . .  nothing! Ye-Haaaaa!!!




Back Into the FIRE

Remember how I told you I was a smart guy? Well, I lied!

The first few years in my retired side gig life were peachy. Mrs. Accountant and I had a new home and my office was in the remodeled basement. Life could not have been better. This is where a medical condition I have affected my so-called intelligence.

I record everything in business. I knew how many returns I did every single day. I still have the handwritten pages next to my desk going back decades. I can tell you how much money came in on any given day and how many returns I prepared that day. It was a sickness. Now the records are computerized in QuickBooks and Excel worksheets so I can micro-analyze the data even better.

There was only one goal I ever had in life: beat last year’s numbers. At first this was a noble endeavor. The numbers were small and tacking a few onto last year’s performance was no big deal. But compounding, as we all know around here, takes on a life of its own.

No longer satisfied with my performance, it was time my side gig went viral. (This is before there was such a thing as “going” viral. Back then viral meant you needed to see a doctor for that little indiscretion you had while traveling overseas.)

I wanted back on the farm so I bought my current office building and farmstead. The year was 1995. A mere five years after starting my serious phase of the tax side gig I was going all-in. The side gig was now a full-fledged business. I had employees working in my basement, but now we were putting on our big girl panties. (This is a family blog so there will be no pictures of people in big girl panties.)

I was back in the fucking rat race. (So much for a family blog.) An office building and more employees meant . . .  WORK! You may not know this, but I have a life threatening allergic reaction to work. I break out in hives and need plenty of rest to recover from any such incident.

Truth is, I was happy. The business had plenty of room to grow. And grow it did. A storefront sent a bulging client list into obesity. It worked for a few years.

Payroll and bookkeeping were minor parts of the company. A one-man (or woman) summer staff was all that was needed. Seasonal help made the office hum like a beehive. I lived for the thrill of tax season.

But I still had the sickness; beat last year. And beat it, I did. Within a few years I blew past 2,000 tax returns and was turning people away. Stress showed up about the same time. It was too much. My disposition was not conducive to this kind of business. I was never going to be a Bill Gates or anyone who would take a small tax practice to a multi-location regional or national firm. I knew what the price would be and refused to play. It was time to stop beating “last year’s numbers”.

I honed the client list down to 700 over the next few years. I was happy again. I was doing what I loved most: reading a lot, preparing taxes and researching tax issues. I was a pig back in the schmoo.

But . . .

Do we see a pattern here?

All that reading and knowledge really should be put to work. Right? Well, smart as I am, I started thinking. I pay property tax for the full year for the full building. I pay for building upkeep. I pay for computers. On ad nauseam. My thinking was simple. Computers cost exactly the same whether I use them for three months a year or if they are used all year long. What a concept!

So I started adding more payroll and bookkeeping clients. I felt I could hire and retain better employees if I could give them full-time work instead of seasonal jobs.

For several years I turned my practice into a job. Bookkeeping and payroll burst through the seams. Since my focus was tax, the payroll and bookkeeping never turned a profit of any size. Toward the end it even lost money. I’m a tax guy and know it.

I built strategic alliances for bookkeeping and payroll (yes, I know I still owe you guys a post on this outsourcing program). Most payrolls are handled outside my firm and bookkeeping is headed in the same direction. Yes, computers don’t cost more if they are used all year, but if there is no profit, why bother? Now the strategic alliances turn a profit, so feel free to contact my office for payroll and bookkeeping. We do it better and cheaper now. No stress for me; better service and price for you. And I make money. And last I checked that is the reason I am in business; side gig or no.

Danger, Will Robinson!

Tax season is over. I am writing from home. The office is quiet. My office manager and one tax preparer are all that remain. Friday’s are very short days. Only one full-time employee will haunt the halls of my practice until the next tax season. Even the office manager is on truncated hours. And me? I am writing, reading and speaking. My schedule is full. Too much traveling for my taste, but necessary for the life of a blogger who wants to turn it into a real business.

Livestock Dairy Farm Cattle Agriculture Milk Cow

And now we get to the real issue of this blog post. I hope you read this far.

I share my story because I want you to understand the dangers of a side gig. There is one last thing I haven’t told you yet. It is the worst possible thing ever anyone is forced to do.

My practice is more a side gig than ever again for the first time in years. The long hours of tax season are over and my lusts have been satisfied. I accomplished a lot and missed a few things I really wanted to get done for clients. Now I look into the maw of a summer without payroll issues. Some tax work still comes in. It is easier to finish a couple hundred tax returns over nine months than a thousand in two and a half. Yet my heart is heavy.

It is not lack of work to fill my days weighing on my soul. It is the people. My employees. Summer work is done and what started as full-time opportunities turned into seasonal work. As this tax season progressed I knew what had to be done. Good people, people I enjoyed working with, would no longer have work to do in my practice.

I am a coward in these matters. My office manager broke the bad news. My front desk: gone. Tax professionals: gone. Karen, my office manager, keeps the place running smooth. Dawn, an undiscovered tax prodigy (Don’t let it get to your head. Dawn likes to read this blog so I need to keep it real for her.) who somehow wandered into my sphere of influence is the sole remaining full-time employee. There is enough work for her to do as long as I send her on research projects for upcoming blog posts and for extensions and wayward taxpayers seeing the light.

Two years ago Mr. Money Mustache gave me a great honor by pointing out my office and work. He meant well and we get along fine. I do his tax work and even advise MMM on tax matters. When I feel punchy I tell people I’m the financial consultant of MMM. It impressed the shit out of people. He is a fine man and I will always be grateful for what he did for me.




Two years ago it created a huge challenge in my business. The side gig became the worst job ever. MMM has a huge following and it is hard to control the flow. A blog is easy by those standards. More readers are relatively simple to manage. Not so a massive influx of tax clients. There are only so many hours in a day and they were then all consumed. I learned new skills from the challenge.

Two years ago some people got jealous of my success. Why did I get such an honor from MMM when they deserved it? Worse, I had two jealous employees sabotage the business. They couldn’t stand an ‘ol farm boy doing well on such a large stage. Those employees went and the ones they poisoned.

New employees arrived and were trained. Life moved on and my practice grew in the right ways. There is still room for improvement and you can expect that from me as we move forward. There was no doubt I was out of my league two years ago when things hit.

And that is the danger of a side gig. Loving something can quickly turn into an obsession. A seasonal or part-time side gig means you will let good people go. Make no mistake, I fully understand the consequence of my actions. Families are affected.

And I never realized how many times I would have to tell people “no.” There is only so much of little ‘ol me to go around.

That is the real danger of a side gig. You do it because you like doing it. Then it takes over. Learn from the experiences of an old accountant from the backwoods of Wisconsin. Love can be very painful. It is not a character flaw; it is life. Know this before going in.

The side gig is the greatest thing on Earth. It will take you further than you ever imagine. Whoever though my practice would do taxes for Americans on the other side of the planet? Not me. Not even a wet dream. (Not even a wet dream.)

It started when I had a great business proposition for MMM that went beyond anything I could imagine. If I would have known how my life changed the second MMM interrupted my presentation three years ago in Seattle, I would have run from the room and never returned. You can’t mentally handle what the world has in store for you. You just have to take it as it come.

I’m still a farm boy from the middle of nowhere. Things like this don’t happen to people like me.

It was just a side gig, for Christ’s sake. What the hell went wrong?



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Keith Schroeder

3 Comments

  1. Jonathan on April 21, 2017 at 6:34 am

    Its hard to win if you don’t know the rules. I love that Wealthy Accountant knows all the rules when it comes to the tax code and consistently applies them to the FI community goals. Optimize Everything. I learn new information from each of his blog post and, Which is saying something because I have a pretty strong baseline due to my own blog/ podcast and the shear amount of time I spend researching FI hacks and Tax Hacks, but I suspect that Wealthy Accountant has years of material to “unpack” and I can’t wait to learn from him. An Accountant that’s focused on Tax Hacking for FI… How powerful is that. Wealthy Accountant presents his information in a clear, innovative, creative way that is easy to grasp and never boring. I look forward to each new blog post and look forward to getting him on my podcast where we can start to turn these amazing articles into conversations. Thanks Wealthy Accountant. We love having you in the FIRE community. Congrats on finishing Tax Season

    • Keith Schroeder on April 21, 2017 at 7:06 am

      And living, Jonathon. Not everybody makes it out the other side without a body bag.

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