Grateful?
What a 1969 computer system, a lost tax return, and zero privacy reminds me about how we treat our customers.
I showed up at 1:20 for a 1:30 appointment — $7 for parking, paid upfront before you even walk in the door. That should’ve been my first sign.
Turns out, 1:30 just gets you through the door. From there, you are given a number and wait. Like a deli counter, except instead of ordering your Italian sub, you’re waiting to find out how much money the federal government has lost track of.
The cubicles are supposedly private with half walls, but the noise carries across the room revealing all of the tax secrets being discussed. Everything — and I mean everything — can be heard. The guy in the next cubicle was trying to understand why he was being penalized, and the agent’s tone was the kind of condescending that makes you grip the armrest and breathe through your nose. I sat there thinking, this is what we’re doing? This is how we treat people who are trying to get it right?
But I wasn’t there to observe. I was there to fight.
Here’s the short version: the IRS has been losing my files for years — literally every few years from 2012 forward. Even when they’re digitally filed. Even when — and this is the part that makes me want to scream — I send them via certified mail because I no longer trust the system.
My 2024 return had to go by mail because one specific form couldn’t be filed electronically. Fine. So we sent it certified. I have the tracking number. I have proof it was signed for. Delivered. Done.
Guess what? They say they never received it.
For the love of God. Please grant me patience.
So today, I came armed. Four years of issues. Tracking numbers. Digital verification receipts. Every piece of documentation I could carry. And here’s the maddening part — the moment I laid the proof on his desk, he found the returns. In their own system. They were there the whole time. Now they’ll be processed.
But it doesn’t end there. Because while they were “missing” my returns, they were also applying penalties and interest. And taking refunds from other years to pay toward the years they said I owed — years where they already had my money but said they didn’t. So they took money I was owed to cover money they already had.
If you’re confused, welcome to the club.
The gentleman said I can now reach out to a taxpayer advocate through a separate organization and open a case. Thirty to forty-five days from now, I can start petitioning.
Let that land. I did everything right — filed correctly, sent it certified, kept the receipts — and the resolution is that I get the privilege of petitioning to prove it.
At some point during our conversation, I made a comment about the level of patience he must have. He told me he’s worked at the IRS for 28 years and that their system can’t be hacked because it’s from 1969.
He said this like it was a good thing.
He’s not wrong about the date. The IRS’s primary tax processing system — the Individual Master File — was built in the late 1960s. It runs on COBOL, a programming language so old that the government is running out of people who know how to maintain it. The GAO has reported that this system won’t be fully replaced until 2030 at the earliest — at which point it will be over 60 years old. A third of the IRS’s applications are considered legacy technology. Some are running software 15 versions behind current updates.
And they’re proud of this.
Regardless of where you stand politically, I think most of us can agree on one thing: the tax code needs to be simpler, and the system that administers it needs to work. This isn’t a left or right issue. It’s a functioning government issue.
But here’s what really gets me — and this is where I need to talk to the business owners reading this.
I once followed a well-known tax advisor online. Attended her webinars. Was genuinely impressed — until she said something that I still can’t shake. The gist was that we should feel grateful to have businesses successful enough to pay taxes.
Grateful.
Let me tell you what gratitude looks like for a small business owner. It looks like navigating a system that wasn’t built for you. It looks like watching corporations — the Amazons and Teslas of the world — pay effective federal tax rates in the single digits while you’re writing checks that make your eyes water. In 2025, four of the largest tech companies in America collectively paid about 4.9% in federal corporate income taxes on $315 billion in U.S. profits. Meanwhile, you’re a small business owner trying to figure out if your quarterly estimated payment was enough to avoid a penalty.
The playing field isn’t just uneven. It’s a different sport entirely.
Private equity firms restructure to minimize tax exposure. Family offices route capital through favorable jurisdictions. Corporations get years of tax incentives to relocate to a new city. And the small business owner — the one creating jobs in their community, the one who can’t afford a team of tax attorneys — is left holding the bag.
Don’t tell me to be grateful. Tell me to be smart.
So let’s be smart. Here’s what I want you to think about if you’re building a business right now:
Invest in a great accountant early. Not eventually. Not when you “get bigger.” Now. The difference between a good accountant and a mediocre one is hundreds of thousands of dollars over the life of your business. Your goal is to keep as much money in your business — or reinvested in your business and your team — as legally possible. Master that, and you’ll rinse and repeat.
A big name doesn’t mean a better fit. I once worked with a firm that had the prestige, the price tag, and all the bells and whistles. I paid a small fortune. And they weren’t advocating for me as a small business owner — they were running me through the same playbook they used for everyone. Bigger doesn’t mean better. Better means better.
Ask the hard questions upfront. What’s their philosophy on tax strategy? How will they advocate for you? If you get audited — will they hold your hand through it or hand you a bill and wish you luck? And here’s a gut check most people don’t think to ask: how many of their clients have been audited in the past ten years? Firms with higher-than-average audit rates become automatic targets — and every client on their roster gets pulled into that spotlight. You need to know this before you sign.
Outsource your monthly bookkeeping. This is a no-brainer. For usually $100 to $500 a month — depending on the number of accounts and transactions — you can have an outside service handle your bookkeeping and reconciliation. Always maintain control of your money — nobody signs anything but you — but the paperwork? Let someone else handle it. If you need a referral, reach out. The bookkeeper we use only takes clients by referral and word of mouth. She is good, fast, and on track.
Know what’s inevitable — and what’s negotiable. Payroll taxes, real estate taxes, licensing fees, property taxes — those are coming no matter what. But your federal tax strategy? That’s where the game is played. Pay what you are legally obligated to pay. Not a penny more. That’s not being shady. That’s being a responsible business owner.
And if you need a recommendation on who to work with — let me know. I’ll make the introduction personally. Their motto is literally #IRSSucks.
Now — here’s the part I didn’t expect to come out of today. But it might be the most valuable thing I took from that building.
Sitting in those uncomfortable chairs waiting for my turn to go into the little cubicle, and watching how the IRS interacts with the people it serves, I couldn’t stop thinking about customer experience. About our businesses. About how easy it is to let your systems become someone else’s version of that waiting room.
Bragging about a system from 1969 is not a flex. Technology is moving at a speed that makes two years ago feel like a decade. And yet, how many of us are running our businesses on processes we haven’t looked at in months — or years?
Put yourself in your customer’s shoes. Not once a year. Not biannually. Every month. What is it like to navigate your system? How are they introduced to you and your company? How are they onboarded? Do they feel valued — or do they feel like they’re taking a ticket and waiting?
If your customer has to ask you a question that you should have anticipated, you’ve already missed the opportunity to wow them. This is especially critical in service-based businesses, where the experience is the product.
Shop your own service. Shadow your team — in person and from a distance. Watch what’s actually happening, not what you assume is happening. Does the experience match what you advertise?
And never — never — underestimate the power of a proper introduction and a genuine thank you. The basics aren’t basic. They’re everything.
I left the IRS today frustrated. Some things were resolved, but the effort was still put back on me. I’m the one who gets the luxury of petitioning. I’m the one who now needs to enlist an advocacy organization to fight on my behalf for money the government already has.
Make it make sense.
But here’s what I know. This isn’t the first impossible system I’ve had to navigate, and it won’t be the last. The IRS didn’t break me today — it reminded me why I build the way I build. With receipts. With documentation. With the kind of stubborn, detailed, refuse-to-quit energy that has gotten me through worse.
And if you’re building something right now — a business, a life, a comeback — take this from someone who spent her Tuesday afternoon in a government cubicle proving that the mail was, in fact, delivered:
Keep the receipts. Fight the fight. And build something they can’t break.
If this resonated, subscribe to The Jenn Files. I write about business, money, resilience, and grit — cutting through the noise so you can build something that can’t be broken.