The First Time You Had to Do Your Own Expense Report

In my school job, I never thought much about expense reports. I’d submit receipts to the business office, maybe fill out a form, and the rest just happened. Money appeared in my account. The numbers reconciled somewhere. Someone else made sure the math worked, and the records were kept properly. It was like magic, except it wasn’t magic at all. It was an entire team of people doing work I barely noticed.

Three and a half years into running my own business, I notice it now.

The Invisible Infrastructure

Here’s something nobody warned me about when I made the leap from school employee to entrepreneur: you are now the finance office. You are both the accounts receivable and accounts payable departments. You are the person who tracks expenses, sends invoices, follows up on late payments, manages receipts, figures out quarterly taxes, and tries to remember which software subscription renewed this month and which one is hitting next week.

All those systems that hummed along in the background at your school? The ones you never had to think about because someone else was thinking about them? Those are your responsibility now. Every single one.

I knew, intellectually, that running a business meant handling the business side. But knowing it and living it are entirely different experiences. The sheer volume of small financial tasks that pile up when you’re on your own is something I genuinely did not anticipate.

Everything Takes Longer Than You Think

The other thing I underestimated is how long all of this takes when you’re not an expert. At school, the business office had people who’d been doing this work for years. They had systems, institutional knowledge, and the kind of efficiency that comes from repetition.

I had none of that. I had Google searches, YouTube tutorials, and a lot of trial and error. Setting up accounting software that someone with experience could configure in an afternoon took me the better part of a week. Tasks that should be routine still require me to stop and think, to double-check that I’m doing it right, to fix the mistakes I made because I didn’t fully understand what I was doing the first time.

This isn’t a complaint. It’s just the reality. When you leave the infrastructure of a school, you’re not just losing colleagues and a steady paycheck. You’re losing an entire support system you probably didn’t even realize was there.

The Learning Curve Is Real

I eventually got smart enough to hire an accountant, which was one of the better decisions I’ve made in this journey. I also invested in software to handle some of the tracking and invoicing I was doing manually (badly) in spreadsheets. These things helped. A lot.

But even with help, there’s a baseline level of financial literacy that running a business requires, and I’m still building it. I’m still learning terminology I never needed to know before. Still figuring out which expenses go in which category and why it matters. Still discovering things I should have been doing six months ago that nobody told me about, because why would they? Everyone assumed I already knew.

If you spent decades in education, you probably didn’t spend a lot of time thinking about invoicing or bookkeeping or the finer points of estimated tax payments. I certainly didn’t. And now I think about them all the time.

A Heads-Up, Not a Warning

I’m not sharing this to scare anyone away from the leap. The freedom and autonomy of running your own business are worth the administrative hassle. But I do think people making this transition deserve an honest picture of what “being your own boss” actually entails day-to-day.

It’s not just the exciting parts. It’s not just landing clients and doing the work you’re passionate about. It’s also the unglamorous hours spent reconciling accounts, chasing down receipts, and figuring out why your numbers don’t match up.

If you’re still in a school job and considering the move, take a moment to appreciate the finance office. The HR department. The IT team. All those people are doing work that makes your job possible without you ever having to think about it. You’re about to become all of them, at least until you can afford to hire help.

The Expense Report Moment

There’s a specific kind of moment that captures this transition for me. It’s the first time you realize that nobody is coming to handle the thing you used to hand off to someone else. The first time you sit down with a pile of receipts and think, “Okay, what do I actually do with these?”

That moment is humbling. It’s also clarifying. You start to understand just how much invisible labor was happening around you, and you develop a new respect for the people who do this work professionally.

I’m still learning. Still getting better at the back office stuff. Still occasionally discovering that I’ve been doing something wrong for months.

But at least now I know where the expense reports go. They go to me.