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It started with a stack of invoices
Why I automated the most annoying process first — not the most impressive one.
Sunday evening, end of the month. 120 rows waiting in the hours spreadsheet. Eight clients. Three billing tiers. Two number ranges. A process that lives only in my head. Here we go again — my monthly highlight. I advise companies on digitalization and automation. By day. In the evening I sort time entries by hand — row by row: which project? which tier? billable or not? For years, my fix wasn't automation. It was perfection. One more column, one more naming convention, one more sticky note for the next invoice number.
The spreadsheet grew ever more elaborate; the end-of-month evening never got shorter. I hadn't solved the pain — I'd furnished it. By now it had curtains. The turning point was my own line in a client meeting: "Automate the process that hurts most first — not the one that sounds most impressive."
On the drive home it hit me: I'd been selling that sentence for years and never followed it myself. I had visions of AI-enabled consulting — and a stack of invoices. So: theory back in the drawer, invoices on the desk. The next thing to automate wouldn't be the exciting one. It'd be the annoying one: the monthly billing. T
hat unspectacular decision set off everything I tell in this series: the invoice automation became a company portal, the portal became a firm with a new colleague — one who never tires but forgets everything every night.
Told honestly, with real numbers and every failed attempt. I learned almost only from those.
A quick trip to the engine room
A bit of tech talk for the curious: the "system" was a single Excel file — database, workflow and archive in one. 20 columns, 2 separate number ranges, 3 billing tiers. A quarter is 295 time entries for us;
June alone brought 120. Every row categorized and assigned by hand — and the knowledge of how lived nowhere.
Back then a project lead, today at the controls
Years ago I coded myself. Since then I've led countless software and transformation projects — always to the same beat: gather requirements, get a quote, commission the build, test, bugfix, re-test.
That beat was spot on and still is. I just always sat at the head of the table — never at the controls. How radically that would change, I had no idea that Sunday evening.
What I wish I'd known earlier
Keep an "annoyance list" for a week: note every task that feels like waste. Just collect, don't fix. That list is your automation backlog — and the most honest project plan you've ever had. And: make a note — that list itself could be your first automation.
Automate your biggest pain, not your biggest vision.
my new colleague's first day on the job — and why his first success was exactly ten calendar entries.