The Client I Kept Billing During the Worst Month of My Life

The month everything fell apart

My dad went into the hospital in October. Nothing dramatic to explain here. Just the kind of thing that rearranges your entire life in about four hours.

I kept working. I had to. Rent doesn't care about emergencies, and neither do retainer clients who expect deliverables on Friday regardless of what happened to your week.

I was logging in from waiting rooms. Answering emails from parking garages. Finishing a client deck on my phone while sitting in a hallway that smelled like floor cleaner.

I thought I was keeping up. I was not.

What I didn't notice until it was over

When things settled down about three weeks later, I opened my time tracker and looked at October. There was almost nothing there.

I had worked. I know I had worked. I had the Slack messages to prove it. I had the delivered files. I had the client replies saying thanks.

But I had almost no tracked hours because I had no system that worked when I wasn't functioning at full capacity.

At the time, I was using a browser tab for time tracking. You had to remember to open it. You had to remember to start it. You had to remember to stop it and assign it to the right project.

In a normal month, that's mildly annoying. In October, it was invisible. I simply didn't do it. I was in survival mode and the tab never opened.

The invoice I couldn't write

At the end of the month I tried to invoice three clients. I had partial logs, some notes in a notebook I half-remember writing, and a vague sense of how much I had done.

I billed about 60 percent of what I actually worked. Maybe less.

I didn't fight for the rest because I couldn't prove it. I had no screenshots. No timestamps. No log entries. Just my memory, which was not reliable that month for obvious reasons.

I lost somewhere between $2,800 and $3,400. I'll never know the exact number because the data doesn't exist.

The thing I changed after

I needed a tracker that worked when I wasn't thinking about tracking.

The browser tab was out. I needed something that lived on my desktop. Something I could start with one click and forget about. Something that would keep running even if I closed everything else and walked out of the room.

I also needed screenshots. Not because I was worried about clients doubting me. Because I needed to doubt myself less. Having a record that said "at 2:14pm on October 9th you were working in this document" is worth more than any handwritten note when you're operating on four hours of sleep.

Time-Trak ended up being what I switched to. The floating timer widget sits on top of everything. I don't have to go find it. I don't have to remember it exists. I just have to click it once and it runs.

The automatic screenshots meant that even on the days where I worked in a fog, there was a record. A real one. Timestamps and everything.

What I'd tell someone in a hard month

Your system needs to work when you don't.

Good months are easy. You're focused, you're remembering things, you're opening the right tabs. Any tracker works in a good month.

The test is October. The test is the week where you're holding things together with tape and still trying to deliver for clients who don't know anything is wrong.

If your tracker requires you to be at full capacity to use it, it will fail you exactly when you need it most.

I won't get that $3,000 back. But I haven't lost a month like that since, and it's not because my life got easier. It's because my system got simpler.

Track your time, bill every minute.

Time-Trak is a native Mac and Windows time tracker with a floating timer, automatic screenshots, and one-click invoicing.

Free during beta.

macOS + Windows · Floating widget · Auto screenshots