I spent $420 on to-do apps. I ended up back in Google Calendar.

Nineteen to-do apps. $420 in subscriptions in a year.

Google Calendar was the one I kept. I thought I just wasn’t good at keeping things organized. Looking back, keeping my to-dos and my schedule in separate places was wearing me out.

Find the task in one app. Open the other to check the time. Put the two together in my head. Several times a day.

At first, picking a new app was fun

I’m a freelance photographer working with a few teams. Brand shoots, client meetings, and plenty of time on my own selecting, editing, and delivering photos.

I made project lists in my to-do app. Flagged urgent work. Checked things off. One app looked great; another had a list setup I liked. I changed colors and rearranged the view.

Finding an app that felt like mine was fun. I felt like someone who had things together.

At first.

“Are you free Wednesday?” shouldn’t have taken two apps

A designer I work with asked whether we could talk about the next shoot on Wednesday afternoon.

I opened Google Calendar. Nothing there. I was about to say yes, then opened my to-do app too.

Oh. Those photos I needed to deliver Friday. Wednesday was when I’d meant to select and edit them.

The work was on my list. It wasn’t on my calendar. The designer had checked my shared calendar and reasonably figured I was free.

This kept happening.

• The shoot went in Google Calendar.
• The shoot preparation went in the to-do app.
• The delivery deadline went in the to-do app too.
• The time I needed to select and edit photos stayed in my head.

Each app looked organized on its own. But “Am I free Wednesday?” still took some figuring out.

Two apps. I was the one putting the day together.

In the morning, I opened the calendar. What time was the meeting? Then the to-do app. What needed finishing before it?

A new message came in. Back to the calendar. Wait, what else did I need to do that day? Back to the list.

Getting the dates wrong wasn’t the whole problem. Even when I’d entered everything correctly, I still needed both places.

New work meant another small decision. Is this a to-do or an event? If I put it here, do I need it over there too?

On a busy day, even that felt like effort. I’d put it somewhere and get back to work. Later, I had to remember where.

I’d started using these apps so I wouldn’t have to remember everything. Now remembering what lived in each app was part of the job.

A new app helped for a few days. Move the lists, set it up, decide this was the one. Get busy and end up in the same place.

The money bothered me. The hours I’d spent doing this over and over bothered me more.

Fine. Delete the to-do apps. Keep Google Calendar.

Without a to-do app, things felt a little off. Sometimes inconvenient.

Without my calendar? I miss a client meeting. Arrive late to a shoot. Book two things at once. I can’t work like that.

Colleagues used my shared calendar to arrange meetings too. The choice was pretty clear.

I deleted the to-do apps and started cramming the work into Google Calendar.

“Deliver photos by Friday” went there too. I didn’t know when I’d send them yet. I just needed to see the reminder in Friday’s column.

Eventually, the calendar looked like this:

• Tuesday, 2 p.m. — client meeting.
• Wednesday — select photos.
• Thursday, 10 a.m. — new brand shoot.
• Friday — deliver edited photos.
• Update my portfolio sometime… put that on next Monday for now.

Appointments, deadlines, things I might do someday. Everything was in one place, but now I had to work out what each entry actually meant.

Had I actually set aside time for “select photos,” or just left myself a reminder? Was I really updating the portfolio next Monday?

Still, I didn’t want to maintain two apps again. I made it work, awkward as it was.

This time, I told the AI before organizing anything

So I was skeptical when I tried thrw. Was I really about to give myself another app to maintain?

I connected Google Calendar to thrw, opened its AI chat, and put in the week all at once.

help me sort out this week
client meeting tues 2 to 3
new brand shoot thurs 10 to 1
need to send photos from the last shoot by friday
before that gotta pick the photos so block wed 4 for an hour
pack lenses and memory cards the day before the shoot
also want to redo the portfolio homepage but no date for that yet

Previously, I’d have opened the calendar for the appointments, the to-do app for the preparation, then the calendar again to block off work time.

This time, I sent one message.

Here’s what the AI made of it.

• Client meeting — Tuesday, 2–3 p.m.
• Brand shoot — Thursday, 10 a.m.–1 p.m.
• Select photos for delivery — work time Wednesday, 4–5 p.m.
• Pack lenses and memory cards — preparation due Wednesday.
• Deliver edited photos — due Friday.
• Update the portfolio homepage — no date.

It had separated appointments, time I’d set aside to work, a delivery deadline, and an idea with no date.

I hadn’t filled out six separate forms. I’d told it what my week looked like, and the result was a plan I could actually use.

I checked the proposed changes and applied them. Then opened Google Calendar. Once it synced, the meeting, the shoot, and Wednesday’s photo-selection block were there.

Wait. I’d just told it what was going on, and this was the result?

My calendar finally showed the work between meetings

The next time someone checked my availability, they had a better picture.

The 4–5 p.m. photo-selection block appeared on the Google Calendar I shared with the team. They could see I was working then before I had to explain it. (Meetings aren’t the only work.)

The Friday delivery stayed on my to-do list with its deadline. The portfolio stayed there without a date. I didn’t need to put everything on the calendar just to remember it existed.

I checked calendar sharing and event visibility for the things the team needed to see. My personal to-dos didn’t all need an audience.

I prepared for the next shoot the same way. Work that came up in conversation, appointments already agreed on, ideas without dates yet. I stopped trying to classify everything before entering it. Told the AI together, then checked what came back.

The busier the week, the more I noticed the difference. Instead of switching apps and filling out dates for every new item, I could talk through the week once.

I still use Google Calendar. I spend less time bouncing between it and a to-do app, trying to assemble my day in my head.

Now when someone asks, “Are you free Wednesday?” I don’t start by hunting for the place I wrote down my work.