Trello and I had a long run. Five years, hundreds of cards, dozens of boards, one for every client. It was the first piece of “real” software I ever used to run my business, and for a long time I thought it was perfect.

Then about eighteen months ago, I sat down to add up what Trello was actually costing me. Not the £10 a month subscription. The hidden costs. And the maths was bad enough that I migrated everything off within a quarter.

If you’re currently running client work in Trello, this might be useful.

What Trello is genuinely good at

Let me be fair to a tool I used and liked for a long time.

Trello is brilliant for visual task tracking. Drag a card from “To Do” to “In Progress” to “Done” and your brain rewards you with a little hit of clarity. It’s brilliant for solo or small-team workflows where you mostly need to remember what you’re doing this week. It’s brilliant for personal projects, content calendars, anything where the “thing being tracked” is genuinely just a task.

If those are your needs, stick with it. The rest of this article doesn’t apply to you.

What I was actually doing with Trello

Where it broke down for me was that I wasn’t really managing tasks. I was running an entire business pretending to be a task manager.

My workflow looked like this:

One board per client
Lists for “Quoted,” “Approved,” “In Progress,” “Awaiting Feedback,” “Done,” “Invoiced”
Cards for each piece of work
Custom fields for hours worked, deadline, budget
Comments containing the project’s entire history

This worked, in the sense that I could see things. But it had problems I learned to ignore:

Quotes weren’t really quotes. They were Trello cards with prices in the description. Sending one to a client meant exporting the description, copying it into a Google Doc, formatting it, exporting as PDF, and emailing.

Invoices weren’t really invoices. Same process. Card description → Google Doc → PDF → email → manual track of who’d paid → mark card as “Invoiced” → forget which clients still owed money.

Time tracking was bolted on. I used a separate timer tool, then manually entered the hours into a custom field on the relevant card. Half the time I forgot.

Reporting was impossible. “How much did I bill last month?” — open every client board, count the cards in the “Invoiced” column, add up the prices, hope I hadn’t missed any. I was running a business and I genuinely didn’t know how much I was making at any given moment.

The day it all clicked

The moment I knew Trello had to go was when a client emailed asking what their outstanding balance was, and it took me an hour to answer. An hour. Because I had to:

Find their Trello board
Find the cards marked “Invoiced”
Cross-reference with my bank statement to see which had been paid
Add up the unpaid ones
Email the answer

Any reasonable system answers that question in two seconds. Mine took an hour. That hour wasn’t an outlier — that was every quarterly check-in I did with every client, every time someone asked me a financial question.

I was paying for Trello (fine) and Google Workspace (fine) and a time tracker (fine) and an accounting tool (fine) and stitching them all together with my own time, which was the actually expensive bit.

The migration

Migrating off Trello was less painful than I expected. Three steps:

Export each board as JSON or CSV. Trello makes this straightforward.
Identify what’s actually a quote, what’s a job, and what’s an invoice. Most of my cards mapped cleanly to one of those three.
Import them into the new system, structurally. So a card called “Brand identity for Acme — £4,500” became a quote with line items, which became a job with tasks, which became an invoice. Same record, three states.

The whole migration took a long weekend. The benefit hit immediately the following Monday.

What changed in the first month

Two things, mostly.

First, the financial questions had instant answers. Outstanding balance per client, billed-this-month, average days-to-payment — all visible without me opening anything. The hour I used to spend assembling each answer was gone.

Second, I stopped losing things. The shape of work in Trello — board, list, card — turned out to be very good at letting cards quietly slip into “I’ll get to it later” purgatory. The new system pinged me when something had been in a stage too long. Quotes stopped expiring without me knowing. Jobs stopped sitting “awaiting client feedback” for three weeks because I’d forgotten to chase.

The honest downside

I miss the simplicity. Trello has an interface my parents could use. The new system has more in it — pipelines, quotes, invoices, automations, reporting — and that takes a few hours to learn properly.

But “more capability with a learning curve” beats “less capability that I’ve now outgrown.” The frustration of being limited by your tool is worse than the frustration of learning a new one.

Should you switch?

The test is the same as the Notion one I wrote about. If someone asked you “what’s our outstanding balance across all clients right now?” — could you answer in five seconds?

If yes, your tool is fine. Stay where you are.

If no, you’re probably ready for something that treats your work as a connected business, not a series of disconnected boards.

stedd.io is what I switched to. The migration story above is genuinely how it went.