I switch tools, perhaps too much.

Over the summer, I switched from Dropbox to Google Drive because they told me the plan I’d been using for my business for a decade suddenly wasn’t for business anymore.

I switched from Bonjoro to Senja recently because it cut several steps out of my workflow.

And now I’m considering moving from Cal.com BACK to Calendly.

Why?

Some time between when I signed up and a month ago, they turned reminder email editing off for the free plan.

I get that I’m using a free tool — the only paid options are for teams and enterprises.

But the problem is I made edits to those emails, and now I can’t change them at all.

Even worse, support told me there is “nothing they can do.”

This is software, not a terminal disease. Surely there’s something they can do.

But that’s beside the point. The real question is, should I switch, or not?

Weighing the Pros and Cons

To figure out if it’s worth me moving from Cal back to Calendly, let’s weigh the pros and cons:

Pros of switching

• I can edit these emails that I need to edit.
• There’s pretty strong feature parity between them, so I won’t be missing something I absolutely need.
• Paid software is generally more stable than free software. I mean…I don’t have much room to complain about something I’m not paying for, right?

Cons of switching

• It will take me time to move all of my calendars over and test them (est: 60-90 minutes)
• I’m going to have to rebuild and test automations — potentially moving them to Zapier from Make (est: 90-120 minutes)
• My costs increase from $0 to $120
• I will have to update all of the places where I use Cal.com links or embeds, and replace them with Calendly (est: 30-45 minutes)

Luckily for that last one, I use redirects (a lesson learned by a guy who switches too much), so it’s a lighter lift than it could have been.

All-in, I’m looking at about 4 hours of work + $120 out of pocket.

How to Figure Out if You Should Switch

So what should I (and you) ask to figure out if switching tools is worth it?

1. Does the pain of using the current tool outweigh the effort to switch?
2. Does the new tool have a feature you absolutely need?
3. Is the level of effort to switch nearly zero?

Based on that criteria, I’m not switching. The effort is too high and the benefit is not there. If we convert my estimated time to billable hours, I’m looking at it costing over $800 to move.

What should I do instead?

Upgrade to Teams for $15 for one month to make the changes to the emails, and then downgrade when I’m satisfied with them.

What about you? When do you know it’s time to switch tools?