Why double-bookings happen and how to avoid them

I used to think double booking was just part of the job. A meeting here, a client call there, and suddenly, two things are fighting for the same hour in my calendar. Sound familiar?

The truth is, overbooking doesn’t happen because we’re careless. It usually comes from trying to do too much with too little time—and too many places to manage it all. If you’re like me, you’ve got emails, calendar apps, Slack pings, and probably a few sticky notes somewhere in the mix. It’s no wonder things get messy.

The real reason double-booking happens

In my experience, overbooking usually comes from one of three things. First, there’s having too many calendars—personal, work, shared projects—and not keeping them in sync. Second, there’s saying “yes” to something without checking what’s already on the books. Third, and maybe most common, is not having a simple way for others to book time with me that actually reflects when I’m free.

Before I sorted this out, I missed calls, rushed meetings, and more than once had to send the dreaded “sorry, I double-booked” message. It wasn’t just embarrassing. It also made me look less professional than I wanted.

What finally helped me fix it

What changed for me wasn’t more discipline. It was switching to Doodle. I haven’t had a single overbooking since. Doodle connects to all my calendars and only shows my clients the time slots where I’m truly available. That means no overlaps, no double-bookings, and no surprises.

Instead of hoping things don’t conflict, I can finally trust that what’s on my calendar reflects reality. It saves me time, but more importantly, it saves me stress.

A small change that makes a big difference

If you’re running a business, juggling clients, or managing a full teaching schedule, overbooking can feel like just one more fire to put out. But it doesn’t have to be. The proper scheduling setup turns the chaos into something manageable. You don’t need to overhaul your entire system—pick a better time management method.

I recommend Doodle. It’s the tool I use when I want people to book time with me without all the back and forth. It’s simple, reliable, and actually respects my calendar. I don’t worry about double-booking anymore—and that’s been an enormous relief.