Calendly

Calendly claims it makes "finding time" a breeze, which immediately tells me everything I need to know about their relationship with the English language. If finding time were actually difficult, wouldn't we have solved temporal physics by now? But here we are, drowning in a sea of corporate speak that treats basic calendar functionality like it's some kind of revolutionary breakthrough. The homepage reads like it was written by someone who just discovered the concept of appointments and decided to evangelize about it with the fervor of a recent convert. "When connecting is easy, your teams can get more done" – a sentence so aggressively bland it could serve as the mission statement for every SaaS company that's ever existed.

The visual design follows that insufferable modern playbook where everything must be clean, minimal, and devoid of personality. White space everywhere, gentle gradients, and those goddamn rounded corners that have infected every interface since 2018. It's the digital equivalent of a WeWork office – professionally inoffensive and soul-crushingly sterile. The color palette screams "we hired a design agency that charges $200k for rebrands," all blues and whites that whisper "trust us, we're competent" while simultaneously putting you to sleep. Even their illustrations look like they were generated by an AI trained exclusively on stock photography from 2019. There's nothing technically wrong with any of it, which somehow makes it worse.

Functionally, Calendly does exactly what it promises, which is both its greatest strength and most damning weakness. Yes, it connects to six calendars. Yes, it automates scheduling. Yes, it integrates with every productivity tool your company already overpays for. But using it feels like being trapped in someone else's efficiency fantasy, where human interaction has been optimized into a series of dropdown menus and time slots. The "custom event types" feature is particularly soul-crushing – imagine reducing every possible human meeting to a template. Coffee with an old friend? There's a template. Performance review that might end your career? Also a template. It's functional in the way that a vending machine is functional.

The pricing structure, while not explicitly detailed on the homepage, lurks behind every "Pick the perfect plan for your team" button like a used car salesman's smile. They boast about serving "86% of Fortune 500 companies," which tells me their enterprise pricing probably costs more than my rent. The free tier exists solely to get you hooked before they start charging you monthly fees for the privilege of letting other people book time with you. It's the freemium model perfected: give away just enough functionality to make you dependent, then charge you for features that should have been included from day one. The whole business model depends on convincing people that coordinating calendars manually is somehow beneath them.

What bothers me most about Calendly isn't what it does wrong – it's how efficiently it does everything right while completely missing the point. Scheduling shouldn't need to be "revolutionized" or "simplified" or whatever other buzzword they're using this quarter. Sometimes the friction of coordinating schedules serves a purpose; it forces you to consider whether a meeting is actually necessary. Calendly removes that friction entirely, enabling the very meeting culture it claims to improve. It's a beautifully engineered solution to a problem that didn't need solving, executed with the kind of corporate precision that makes you long for something, anything, with a little more humanity baked in.