Calendly Culture
Are We Scheduling Ourselves Out of Connection?
Originally published on my Blogger site on May 16, 2025. Preserved here on Substack.
Here’s something that hit me recently. Harder than I expected.
I started reaching out to old colleagues. People I used to just call. You know the kind. Ring them up, say hey, catch up for a bit. Sometimes it turned into a new idea or an unexpected opportunity. Sometimes it was just a good conversation.
This time, I didn’t get conversations.
I got links.
“Here’s my Calendly.”
“Schedule a 15-minute slot.”
“Pick a time that works.”
Click here to become an obligation on my calendar.
Look, I get it. We are all busy. Calendly is efficient. I use it too. But let’s be honest. When did catching up with another human start feeling like booking a root canal?
That moment surfaced something deeper for me. A realization that we have professionalized almost everything, including friendship. Connection is now filtered through tools built for efficiency, and somewhere along the way, the human part has been edited out.
I want to unpack that. Not to bash tech. I love automation when it serves us. But to ask some uncomfortable questions.
Have we over-optimized the way we connect?
Is convenience costing us warmth, trust, or opportunity?
What happens when relationships get reduced to calendar slots?
This is not a rant. It’s a reflection. Maybe even a small wake-up call for me, for you, for anyone navigating this strange digital dance where every conversation begins with a link.
Let’s talk about Calendly Culture, and why it might be time to bring a little humanity back to the schedule.
From Cold Calls to Calendar Links: The Evolution of Professional Networking
There was a time, not that long ago, when “let’s catch up” actually meant catching up.
You would dial someone’s number. Maybe leave a voicemail if they didn’t answer. And then suddenly you were in a conversation that wandered from work to life to that random video you both saw years ago. No friction. No formality. No availability grid.
Now you send a message and, almost instantly, a scheduling link lands in your inbox.
No shade to the tool itself. It’s useful. But it also sends a signal. This isn’t a conversation. It’s a booking request.
Professional networking used to have texture. It was fluid, spontaneous, sometimes a little messy. That messiness was part of the magic. Today it is optimized, templated, and timestamped. Everyone is guarding their time like a startup pitch, and you are just another request in the queue.
Somewhere between remote work becoming default and time-blocking becoming doctrine, we stopped leaving space for unstructured connection. That shift may be more expensive than we think.
This is not about nostalgia for phone calls or walking meetings. It’s about trust. About those small moments that only happen when no one is watching the clock or counting minutes.
The tools we built to protect our time are quietly reshaping how we value each other’s. When every interaction has to pass through a scheduling filter, we are not just removing friction. We are removing the signal that says, “You matter enough for me to just reach out.”
So yes, we have evolved. We have streamlined. But in doing so, we may have sterilized a core part of what makes professional relationships work.
The question is whether we are actually okay with that.
Why “Let’s Chat” Now Requires a Scheduling App
Let’s be honest. When someone drops a Calendly link into a casual conversation, it has a vibe. And it is not always a warm one.
People mean well. It is convenient. Everyone is juggling too much. Still, when the response to “Hey, want to catch up?” is “Here’s a link to book me,” it can feel transactional.
It’s like saying, “I’m open to connecting, but only if you pass through my scheduling firewall first.”
Calendly solved a real problem. Endless email threads, time zones, meetings that never happened. But in solving that problem, something else got stripped away.
There is a subtle power dynamic embedded in these tools. Sending someone your link, especially someone you already know, can unintentionally communicate, “I’m the one in demand. You do the legwork.” What could have been a simple five-minute call suddenly feels like applying for a slot at the DMV.
It’s especially jarring with people who used to text you or call while walking their dog.
Maybe this is just how things work now. Maybe everyone is trying to protect their bandwidth and avoid burnout. I respect that. But when even our most human interactions get outsourced to an app, something gets lost.
Warmth. Spontaneity. The quiet message that says, “You matter enough for me to meet you halfway.”
Calendly has its place. I am not advocating a return to random cold calls like it’s 2009. But there is a difference between using a tool for efficiency and letting it define how we value a relationship.
Because if “let’s chat” requires a form, an open Tuesday three weeks out, and an automated reminder, we are not really chatting anymore.
The Hidden Cost of Efficiency: Losing the Human Touch
Here’s the part we rarely say out loud.
We have optimized ourselves into emotional flatlines.
Yes, it’s impressive that we can schedule a meeting in thirty seconds. But what disappeared in that speed?
The “How are you really doing?”
The pause.
The vibe check.
The chance to be more than a calendar entry.
Efficiency is seductive. I get it. I love a good flow state as much as anyone. But the more we automate the connective tissue between us, the more brittle it becomes.
That small friction we removed, asking if now is a good time, sensing someone’s energy, letting a conversation breathe, used to be a feature. Not a bug.
Now conversations feel scripted. Outreach feels templated. Sometimes an assistant or an AI sets things up before you even speak. And you find yourself thinking, can I just talk to you, not your system?
There is something deeply human in the inefficient moments we engineered away. The spontaneous check-in. The unplanned thirty-minute detour. The moment someone opens up because the conversation was not boxed into fifteen minutes.
Tools are not the problem. Pretending they are neutral is.
When we default to structure over sincerity, we send a message, even if we don’t intend to. “I’ve optimized everything, including you.”
That sounds dramatic. Maybe it is. But ask yourself this. When was the last time you had a real conversation that wasn’t framed by a countdown timer?
We are so focused on protecting our time that we have started commodifying the people in it. The cost is not just missed connection. It is trust. Depth. Momentum. The things that never show up in productivity metrics but define real relationships.
Efficiency delivers output. Connection builds legacy.
Are We Optimizing Ourselves Out of Meaningful Conversations?
At some point, the line between productivity and disconnection blurred.
We are all optimizing. Time-blocking. Tool stacking. Automating workflows. I am not immune. I love optimization loops.
But I keep coming back to this question.
When everything is optimized, where does the meaning go?
Connection has become a KPI. Every call needs an agenda. Every conversation needs a deliverable. Every message gets reduced to, “What’s the ask?”
There is a place for structure. Not every conversation needs depth. But when every interaction is flattened into a calendar slot, we lose unpredictability. And unpredictability is where trust, creativity, and collaboration actually live.
Here’s an analogy. In physiology, not all stress is bad. Some friction triggers adaptation and growth.
Conversation works the same way. A little spontaneity. A little discomfort. That is often where the breakthrough happens.
When we optimize every inch of communication for efficiency, we remove the space where surprise and insight live. No randomness. No misfires. No magic.
Some of the most important ideas, friendships, and collaborations in your life did not come from a scheduled fifteen-minute call. They came from the extra five minutes. The laugh after the meeting. The question that came once the agenda ended.
Use the tools. Sync the calendars. But remember this.
Your most valuable asset is not your time.
It’s your presence.
And presence is not optimized. It is felt.
Bringing Back Warmth: Human-Centered Networking in a Digital World
If Calendly is not the villain and tech is not the enemy, where do we go from here?
We adapt. We change how we use the tools, not just which tools we use.
The answer is not burning calendar apps or cold-calling people like it’s the late nineties. It is layering back what got lost. Warmth. Intention. Humanity.
It is about how you show up, not just when.
Here’s what I’ve been experimenting with.
Instead of dropping a link with no context, I add a sentence. “Would love to catch up. Totally understand how busy things are. Here’s my link, but happy to meet however works for you.” That one line changes the tone. It feels like an invitation, not a command.
Sometimes I skip the link entirely and send a short voice note. Thirty seconds. No scheduling. Just, “Hey, thinking about you. Want to connect?” It lands differently, especially in a world full of automated messages.
If I am trying to nurture a relationship, I send a quick video message. Not polished. Not produced. Just human.
Human-centered networking is not about more effort. It is about more presence. That pause before hitting send. That sentence that says, “I see you, not just your title.”
You do not need to manufacture warmth. You just need to stop outsourcing it.
In a hyper-productive, automated world, this approach can feel excessive. That is precisely why it works.
People do not remember perfect pitches. They remember how you made them feel.
So keep the tools. Just wield them like someone who values time and people.
Wrapping Things Up: Making Space for Serendipity Again
This post may have started with a few scheduling links, but it is really about something bigger.
It is about noticing how connection slowly turned into coordination. How spontaneity got replaced by structured availability. How “let’s catch up” now requires multiple clicks, confirmations, and reminders.
We did not plan for this. But here we are.
I am not suggesting we abandon modern tools or go fully analog. I am suggesting we leave room for the unexpected. White space between calendar blocks.
Because no app can replicate an unplanned conversation that sparks an idea.
An unscheduled call that rebuilds trust.
A casual message that opens a door neither of you knew existed.
Serendipity needs space. And space does not always fit into a thirty-minute slot.
As we navigate an AI-augmented, hyper-efficient world, maybe the real flex is staying human.
Bringing warmth back into cold workflows.
Letting presence win over productivity sometimes.
Reaching out not because you need something, but because you felt like it.
So here’s my ask. This week, reach out to someone without a link. No agenda. No calendar invite. Just check in. Say something real. Make it a little awkward.
Let’s bring the human back.
References
Malkoc, S. A., & Tonietto, G. N. (2022, August 23). The Case Against Scheduling Your Fun. The Art of Manliness.
https://www.artofmanliness.com/living/leisure/the-case-against-scheduling-your-fun/Blair, L. (2022, July 1). Go ahead, be a little spontaneous. Vox.
https://www.vox.com/even-better/23172589/spontaneous-benefits-scheduleThriveworks. (2024, April 12). Understanding Transactional Relationships: Insights and Impact.
https://thriveworks.com/help-with/relationships/transactional-relationships/Kao, W. (2023, December 13). The unspoken power dynamics of Calendly. Wes Kao’s Newsletter.
Medens Health. (2024, November 7). Human Connection in the Digital Age.
https://www.medenshealth.com/blog/human-connection-in-the-digital-ageLüdtke, T., et al. (2023, March 4). The importance of high quality real-life social interactions during the pandemic. PubMed.
https://pubmed.ncbi.nlm.nih.gov/36871079/