Calendly Culture: Are We Scheduling Ourselves Out of Connection?

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… ring them up, say hey, chat a bit, maybe spark a new opportunity or two.

Instead, I got links.

“Here’s my Calendly.”
“Schedule a 15-minute slot.”
“Pick a time that works for you.”

Just… click here to feel like an obligation on my calendar.

Look, I get it. We’re all busy. Calendly is efficient. I use it too. But let’s be real: when did catching up with a human start feeling like booking a root canal?

That moment triggered something deeper for me—a realization about how we’ve professionalized everything, including friendship. Connection is being filtered through tools designed for efficiency, and somewhere along the way, the actual human part is getting edited out.

I want to unpack that. Not to bash tech—I love automation when it serves—but to ask some real questions:

👉 Have we over-optimized the way we connect?
👉 Is convenience costing us warmth, trust, maybe even opportunities?
👉 And what does it mean when relationships get reduced to calendar slots?

This isn’t a rant. It’s a reflection. Maybe even a little wake-up call—for me, for you, for all of us navigating this weird digital dance where every conversation starts 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’d dial someone up, maybe leave a voicemail if they didn’t answer (remember those?), and the next thing you know you’re deep in a conversation that meanders from work to life to that random YouTube video you both saw back in 2014. No friction. No formality. No “please select a time from my availability grid.”

Now? You send a message and—boom—you get a Calendly link. No shade to the tool itself; it’s slick, sure. But it also signals something else: This isn’t a friendship, it’s a booking request.

Let’s zoom out for a sec. Professional networking used to have texture. It was fluid, spontaneous, sometimes a little messy—and that was the magic. Today, it’s optimized, templated, and timestamped. Everyone’s operating like their time is a startup pitch, and you’re just another meeting request in the queue.

Somewhere between remote work going mainstream and “time-blocking” becoming a religion, we stopped leaving space for unstructured connection. And honestly? That shift might be more costly than we realize.

It’s not just about nostalgia for phone calls or walking meetings. It’s about trust. About those little micro-moments that only happen when we’re not watching the clock or glancing at our calendars every five minutes.

And here’s the thing: the tools we’ve built to protect our time? They’re quietly reshaping how we value each other’s. When every interaction has to pass through a scheduling filter, we’re not just removing friction—we’re removing the signal that says, “You matter enough for me to just reach out.”

So yeah, we’ve evolved. We’ve streamlined. But in that evolution, we’ve also sterilized a part of what makes professional relationships work: the human part.

The question is… are we 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’s got a vibe. And not always the warm, fuzzy kind.

I know, I know. People mean well. It’s convenient. We’re all juggling ten thousand things. But still—when the response to “Hey, let’s catch up” is “Here’s a link to book me,” it hits a little… transactional, doesn’t it?

It’s like saying, “Sure, I’m open to connecting… if you can pass through my scheduling firewall first.”

And yeah, I get the other side too. Calendly was born out of chaos. Back-and-forth emails, missed time zones, meetings that never happened. Scheduling links cleaned that up. But in cleaning it up, they kind of cleaned out the soul of it too.

There’s a subtle power dynamic embedded in these tools. When you send someone your link—especially someone who knows you—it can unintentionally signal, "I'm the one in demand here. You do the legwork." And suddenly, what could’ve been an easy “grab five minutes?” now feels like applying for a time slot at the DMV.

It’s a weird shift, especially among people who used to just text you a time or randomly call you while walking their dog.

And maybe this is just how things work now. Maybe everyone’s just trying to protect their bandwidth and avoid burnout. I respect that. But when even the most human interactions get outsourced to an app… something gets lost.

Warmth. Spontaneity. That unspoken message of, “Hey, you matter enough for me to meet you halfway.”

So yeah—Calendly has its place. I’m not saying we should all go back to cold-calling each other at random like it’s 2009. But there’s a difference between using a tool for efficiency and letting it define how we value a relationship.

Because if “let’s chat” now requires filling out a form and finding an open Tuesday in three weeks… we’re not really chatting anymore, are we?

The Hidden Cost of Efficiency: Losing the Human Touch

Let’s talk about the thing nobody really says out loud:

We’ve optimized ourselves into emotional flatlines.

Yeah, it’s great that we can schedule a meeting in 30 seconds with zero back-and-forth. But you know what also got deleted in that speedrun?

The “Hey, how are things really going?”

The pause.

The vibe check.

The chance to be more than just a line item on someone’s Outlook Calendar.

Efficiency is addictive. I get it. I love a good time-blocked flow state as much as anyone. But the more we automate the connective tissue between us, the more brittle it becomes. That little bit of friction—reaching out, asking someone if now's a good time, sensing the energy on the other end—it used to be a feature, not a bug.

Now? We’ve smoothed it all out. Conversations are templated. Outreach feels scripted. Half the time it’s an AI assistant setting things up on someone’s behalf. Like, damn—can I just talk to you, not your robot?

There’s something deeply human in those “inefficient” moments we’ve engineered out. The spontaneous check-in. The unplanned 30-minute rabbit hole. The moment someone opens up because the conversation wasn’t rigidly time-boxed.

And look, I’m not saying throw away your tools. I use them too. But let’s not pretend they’re neutral. When we default to structure over sincerity, we send a message—even if we don’t mean to:

"I’ve optimized everything… including you."

That sounds harsh. Maybe even a little dramatic. But think about it: when’s the last time you had a real conversation that wasn’t framed by a countdown timer?

We’re so focused on protecting our time, we’ve started commodifying the people in it. And the cost? It’s not just missed connection—it’s trust. Depth. Momentum. All the things that don’t show up in a productivity report but make the difference between good networking and real relationships.

So yeah—efficiency gets results. But connection builds legacies.

Are We Optimizing Ourselves Out of Meaningful Conversations?

At some point, the lines between productivity and disconnection got blurry.

I mean, we’re all optimizing, right? Time-blocking. Stacking tools. Automating workflows. Hell, I’ve got peptides for brain performance and a PEMF mat to recover while I sleep. So trust me—I love a good optimization loop.

But here’s the thing I keep bumping into:

When everything’s optimized, where does the meaning go?

We’ve started treating connection like a KPI. Every call has to have an agenda. Every conversation needs a deliverable. Every invite gets boiled down to: “What’s the ask?”

And sure—there’s a place for that. Not every convo needs to be a soul dive. But if every interaction gets flattened into a slot on a calendar, we start stripping away the unpredictability—the humanity—that actually fuels trust, collaboration, even innovation.

Here’s a weird analogy, but roll with me:

In biohacking, we know not all stress is bad. Some friction—hormesis—is good. It triggers adaptation. Growth. Resilience.

Well, conversation’s kind of like that too. A little spontaneity? A little discomfort? That’s where the magic happens.

But when we optimize every inch of our communication flow for “efficiency,” we rob ourselves of that adaptive space. No randomness. No misfires. No breakthroughs.

We’re so focused on not wasting time that we forget the best stuff in life usually shows up unplanned.

Think about it—some of your best ideas, most important friendships, most pivotal collaborations… they didn’t come from a scheduled 15-minute Zoom call. They came from the extra five minutes. The unfiltered laugh. The question that came after the meeting ended.

So yeah, optimize your inbox. Sync your calendars. Use the tools. But don’t forget—your most valuable asset isn’t your time.

It’s your presence.

And presence doesn’t get optimized. It gets felt.

Bringing Back Warmth: Human-Centered Networking in a Digital World

Alright—so if Calendly isn't the villain and tech’s not the enemy, where do we go from here?

We adapt. We upgrade the way we use the tools, not just the tools themselves.

Because the solution isn’t to burn your calendar app or start cold-calling people like it’s 1998 (though, low-key, a random voice memo might hit different these days). It’s about layering back in what got lost—warmth, intention, humanity.

It’s about the how, not just the when.

So here’s what I’ve been experimenting with—and honestly, it’s made a difference:

• Instead of just dropping a link, I’ll add a line of context first. Something like, “Would love to catch up. Totally get how busy things are—here’s my link, but happy to work around your schedule if that feels better.” That one sentence? Shifts the whole vibe. Now it’s a conversation, not a command.
• Sometimes I skip the link altogether and just send a quick voice note. 30 seconds. No calendar needed. Just, “Hey, thinking about you. Want to connect?” It hits different. Especially now, when people are drowning in cold DMs and LinkedIn spam.
• And if I’m really trying to nurture a relationship? I’ll drop a custom video message. Doesn’t need to be fancy. Just authentic. Just... human.

Because here’s the truth: Human-centered networking isn’t about more effort—it’s about more presence. It’s that pause before hitting send. That two-sentence note that says, “I see you, not just your title.”

You don’t have to fake warmth. You just have to stop outsourcing it.

And yeah, in a world of hyper-productivity and auto-everything, showing up like this might feel “extra.”

But you know what? That’s the exact reason it stands out.

People don’t remember the perfect pitch. They remember how you made them feel.

So let’s not ditch the tools. Let’s wield them differently—like someone who knows the value of time but never forgets the value of people.

Wrapping Things Up: Making Space for Serendipity Again

So yeah… maybe this whole post started with a few Calendly links. But really, it’s about something bigger.

It’s about noticing how we’ve slowly replaced connection with coordination. How spontaneity got replaced with structured availability. How we turned “let’s catch up” into something that requires three clicks, two confirmations, and a reminder email just to make it onto someone’s radar.

We didn’t mean for it to get like this. But here we are.

Again, I’m not saying we torch our tools or go full analog. I’m just saying… maybe we leave a little room in our lives for the unexpected. A little white space between the blocks on our calendar.

Because you know what no app can replicate?

• That unplanned conversation that sparks an idea.
• That unscheduled call that rebuilds trust.
• That casual message that opens a door neither of you even knew was there.

Serendipity needs space. And space doesn’t always show up in a 30-minute time slot.

So as we keep navigating this fast, AI-augmented, hyper-efficient digital world, maybe the real flex… is staying human.

Maybe it’s bringing warmth back into the cold parts of our workflows.

Maybe it’s letting presence win over productivity once in a while.

Maybe it’s reaching out not because you need something… but because you just 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 weird, even.

Let’s bring the human back.

10 Years with Kanban: A Journey of Simplicity

A decade ago, I was introduced to a tool that would revolutionize how I approach work—Kanban. I started with Trello, moved through GitHub, and now I’ve integrated it into Notion. Over these years, I’ve come to realize that Kanban is more than just a productivity hack; it’s a philosophy of work management that remains as relevant in 2024 as it was when it first took shape.

What is Kanban?

At its core, Kanban is a visual system for managing work as it moves through a process. Originating from Toyota’s manufacturing line in the 1940s, Kanban was designed to improve efficiency and reduce waste by visualizing workflow and limiting work in progress (WIP). The word "Kanban" literally means "signboard" or "billboard" in Japanese, reflecting its emphasis on clear, visual communication.

But let’s strip away the jargon. Kanban is simply about making your work visible. It’s about knowing what’s being worked on, what’s up next, and what’s been completed. This visibility drives focus and clarity, helping you to prioritize effectively and avoid the chaos of multitasking.

How to Kanban: The Basics

Whether you’re leading a team or managing your own workload, Kanban can be a game-changer. Here’s how to get started:

1. Visualize Your Workflow: Start by mapping out the steps your work typically goes through—from the moment a task is conceived to its completion. In Trello, GitHub, Notion, or any other tool, this usually involves creating columns that represent different stages like "To Do," "In Progress," and "Done." For individuals, think of these columns as your personal task pipeline. By visualizing your tasks, you turn your workload into something tangible, making it easier to track progress and identify what needs your attention.
2. Limit Work in Progress (WIP): One of Kanban’s most powerful principles is limiting the number of tasks in progress at any given time. This focus prevents the cognitive overload of juggling too many things at once and pushes you towards completion before starting something new. As an individual, a good rule of thumb is to limit yourself to 1 to 3 "In Progress" tasks at a time. This way, you stay focused and ensure that each task receives the attention it deserves, ultimately leading to higher quality work and less stress.
3. Prioritize What Moves from "To Do" to "In Progress": With your WIP limits in place, the next crucial step is prioritization. Not every task in your "To Do" column carries the same weight or urgency, so it’s essential to determine which tasks should move into "In Progress" first. To do this, consider factors such as deadlines, the importance of the task, the potential impact, and any dependencies that might affect other tasks. By prioritizing effectively, you ensure that your most critical or high-impact tasks are addressed first, allowing you to maximize your productivity and achieve your goals more efficiently.
4. Manage Flow: Managing flow is about ensuring that tasks move smoothly from one stage to the next without unnecessary delays. Picture your workflow as a pipeline: tasks should move steadily through it, like water through a pipe. When a task reaches the "Done" column, it creates a vacuum or open space in your workflow. This space is crucial because it signals that you’re ready to take on a new task from your "To Do" list. By continuously monitoring this flow, you can identify and address any bottlenecks—points where tasks are getting stuck or moving too slowly. The goal is a smooth, steady flow of tasks, ensuring that your personal productivity remains high and that you’re always moving forward.
5. Make Process Policies Explicit: Clarity is key in Kanban, even when working alone. To avoid confusion and ensure consistency in how you handle your tasks, define and agree on the rules for moving tasks between stages. For instance, you might decide that a task can only move from "To Do" to "In Progress" if it’s clearly defined and you have the necessary resources to complete it. By making these rules explicit, you create a personal workflow that’s predictable and efficient, helping you avoid unnecessary delays and ensuring steady progress.
6. Implement Feedback Loops: Continuous improvement is at the heart of Kanban. Regularly review your Kanban board to assess what’s working and what isn’t. This is where feedback loops come into play. Set aside time for personal reflection—whether daily, weekly, or monthly—to analyze your workflow, identify any recurring issues, and brainstorm ways to improve. For example, if you notice that certain tasks consistently get stuck in "In Progress," you might need to adjust your WIP limits or tweak your approach to those tasks. The goal of feedback loops is to foster a habit of continuous improvement, ensuring that your personal productivity continues to grow over time.

Now, let’s step outside the conventional wisdom. Most people view Kanban as a tool for software development or manufacturing, but its principles are universal. Whether you’re leading a team, managing your own work, or even balancing personal projects, Kanban’s adaptability makes it incredibly powerful across various domains.

What’s often overlooked is Kanban’s potential to foster not just efficiency, but intentionality. In a world obsessed with doing more, Kanban teaches us the value of doing less, better. It’s a reminder that productivity isn’t about how much we can cram into our day but about making meaningful progress on the things that truly matter.

Why You Should Kanban

In 2024, where the pace of work and life continues to accelerate, Kanban offers a counterbalance. It’s a simple yet profound approach to work management that encourages focus, clarity, and continuous improvement. By making your work visible, limiting distractions, and fostering intentional progress, Kanban can transform how you approach both your professional and personal life.

If you haven’t tried Kanban yet, or if you’ve been using it only in a narrow context, I challenge you to expand your perspective. Think of Kanban not just as a productivity tool but as a way to bring more intentionality and purpose into your work. It’s more than just moving cards across a board; it’s about mastering the flow of your life’s work.

Pwned Passwords

On February 22, 2018, Troy Hunt released the V2 update to Pwned Passwords.

Pwned Passwords is a service that checks to see if any of your passwords have been leaked in any third-party security breaches. Troy also provided a new API that allows you to lookup a password by using its hash. That means you don't have to send over the password that you want to check.

I created a short Python script that performs the check against the API. It'll hash your password on your local system and check the hash for you against api.pwnedpasswords.com.

The code repository can be found on github.

As an example, here I'm checking for  `password` as the password. In this example, Over 3 million accounts have been found from third-party breaches using the weak password of `password`.

Retrieving a Stolen iPhone in Under 72 Hours

Image via streamingmedia.com

Within 53 hours I was able to get a stolen iPhone safely into police custody. Here's a rough timeline of the steps I went took to get the phone back to the rightful owner:


Saturday, 2/4/2012 @ 8:45 AM -- iPhone was "lost" (i.e., stolen).

• Called stolen iPhone and it rang four times before going to voicemail, suggesting that it was powered on and had reception. Used the "Find iPhone" app to locate the phone using the Apple ID credentials of the stolen iPhone, but it was unable locate the phone.
• Using the "Find iPhone" app, sent lock code to stolen iPhone to ensure that it was locked and required an unlock code to access the phone.
• Using the "Find iPhone" app, sent messages with sound to the stolen iPhone stating that the phone was lost and to call ###-###-#### (my Google Voice number). No response.
• Shortly thereafter the iPhone was powered down by the "someone" who had possession of the phone.
• I had the owner of the stolen iPhone change passwords to accounts accessed by the iPhone (e.g., Gmail, Dropbox, etc).
• Setup the email account used as the Apple ID of the stolen iPhone to forward a copy of all mail from "noreply@me.com" to an account I setup at Boxcar. The reason for doing this was to have push notifications sent to my phone moments after the stolen iPhone would be powered on and receive the commands that I sent from the "Find iPhone" app.
• There's a Boxcar iOS app that I installed on the device that I was doing the tracking from.
• Opted not to report the phone as stolen with AT&T yet since I wanted to be able to continue tracking the phone. 
• Also opted not to remotely wipe the iPhone via the "Find iPhone" app for the same reason.
• The "Erase all data on iPhone after 10 failed passcode attempts" option was turned off on the iPhone. This was a good thing since it prevented the stolen iPhone from being wiped by 10 failed passcode entries and becoming un-trackable. 

Sunday, 2/5/2012 @ 10:00 AM -- the iPhone was powered on by "someone" and the location of the phone was identified.

• I received a push notification from Boxcar showing that an email from noreply@me.com was received. That meant that the stolen iPhone was powered on and was now locatable.
• Used both the "Find iPhone" and "Find Friends" iPhone apps by Apple to track the location of the phone.
• Another option was logging into iCloud with the Apple ID and password associated with the stolen iPhone ... which I did.
• Location of the phone tracked to a residential address.
• Used Google maps and street view to look at the house.
• Identified the owner of the house using PropertyShark.
• Gathered information about the owner using Intelius.
• Again, sent messages with sound to the stolen iPhone stating that the phone was lost and to call ###-###-#### (my Google Voice number). No response.
• The phone was powered down by the "someone" who had possession of the phone roughly five minutes after it was powered on.
• Checked AT&T for any unauthorized calls. There were no unauthorized calls.
• A police report was submitted online to the police department where the phone was stolen. 
• The police department where the phone was currently located (different city than where the phone was stolen) would not accept a report directly since the theft occurred in a different city.

Monday, 2/6/2012 @ 10:46 AM -- the iPhone was powered on and left on.

• Using both the "Find iPhone" and "Find Friends" apps, the GPS location of the stolen iPhone was the same address as the address that was identified on Sunday.
• A police report was submitted online to the police department. The location of theft was intentionally left vague, implying that the theft occurred in the city where the phone was currently being tracked to. The police department was willing to accept the incident report.

Monday, 2/6/2012 @ 1:04 PM -- Called the records and dispatch departments of the PD from the city where the stolen iPhone was currently located.

• Gave the incident report tracking number to dispatch.
• After a lengthy conversation, dispatch agreed to send an officer to the house and that the officer would call me back if I needed to cause the stolen iPhone to make a sound.

Monday, 2/6/2012 @ 1:36 PM -- Received a call from the responding officer.

• The police officer stated that he went to the residential address.
• The officer stated that the owners of the house were at the residence.
• The police officer gained possession of the phone.
• The police officer asked me for the unlock code and some contact data that was on the phone to verify ownership.
• The officer relayed the convoluted story that the individual who had stolen the iPhone told him.
• We agreed to check the phone into the police department's chain-of-custody and the stolen iPhone will be picked up by the rightful owner soon.
• Called the police department from where the phone was stolen, stated that the iPhone was retrieved by another police department, and the case was closed.

... and that's a happy ending.

Apple has more information about locating a lost or stolen iPhone here.

Related articles

• NYPD meets FMI: Cop nabs iPhone thief in NYC (tuaw.com)
• Home invasion suspects caught with iPhone's help (tuaw.com)
• Find my iPhone/iPad2 in iCloud (phobe2phile.wordpress.com)

Koobface Analysis

Today Facebook announced that it will share the data it has collected about the group of people behind the Koobface virus. Facebook didn't provide any details about the "Koobface gang". However, in a separate blog post independent researchers Jan Drömer and Dirk Kollberg of SophosLabs did provide details of their analysis. I found the SophosLabs article a very interesting read in that it details the painstakingly slow process investigators must endure to piece security incidents together and that given enough time and resources "cybercrimes" can be solved.

"Up until now, Drömer and Kollberg's research has been a closely-guarded secret, known only to a select few in the computer security community and shared with various law enforcement agencies around the globe" ... "At the police's request we have kept the information confidential, but last week news began to leak onto the internet about Anton 'Krotreal' Korotchenko - meaning the cat was well and truly out of the bag." -- Graham Cluley, Sophos analyst

Link to Analysis: http://nakedsecurity.sophos.com/koobface/

Related articles

• Twitter worms (ggl): Web Gang Operating in the Open - New York Times (nytimes.com)

DHS Cybersecurity Strategy and New California eCrime Unit

Image by Getty Images via @daylife

A couple of interesting items within the information security world...

I. The Department of Homeland Security has released a new cybersecurity strategy document with a two-pronged approach:

1. Protecting critical infrastructure today
2. Building a more secure cybersecurity ecosystem for the future

Download the Blueprint for a Secure Cyber Future document (PDF).

II. California Attorney General Kamala D. Harris has announced the creation of a new eCrime Unit to investigate and prosecute technology crime.

"The primary mission of the eCrime Unit is to investigate and prosecute multi-jurisdictional criminal organizations, networks, and groups that perpetrate identity theft crimes, use an electronic device or network to facilitate a crime, or commit a crime targeting an electronic device, network or intellectual property." READ MORE

Related articles

• Blueprint for a Secure Cyber Future: The Cybersecurity Strategy for the Homeland Security Enterprise (bespacific.com)
• DHS Releases Blueprint for Cybersecurity (govsellingsolutions.com)
• California targets cybercrime, identity theft (sfgate.com)
• State attorney general launches eCrime Unit (sfgate.com)
• California unveils new unit to fight cybercrime (news.cnet.com)
• California Creates Special Unit to Fight Computer Crimes (bits.blogs.nytimes.com)
• California Forms Cyber Crime Unit (informationweek.com)

America the Vulnerable

Image by formalfallacy @ Dublin (Victor) via Flickr

During my commute to and from work I recently began listening to the audiobook, "America the Vulnerable: New Technology and the Next Threat to National Security" by Joel Brenner, narrated by Lloyd James. The audiobook was downloaded from Audible.com.

I’m currently half-way through the unabridged audio and am enjoying it. The book is an eye-opening reminder of what many of us within the InfoSec industry are already aware of as we analyze security events on a daily basis. American national security, our economy, physical and energy infrastructure, financial system and our own privacy are at risk and that if security isn't built into our systems, our systems won't be secure. From what I’ve listened to so far, Brenner does a good job of laying out the cyber-threat facing the United States.

I hope to finish the audiobook by the end of this week as I’m interested in hearing what Brenner has to prescribe as a solution to the problem. Though I have yet to finish the audiobook, I recommend it as a must read for anyone interested or with career in cybersecurity.

Related articles

• Normative Cyber Security (bloginfosec.com)
• America the Vulnerable (csmonitor.com)