My daughter has one more week of winter break than I have PTO, which means today she’s my office sidekick. Getting a teenager and myself out the door on time is its own project management exercise – packing lunches, making sure everyone eats breakfast, locating all the things that somehow migrated overnight.
Thank you, Alexa, for the 6:15 AM reminder that I needed my laptop today. I’m working from my alternate office where there are no spares, and that would have been a spectacular way to start day one back.
We roll into the office at 7:38 AM and I immediately send my kiddo on the most important mission of the morning: Starbucks. Half a block away, bless this location. We were in too much of a rush to make coffee at home, and I’m not about to face this inbox uncaffeinated.
While the Coffee Run Happens
I open PowerShell 7, CD into my first client folder, and have Claude Code run fresh reports for the clients under my care. I need an overview of what happened while I was gone. I did attempt to stay out of my inbox during PTO. We all know how that actually goes – I checked it approximately seventeen times while pretending I wasn’t checking it. (I also got a few emergency calls as well while off, so work still happened.)
Then it’s over to VS Code with Claude Code to tackle the improvement requests and bug reports my team pushed over for SmartDispatch while I was out. This is the nice thing about having a well-documented backlog – I can jump right into context without playing detective. A few edge cases that needed handling, one feature request that’s actually reasonable, and a bug that only shows up on Tuesdays for reasons I’ll eventually understand.
By the time my kid returns with coffee, I’m scanning my calendar for the day’s meetings and asking Copilot to get me up to speed on what I need for each one. Meeting recordings, summary emails, context I missed – Copilot pulls it together so I’m not walking in blind.
Meanwhile, My Automations Have Been Living Their Best Life
Here’s the thing about taking time off when you’ve spent months building automation infrastructure: it keeps working without you. My n8n workflows have been humming along while I was gone, which is both reassuring and slightly unsettling. The automated ticket categorization kept categorizing. The client report generation kept generating. AutoDispatch kept dispatching.
I pull up the logs and everything looks… fine? Good, even? It’s like coming home to find your house didn’t burn down, but also your house has been living its best life without you. The plants are watered. The dishes are done. You’re not sure whether to be relieved or slightly offended.
And Then Microsoft Had Opinions
Sometime during all of this, Microsoft 365 decides to have a moment. Exchange, login issues, the website – nothing catastrophic, but enough that Downdetector lights up and my Teams starts acting sluggish. Classic first-day-back energy from the entire Microsoft ecosystem, apparently.
So I pivot back to Claude for planning the rest of my day while the M365 gremlins sort themselves out. This is why you don’t put all your eggs in one AI basket – when Copilot is having a rough morning because its house is on fire, Claude is right there ready to help me triage.
The 9 AM Team Catch-Up
I hop on a Teams call with my team to get the real scoop – the stuff that doesn’t make it into tickets or emails. The vibe check. The “how are we actually doing” conversation.
Someone mentions a “small issue” with a client’s Azure environment that turned into a “learning opportunity” involving a 2 AM call. The way they say “learning opportunity” tells me everything I need to know about how that night went.
I make a mental note to check on that engineer’s wellbeing later. I also make a mental note to build another automation so this doesn’t happen again – or at least so we catch it before it becomes a 2 AM problem. Half of my job is fixing things. The other half is making sure we never have to fix the same thing twice.
The call ends on a high note though – one of my team leads in South Africa thanks me for the emotional support pizza stuffies that arrived while I was out. Thank goodness Amazon ships internationally. Look, it’s an MSP. You need some kind of emotional support to get through the day, and if that comes in the form of a plush pepperoni slice with a friendly face, so be it. We take our wins where we can get them.
The 11 AM Interruption (The Good Kind)
My daughter emerges from her hidey hole – she’s commandeered a conference room with her laptop and headphones – and walks into my office. “Hey, can you help me with my resume?”
She’s working on one for the first time. College applications, job applications, the whole growing-up thing happening in real time.
This is the part of the “day in my life” content that people don’t usually show – the part where you’re a CIO and a mom and sometimes those things happen in the same five-minute window. I’ve got a client proposal half-drafted in one tab and I’m about to help my kid figure out how to describe her volunteer work in a way that sounds professional.
We spend fifteen minutes on it. It’s a good fifteen minutes. Then she retreats back to her conference room and I return to my 23 open tabs.
The Lunch That Almost Didn’t Happen
It’s suddenly 1:30 PM. How is it 1:30 PM?
I’ve processed maybe 60% of the backlog. I’ve used Claude to draft three client proposals, had Copilot summarize two hours of recorded meetings I missed, and discovered that my ConnectWise board has opinions about my absence. The tickets have multiplied. The service board is giving me a look.
I throw something from my heated lunch bag onto my desk – meal prep from before vacation, because past me occasionally has her act together. One of the best purchases I’ve made for office days: actual hot food that doesn’t require a microwave trip or sad desk salad energy. I keep plowing through while I eat because that’s how first days back work.
The Afternoon Question
Someone asks me how I manage it all.
I gesture vaguely at my screen, which currently has 23 tabs open across two monitors, four VS Code windows, a Zapier workflow that’s doing something I’ll remember later, and a sticky note that just says “CHECK THE THING” in my own handwriting. I have no idea what thing.
The honest answer is: I don’t manage it all. I manage enough of it, with a lot of help from tools that are smarter than me at remembering things and faster than me at processing data. The AI doesn’t replace the work. It replaces the busy work, which frees me up to do the actual work – the thinking, the strategy, the conversations that matter.
Also, I write everything down. Everything. Because I will not remember the thing.
The Wrap-Up
By end of day, I’ve made a dent. Not a crater, but a dent. The inbox is down to manageable. The urgent things got handled. The less urgent things have been triaged for tomorrow.
My daughter finished her resume. Microsoft recovered from its morning drama. The engineer who had the 2 AM call took a long lunch and seems to be doing okay.
Was taking PTO worth the re-entry chaos? Absolutely. Because here’s the thing about coming back – you remember why you built all these systems in the first place. The AI tools, the automations, the workflows – they’re not just about efficiency. They’re about creating space to step away and trust that things won’t completely implode.
They mostly won’t, anyway.
And when they do, well – that’s what the 2 AM learning opportunities are for. And the emotional support pizza stuffies. Also, have I mentioned that Uber Eats delivers internationally?