My Post Microsoft Subscription Crisis

Trying to retire without downgrading my tech life

After nineteen years as a Microsoft employee, and a few vendor years before that, you get spoiled. Not in the “free snacks” way, although those were nice, but in the dogfooding way. You live inside a world where new tools appear early, integrations show up before the marketing pages do, and you stop thinking about which model is powering what because everything simply works.

But now I’m retiring. And suddenly I’m looking at my digital life choices, starting with my AI choices. What do I actually need? What do I want? And what will keep me from feeling like I’ve stepped backward?

This is my early attempt at answering that.

M365: The First Non Negotiable

Let’s start with the obvious. I’ve lived in the Office desktop apps for decades. I know Google has come a long way, but muscle memory is a powerful thing. And in the past few months, I’ve fully embraced M365 Copilot, not as a novelty but as a thinking partner.

My daughter asked if she would lose access to her own Copilot when I retire. I told her she is safe. Some things are sacred, like her thinking partner.

GitHub Copilot: My VS Code Companion

I live in VS Code now. It took me forever to move there, so I’m not about to jump to a CLI only life. Paying for GitHub Copilot felt like a simple decision, right up until the pricing announcement landed days after I subscribed. Timing is everything.

Still worth it. Still staying.

Adobe Firefly and the Eight Hundred Dollar Question

Two weeks ago I started playing with Adobe Firefly. It is part of the full Adobe Suite, which I have actually had for several years. The girls used it occasionally for school projects, and I use the mobile apps to edit photos on my phone. But if I am honest, I doubt we have ever gotten eight hundred dollars of value out of it in a single year.

That is why this year feels like a test run. I want to push the tools harder, see what Firefly can really do, and figure out whether the full suite earns its keep as we build our new company. This year is the experiment. Next year is the verdict.

Canva and Figma: The “Everyone Says I Should Try These” Tools

I dipped into Canva. Made an infographic. It was fine. It never quite landed the way I wanted, but I will keep a free account around.

Then came Figma. Everyone insists I need it. I opened it, got distracted, wandered off, and never came back. Classic me. I will return eventually. If someone wants to explain why I must have Figma when I already have the Adobe Suite, I am listening.

Mermaid: My New Diagramming Crush

I am still a Visio girl at heart, but Mermaid has been sneaking up on me. It is lightweight, it is right there in VS Code, and it scratches the “diagram something quickly” itch beautifully.

I have the basic account. The Plus plan is one hundred twenty dollars a year. I am not convinced I need it yet. Mermaid fans, feel free to make your case.

Claude, ChatGPT, Copilot, GHCP: Is This Excessive

I have:

• M365 Copilot

• GitHub Copilot

• Claude on the entry level annual plan

• ChatGPT on the entry level monthly plan

On paper, this looks excessive. In practice, each one has a different personality and strength profile. Claude is my long form, emotionally precise writer. ChatGPT is my fast twitch generalist. M365 Copilot is my integrated productivity layer. GHCP is my coding brain.

In June, I am going to track my usage at home. I want to see when I am happy, when I am frustrated, and when I switch tools. I suspect the patterns will be revealing.

The Gemini Question

You will notice Gemini is not on my list. Marlowe and I talked about this. I live in Gmail and Google Docs for my personal life, so you would think I would be all in. But right now, I am not sure what I would be missing without it.

Someone told me to try NotebookLM. Fine, it is on the list. But I am not convinced I need another subscription just to avoid FOMO.

Local Models: My Next Exploration

Next week I am diving into local models. I have a list. I want to understand what is possible on device, what is practical, and what is simply hobbyist fun.

This is the part of the journey that feels like early computing again, full of tinkering, experimenting, and discovering.

Database Tools

I used to rely on a whole suite of database design tools. Now, with the combination of Copilots, Claude, ChatGPT, and the creative tools I already own, I can generate everything those tools used to give me and more. Even better, I can build my own custom tools on top of these models.

Your Turn

Retirement is not a step backward. It is a shift from “what Microsoft gives me” to “what I choose to build.” And honestly, that feels exciting.

If you have thoughts on the tools I mentioned, or if there is something you think I should absolutely try as I build my post‑Microsoft toolkit, I would love to hear it.