Building (Software) Things in Retirement – My Next Chapter: A Retirement Journey

It’s hard to explain the magnitude of what’s happened the past few months around writing software.

“Software Bonkers” is how writer Craig Mod put it recently. “I can’t stop thinking about software. And I can’t stop building software. . . . There’s an energy around all this that is – truly – epochal.”

Developer Simon Willison points to last November as “an inflection point - one of those moments where the models get incrementally better in a way that tips across an invisible capability line where suddenly a whole bunch of much harder coding problems open up.” He’s now posted close to 200 tools he’s built with AI, and no doubt more are on the way.

Projects which used to seem impossible – either because they were beyond my skill set or they would have taken way more time than they were worth – are suddenly doable.

And that’s pretty wild.

Some people in the field are getting a bit obsessed. “I replaced Netflix with Claude Code,” venture capitalist Nikuni Kothari blogged last month. “I lie in bed thinking about what I can spin up before I fall asleep, what can run while I’m unconscious.”

OK, that’s not necessarily healthy. And Kothari admits that “Everyone here [Silicon Valley] knows they should step away more”.

But it’s hard to resist when (tech) things you’ve wanted for years have become not only possible, but easy. And after one project comes to life, other ideas do, too.

Even if you’re retired.

Which is why I’ve spent much of the last couple of weeks working with Claude Code on software.

It started with a project I began around 10 years ago: an easy-to-search local events listing page.

I automated some of that work, but still ended up spending lots of time adding events manually to the calendar. That took a lot of time, though, and it was unpleasant drudge work. So I scaled it back.

Now?

At my direction, Claude Code built me a bunch of tools to make the updates simple, and almost fun. I can point Claude to a URL and have it 1) extract event info, 2) ask for my approval, 3) add it to a spreadsheet, and 4) run some code to update multiple calendar websites.

In less time than it took me to handle one calendar, I can now run three – including one just for me, tailored to the sources and event types that I choose.

And, these calendars have evolved for 2026. Claude helped me add chatbots where I can ask natural language questions like “Are there any mindfulness events this week?”

But wait, there’s more!

I can also ask Claude Code to build custom applications for my Windows PC, using programming languages I don’t even know.

For instance, I use a somewhat ancient Windows application called AutoHotKey that lets me set up typing shortcuts, such as “;fr” turning into “Framingham”. It works, but it’s a bit complicated to 1) see what snippets I already have and 2) add new ones.

I’ve tried alternatives, but nothing quite fit what I wanted.

Now?

I asked Claude Code to custom build a graphical user interface for AutoHotKey exactly to my specifications. And it works.

This is hard to resist.

“The second or third time you catch yourself thinking ‘it’d be great if there was a tool that did this,’ you realise that you can just build it. You are a toolmaker now,” Nic Hodges posted on LinkedIn. “Tools for an audience of one. Tools for a team of two.”

This can happen a lot. And it can get addictive.

Fortunately, I’m not working for a company that will pay for me to spend thousands of dollars a month on Claude Code “tokens” and even encourage me to do so – which apparently is now a thing in Silicon Valley.

Instead, I’ve got a $20/month account that regularly bumps up against usage limits. It’s a wonderful way to force myself to step away from the keyboard and do something else.

I ran out of Claude Code tokens for the week last Thursday. That ended up being perfectly timed for a planned visit to the Harvard Art Museums the next day. I didn’t even have to squash the urge to rush home and see how Claude could improve my latest projects!

(Local folks: The art collection at Harvard is great if you like Impressionist paintings, and art museum admission is free [although getting there from the suburbs is not]).

Saturday we had a lovely visit with family, plus I heard some inspiring speeches at a local No Kings pro-democracy rally.

And then Sunday I got back to work on my next Claude project, and how I might turn it into a freelance article. 😅

But after my initial burst of enthusiasm, I’m trying to keep this in perspective. Because I didn’t finally achieve space for better work/life balance in retirement only to lose screentime-to-real-life balance from AI.

So I’ll be sure to make plans to get away from the keyboard this week, too.

Below: Renoir’s Spring Bouquet at the Harvard Art Museums