A Strange Christmas Choice

On choosing difficulty when freedom feels easy

The Christmas holiday break arrived with all the usual signals of rest. No meetings. No half-workday commitments. An empty calendar. Simply having the time to chill.

And yet, instead of switching off ( my usual struggle) , I found myself choosing something demanding.

I drifted back to a dormant business idea — an old solution that had been quietly parked for some time. A retail analytics platform we once built: technically dated, but conceptually still sound. With time suddenly available and no one expecting anything of me, I began redesigning it. Not because I had to, but because I wanted to see what it could become if rebuilt on new technology, using modern tools and fresh thinking.

At first, it was fun — refreshingly challenging, engaging, absorbing — the kind of activity where time slips past unnoticed.

But the deeper I dived, the more demanding the challenge became. The elegance of the idea was gradually trampled under the weight of architectural trade-offs — necessary, but now requiring more discipline and less enthusiasm. What had begun as play started to feel like work.

So I downed tools — for a day at least. Once a dog with a bone, always one (he he).

After days of focused work, I felt a pull towards the outdoors. It seemed as if I was the only one not at the beach. The contrast struck me — my self-enforced discipline set against the rest of the holiday-makers enjoying the sun, sand, and sea.

And that’s when it became clear: retirement isn’t about not having to work, or even about doing part-time work. It’s about having the freedom to choose what you do — and when you do it.

Perhaps this is one of the lessons of this phase of life: freedom doesn’t eliminate the desire to be challenged, but it does expose how finely balanced that desire really is.