Returning to Work After Summer Holiday

Introduction

This has been a bit of a strange year for me personally and I have to admit I have struggled a bit mentally — so when summer came and it was time for a break, I was really ready for it.

I usually don’t take a long vacation, but this year I decided to work early summer and then have a good break at the end. Working when most people are on holiday can be lonely, but also very productive — you can work long spells uninterrupted. Combine this with agentic coding and you can be super productive on all those chores and technical debt that never gets tackled.

Anyway, back to the much-needed vacation. When it came I pretty much closed the computer and handed over the reins of the team to a colleague and really went on holiday. But now the holidays are over and things start ramping up at work again — I really struggle to find my groove and get motivated again. So how can we get back into the groove knowing summer is at an end and we are heading into a darker and colder time of year?

Getting Back Into the Groove

Start with small wins. Don’t try to be a hero on day one. Pick a task you know you can finish — something that has been sitting on the backlog forever but never gets prioritised. One thing I did was use my trusted AI companion to document all our services properly (yes, some people still read documentation). It felt productive, it was genuinely useful, and it warmed up my brain without requiring full creative capacity.

Review before you react. Before you dive back into Slack, emails, and stand-ups, spend 30 minutes reviewing where things stand. What did your team ship while you were away? What is on the horizon? Going in blind means you spend the first week reacting instead of leading.

Re-connect with your team as people, not just colleagues. Coming back after a break is a great excuse to have a few informal chats — grab a virtual coffee, ask how their summer was. It rebuilds the social fabric of the team and, honestly, it makes coming back feel a lot less cold.

Block some focus time early. The calendar fills up fast when you return. Block at least a couple of hours of deep work time in your first week before everyone else does it for you. If you want a refresher on why this matters, I wrote about it in my Deep Work post.

Key Takeaways

It’s OK to struggle a bit in the first weeks back — that’s completely normal, and you’re not alone in feeling it. The trick isn’t to fight it, but to work with it.

• Be kind to yourself. You just had a holiday. Your brain needs a warm-up lap, not a sprint.
• Small wins unlock momentum. One finished task beats five half-started ones.
• Know the landscape before you react. Know where things stand before you start making decisions.
• Protect your focus time before others steal it. Block it early, guard it fiercely.
• People first. A five-minute chat with a colleague does more for your motivation than any productivity hack.

The darker months are coming whether we like it or not — so the question isn’t really how do I get back into it, but how do I set myself up to sustain it. What’s the one thing you’ll do differently this week to make sure September doesn’t derail you?