The win: A fun way to build connection before your next meeting with zero prep needed. Laughs guaranteed.
First Job, Worst Job
This icebreaker takes about 10 minutes, works for any size of team, and can be done in person or virtually.
How it works:
Step 1: First Job
- Split into groups of 3-5.
- Each person shares their very first job ever.
- Leave a few extra minutes for group dialogue.
Step 2: Worst Job
- Reshuffle into new groups of 3-5.
- This time, everyone shares their worst job ever.
- Leave time for group questions and a few laughs.
Why it works: hearing where someone started builds a kind of instant humanity. It’s hard to stay guarded with someone once you know they spent a summer in a fast food drive-through or cleaned porta-potties at a fair.
The win: a good laugh after a long month.
The win: A key idea with a practical tool to help you and your team thrive at work AND home this summer.
You Can’t Thrive at Work if You Never Actually Leave
TLDR: Leaders who unapologetically step away for breaks give their teams permission to do the same. You don’t need to pick sides – either killing it at work OR being fully present at home. The key leadership move is learning to thrive at both. We’ve got a tool to help you do just that.
Here’s something worth saying out loud: the way you spend your summers sends a message to your team. Not just what you say, but what you do.
When leaders check emails on vacation, respond to Slack at 9pm, or never really “leave” even when they’re away, it creates unwritten expectations. The team sees it. And many of them will follow your lead, even if you haven’t asked them to.
The tension to manage here is thriving at work AND thriving at home. Not choosing one. Managing both on purpose. When you never fully check out, your brain and body don’t get the recovery they need to perform at their best. You return from vacation not fully rested, and not fully present while you were away. That’s a lose-lose.
Want a simple tool to actually stop your brain from clocking in? Tell your team where you’re at before you step away. Create clarity around your availability, and give yourself real permission to be off.
Try the Stoplight System
At Leaders for Leaders, we use a simple stoplight to communicate availability during time off:
Green: Reachable as normal.
- Maybe you are working a normal day, you just happen to be at the cottage. Green lets your colleagues know it’s okay to reach out to you, even if there IS a sparkling lake and loon calls in the background of your Zooms.
Yellow: Textable for urgent matters.
- Some roles, seasons, or current project work call for this. We get it, but don’t let this be every single vacation day you take this summer (yes, we’re talking to you entrepreneurs).

Red: Not available for work matters.
- You might be ‘red-light’ because you are physically unable to access cell service or wifi – ie. hiking the Alps, backcountry canoeing in Algonquin, or soul searching at a Tibetan monastery.
- AND there are times you need to give yourself permission to be ‘red-light’ even if you can access your email on a staycation. It’s less about where you are, and more about what you need to refill your tank.
So, before your next vacation or long weekend, let your team know which light you’re in. And model red light yourself whenever you can.
For red-light breaks, make sure the person you’ve left in charge is set up for success and knows they are empowered to make calls in your absence. View it as a development opportunity. That’s not just good boundaries. That’s good leadership.
Your action step:
Before your next time away, send your team a one-liner like this:
“I’ll be red-light off from [date] to [date]. [Name] has the keys. Reach them if something urgent comes up.”
That’s it. Clear. Simple. And it gives everyone, including you, actual permission to be off. This simple stoplight tool can help make or break your summer.
Want to help your team learn to thrive at work AND home?
Our Masterclass on Thriving at Work AND Home gives leaders tools like this and a practical framework to manage this tension all year long, not just in summer.
Participants shared with me how the leadership sessions were the highlight of their month, providing a respite to their work, and inspiring them with a way forward."

