Beer Budgets, Bug Spray, and Big Leadership Lessons

The long weekend is coming up, and like many Canadians, I’m heading north, where the WiFi gets weaker and the leadership lessons get a little stronger. 

I don’t own a cottage, but I’ve spent decades soaking up summer weekends at other people's. Growing up, my family spent summers at a trailer park. These days, I’m lucky to have friends—and a sister—who generously share their cottages with me. Over the years, I've learned that what looks like a peaceful escape often hides a surprising amount of logistics, coordination, and people management. 

And the more time I’ve spent dockside, the more I’ve come to see how many of the same principles we talk about in leadership show up in cottage life. 

1. Project Management Is Real 

It’s easy to laugh at the idea of “managing” a long weekend—but when you look closer, it’s exactly that. Food needs buying, people need beds, the fridge needs room for six types of drinks and one vegetable tray, and somehow, there’s never enough ice. 

Someone is making all of this happen, and more often than not, they’re managing invisible moving parts. Most of the time this burden falls on the shoulders of one ring leader. 

You wouldn’t call it a project plan, but it might as well be! I have so much respect for the people who make this happen! Never missing a single detail and keeping everything running on time and efficiently.  

At work, project management is about anticipating needs and staying two steps ahead. At the cottage, it's making sure you have enough lifejackets and no one forgot the mustard. Both matters. 

I think that when you reframe a cottage weekend as a short-term high stakes project that requires a plan and timeline you begin to think differently. Now I am not suggesting that you should treat the weekend like work, but when you plan and prep ahead of time, collaborate with your stakeholders (your partner, kids, and guest) it makes it easier to distribute tasks, promote buy-in and help relive a lot of the stress that goes into these epic trips. 

When’s the last time you planned something “casual” that turned out to need real coordination? 

2. Crisis Management (a.k.a. The Dock Is Floating Away) 

It's a universally known truth that things will go sideways at some point. A thunderstorm hits while you're on the lake, the power flickers out mid dinner prep, the boat won’t start, and someone slips on the rocks. Cottage weekends are full of small (and not-so-small) moments where things don’t go to plan. 

You learn quickly: yelling doesn’t help. Pointing fingers doesn’t fix the problem. What does? Staying calm. Thinking clearly. Doing what you can, with what you’ve got. 

At work, the same rules apply. Teams look to leaders not just for answers—but for steadiness. You don’t have to know everything, but how you show up in the moment and change the outcome. 

What kinds of methods can you take to try and minimize these crises? Do you check the weather regularly? Do you have your emergency kit restocked and ready for the summer? How about your BBQ? When did you last clean it? Crisis management starts at prevention.  

3. Vision & Planning Matter—Even at the Lake 

Sure, cottage weekends are supposed to be easygoing. But the best ones. They don’t happen by accident. 

Someone had a vision: the campfire, the tubing, the morning coffee on the dock. And someone made a plan to make it possible. That’s leadership too. 

It’s the same in our roles. Whether you're launching a product, building a team, or just trying to improve one part of your operation—you need clarity. You need to know what great looks like, and work backwards from there. 

What tools do you need to make it happen? What resources are required? What's your timeline! This is a Biggy! You can’t go on a beer run when you and your buddies spent the morning drinking, I mean, emptying out the beer fridge. You’ve got to plan for that! 

What would happen if you approached your next work week like a long weekend: with intention, a few anchor moments, and enough flexibility to enjoy it? 

4. Boundaries Aren’t Just for the Property Line 

Every cottage has rules—written or unspoken. Shoes off in the cabin. No wet towels on the couch. Quiet time after 10. Don’t touch the host’s special bourbon. These aren’t just about cleanliness or comfort—they’re about respect and keeping things running smoothly when people are sharing space. 

And yet, not everyone naturally follows them. Some guests pitch in without being asked. Others treat it like an all-inclusive resort. If you’ve ever found yourself cleaning up solo while someone else cracks another drink, you’ve seen what happens when boundaries aren’t set—or enforced.  

And here’s the thing about rules—they only work if people actually know about them. 

Setting boundaries isn’t just about enforcing rules when they’re broken; it’s about communicating expectations before the weekend even begins. The best cottage hosts don’t just hope everyone will show up with food, help clean, and be respectful—they create a group chat, share itineraries, lists and schedules, they make a signup sheet and/or a chore chart, they say, “Hey, can you bring X?” They’re clear. They’re fair. They’re intentional. And when someone doesn’t follow through? You learn. 

Maybe they forgot to bring the groceries they promised. Maybe they disappeared when it was their turn to make dinner. Maybe they treated the weekend like a getaway but forgot it was also a shared effort. 

You can’t control people. But you can make decisions based on patterns. Sometimes accountability at the cottage looks like not extending that same invite next time. And sometimes, it looks like letting go—accepting someone’s limits and adjusting your expectations accordingly. It’s always good to have a backup plan! (see project management) 

The same goes for leadership. Not everyone will rise to the occasion. Some team members will drop the ball. Some won’t read the room. It’s not about taking it personally—it’s about noticing what’s consistent, being clear in your communication, and holding people accountable through action, not just feedback. 

Boundaries aren’t about being rigid. They’re about making the experience better for everyone—so that the people who do show up, contribute, and care. Don’t burn out carrying the whole load. 

How clearly have you communicated the “cottage rules” on your team? And what do you do when someone just keeps showing up empty-handed? 

5. Saying No and Finding Time to Relax 

There’s a point in every cottage weekend when the host starts to hit their limit—whether it’s too many people, too much noise, or not enough sleep. I’ve seen it in friends, in family, and I’ve felt it myself: the quiet exhaustion that comes from being “on” for too long.

And yet, so few people say it out loud. 

At work, the same thing happens. Leaders stretch themselves thin trying to make everything go smoothly—for everyone but themselves. But saying “no” or “not this weekend” is often the bravest and wisest thing you can do. 

Setting boundaries, especially with family can be tricky! There seems to be a strange Canadian phenomenon that the second you get a cottage you are suddenly expected to host everyone you’ve ever met every week for the whole summer! It’s important to prioritize and protect your peace. Just like at work, block time in your calendar. These weekends are family weekends but these ones are available, first come first serve! 

Remember to say no by saying-

YES: Yield,  Explain, Suggest.  

• Yield to emotions, yours and others. Acknowledge emotions, “I know Jimmy and the kids love to visit the cottage this weekend and will be disappointed...” “Yes I know it's a tradition that you visit every year” 
•  
• Explain briefly: Don’t provide too much information or make excuses. “We have other commitments this weekend.”
•  
• Suggest alternatives: find an alternative or offer a compromise. “What about the long weekend in August?”  

One of the best parts of being at the cottage is the downtime. Sometimes it’s busy and the weekend flies by but within the chaos you have these pockets of time to sit and reflect. You watch the sun set sitting on the dock, you enjoy the early morning stillness with your first cup of coffee in the morning before anyone else is awake. The spaces of companionable silence that emerge while sitting around the campfire. These moments recharge us and remind us what we are doing it all for. 

When was the last time you took a moment at work to be fully present? To set aside time to think on your project trajectory and have space for some creative thinking and problem solving? Why can’t that fit into the little pockets of your day? I highly recommend you try. Find those calm moments in the eye of the storm and take a moment to think and reflect.  

Conclusion 

Cottage life reminds me that leadership isn’t always about big speeches or strategic plans. Sometimes, it’s how you react when the propane runs out. Or how you carve out 30 quiet minutes on the dock before the day begins. 

Whether you're heading north this weekend or staying home, I hope you find a little space to recharge—and maybe reflect on the kind of leader you’re becoming. Not just the one who gets things done but also the one who brings calm, clarity, and care to the people around them. I urge you to take some time to think about how you can bring these cottage leadership lessons back to the city.