Taking a proper holiday is one of the best things you can do for you and your business.
I don’t mean a half-holiday where you’re still on Slack, still replying to emails, still “just doing that one thing”. A real holiday. Clean break. Phone down, laptop closed. Proper switch off.
Here’s why.
See what breaks
When you go away properly, it forces the business to run without you. And that’s the test every founder secretly avoids. 1) Because you probably secretly enjoy being needed. 2) You don’t know who you are without your work. 3) You are sh*t scared something will break.
Maybe it’s one, or maybe it’s all three, but if those reasons for avoidance resonate, all the more reason to lean into them. I believe taking a proper holiday is actually a way to grow both you and the company.
I have a weird relationship with holidays. I always resist them and always have; I suppose I’m afraid to let go. But every single time I take a proper holiday something good happens. In my last startup we’d always, and I genuinely mean this, always land a big customer when I went on holiday. It was so surreal. And, of course, I’d leave feeling like I had some major problems that were stressing me out and after a week in the sun realise that they didn’t matter that much.
Before you leave, you have to hand things over. Delegate. Write the processes. Trust other people to make decisions. In other words: let go.
When you come back, one of two things will have happened:
- Something has broken.
Great. Now you know where the operational hole is. You’ve got a clear signal on where the business actually relies on you. What needs fixing. - Nothing has broken.
Even better. You’ve just learned you can step away. Which means you’re free to take on bigger, more important problems.
That’s the magic of a holiday. It’s not just sun and chill. It’s also stress-testing your business.
The art of the handover
Doing this is actually really hard. It’s a massive point of resistance for founders and many founders will go years without a holiday. Some might even go their entire startup journey without taking a proper break. But you can do a few things to make this transition easier:
- Book in a handover meeting where you pass over key tasks, projects and responsibilities to people on the team. Look at this as a test of their abilities.
- Get the blessing of your cofounders (if you have them). Discuss your break with them in advance and plan your holiday with and around them so that you don’t have key people off at once.
- Delete your email and instant messaging apps for a week. Delete any app on your phone that plugs you into the startup mainframe: Hubspot, Shopify notifications… anything that will keep you switched on. Your back up should be a phone call; if people really urgently need you, they’ll call.
- Take a notepad and pen. Reframe the time away to let creative, big picture thoughts bubble up. Yes, it’s a holiday, but you’re still a founder after all…
Make yourself dispensable
Not being able to switch off isn’t just an emotional weakness. It’s a systems problem. It’s proof your business can’t function without you. And if your business can’t function without you, you don’t actually own a company, you’ve just made a really stressful job for yourself.
Your job as founder is to constantly make yourself redundant. Every three to six months, if you’re growing, you should be handing off another chunk of your role. Holidays force you to do that.
That’s why taking regular, proper breaks, at least 2-3 times a year, is so powerful. They build resilience into the systems of your business. They accelerate its maturity. Your business (and your family, and your brain and your health) will thank you.
If you’re really struggling to do this. Here are a few coaching/journalling questions you can ask yourself:
- What am I avoiding, in not taking a holiday?
- When was the last time I truly switched off from work?
- Who am I without my business?
- What’s the worst that could happen?
