Here’s how I prepared for a week OOO

I took a week off in August for a family road trip out into the mountains. It was a much needed opportunity to unplug—I left my laptop… and shampoo… at home. All that space inspired these thoughts: A messy kind of reflection about taking vacation as an entrepreneur.

I regularly take time away from work, but I know the same isn’t true for many others who are self-employed. Not only do I think vacation is important for your wellbeing, but it’s critical to your professional growth too.

The following is the what, why, and how attached to all of the above.

Taking vacation as an entrepreneur: Getting ready

The time away from the city was much needed. I mentioned the space was welcomed. Which is kind of funny because we live in what I think is one of the most beautiful cities in Canada. I’m typing this while looking out the window to see mountains and the Okanagan Lake in the view peeking from behind our neighbour’s home. It’s funny that even living here, we craved more space.

So we packed up and hit the road.

You don’t need shampoo when you’re living between the trees. I embraced the braids, hat, and messy bun looks. It was our first overnight trip as a family of 4 (plus the pup), and overall it was a success. We drove home on Sunday tired, but happy. Ready to get back to civilization and a shower.

Before we left though, I almost got caught up in my old hustle habits.

Everything needs to be perfect before I leave.

I need to pre-schedule a bunch of stuff to go out.

I should get ahead.

Not so shockingly, the above didn’t happen. I just didn’t have the capacity to do it all before we left. My youngest has been giving me a run for it overnight, then my oldest runs all day long from the moment he wakes until he crashes at bedtime.

The big lesson here is that, despite my lack of hustle prior, everything was okay. Even though I didn’t properly “get ready” for my time OOO, it worked out fine.

I think that warrants a note that as business owners, freelancers, and entrepreneurs, we often place unrealistic and unnecessary expectations on ourselves.

Your business won’t burn down in a few days

At least, it shouldn’t burn down if you take a few days off. Even if your revenue is still closely tied to the hours you work, you can hopefully at least clock out for a few days to a week without your stress levels sky rocketing.

Tough love: If that’s not the case, then something needs to change.

A few cool things happened even though I didn’t “properly” get ready for taking vacation as an entrepreneur…

✅ My clients got information and support they need because I focused on pre-scheduling their homework and comms vs anything else in the business.

✅ My long-form content is really working for me, and Google Analytics notified me that my website passed another traffic milestone while I was away.

✅ No one even knew that I was really gone.

✅ You probably didn’t mind that you didn’t read an email last week, and I get to pop into your inbox refreshed now.

✅ Stripe notifications, yay!

Some of my clients also took time off too… 1 is moving into her new home. Another is enjoying her annual sabbatical. I love working with people who recognize the need to live their lives away from their desks.

Consistent effort over time pays off

The above wins won’t happen overnight. If you’re new to business, you probably need to push a little more in general, but also to take time off. Maybe you’re in a season where you truly do need to triple check your to-do list and clock a few extra hours before taking a break. That’s okay, and I’ve been there too. Most of us have.

I realize the contradictions here, but I think the most important message is this: Regardless of your season in business, you need to prioritize taking vacation as an entrepreneur. Then prepare accordingly, while also keeping your wellbeing in mind.

Ie. Is vacation really going to help you if you stress yourself up for weeks prior? Probably not. It’s likely an opportunity for you to check your expectations as you prepare for time off.

My business is established. I have a client roster. I have digital products that people can purchase when I’m OOO. And systems in place to create buffers if I’m away for any period of time.

So with that context in mind, it’s clear that consistency means more than just the days or weeks leading up to your vacation time. It’s how you operate your business on the day-to-day to allow yourself space when you need it.

I realized in the days leading up to my vacation that certain stuff I wanted to do didn’t really need to happen. So I let it slide.

The lesson: To-do lists never truly end

When you recognize that your to-do list will never truly end, that understanding can be relieving. If it’s never going to end, there’s no pressure to try to check everything off.

Instead, you just need to learn how to prioritize your days to achieve the life you want, and reach the goals you’ve set. This applies to taking vacation as an entrepreneur too.

Yes, consistency is important. Yes, sometimes you need to work ahead to get ready for time off. But you also don’t need to do everything. You can achieve your goals without running yourself into the ground. Diminishing returns are real, so sometimes you need to be harsh with your priorities and skip the shit that doesn’t matter.

Book the vacation.

Cut everything from your list that doesn’t really need to happen right now.

Log out early.

Give yourself space to breathe. Then watch the difference it makes. I promise you that you’re deserving of a break even if everything isn’t perfectly ready for your time off. With just a few more weeks left of summer on my side of the world, I’ll be taking my own advice more.

Taking vacation as an entrepreneur means leaving the laptop at home

I often see entrepreneurs saying they’re on vacation, but they still bring their laptop. They still log in. I’ve been there! I’m not above this.

But an intentional decision I’d love to see you make is this: Do I want to and intend to work on this vacation? Is that the point to have this work-life integration? Or do I need the time to be offline?

If you’re only bringing your laptop because you feel like you need to, that’s not an intentional decision.

That’s falling for hustle culture, and continuing to grind when you should be resting.

Often, I prefer to leave my work at home. However, sometimes it makes more sense to not officially book the time off and just run things light for the time away. Maybe “light” means just responding to timely emails (not all… only the time-sensitive ones). Maybe posting on social media.

But I decide this intentionally prior to the time away, and prepare accordingly.

The most successful business owners I know are intentional with their decisions around time and priorities, and that includes things like taking vacation as an entrepreneur. They aren’t reactionary. They don’t let things happen to them. And they lead and make intentional decisions for themselves.

When you can’t take time off, you’re an employee, not a business owner

A challenge I see so many entrepreneurs face is they think they start their own business, freelance or otherwise, for freedom. But instead of having true freedom and being their own boss, their clients become multiple bosses. They feel like they can’t live or take time off because they’re not in charge of their schedule.

No wonder you find yourself stuck in the constant grind. You want to plan time away, but you don’t even know where to start with taking vacation as an entrepreneur.

If this feels like too much of a challenge, I hope it helps you revisit how your business operates at the very least. Are you able to take time off? Or are you kinda stuck?

Maybe the answer to this question will motivate you to change how you do things, so you can live your life more away from your desk.

It’s about more than taking vacation as an entrepreneur

I’ve seen articles floating around the internet about the optimal vacation time for entrepreneurs. Apparently 4 weeks is a magic number for vacation time, among other suggestions. But I don’t buy it. I think your fulfillment and feelings of content you want from your work come from truly integrating your work and your life in a way that feels balanced and rewarding, not like your work precedes everything else worth living for.

I talk a lot about all things work-life integration. Honestly, it’s about more than taking vacation as an entrepreneur. I think you can still be hustling too much… Just surviving on the brink of burnout… Even if you do plan time away.

What’s more important is working towards work-life integration. Specifically, designing your work and how your business operates to fit around the ideal lifestyle you want to live.

What really matters to you? And how are you going to build a business that supports those dreams? That’s the question I want answers to.

Hopefully this winding reflection inspires you to think differently about how you run your business and taking vacation as an entrepreneur too.