TL;DR: Taking time off as a business owner doesn’t have to be stressful. By implementing six-week planning cycles, weekly time budgets, clear out-of-office messages, and actually unplugging from email, you can enjoy guilt-free vacations without returning to chaos. The key is building systems that protect you from work overload before, during, and after your time away.
When I talk about systems, I tend to frame them in the context of the broader goal: to have a calmer, steadier business and life.
If you think of your home, you’re surrounded by systems that allow you to focus your attention on other things. Without plumbing, you’d have to spend hours every day going to get water and then moving it around your house. Without refrigeration, a significant portion of your year would go to preserving food. For most of human history, this was true. We’re so used to having these conveniences now that we forget about them entirely.
I’d love for you to experience this in your business, too. I don’t want you to spend hours on a random Tuesday just trying to figure out who owes you money. I don’t want you waking up in a cold sweat at 2 am because you just remembered that you missed a deadline.
And, I want you to be able to take time off. So, let’s talk today about the systems I have in my business to make time off more possible and less stressful. I’m writing this in January, so the holidays are fresh in the rearview mirror.
How Can You Avoid Stressful Vacations as a Business Owner?
Like most other people, I’ve had my share of stressful ‘vacations’ from work. Fun elements of these included:
- Scrambling in the days before the vacation to try to get everything done
- Still checking my inbox while I was away, or worse, still sneaking in a couple of calls
- Returning to a mountain of things I was ‘behind on.’
- Allowing a couple of clients to subtly guilt-trip me for being unavailable to them
Have you ever felt that taking time off isn’t even worth it because of all this stress around it? I definitely have.
What Systems Actually Work for Taking Time Off?
I’m not perfect about taking time off to this day, mainly for mindset reasons. I know myself and my workaholic tendencies, which is why systems are so helpful – they can save me from myself to some extent.
Here are the puzzle pieces that I’m finding most helpful:
6-week planning cycles
I talk about this more in my blog about big picture planning, but the gist of it is this – I plan my work in 6-week cycles, with two weeks for buffer and reflection, so each cycle expands out to a clean two months. When I look at a smaller frame of time like this, I can see when my vacations are and adjust my plans accordingly before the cycle even begins. For example, going into Christmas this year, I decided in November about multiple things I would be pushing into 2026. It felt a lot better than trying to plow through an impossible list between wrapping presents and packing for our trip.
Was December still A LOT? Yep – I have two little kids. But it was better than it could’ve been because November me was looking out for December me.
Weekly time budgeting
I have a whole blog about this too – the beauty of weekly time budgets for me is that it smooths out that mountain of tasks after a vacation is over. I can only plan to do the amount of work that my time budget allows. If it doesn’t fit, it doesn’t make the cut for the week. The process forces me to pick things to delay or cut entirely before the week even begins. I get the opportunity to feel like I’m winning because I did everything on my list for the day, and I can step back into work with far less stress.
Out of office messages
This is a given I know, but out of office messages are also easy to forget about. 8 times out of 10, communication is more important than speed for most types of work. When people know that you’re gone and won’t get back to them right away, they’re less likely to feel angsty about it. You’re also less likely to get the ‘just checking in’ emails that clog up your inbox even more.
Imagine you have a 6 pm reservation for a fancy restaurant. You and your date arrive right on time and the host simply says, ‘Have a seat.’ You then proceed to wait for 15 minutes while no one acknowledges you or even glances your way. That 15 minutes will feel long and frustrating – you have no idea how long to expect and may even start to suspect that they’ve forgotten you.
Now imagine the same scenario but with better communication. If they tell you when you first arrive that there will be a 15-minute delay, and then check in after 10 minutes to confirm that you only have a few more minutes to wait, you’ll feel much better about it. It’ll probably be a non-event.
Just let people know what to expect, and it will take the pressure off. I’ve even seen people do this with internal planning days or one-day absences. You can also make them silly!
Of course, I don’t surprise people with these. I make sure my clients and team know about longer absences several weeks in advance.
Why Is It Important to Actually Unplug During Time Off?
If I want a vacation to feel like a vacation, I can’t check my email. At all. If I look, even if I don’t respond to anything, it keeps my brain in ‘work mode’ – and I also run the risk of getting stressed out if there’s something less than stellar in there.
In my last job, unplugged vacations were rare across the team. Working yourself to the bone – even to the visible detriment of your health – was a badge of honor. I remember once, a Director left for a vacation. She continued to be copied on emails that people felt she would like to see on her return. A few days in, we received an angry email from her demanding that we stop emailing her. This isn’t how things work.
As we all know by now, getting people to stop emailing us is well nigh impossible (I love the unsubscribe button, but there’s only so much you can do). We can’t blame our inboxes (or our Slack messages, or whatever) for keeping us thinking about work. We have the power to turn them off.
If I’m worried about it, I’ll include an alternative team member for people to reach in an emergency (I’ve been gone for two maternity leaves since starting this business – it’s wild how few of these there truly are). Or I’ll let people know they can text me if needed. Thankfully, this almost never gets used, but it can help me feel like I don’t have to check in ‘just in case something major is wrong.’
As for the minor guilt trips, the only solution I have right now is to not let side comments get to me. If I have a good relationship with someone, I can even remind them that I want them to start taking guilt-free vacations, too. Usually resentment over someone else being unavailable only crops up when one’s own boundaries aren’t where they should be.
How Do You Make Time Off Sustainable as an Entrepreneur?
I’m pretty sure Europeans have a lot to teach us Americans when it comes to taking meaningful time off. Sometimes I think about their out-of-office messages that will simply ask people to email again after their breaks because they won’t be reading anything that came in while they were out. I can’t quite do that – yet – but I like to remind myself that so much of the stress I’ve felt around taking time off is culturally informed. It doesn’t have to feel awful, and we don’t have to ‘earn’ the right to step away for a few days. We definitely shouldn’t do the same amount of work we would’ve done without the vacation. That misses the point entirely.
Most people who start their own business note that having autonomy over their time is a main attraction. Autonomy comes with responsibility – no one else is there to help us unplug and recover. Rest is critical for us to have the staying power for the roller coaster of entrepreneurship, and we have to put in the guardrails we need to make our own working life sustainable.
I’m cheering you on as you think about the best things to put in place for yourself!
Frequently Asked Questions
Q: How far in advance should I notify clients about time off?
A: I make sure my clients and team know about longer absences several weeks in advance. This gives them time to plan around my absence and reduces last-minute stress for everyone involved.
Q: What should I do if I’m worried about emergencies while I’m away?
A: Include an alternative team member for people to reach in an emergency in your out-of-office message, or let people know they can text you if absolutely needed. You’ll likely find these options are rarely used, but having them in place will turn down the volume on the voice in your head telling you to check on things ‘just in case.’
Q: How do I handle the workload when I return from vacation?
A: Weekly time budgeting is key. You can only plan to do the amount of work that your time budget allows when you return. This forces you to prioritize and prevents the overwhelming ‘mountain of tasks’ feeling that can make vacations feel exhausting.
Q: Is it really necessary to completely avoid checking email on vacation?
A: Yes, if you want the vacation to actually feel like a vacation. Even just looking at email without responding keeps your brain in work mode and risks stressing you out. The power to turn off notifications is in your hands – use it.
Q: How do 6-week planning cycles help with taking time off?
A: Planning in 6-week cycles (with 2 weeks buffer) lets you see upcoming vacations in advance and adjust your workload before the cycle even begins. This means you can proactively push tasks to later periods rather than scrambling to finish everything before you leave.
