How to Take Time Off and Tell Clients You’re on Vacation
If I had a dollar for every “7-figure coach” who promises you can travel the world while your business runs itself, well, I’d probably have enough to take a really great vacation. Here’s the thing: for the rest of us—ordinary but thriving business owners without celebrity-sized teams—taking serious time off can feel impossible. What happens if a client needs you? Will everything fall apart? Will there be money when you get back? Cue late-night panic-Googling.
My solution is far from glamorous. There’s no million-dollar team, no “passive income empire,” no magic calendar app that makes leads sprout from thin air. But somehow, I take 5 to 7 weeks off every single year. And no, I don’t mean two months in Bali (though, friends, wouldn’t that be dreamy?). I mean practical, honest, it-makes-sense-for-my-life kind of time off. And my business is still here, chugging right along.
If you’re a service provider, a solopreneur, or just plain allergic to those exhausting business “crush it” mottos, grab your favorite beverage. I’m pulling back the curtain on how real business owners (your people, just like you) can build downtime into their lives… no empire required.
How to Take Time Off As a Business Owner
If you peeked at my calendar, you’d see a patchwork of regular breaks—not just the annual vacation with my husband, but strategic long weekends, conference trips, and even carefully timed “just-because” days. It might look indulgent from the outside, but here’s my reality: I set up my business to support my life, not the other way around.
Could I work more? Probably. But after more than 30 years living with Type 1 diabetes (I’m 35, in case you’re counting), I don’t have the luxury of assuming that “someday” will be here for all the adventures I want. I’m healthy today, and I want to use that. I want memories, not just invoices. That’s why I don’t let business guilt or outside expectations rule how I use my time.
The Not-So-Secret System: The Power of the Calendar
Here’s where the “secrets” start—if you can even call them that. Every single vacation, family trip, or random pocket of time off goes first on my calendar. It’s my business version of “if it’s not scheduled, it’s not real.”
When my husband and I decide on a vacation (usually around our anniversary), I literally book it by March or April, and as soon as it’s set, it gets blocked off. Same goes for conferences, school breaks for my daughter, camping weekends… you get the idea. If anything feels “random,” I make it matter by making it official.
Parent friends, lean in: if you get your kid’s school calendar and it’s buried under leftover takeout on the fridge, time to upgrade. I love taking a picture and uploading those dates into Google Gemini or even having it auto-create busy days for me. Why? I’m protecting my time from the accidental “whoops, you booked a client call on the first day of fall break!” moments. Even if I might work part of that day, there are NO calls, period.
Simple Project Timelines Before Vacation
Here’s one that ordinary business owners will love: my client projects are almost always two or three weeks long. That’s it. Occasionally (and I mean very rarely), a huge project might need a little more. But generally, this lets me clearly see when a project starts… and when it ends. And I do not—repeat, do not!—start a big website build right before running off to Europe. If a trip overlaps, I push the start date. No drama, no guilt.
Sometimes that means I land with a random empty week before vacation. And honestly? I love it. That’s my time to catch up on admin, sneak in a small “jumpstart” project, or just breathe a little. The myth that “every idle day kills your business” needs to be politely shown the door.
Vacation Mode vs. “Reachable” Mode
Not all time off is created equal. Some trips are sacred: when I’m on a “real” vacation (especially in Europe), I’m unplugged. Inbox closed. Slack silenced. The only thing I’ll post is a cheerful “here’s my pizza in Italy” photo for the ‘gram, because, let’s be honest, I want to remember that too.
But for mini getaways—conferences, friend-visits, camping—I sometimes check email for 30 minutes or so, maybe respond if it’s really easy. The world doesn’t end. The business engine keeps humming. And for anyone who wants to be 100% unplugged even during short breaks, let that be your call! The point is, you get to decide. Ordinary doesn’t mean powerless; it means you’re the boss of your time.
Prepping for Time Off: No Fancy Systems Here
Contrary to all those “10-step vacation prep workflows,” mine is… not like that. The week before I leave, I’ll:
- Turn on my out-of-office autoresponder (yes, even for Dubsado onboarding sequences—reminders matter!)
- Add a note to client communications about time off
- Schedule out content (YouTube, podcast, etc.) not only for the week I’m gone, but ideally for a week or two after, so I’m not in a mad scramble upon returning.
No frantic pre-vacation sprints. No spreadsheets. Sometimes, simplicity wins.
Keeping The Money Coming In While on Vacation
Here’s a little “real talk” on income: my business isn’t one big “eat-or-famine” launch. Clients pay in installments, spaced across several months. That means even when I’m not working, payments drop in like clockwork. I also have recurring SEO retainer clients—not because I set out to “replace my salary while I nap,” but because they genuinely needed ongoing support.
My leads are steady, coming in from SEO, word of mouth, and content (like this podcast). I worked hard to create margin—so “out of office” doesn’t mean “out of money.”
And, because all the experts say “clarity matters,” let me say: even with 5 to 7 weeks off a year, my in-office weeks aren’t bananas. I don’t stack them with 80-hour heroics. I protect Mondays and Fridays from client calls, and I deliberately block off every other Tuesday for breathing room. You can do this, too—it’s not luck, just intention.
Coming Back: The Gentle Re-Entry
I’ll admit it: on the way home (usually sitting at the airport), I’ll skim my inbox and nudge out 113 newsletters so the first real workday isn’t a wall of digital noise. But I never book calls immediately after time off. I give myself a day (sometimes two) to catch up, stretch, and get back in the swing before jumping into meetings and heavy client work.
I’m a big believer in making your “come back” as gentle as your “see you later.”
Why Ordinary Boundaries Aren’t “Less Than” (They’re Everything)
If you’re still thinking, “Jessica, this sounds great, but what about the money? What about missed opportunities?”—I hear you. But if the last three decades have taught me anything, it’s this: we don’t know how many healthy years we get. I take time off now because I want to live my life while I can, and I built my business to make that possible.
Point blank: “Ordinary” isn’t an insult here. It’s the most freeing thing in the world. The ordinary-but-thriving business owner’s path is painfully honest, wildly flexible, and (maybe most important!) actually enjoyable. No huge teams, no “sales machine” needed. Just a business that works for your life—and your loved ones.
So, go ahead. Mark your trip on the calendar. Block off your kid’s fall break. Build in margin, not just meetings. Your people are doing it, I’m doing it, and you get to, too.
FAQs: 5 Things I Get Asked All The Time
1. Do you really take 5–7 weeks completely off every year?
Yes! Sometimes that looks like scattered vacations, long weekends, or trips for conferences. But I make sure they’re actually blocked out (in advance!) on my calendar—and I stick to it.
2. What if a client project overlaps with planned time off?
I plan projects in 2–3 week blocks. If the timeline bumps into time off, I simply start the next client afterward. No moving people around or working from the airport to “close the gap.”
3. How do you keep money coming in when you’re not working?
Clients pay in installments, so income continues even during time off. Plus, referrals, SEO, and content keep inquiries flowing. Most of my clients are one-off, but retainer work provides a nice bonus.
4. How do you make sure business stuff doesn’t creep into vacation?
For “real” vacations, I fully unplug—autoresponders on, access off. For conferences or small trips, I might check in, but I set boundaries so business doesn’t dominate my personal time.
5. What’s your best tip for someone scared to take more time off?
Start small. Block off the dates, even if it’s just a half-day or a random Friday. Build boundaries with clients and practice breathing room. Ordinary business is about steady, honest steps!
6. Is it possible to do this without a team or fancy systems?
Absolutely. I’m proof: no team, no endless automations. Just old-fashioned planning, boundaries, and a willingness to say, “My life matters just as much as my business.”
Ready to claim your own version of time off? I’d love to hear how you’re making space for real life inside your ordinary but thriving business. DM me, find your people, and enjoy that well-earned break—you deserve it.