How I Prepared My Business for a Two-Week Vacation in Italy (Without Stressing Out)
The Truth: This Didn't Happen Overnight
In this post, I'm breaking down exactly what I did to prepare. You'll find tips for both product-based businesses (especially Etsy sellers!) and coaching/service-based businesses, plus the bigger picture mindset work that's made this kind of ease possible.
Before we get into the logistics, I want to stress something important:
There honestly wasn't that much I had to do before leaving.
And that's because I've been preparing for this for years.
Over time, I've intentionally shifted my business to a place that doesn't rely on me working 24/7 — a business that can support me, not the other way around. That transition has been a blend of:
Setting clear boundaries and policies
Building systems and support
Shifting my offers and business model to allow for this.
Even my clients who are still doing custom stationery work are able to take extended time off because they've built businesses that are mentally and operationally ready for it. That's the real work here, not just prepping for vacation, but creating a business that supports your life in all seasons.
The Backstory: Moving Away from Custom Work
A big part of this shift for me started when I realized I didn't want to keep doing custom work forever. Early summer 2021, I made the mental decision to phase it out — and over the following year, that slowly became a reality.
Before Thanksgiving, we took all our custom listings off Etsy to prepare for Black Friday. (that's our busiest time of year!) We wrapped up custom orders and put more energy into products like Vellum, which I had originally launched back at the start of 2021. It became a strong, steady source of revenue that helped me confidently make the shift.
If you're in the middle of a transition yourself, know this: it can absolutely feel weird, hard, or uncertain, but every small step makes the next one easier.
Preparing the Etsy Shop for Vacation
Okay, let's talk about the tangible stuff.
Here's what I did on Etsy to prepare for being gone for two weeks:
1. Lowered My Ad Budget
A few weeks before leaving, I reduced my Etsy ad spend. Ads are a great way to control how many orders come in + and I knew I didn't want a surge of last-minute orders that would need to be fulfilled while I was away.
2. Planned Around a Slow Season
I didn't even plan this consciously, but our vacation ended up landing right after August, which is always our slowest month in the wedding stationery world. Perfect timing!
Knowing your industry's natural ebbs and flows makes this kind of planning so much easier.
3. Updated My Snippets and Lead Times
This was long overdue. I updated all my canned responses (snippets) so my mom could easily handle questions while I was gone.
I also extended my lead times — not just for the trip, but to give myself more breathing room overall. (Pro tip: do this at least a couple weeks in advance, not the day before!)
4. Finished Orders Early + Prepped Products
Before leaving, we finished as many orders as possible and prepped products for easy fulfillment. My mom can ship things while I'm gone, and when I return, I won't be buried under a pile of work.
When you're preparing for a trip, think about the four-week window around it: the week before, the vacation itself, and the recovery week after.
5. Set Up an Auto Response and FAQs
Etsy allows you to create automatic replies, so I added an out-of-office message with answers to the top three questions we always get. That way, customers get instant info — and anyone who messages knows we're temporarily out of office.
Here is what that message said:
“Ciao from Italy! I am currently vacationing in Italy, so there may be a delay in communication; however, orders are shipping normally while I am gone!”
Here are some FAQ to help while you await a response :)
Q: Do you have rush options?
A: At this time, no. The turnaround time is reflected at checkout, and we'll always get it in the mail as soon as we can!
Q: Does this come in other sizes?
A: We currently only have vellum to fit 5x7 (A7) invitations.
Q: When will my order ship?
A: The turnaround time is reflected at checkout. If your question was about when your order will ship, it's already in process to ship out ASAP! You'll receive tracking when the order ships. Shipping takes as little as two days.
Thanks so much!
Carley”
Pro Tip💫: Grab my free plug-and-play Etsy templates that give you exactly what to say. Copy, paste, & sell more. Snag those here.
6. Decided Not to Use Vacation Mode
I've used vacation mode before, and it's never been a big deal. But since my mom can manage orders, we decided not to use it this time.
Generally, I don't recommend using vacation mode unless you're gone for extended periods of time. With the auto replies and easy-to-change lead times, that is always where I would start! I have used Vacation mode successfully, getting an order in as little as 6 hours after opening my shop from vacation mode!
Wondering if Vacation mode is right for you? Check out this blog post: Etsy Vacation Mode: How to Take a Break Without Hurting Your Sales
Read this blog or listen to this podcast episode on Apple or Spotify before you turn on caption mode!
7. Set Hard Deadlines
I gave clear order cutoffs to custom clients and leads ("You'll need to order by today to get it by [date]."). It's a win-win: customers know what to expect, and I protect my time without guilt.
Grab my Plug & Play Etsy Templates to see this in action! {Here}
Preparing My Coaching & Digital Business
For the other side of my business — coaching, courses, and the Tipsy Business Podcast — the prep looked different, but the intention was the same: ease.
1. Client Communication
All my coaching clients knew I'd be gone well in advance. I reminded them that I'd still be available on Voxer but with a time delay (thanks to the 6–9 hour time difference).
Because I work with established, confident business owners, they don't rely on me for emergencies — they hire me to help them grow. That makes it easy to take time off without anyone feeling unsupported.
2025 edit: Now that I have a child, I would not be available to my clients on vacation. This was a different season of life, and it worked out well! They rarely messaged me and respected my vacation!
2. Automated Payments
All recurring payments are set up automatically. No manual invoicing, no scrambling. This means I was making money while in Italy!
3. Podcast & Content
I batched and pre-scheduled podcast episodes so I could fully enjoy my trip. For simplicity, I skipped guest interviews for a few weeks, so I didn't have to worry about coordination or promotion while traveling.
4. Team Prep
I let my team know the exact dates I'd be gone, asked if they needed anything from me ahead of time, and made sure nothing was waiting on me. Clear communication solves 90% of potential issues.
The Bigger Picture: Why This Feels Easy Now
If you're reading this and thinking, "That sounds nice, but it doesn't feel possible for me yet," ...I've been there.
A few years ago, I couldn't imagine stepping away for two days, let alone two weeks in Europe. But that feeling was actually my sign that I needed to start building a business that supported my life, not the other way around.
Because the truth is: I've been designing for ease all along. The longer I've practiced that, the easier it's become.
Final Thoughts.
A business that allows freedom like this is something you prepare for, one boundary and one system at a time.
So whether you're planning your next trip, a season off, or to grow your family (read this blog post about how I ran my Etsy the month I became a mom), start now. The earlier you begin creating ease in your business, the sooner it becomes your new normal.
🔊You can also listen to the episode on apple podcasts or spotify!
Watch me answer messages in 7 seconds (yes, really.)
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