Taking a real vacation as a freelancer or self-employed person isn’t easy, but it is possible to take time off. It does require planning down to the last detail, balancing money, client expectations, getting over the nagging worry of “What if my clients never hire me again?” and drawing some hard boundaries.
Now, this plan isn’t for the spontaneous trip. This is for the trip you want to take in a few months from now. So by the time you’re reading this, you’re probably thinking of a trip that’s four to six months away. Here’s how you can prepare to step away from work for a full month and truly unplug.
Budget, budget, budget
First things first: you need to plan your finances to cover both your vacation costs and your regular expenses. Your essentials—housing, retirement, insurance, utilities, credit card bills, phone, internet—all still need to be covered, with enough extra saved for two weeks to a month after you get back.
How to Handle It: First, either look at your monthly budget to see how much you need to cover your basic expenses. Then, take that total number and divide it by the number of pay periods between now and when you plan on taking your vacation. That should give you the number you need to put away per pay cheque.
Then create a separate, no-fee account dedicated to your vacation savings, and set up an automated weekly deposit. This way, the money builds up without you having to think about it, and you’re less tempted to dip into it. Out of sight, out of mind.
Cover essential bills and obligations
Some payments may not be automated like taxes and property taxes. Make a list of these bills and add reminders to your calendar. This way, everything’s handled before you leave, and you don’t come back to surprise expenses.
Essentials checklist:
● Taxes and HST: If you’re using accounting software, check your income and estimated taxes. You might need a quick meeting with your accountant to get a handle on this.
● Property taxes: Make sure you’ve saved for any increased bills. Hold off on paying until the last minute, but have it ready.
● Non-automated bills: Mark these on your calendar so you don’t miss anything.
Stick to a savings plan
Having a separate account for vacation funds ensures that your trip doesn’t affect your regular finances. You can either set up automatic savings transfers or assign funds in your main checking account a specific role—but the separate account is often easier.
Savings strategy:
● Automate savings: Set a weekly deposit into your vacation fund. This keeps it growing without you needing to remember.
● Avoid roaming fees: Managing finances on your phone is possible, but avoiding the need for daily check-ins keeps costs low and helps you truly unwind. You can buy an eSim to avoid roaming costs. If you have two-factor authentication, you may need to disable them temporarily to get access to certain accounts. Definitely check that before you leave as it can leave you open to scams. Consider getting a VPN if you’re checking sensitive personal information on your devices so scammers can’t access your
information.
Let clients know in advance
Taking a month off without blindsiding clients means giving them as much notice as possible. Start communicating your plans a few months in advance, so it’s clear when you’ll be away. We suggest letting them know at least three months in advance as they have enough time to adjust their calendars. Then remind them monthly and finally the week before you leave. Coordination is key here—you may need to adjust deadlines or even double up on assignments to meet their needs.
Client communication tips:
● Advance notice: Start sending emails and updating your email signature with the dates you’ll be unavailable.
● Workload adjustments: For some clients, you might need to double up on work before your break. Others may be okay skipping a month, so communicate and plan around their preferences.
● Planning for your return: Also, to prevent the ‘I’ll never work again’ anxiety, you can send some pitches to your clients so you’ll have assigned work when you’re back and working your way through the jet lag.
Set clear boundaries and out-of-office message
We know self-employment often means being surgically attached to our phone but it’s not a vacation if you keep answering emails and texts. Set a solid out-of-office auto-response with your vacation dates and alternative contacts (if applicable) to ensure clients know not to expect responses right away. If possible, avoid the temptation to “just check in” while you’re away.
How to disconnect:
● Email auto-reply: Create a clear auto-responder with dates and details so clients know your schedule. If you have back-up, send them there.
● Minimal communication: Give yourself permission to disconnect. Setting limits can help keep your vacation a vacation.
If you have a client who “just wants to hop on a call really briefly,” how you react is up to you based on the size of the project and if it’s a repeat, long-time client. Personally, I’ve had to point out that I’m not going to have internet as I’ll be traveling. Or another time I pointed out that I’d have to buy the fancy internet that allows for video calls and are they comfortable with me billing them for that? Or you can temporarily disable all video apps on your phone or computer, if you even have your computer. Our point is, draw some serious boundaries and pull up the drawbridge. Say no and keep repeating it.
Back-up, delegate, and document
Some tasks might need attention in your absence, so consider delegating. Handing over responsibilities to an assistant, virtual or otherwise, a trusted fellow freelancer, or colleague can help ensure everything runs smoothly while you’re away. Documenting key processes and storing files in the cloud also helps you avoid any issues.
Back-up and delegation plan:
● Document key processes: Even if you don’t delegate, having a checklist of must-dos can help smooth out your reentry.
● Backup files: Store critical files in the cloud for easy access, just in case someone covering for you needs them.
Plan for post-vacation re-entry
To avoid burnout the moment you’re back, ease yourself into work slowly. Block off the first few days to catch up on emails and admin tasks before diving into your full workload. This way, you get back into the groove gradually.
Re-entry strategy:
● Ease back in: Plan light workdays your first week back to give yourself breathing room.
● Admin catch-up: Set aside dedicated time to catch up on emails and client updates, so you’re not overwhelmed.
Mentally prepare to disconnect
Taking time off means stepping out of the freelancer mindset of “always being available.” Remind yourself that this break is not just okay—it’s essential to prevent burnout. This mindset shift will make it easier to truly unplug. It’s self-care. Taking the time to refresh yourself mentally, emotionally and physically makes you a better freelancer and entrepreneur. You have the clarity and the time to think of new ideas to grow your business.
Mindset shift:
● Embrace the break: Remind yourself that you’ve planned, saved, and worked for this. Taking time away is crucial for your well-being and productivity.
● Unwind activities: Plan screen-free activities—think hiking, reading, or people watching—to help you actually relax and enjoy your time away.
Preparing for a month off as a freelancer takes patience and discipline, but with a savings plan, clear client communication, and boundaries in place, you can take a break without stress. A well-planned vacation isn’t just a luxury—it’s the reset you need to return to work refreshed and ready to dive back in.
