They say that freelancers never go on holidays. And, if they do, it is never 100% holiday. It is rather half work, half remorse for being unproductive. Do you agree? Are you a freelancer who never dares to take a break out of fear of losing your clients? Or the fear of missing “the chance of your life” to get the best client ever? Well, let me prove to you why freelancing doesn’t mean sacrificing your holidays! I’m writing this article a couple of weeks before I leave to visit my friends in Germany for a 9-day break, so I know what I’m talking about!

These are the steps that I’d suggest you take to start enjoying the time and location independence that your freelance lifestyle should offer:

1. Identify your periods of low workload
2. Plan your time ahead
3. Plan your finances ahead
4. Keep an open communication with your customers
5. Change your mindset

Step 1 – Identify your periods of high and low workload

When can I go on holiday? If this is the question that is killing you, I get you! Trying to find the best moment to take a long break from work seems an impossible task, but it doesn’t have to be!

If you have no obligations – ahem, kids -, choose your holidays according to your workload. Before I had kids, leaving in August was for me a no-go. That was THE month to get new clients! Why? Because everyone else goes on holiday in the summertime, and companies feel forced to search for new outsourcing options – either to cover the work of their employees or even their freelancers. And that is when I’d come into play!

In some cases, customers would be so grateful that someone “saved” them, that they’d keep me as their regular freelancer. In other cases though, they would only contact me again for the next holiday season. But that was OK with me because my holiday wouldn’t depend on school breaks 😉

So when would I go on holiday then? In those months when I used to have a low workload. Whenever I’d notice that I didn’t have as many projects coming in as usual, I *tried* not to panic and checked whether this was a yearly trend. If it was, that month would become a very good “holiday candidate” 😅

By the way, I’m writing in the past tense because I now have a sense of when my recurrent high and low phases are, but my process is still the same! Only that now I have kids… and their school calendar.

If you have kids and have to stick to their school calendar, consider going on shorter holidays more often than taking a long break when you know your customers need you most. Or you can also travel for longer periods of time, take one or two weeks REALLY off, and work part-time for the rest of the trip. Check this post on how to freelance while traveling with your family.

Step 2 – Plan your time ahead

Planning a holiday as a freelancer isn’t just writing a list with stuff you want to pack in your luggage. It’s rather a long-time task that will help you avoid what Germans call “pre-holiday stress.”

• Each year, turn it into a routine to schedule your holidays and any other specific days that you’d like to take off. Think birthdays, anniversaries, Christmas… Write those dates into your planner and take them always into account when taking on new projects.
• Always work ahead. If you “love” working under pressure and tend to finish your projects on the very last minute to meet the deadline, you’d better change that right now! The sooner you can deliver your work, the more time you’ll have to work on any interesting new projects that may arrive short before leaving for your holidays.
  And if no financially interesting project arrives, you may want to dedicate that spare time to send invoices, organize your bookkeeping, tax filings… You know, all this stuff you know you have to do but you never find the time. Besides, do you know how good it feels when you come back home and everything is sorted out?
• Last two weeks before your holidays: Don’t overload your weekly to-do list. Plan to do what is 100% important and urgent. If you have something on that list which isn’t both important AND urgent, leave it for later. Or maybe get it off the list all at once?

Step 3 – Plan your finances ahead

Lack of time or lack of money – What is worst, right? Freelancing won’t guarantee any fix income, but this is something you already know. What we can do though is plan our finances ahead to have a security cushion, just in case.

• Each year or quarter, when setting your rates, don’t forget to include 4 weeks of holidays where you won’t be earning any money. If you need help calculating your rates, check out the Work for You Planner. There is a whole chapter dedicated to rates and prices!
• Consider taking on more assignments in the months leading to your planned vacation time. However, as we said before, do not overload the last 2 weeks before leaving. You don’t want to start your holidays all stressed up!
• Each month, set money aside for your holidays. You are your own boss, so be kind to your employee 😉
• Consider opening another source of passive income. Depending on your industry, you might want to work with affiliates, or offer digital goods like workbooks, printables or digital courses. You may not get rich, but it’s quite comforting to get some cash on a monthly basis. Just give it a thought.

Step 4 – Keep an open communication with your customers

Repeat after me: Customers are people. You can talk to them. In fact, the more honest and open the communication, the fewer misunderstandings there will be!

• Let them know that you will be off, and provide them with the exact dates. The sooner, the better. Customers don’t look for other freelancers to punish those who can’t work 24/7/365. They just look for the resources they need to keep their schedule.
  • So don’t be scared of saying that you are taking a break. Talk to them about timelines, show some flexibility and willingness to collaborate with them, and suggest new delivery due dates.
  • If it isn’t going to stress you out, you can check your emails a couple of days per week when on holidays. Make sure you only answer to those emails that really matter. Giving a short answer like “Hi, I am away for [INSERT PERIOD OF TIME]. Let me know if I can help you when I get back” won’t send customers away, quite the opposite: They’ll feel grateful that you took the time to answer from your holidays! And if they don’t, consider changing customers 😉
  • I like to include a personal touch, like “Best regards from Bali / Tokio / Honolulu” or wherever it is that you’re taking your well-worth time 😉
  • Another option is telling them that you are involved in a longer project for another customer. Give them the exact dates when you’ll be available again, and they should understand it.
• Set an out-of-office reply. Your customers may forget that you are away, and it is also very helpful if any new customer reaches out to you for the first time!
• When you are back home, send them a quick notice reminding them that you are up and running!

Step 5 – Change your mindset

As a freelancer, you will always have something to do for your business. But I bet this isn’t why you started freelancing in the first place, right? So give yourself some grace! Everybody needs a break after spending months with long working hours. You will come back with recharged energies, and, besides, a time out will most likely help you come up with new ideas!

So what are you waiting for? Start planning your next holidays and enjoy your freelance life!

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