Taking Vacation When No One is Paying You to Take Time Off

Avatar of Geoff Graham
Geoff Graham on (Updated on )

DigitalOcean provides cloud products for every stage of your journey. Get started with $200 in free credit!

My family usually takes two “bigs” trips each year: one spent visiting family across the country and another to explore places that are new to us. This is no problem for my wife. Her employer gives her four weeks of paid vacation every year and she can bank on that when we’re planning where we want to travel and how long we want to spend there.

So lucky!

The problem for me, however, is that no one is paying me to take time off. It’s kind of ironic in a way because my wife has one employer who pays her to not work for a limited amount of time, but I have many employers who do not do the same for me. That’s one of the many benefits that often comes with full-time employment and something we may even expect an employer to provide. For me and others who call themselves freelancers, that is a benefit we either have to forgo or intentionally manage ourselves.

The way my family has dealt with this in the past has to call these “working” vacations where we make billable, working hours part of our vacation agenda. If you’re thinking this sounds awful, it kind of is, and that’s because it makes no one happy. My kids are not happy that I’m not spending time with them. My wife is not happy to be solo-parenting during vacation. I’m certainly not happy knowing there is a lot of fun to be had just outside my makeshift office. It’s a no-win situation.

We’re not going to be looking at CSS in this post but we are going to talk about tricks for taking paid vacations when no one is paying you to take time off. I suspect that there are a number of us in the front-end development community who face similar situations and addressing is one way we can figure it out together and hopefully glean ideas that make our work-life balance much healthier.

Why paid vacations are a big deal

I realize this might go without saying, but let’s get it out of the way: taking time off is important to our overall well-being. No one wants to be Richard Hendricks in Silicon Valley after pulling an endless string of all-nighters.


Seriously, though, taking time-off allows us to recharge and decompress from the stresses of our normal working lives, enjoy things that are not directly tied to work, and even return to our desks much happier and more productive than we were when we left. For me personally, I tend to resent my work the longer I go between vacations and that resentment most definitely carries into my personal life which is unfair to me and my family alike.

Forming a mindset for taking time off

Let’s be real about this: there is no trick for getting other to pay the tab for your vacation when you run a freelance business. What we’re talking about instead is changing our way of thinking and forming habits that provide us with indicators for when we can afford to take a vacation. This requires a little bit of planning, a smidge of budgeting acumen and a lot of self management.

More specifically, let’s go over three actionable things we can do to form good habits for knowing how much we work, how much we earn, and how we can set funds aside that allow us to take time off when we’ve earned it.

Start by tracking your time

I cannot advocate enough for tracking the time you work. By this, I mean creating a record of the amount of time you spend working each day and noting what that time was spent doing. If your freelance work is billed on an hourly basis, you probably already do this to some extent, but I would even recommend it for those who work on retainer, contract or flat-rate projects. The benefit is you know how many hours you typically work in a day, how much of it was billable, and where you are spending most of your time.

There are other hidden benefits to time-tracking and those may even make for a fun follow-up post. Suffice to say, tracking time is the foundation for knowing whether or not you are even eligible to take a vacation in the first place. It’s your gauge for knowing how much time you have put into work and when you should consider taking time off.

I use Harvest for time tracking (you can use my referral link for a trial and discount) but I have heard great things about Toggl, Timely and FreshBooks. If you have one you’re particularly in love with, then please share it below and I’d be happy to consider adding it to the list.

Pay yourself a salary

Freelancers do not always have the luxury of being paid regularly or even on time, but we can pretend like we do. If you’ve been in business for yourself for any amount of time, then you likely have a feel for what you bill clients on an average month and that’s a decent place to start for giving yourself a paycheck.

I know it can be different for everyone and not all freelancers can bet on having a regular stream of income. In those cases, I would likely start by adding up your monthly living expenses and using that as your monthly payments to yourself.

I’m far from being a financial advisor or anyone to instruct others on how to manage their money, but one trick I’ve learned for myself is to keep all my client payments in their own separate bank account and set up a recurring transfer from it to my personal account on the first of every month. That ensures I am paying myself, that I have my living expenses covered, and that I am not immediately blowing any extra money I might be fortunate enough to made above my expectations.

Regardless of what trick works best for you, the important thing is having an idea of what a “normal” month looks like for you and allowing yourself to stash some cash away to use to pay yourself when you are not technically working.

Establish a vacation fund

My wife’s employer gives her a specific number of days off each year, but she has to earn them. In other words, she gets a credit towards paid time off for every day she works up to four weeks in a given year. It’s sort of like they’ve set up a fund for her that rewards her for showing up to work and they draw from it whenever she chooses to use the credits for vacation.

I think freelancers can do a similar thing as long as we are taking the steps we mentioned above of tracking our time and paying ourselves. If we know how much time we need to work to earn a baseline amount of money to cover our expenses, then we skim the top off what we earn in excess of that to pay for time we decide to take off of work. In a way, it’s like we are putting in extra work and using the credits from that work for well-deserved time off. It’s not a perfect analogy, but allows us to mimic the same sort of benefit my wife gets.

The same goes for the other way around: if we earn less than we expect then the chances are (and, yes, this is a big assumption) that we worked less than we expected and that counts against our paid time off. That’s not a fun thing to talk about but certainly is one of the risks that comes with self-employment. Where my wife cannot lose her paid time off if her employer has a bad month, that is a distinct possibility with freelancing.

Calculating and tracking vacation

I put a spreadsheet together to help put the concepts we’ve covered in this post together for the sake of tallying up vacation hours.

View Spreadsheet

All cells highlighted in yellow mean you can edit the values. The others calculate on their own.

Spoiler Alert: It’s not a silver bullet that is going to work for everyone and your mileage may vary. That said, it might be a decent starting point for you to plug in a few numbers, track your client payments, and spit out a result that gives you affirmation for deciding when to take time off. You’ve put the hours in and deserve to at least treat yourself every now and then.

Aren’t there other ways to calculate this?

You bet. As mentioned, the spreadsheet above is not going to be perfect for every need or situation. For example, if you absolutely have no way of defining a salary for yourself, then the spreadsheet is going to fall apart right away.

Another idea might be to use your hourly rate, calculating your revenue based on the number of hours you work in a month, then taking a percentage of that to fund your paid time off. I made another spreadsheet of how that might work. Again, all cells in yellow are ones you can change to suit your needs.

View Spreadsheet

Wrapping Up

We all know the saying “with great power comes great responsibility” and the same can be said of freelancing. We have a lot of say in how we defining what we work on, who we work for, and when we work, but there’s a lot of self-management, overhead and responsibility that comes with the territory.

Taking time off is one of those responsibilities. No one is going to tell you to take time off as a freelancer and none of your clients are obligated to continue paying you when you do. Hopefully the ideas we covered together in this post help encourage you to take well-deserved time-off, or at least fuel some ideas for how to do it.

And, of course, if you have different ways of dealing with this that work well for you then please do fill out the form below and we’d be happy to share them.