How to take vacations when you're the boss

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Freelancing requires balancing multiple projects, plans, and priorities at once, which can be a slippery slope into overworking yourself to get it all done. Been there before and not a fan!

Taking time off, whether extended breaks, long weekends, half days, or vacations, is one of the best ways to find your own version of balance so you’re not taking on too much at once.

The goal with prioritizing downtime is to rest for your continued health, reset to replenish your energy and motivation to continue forward, and refresh your perspective to make room for strategic thinking that’s easy to miss out on when working on the day-to-day details.

Since your time off isn’t paid for by an employer, it’s easy to put it on the back burner in favor of bringing more cash in the door by working on that next project.

And while we’re happy to not have a boss dictating the details of how often we take off, sometimes this lack of structure leads to freelancers taking off less time than they would with a capped PTO policy.

Fear is also a driving force behind the notion that too much time off will lead you to missing out on important opportunities that’ll get you ahead, like not having enough time to deliver exceptional service to your clients or properly marketing yourself to attract new business.

That’s usually just hype as a “regular” cadence of both work and leave is not likely to have a negative impact on your practice as long as you’re not vacationing more than you’re working. :)

Feeling this way is normal as a portfolio career of different clients and projects makes it more complicated for a freelancer to find the right times to go on holiday. It’s also likely that you’ve had a moment where you’ve realized you haven’t taken time off in wayyyy too long.

Don’t dwell on it and instead recognize it’s time to more intentionally incorporate regular breaks, holidays, and recharge days as part of your work routine.

Here’s how I’ve handled taking breaks over the last 13 years of freelancing and approaches I’ve seen from other self-employed pros striking their own balance between work and play.

Quite simply, block time on your calendar for rest days and plan your work commitments around these breaks. It’s more common to plan time off around your work availability, but why not the opposite, especially when you have more control over your schedule when freelancing.

Each year, I get better at prioritizing vacations on my schedule not as a secondary consideration but as a fundamental part of maintaining my well-being and performance.

My suggestion is to make it a habit of scheduling a few shorter breaks each month and two lengthier breaks once a quarter.

The shorter ones serve to more regularly break up your routine for rest, but without being too disruptive to your ongoing work commitments.

While lengthier breaks of multiple days and weeks happen less frequently, they’re incredibly beneficial for fully detaching from work and returning with higher energy, focus, and motivation.

The best moment to let a client know of the dates or times when you’ll be unavailable is at the very beginning of an engagement. Give notice ahead of time when the project timeline is being finalized during the drafting of a contract or less formally in initial conversations with a client.

This is less about getting their approval and more about alignment. Here’s one way to quickly explain this in writing:

“The Contractor shall perform the Services during the term of this Agreement, commencing on January 9, 2026, and terminating on April 9, 2026, during the Standard Working Hours of 9:00 AM to 4:00 PM Eastern Standard Time (EST), Monday through Friday. The Contractor shall not be required to attend meetings or perform services on the following Unavailable Dates: January 16, 2026; February 23, 2026; February 24, 2026; and March 18, 2026, through March 24, 2026 (inclusive). Any required work outside the Standard Working Hours or on Unavailable Dates shall be subject to prior written agreement between the Contractor and the Client.”

When, how, and if you inform a client of your availability depends on the structure of the project. In certain instances, you will define regular meeting times across the project timeline, sometimes your contributions will happen as-needed during the agreed-upon working hours, and occasionally, the focus will be on turning over deliverables across a series of deadlines.

The point in clarifying these details early is to reserve your personal leave ahead of time and consistently land projects where open communication is built in from the start.

No matter how much you plan ahead, life happens and you’ll unexpectedly need to take off. Whether you’re sick, you need to care for a loved one, or a last-minute trip pops up, it’s important that you inform select clients right away.

Not every partner or customer needs to be notified, just the ones where your time off conflicts with the timeline, the turnover of any agreed-upon deliverables is affected, or when they’re expecting you to be available to meet or communicate with them during set working hours.

Whenever you’re sharing a change in your availability, the best case scenario is suggesting next steps to the client when your absence alters the parameters of the project.

If there’s a minor, short-term impact to the collaboration, indicate you’ll complete a deliverable ahead of time, temporarily reassign a task, or lengthen the project timeline to make up for your unplanned leave.

If it’s an extended break of two weeks or beyond that’ll significantly impact a project, then in those rare circumstances, you may suggest pausing or terminating the engagement altogether.

While being mindful of upholding your contractual obligations and how this affects your reputation as a freelancer, you’ll find that most clients are understanding when you provide suggestions on how you’ll work to minimize the impact of your unexpected break.

Not every client you have as a freelancer needs to know you’re taking time off. If your mental health day or vacation has no bearing on the details of your collaboration with a particular customer, then it’s none of their business and they likely don’t care.

I’m not suggesting that you ever mislead a client into thinking you’re working when you’re really not, but with many types of projects, there’s no need to update them on your availability.

For example, I offer coaching sessions to freelancers, marketers, and leaders, typically once a week for one hour. Suppose I meet with a coachee every Monday morning. If I take a few days off later in the week, there is no need to notify the client, since it does not affect our scheduled coaching sessions.

Similarly, for projects where you provide ad-hoc guidance, one-off engagements like speaking or training, or asynchronous support with fewer or no fixed deadlines, short periods of unavailability generally do not need to be communicated. Omission is your friend and keeps things simple.

On the other hand, for a more involved consulting project with multiple deliverables due each month and an expectation of timely communication during working hours, I’ll inform the client of changes to the established schedule.

What’s your approach to taking breaks and managing your downtime when freelancing?

A version of this article first appeared in Career Freelancer, December 2025.

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