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Nearly three years passed after I started freelancing full time before I took a bonafide out-of-office-reply vacation. The ballyhooed benefits of a freelancer’s flexible schedule may pan out during the Monday through Friday workweek, but days solely designed for not working are on altogether different footing.

Just before Memorial Day I happened to meet up with a former client who has lately switched to the freelance circuit. After I shared a story about a recent trip, she asked, somewhat wide-eyed, “How do you convince yourself to go away?” In short, approving my own time off is like assessing any other gig—there’s reviewing the schedule, resolving the pricing, and of course, saying no.

1. Set the date.

There’s no form to fill out, no accrued PTO to calculate, no higher-up to grant approval, but locking down the dates is even more important than my Airfarewatchdog alerts. In periods that I'm booking mostly short-term week-to-week gigs, I firm up my departure (if not my reservations) at least three to four months out, that is to say, well before any clients have asked after my availability.

If I’m on a multi-month project with a planned delivery date, I aim for two to three weeks beyond the scheduled deadline, just in case. When I have ongoing clients, I slot my away time between known busy periods, give loads of heads-up, and if asked, help find a fill-in. Picking the same days that my client is off can also do the trick in a pinch.

2. Always be billing, except when you’re not.

Sitting on a beach and realizing it is payday is a glorious moment. As a freelancer, it sometimes still happens. It’s just that the vagaries of accounts payable departments combine with the brutality of 60-day payment terms so the effect is more half relief and half surprise, since the work itself was completed so long ago I’ve nearly forgotten what I did.

Being completely divested from the concept of work attached to payment on a predetermined schedule means that I tend not to notice any difference in my cash flow for a single week (or two!), lo those many moons later. Vacation time is fundamentally no different than a bunch of Sundays strung together. I’m not earning anything then either—except when I’m taking every assignment in sight because I have a holiday coming up—and they happen every week regardless. Vacation should too.

3. No regrets, even when it means missing out.

Without fail, every time I schedule a trip, a new project comes my way that I would love to be a part of, usually from a much-admired or new client, or maybe one that provides a chance to update some skills or will result in a fantastic portfolio piece. And, gutting though it is, I need to decline. Then I need to get over it.

The instability, not knowing what’s in store, potential pitfalls and rewards, and yeah, being bummed when the timing doesn’t work out—that’s definitely somewhere in the small print of all those 1099s that flutter into my mailbox. Take comfort that you sometimes have to say no and there’s no Mai Tai on the other side.

Kathleen Baxter is a freelance editor and project manager in Brooklyn.