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How to Take a Vacation When You Work for Yourself

  • By Greg Hamill
  • November 25, 2020

We all know the internal monologue—to vacation or not to vacation? All of the hard work it takes to bring clients down through the bottom of the funnel makes it near taboo to suggest a break for personal time. Then there are the concerns over a freeze in revenue.
While there are some dizzying temptations to embrace a blended, “weisure” lifestyle, a concrete vacation away from keyboards, work e-mails, and conference calls results in the obvious re-charging of batteries and even serves as an excellent source of unexpected inspiration. Ample research demonstrates the multiple benefits of R&R.
Most self-employed tend to hustle non-stop. While thought leadership content marketer and freelancer coach Nathan Collier appreciates the motivators behind this behavior, he is positioning himself to be able to enjoy long-term breaks (think months long) in the future.
Just how do you successfully negotiate this seemingly thin ice? Whether mid-contract, or enjoying a healthy, long-term retainer, a successful entrepreneur needs to plan ahead, communicate and stay firm. For those just transitioning into the self-employed lifestyle, Collier points out that, “From a workflow perspective, it’s not that different from going on vacation when you have a regular job.”

Plan ahead

Rather than change retainer agreements or re-negotiate contracts, Collier rearranges his schedule “so I am still providing all the work the client would normally get, even if that means doubling up on their work for a week or something like that.” Ensure all clients have what they need for the duration of your vacation. This will put both client and yourself at ease. As Collier explains, “It’s no good if I have something hanging over my head while on vacation.”
If you aren’t working on a retainer, says Collier, “The bigger challenge is cash flow. Ideally you’d have an account for vacations and time off.” Alleviate some of that stress by automating invoicing, so you can bill clients while relaxing beachside or hiking volcanoes.


If you want to stay in a client’s good graces, make sure you notify each one of them when you plan to be away. “I do this as early as I can, preferably as soon as I know the dates I plan to be away,” says Collier. Excellent communication feeds back into planning ahead, ensuring that your client feels fully covered during your absence.

Stand your ground

Just as he “used to do when I was at the office,” Collier turns on that auto-responder. Only this time, there is no emergency contact number. He protects that precious free time, stating, “I’m just away, and they’ll have to wait.”
If questioned by a client, reassure them that their long-term success is your priority. Keep the lines of communication open prior to your departure, and make sure you plan to accommodate their needs. At the same time, recognize that your client’s success is now tied to your own; optimizing that relationship for success necessitates taking care of yourself.
That’s all there is to it. Now go book that cruise, hit the trails or finally take that epic road trip.

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