Writer. Thinker. Strategist. Creative Tight Rope Walker.

How to Take Vacations as a Freelancer

It’s quite easy to become a workaholic when you take on the role of freelancer or small business owner. I’ve been guilty of that for years, but more recently I’ve been changing my mindset through careful planning and the belief that I deserved to take time off. Everyone needs a vacation because it’s necessary to recharge and top up that motivation.

Yet, as a freelancer or small business owner, it’s not like you are getting a paid vacation. It’s a simple principle in the freelance business: work and get paid. don’t work and don’t get paid. That means you have to save up your money or work ahead or extra to have the money in the bank as though you had stayed here rather than took off for parts unknown.

I’ve worked out an effective system in the last few years that has let me disappear for up to a month to places like Australia and England without taking work with me or losing my monthly income. Here’s how:

  • Start with an annual budget that accounts for the type of trips you want to take. For longer trips like my upcoming month in England, I started planning soon after coming back from previous trip to Australia. There was a two-year gap there between trips where I worked on a budget that helped me save for the plane tickets, accommodations, side trips and more as well as the number of weeks off from paid writing work.
  • Plan and book your holiday well in advance of actually taking it. By committing to the trip by making a deposit, you are more likely to save money to cover it while you are gone plus give your clients plenty of notice to schedule work in advance. This is a good idea for long and short trips. However, there’s always room for those spontaneous weekends out of town when you really shouldn’t be working anyways!
  • Give your clients considerable notice and then regularly remind them as the time off gets closer. They will get busy and won’t necessarily keep your vacation top of their mind. In fact, they most likely will want to ┬ácompletely forget about it. Also let them know you have a plan for getting the work done ahead of time so they won’t even notice you are gone. For me, I use numerous content management systems and tools that let me schedule content to be published at a later date.
  • Create a schedule in advance of any trip that is at least a week or more that details how you will fit in all the extra work you wouldn’t normally be doing. While these end up being long days and even weekends, it’s worth it to get this work crammed in to keep clients happy and maintain cash flow that you need for such a trip.

Using this strategy has helped me cross more things off my bucket list, expanded my perspective for a higher quality of engaging content for my clients, and created a more balanced, satisfying life.


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