5 Myths That Keep Freelancers From Taking A Real Vacation And Leaving Business Behind

Five myths turn freelancers into horrible bosses that avoid the real vacations needed to be their best, most strategic, creative selves. Let's fix that.

Freelance Vacation

Freelancers are the hardest working, most dedicated, committed people I know, doing whatever it takes to get the job done and meet their deadlines, often at the expense of their own health and wellness. While getting their freelance business off the ground, they tend to put work ahead of everything else, never taking breaks or vacations to recharge, refuel, re-energize, or reinvigorate. While that pace can be sustained for a short period of time, when the hustle and grind take over for too long, it does serious damage.

I know the negative effects of that pace first-hand because I was that freelancer. In the first few years of my business, I worked 16-18+ hours a day, at least six days a week, and I never took a vacation — because I didn’t think I could.

  • Working on vacation.
  • Working while your family sleeps.
  • Spending the first few days of vacation groggy and cranky from pulling an all-nighter (or two) before leaving for vacation.
  • Skipping activities to get work done.
  • Dreading the mountain of work waiting for you upon your return from vacation.

I did it all, and the guilt was soul-crushing.

Eventually, I began to take weekends off, then long weekends away, then four-day trips, and then week-long (and longer) vacations. Thankfully, with time, I mastered the art of taking a real vacation and detaching from my freelance business without the stress of insane, unhealthy ramps-ups before-hand or mountains of work waiting for my return.

Today, I take around nine weeks of vacation each year and almost never work on vacation.

In fact, my family is on a quest to visit all 63 U.S. National Parks. We’ve visited 30 so far and most of the time, there is little to no cell service or WiFi, which means I couldn’t work even if I wanted to. It’s glorious.

Taking a break from work gives me the opportunity to relax, reset, and recharge. It allows me to reconnect to my creative self and rediscover my passion for what I do. It ensures that when I am working, my clients, program members, students, and subscribers get my very best.

The more freelancers I talk to, the more I realize how many are exactly where I was — handcuffed to computers and unable to take a real vacation and detach from their businesses, obligations, and clients.

In my conversations, I hear things like:

  • I could never do that.
  • I recently took a vacation too, but I brought my computer and worked a few of the days.
  • My wife and I went away last weekend, but I worked on Sunday.
  • We took a trip last month, but my spouse was on his/her phone working the whole time.
  • I can’t detach like that. We go on vacation, but I always check my email and do a little work every morning.
  • I worked in a lounge chair while my kids played in the pool.

These answers break my heart because I know how that feels! For the good of my family, my business, my clients, and myself, however, I knew I had to overcome the myths I believed and the limiting beliefs I had adopted as truths and change how my business operated.

Damaging Freelance Mistakes

Below I share the five myths I believed that held me back, along with the problems they caused, the changes I had to make, and the results experienced. Squashing these myths led to healthy business growth that allowed me to establish boundaries, protect important relationships, and take vacations without working.

MYTH: If I’m not working, I’m not getting paid.

  • PROBLEM: Following the one and done business model with no recurring revenue and billing only upon project completion meant riding the freelance feast or famine rollercoaster.
  • CHANGE: Accepting all major credit cards, implementing automatic payment plans to create better cash flow, and creating opportunities for reliable, monthly recurring revenue.
  • RESULT: Money is constantly coming in on a regular basis and cash flow peaks and valleys even out to create a steady baseline of income you can depend on.

MYTH: I have to do everything myself.

MYTH: If I am unavailable, my clients may go somewhere else.

  • PROBLEM: Thinking that if you don’t jump when the client says jump, you’ll lose their business forever.
  • CHANGE: Establishing clear expectations, strong boundaries, improved client education, and better communication practices to help clients understand response times and lead times, what happens if you are unavailable, and how things work if they have an immediate need.
  • RESULT: An onboarding process ensures clients feel prepared and cared for. They know what to expect and how your partnership works. If you can’t start right away, clients wait for a spot in your workflow.

MYTH: I have to have my computer with me so I don’t miss anything.

  • PROBLEM: Remaining mentally “on call” and not wholeheartedly present during family activities and vacations — just in case.
  • CHANGE: Leaving the computer at home, building solid relationships with clients, and securing reliable backup/support to handle any emergencies that may arise while on vacation.
  • RESULT: You can truly detach from your business, take a real break, and be present for your family. If an emergency arises, your backup/support team can handle it and if necessary, you can be available for questions, major decisions, or critical client communication using your smartphone.

MYTH: Only the minimum amount of time off is needed.

  • PROBLEM: Stress, exhaustion, and crankiness from pre-vacation prep negatively affect the quality of vacations, and upon return, the need to “get back into the groove” creates unproductive, frustrating work days.
  • CHANGE: Taking 1-2 days off before a vacation to decompress, relax, close up shop, and prepare for the trip, and taking 1-2 days off after a vacation to rescquaint yourself with your business and ease back into a normal workflow.
  • RESULT: Relaxed, stress-free vacations, true detachment from freelance life and running your business, and easy assimilation back into a normal workflow after vacation.

A Requirement for Long-Term Freelance Success

I believe that every freelance business owner needs to take regular vacations and completely detach from their business at least 1-2 times each year.

What I learned from building my business around regular vacations is that the more time off I take, the better work I do.

As a freelancer, I am my business. If I want to show up for my clients as my best self, I need to show up energized, excited, and inspired and be strategic, creative, and focused. To do that I need time to recharge my batteries, which means I need time away from my business.

Now, you may not be able to take nine weeks of vacation every year as I do and that’s okay. I slowly worked my way up to that amount of vacation over time. At first, simply taking an entire weekend off was a big deal and a three-day weekend was HUGE. I still remember my first four-day vacation as a freelancer because it felt like I won the lottery.

You can vacation like a pro and still run a successful freelance business.

Get started by taking baby steps:

  • Create reliable recurring revenue and leverage payment plans to even out cash flow.
  • Document your systems and processes so you can automate or delegate key tasks and still get things done “your way.”
  • Train your clients to be great clients by setting clear expectations and boundaries and communicating how you work with clients.
  • Get some backup! Build a relationship with a strategic partner who will have your back and support your clients when you’re unavailable.
  • Start small and build up. Take a long weekend getaway and work up to a week-long vacation. If you take two weeks of vacation per year now, add one more week, and then next year, add another week.
  • Begin to pad your vacations with an extra day. Start with one extra pre-vacation day. Then add one extra post-vacation day. Then work your way up to two days before and after.

Anything is possible when you’re a freelancer. You just need to believe in yourself and get the right systems and support in place to make it happen.