How to Take a Vacation When You’re Self-Employed

By Kat Boogaard

6 min read

My eyes darted between my calendar and my to-do list, and I immediately felt overwhelmed. I had one week left until I was scheduled to set off on my first vacation in a long time.

Hiking, kayaking, campfires, and limited cell reception—for all intents and purposes, I was preparing for a week full of rest and relaxation. It should’ve been something I was eagerly looking forward to. But, instead, I felt stressed and frazzled.

Why? Because I’m self-employed.

When we booked our trip, my husband was able to put in a time off request at his full-time job and receive his five paid vacation days. But, for me, things weren’t quite so simple. I felt like I either had to work day and night in order to get enough accomplished ahead of my vacation or I had to sacrifice a week’s worth of pay so that I could take any time away.

It’s a relatable issue for nearly any business owner—which is likely why only 57% of small business owners planned to take a vacation in 2014. Oftentimes, unplugging from your work seems like a larger hassle than it’s even worth.

So, what’s the answer here? Is the flexibility that comes along with self-employment really just a myth? Does working for yourself mean you never get to take a vacation? Not exactly.

The Importance of Time Off

Stepping away from your business can inspire plenty of guilty feelings. But, rest assured, vacations are necessary to clear your mind, recharge your batteries, and lead an overall healthier, happier, and more productive life.

The science is there to support this. Reaction times increase by as much as 40% following some time off. An annual vacation cuts the heart attack risk by 30% in men and and 50% in women.

“The impact that taking a vacation has on one’s mental health is profound,” told Francine Lederer, a clinical psychologist, to ABC News, “Most people have better life perspective and are more motivated to achieve their goals after a vacation, even if it is a 24-hour time-out.”

Needless to say, some time away from the daily grind does your mind and body some good. But, that doesn’t change the fact that pulling it off takes some work and coordination when you’re self-employed.

Fortunately, it’s completely possible. You’ll just need to use one (or a combination) of the below methods.

Pay Yourself for Your Time Off

This method isn’t a quick fix if you have a vacation coming up in the next few weeks. But, it’s a great solution in terms of long-term planning.

Being self-employed doesn’t mean you don’t get any paid vacation time—you just need to figure out how to offer it to yourself.

One of the best ways to do this is to build it into your standard fees. For example, let’s say at the beginning of the year you decide you want to offer yourself two full weeks of paid vacation throughout the next calendar year. At that point, you can calculate how many working hours you’re losing and multiply that by an estimated cost per hour.

Then, you can slightly pad your fees and prices throughout the rest of the year to make up for that lost time.

While significant price jumps usually aren’t recommended, spreading a small increase out across the remainder of your working time can help you take some much-needed time off—without feeling guilty about lost wages.

Many self-employed people also have begun diversifying their income streams with products—whether it’s courses, ebooks, physical goods, or something else entirely. After your initial time investment, these are a great way to earn some passive income while you’re on vacation.

Consider a Working Vacation

Sometimes—despite your best intentions—it’s impossible to escape your work completely. And, one of the greatest perks of self-employed life is that you can work from anywhere.

Will you be excited about needing to answer emails or put out fires while your toes are in the sand? Maybe not. However, it is an option if you can’t manage to totally unplug. Before you leave, you can work ahead (more on that in a moment!) or delegate non-essential responsibilities to employees or contractors.

You’ll be left with the bare minimum while on vacation—which you can dedicate a few hours to here and there. Working during your time off might not be ideal, but it is a great option for people who want to try to get the best of both worlds.

The best part? If you need to visit a client, attend a meeting, or do some other business-related activity while you’re on your trip, a certain portion of your working vacation could be tax deductible. (Here’s what you need to know about writing off a vacation.)

Work Ahead of Schedule

Having been self-employed for the past three years, this is typically the method I end up using the most when preparing for a vacation.

A couple of weeks prior to my departure date, I sit down and make a giant list of all of the things that would need to be accomplished during my vacation time. Then, I gather the necessary information and insert those tasks into the upcoming weeks—so that I can get the bulk of them taken care of before my time off.

Depending on what line of work you’re in, this isn’t necessarily realistic for everyone. But, if there are a few standard tasks and duties you can get off your plate beforehand, remember that every little bit helps.

Just Unplug and Relax

As a business owner, this option will by far feel like the most counterintuitive. You put a lot of pressure on yourself—which means you often white-knuckle the reins of your business operations and make things far harder than they need to be.

But, ask yourself this: What detrimental things could really happen if you took some time off? Would everything actually come crashing down if you took a few days, set your out-of-office message, and gave yourself some time to relax?

Chances are, your circumstances aren’t quite as do-or-die as you think they are. So, if you have employees, challenge yourself to delegate more and trust them to keep things running smoothly while you’re away. If you’re a one-person show, give your clients or customers a heads up and then enjoy some time spent truly disconnected.

If you feel like you really need a break, it’s typically worth it to sacrifice that pay and enjoy a few days spent recharging. You’ll be better off for it.

Planning: The Secret to Successful Vacations When You’re Self-Employed

There’s one thing that all of these methods have in common: adequate planning and preparation.

When you’re self-employed, you have a certain degree of responsibility to your business, which means you don’t have the luxury of just submitting a vacation request and hitting the road.

Whether it’s something big like determining a totally new pricing structure or something as small as leaving detailed instructions and setting an out-of-office responder, taking some time off will always involve some thought and consideration.

So, make sure to plan ahead for the vacations you want to take when you’re self-employed. That extra preparation will empower you to actually enjoy your time away—with as little guilt as possible.

Information may be abridged and therefore incomplete. This document/information does not constitute, and should not be considered a substitute for, legal or financial advice. Each financial situation is different, the advice provided is intended to be general. Please contact your financial or legal advisors for information specific to your situation.

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