How to Take a Vacation And Detach From Your Business When You’re A Freelancer

Eleven tips for taking a real vacation from your freelance business without stress, worry, or mountains of extra work to get done before you go or when you come back.

I used to hate vacations. Well, not the actual vacation itself, but everything before and after the vacation — and sometimes during the vacation. I know it sounds horrible, but there used to be a time when the idea of a vacation would come up and I would say, “I can’t go. It’s just not worth it.”

When you’re a small business owner, more specifically, a freelancer, solopreneur, or entrepreneur, taking a vacation is extremely difficult, let alone a vacation where you completely detach from your freelance business and actually leave your work at the office.

The reality of taking a vacation when you’re a freelancer:

  • The amount of work that ramps up before you leave is unimaginable by most people…
  • The work that piles up while you’re gone causes more stress than you can ever explain…
  • The work you feel compelled to do while on vacation makes you feel like taking the vacation was a waste (and frustrates your family).

This inability to take a vacation (or sometimes just an entire weekend off) is often because:

  1. You don’t have the support you need.
  2. You lack the systems your business needs.
  3. You are in a phase of business that requires constant attention.

I’ve experienced all three.

I went through times in my business where I had no support and tried to do everything myself, I built my business to multiple six figures with no systems in place, and when actively launching something new, I’ve needed to be in my business 24/7.

It was rough-going and I don’t recommend it to anyone.

Luckily, I was able change things and you can do the same. You have the ability to eliminate the crazy ramp up before a vacation, establish boundaries while you’re gone, and manage the incoming work that is waiting for your return.

I’ve taken important steps to make big changes in my business to support the kind of freelance lifestyle I want. With these changes, I went from working 16-18 hour days seven days a week and almost never taking a vacation, to never working nights and weekends and taking nearly nine weeks off each year. It wasn’t easy at first… But now I have a vacation system — specific steps I take to ensure that I can leave my business behind, enjoy myself, and not freak out about it.

Here are my best 11 tips for taking a vacation from your freelance business:

01. Prepare Yourself

Prepare yourself mentally to be away from your freelance business. A lot of the stress I had over taking a vacation was mental stress that I created. I was worried about not responding to email fast enough or not handling inquiries fast enough, worried a client may need me or they might hire someone else if I wasn’t available, etc. It was awful!

Set aside time before your vacation to get all of your projects buttoned up, your affairs in order, and a plan in place for your return. Then put your mind at ease, let go of the worry, and embrace the time to relax and recharge.

02. Prepare Your Clients

Part of eliminating vacation stress is preparing your freelance clients for your absence. They need to know when you will be gone, when you will be back, and what to do in the event of an emergency. I provide retainer clients my vacation schedule months in advance and all other clients at least two weeks in advance. I also communicate my availability during travel, what I am available for, and what do do in an emergency.

03. Set Reminders

It is important to remind your clients (and yourself) often about an upcoming vacation or time out of the office.

  • For yourself, get a countdown clock, or do a daily check-in on projects in the weeks leading up to a trip. Finish up everything you can and get all open projects to a good pausing point or to a point where the ball is in the client’s lap.
  • For your clients, never assume they will remember your vacation. Two weeks before your travels, add a big, bold, red reminder with the dates you will be traveling in your email signature on all client communications.

04. Set Deadlines

Give your clients a pre-travel deadline for all requests. This means telling your clients that if they want their project done before you leave, they have to get you everything you need by a specific date. Also, if leaving for vacation on the 21st, tell your clients you won’t be accepting any new project requests after the 14th. This gives you a week to wrap everything up before your trip.

05. Stick To Your Guns

If you give your clients a deadline, stick to it. You are partners and they need to take responsibility for their actions. If you tell a client you need materials on the 14th or you won’t be able to finish the project before you leave, remind them several times, and they still don’t deliver what you need by the 14th, it’s their fault not yours.

An emergency on their part doesn’t constitute an emergency on your part. This was a really tough one for me to learn, but it has made a huge difference. No more all-nighters the day before I leave, ruining the first few days on me vacation!

06. Stay On Top Of Workflow

Be careful to stay on top of your workflow and know exactly what projects you need to finish before you go so you can actively manage client requests. This will ensure you don’t promise too many things to too many people in a short period of time and that you can manage your clients expectations effectively.

07. Leverage Email Automation

Follow up sequences are a freelancer’s best friend while on vacation.

First, set up an autoresponder for your email address, so anyone who emails you while you’re gone, gets a message back letting them know:

  1. You’re on vacation and will respond as soon as you get back.
  2. What to do and who to contact if they have an emergency.

Second, update your website form autoresponders or thank you pages, so anyone who fills out your contact form or inquiry form while you’re gone will receive a message thanking them for contacting you and letting them know you’re on vacation and will be in touch when you get back.

08. Keep Track Of Post-Travel Workflow

Managing your workflow when you get back from vacation is where most people get tripped up. For quite a few vacations, I was good at getting ready to leave, but then I’d almost die from overwhelm and the monstrous piles of work waiting for me when I got back.

It made coming home from a vacation an awful experience!

Keep track of the client projects you’re delaying, new projects you won’t be starting yet, and all of the meetings and phone calls you’re scheduling for when you get back — otherwise you’ll be in for a big mess of too much work, not enough time, and a whole lot of stress upon your return.

09. Plan An Extra Pre-Day

Tell everyone — your clients, your team, your family, and your friends — that you leave one day earlier than you actually do. Give yourself one uninterrupted day alone to wrap up any loose ends, send any last emails, and clean your office.

This day has become critical for me. I use this time to mentally detach from my business and my work. When I clean my office, put everything away, and organize my desk and papers, it is almost as if I am putting my office to sleep until I get back.

10. Plan At Least Two Days To Find Your Groove

The worst experience is coming home from a vacation and having to put in a full day’s work the very next day. With this approach you have no time to catch your breath, get your mind into the right space, or prepare for a productive workday.

The next hardest experience is to only have one day off between your vacation and being back at work full-time. With this approach, you only have one day to unwind, unpack, do laundry, get some groceries, and regroup — it’s not enough time to also relax, refocus, and get in the right headspace for work.

At minimum, I schedule two free days at the end of every trip to allow me find my groove and get back into my normal, productive, daily grind.

  • The first day I spend just regrouping from being gone — I relax, unpack, and just hang around the house.
  • The second day I check my email and get reacquainted with my business, open projects, and what work I have coming up — I start mentally preparing myself to get back into my regular workflow.
  • Whenever possible, I add a third day, which is a secret workday. It’s a day that I’m technically not back in the office just quite yet, so it’s uninterrupted time that gives me a chance to get ahead. With this time, I write responses to emails that have come in (but I don’t send them until the next day), I organize my projects, I complete any small requests that have come in from clients, and I find my productive groove so I can hit the ground running the next day.

11. Accept Who You Are And What You Need

As much as I advocate for vacations away from work — no email, no phone calls and meetings, no client work, and no computers — I understand that the act of detaching completely from your business may cause so much stress that it negatively impacts your mental health.

You have to know what you need to be able to turn work off and you need to honor that.

While I have no problem going on vacation and not checking email, voicemail, and even social media, my husband Brian doesn’t operate that way. Being completely disconnected makes him uncomfortable, stressed, and worried. So he uses a different approach…

Brian is an early riser and a morning person and he greatly values his quiet time and coffee. So while the kids and I get ready for the day, he checks all the work and business things and quickly responds to everything that needs responding to. It only takes 30 minutes at most, and that simple check-in gives him the confidence and peace of mind needed to leave work completely behind for the day.

At the end of the day, while the kids and I are showering and binge-watching Food Network, he quickly checks-in one more time. This allows him to confirm that there are no fires that need to be put out, and in turn, he gets a better night’s sleep.

There You Have It!

If you follow these 11 simple tips the next time you plan a vacation, you’ll be able to truly detach from your freelance business and relax, stress-free, worry-free, and freak out-free.

Some links used on this site are “affiliate links.” If you click on the link and purchase the item, I will receive an affiliate commission. Regardless, I only recommend products or services I use personally and believe will add value to my readers. I am disclosing this in accordance with the Federal Trade Commission’s 16 CFR, Part 255: “Guides Concerning the Use of Endorsements and Testimonials in Advertising.”

About Jennifer Bourn

ABOUT THE AUTHOR: Jennifer Bourn is founding partner at Bourn Creative, a full service design and development company specializing in WordPress. With twenty years in the industry under her belt, she is an award-winning designer who consults on branding, website strategy, and content strategy. Jennifer speaks often, delivering workshops and keynote presentations, blogs about food and travel at Inspired Imperfection, co-organizes the Sacramento WordPress Meetup and WordCamp Sacramento, and writes often for other websites on freelancing, client services, blogging, marketing, websites, and branding.

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