Learn how to run a successful freelance business, leave it behind when you go on vacation, and not have everything pile up or fall apart while you're gone.
Think about it for a minute: What happens to your freelance business, your projects, and your clients when you take a vacation?
When I go on vacation with my family, I don’t check email, Slack, my project management system, or anything else related to work. I walk away from my business, shut off all the things, and even remove some apps from my phone! I truly detach, rest, relax, and recharge without any worry, and it’s pretty freaking fantastic!
What’s even more fantastic is that while I play board games, eat yummy food, go on hikes, explore national parks, visit beaches and waterfalls, and go to concerts, my clients are communicated with, educated, and cared for, and my projects keep moving forward without me. Not because I have a team, but because I have systems, software, and automations that handle everything for me.
During my last vacation, here are a few things that happened while I was gone:
- A new client received, completed, and sent back their intake form for a new project.
- A client followed instructions to review design revisions and a concept extension and provided their feedback.
- Someone new booked an ad-hoc consulting session and sent me their prep materials.
- A client sent me the results of their voice-of-customer homework.
- A client shared an incredible testimonial with me that hit every point I’d hoped for!
And I didn’t have to lift a finger to make any of this happen — and that is true freedom.
A Freelance Job Vs. A Freelance Business
When you can step away from your business and it still runs without you… that’s when you know you have built a true business rather than a job you’re in charge of.
When you can step away without worry, guilt, or stress because everything still gets done and projects keep moving forward, you don’t come back to a mountain of work that makes taking time off more trouble than it’s worth. You come back to progress.
When you can step away without fearing collapse or lost business, it’s so much easier to take that vacation or turn off your business for a long weekend and give yourself the time you need to recharge and your loved ones the time and attention they need as well.
I know this first-hand because I used to hate vacations.
Well, not the actual vacation, but everything that happened leading up to it, and after it, and sometimes what popped up unexpectedly during it! I know it sounds horrible, but there used to be a time when the idea of a vacation would come up and I would feel overcome with dread, and just say, “I can’t. It’s just not worth it.” Clearly, I had a lot less experience back then!
When you don’t know what you don’t know, the reality of taking a vacation when you’re a freelancer can suck.
- The amount of work that suddenly ramps up before you leave is often unimaginable by most people. I mean, it seems like every client you’ve ever spoken with only wants something the week before you go on vacation!
- Everything that piles up while you’re gone causes more stress than you can ever explain to your loved ones with traditional jobs.
- The work you feel compelled to do while on vacation makes you feel like taking the vacation was a waste. It also frustrates your family and friends who want to spend time with you doing fun things.
From Hustle Hell to Freedom: My Journey
Learning how to do better business, surrounding myself with like-minded freelancers and entrepreneurs, and investing in the systems that run my business was the BEST decision I have ever made in terms of my own sanity, health, and happiness — and the health and happiness of my relationships and family.
- I went from never taking a vacation to getting away every 6-8 weeks.
- I went from being forced to work weekends, to never having to work weekends.
- I went from working 16-18+ hour days to working a roughly 30 hour week.
- I increased my gross revenue and doubled my net profits.
- I designed a consistent client experience that creates happier clients that spend more money and send more referrals my way.
- I did it with systems and software and content, and without hiring a single person.
Phew, that’s a lot of I statements! And here’s one more: I am proud of what I built!
The initial driver behind documenting every part of my business, and systemizing and automating as much as possible, was to avoid hiring an admin employee or virtual assistant that I would have to manage. Instead, I invested in software that did everything a person could do.
Eventually, I did hire actual employees. I hired my husband full-time then grew the business to a team of five. But freedom is one of my top values and drivers — and managing a team (even while on vacation) didn’t support the level of freedom I needed or wanted.
Luckily, as the boss, I get to create the business I want.
So over time, my business dropped back down to a team of two, and now it’s just me running the whole show and again, leveraging software to handle everything possible. The systems and processes I developed are what make it possible. They are how I manage both the services side of my business and the courses/events side of my business. They’re also how I take an average of nine weeks of vacation away from my business every year without stress and worry — and without a mountain of crap to slog through every time I get back.
Again, that’s a glorious feeling that I want you to experience too!
But first, you’ve got to get your mind right!
5 Myths That Keep Freelancers From Taking Real Vacations
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 rarely ever took a vacation because I didn’t think I could.
- Working on vacation?
- Sneaking open your laptop 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 wasn’t lying before. I did it all. And the guilt was soul-crushing.
But 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.
Now? I take around nine weeks of vacation each year.
My family is on a quest to visit all 63 U.S. National Parks. We’ve visited 41 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. 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, community members, students, and subscribers get my very best.
Unfortunately, the more freelancers I talk to, the more I realize just 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 had adopted as truths, shift my mindset, and change how my business operated.
Here are five freelancing myths I had to squash:
Myth 1: 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 roller coaster.
- 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 2: I have to do everything myself.
- Problem: Believing no one can do it as well as you can, which means you have to do everything or it doesn’t get done.
- Change: Creating documented systems and processes for repeating tasks to streamline workflows and ensure consistent outcomes regardless of who is doing the work.
- Result: Many client management are automated and others can be successfully delegated to and completed by other team members and contractors.
Myth 3: 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 4: 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 5: 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 reacquaint 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.
11 Tactics That Help Freelancers Take Vacations
The inability to take a vacation, or sometimes just the weekend off while freelancing, is often due to not having the support you need, lacking the proper systems, or sitting in a phase of business that requires constant attention.
I’ve experienced all three of these scenarios:
- Early in my business, I had no support and tried to do everything myself.
- I built my business to multiple six figures with no systems in place.
- When launching something new, I’ve needed to be in my business 24/7.
It was rough and I don’t recommend it. Luckily, over time, I learned to do things differently. It wasn’t easy. But now I have a vacation system — specific steps I take each time I travel to ensure that I can leave my business behind, enjoy myself, and not freak out about it.
The good news is that you too can take a vacation without bringing with you!
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. The key is building your freelance business around the lifestyle you want.
Here are my best 11 tips for taking a vacation while freelancing:
1. 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.
2. 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.
3. Set Reminders
It’s 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.
4. 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. For example, 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.
5. Stick To Your Guns
If you give your clients a deadline to submit pre-vacation requests, 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.
Remember, 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!
6. 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.
7. 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:
- You’re on vacation and will respond as soon as you get back.
- What to do and who to contact if they have an emergency.
Second, update your website form thank you pages and autoresponders. Make sure anyone who fills out your contact form or inquiry form while you’re gone will receive a message that thanks them for contacting you and lets them know you’re on vacation and will be in touch when they get back.
8. 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!
What I learned is that keeping 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, is a must! 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.
9. Plan An Extra Pre-Day
Tell everyone — your clients, your team, your family, and your friends — that you leave for vacation 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, organize my desk and papers, and prep my work for when I get back, it is almost as if I am putting my office to sleep while I’m gone.
10. Plan At Least Two Days To Find Your Groove
I don’t know about you, but the worst experience for me, is coming home from a vacation and being forced to put in a full day’s work the very next day. With this approach you have no time to catch your breath, get into the right headspace, or prepare for a productive workday.
The second-worst 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.
Today, I try to always 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. It’s not always possible but wow, does it make a difference!
When it works out:
- 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.
And, whenever possible, I add a third day, which is a secret workday. 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 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, I don’t always detach completely. I do what works for me in the moment and current context of what’s happening around me.
I also know that the act of detaching completely from your business may cause so much stress that it negatively impacts your mental health. It’s why you have to figure out what you need to be able to turn work off and honor that.
- If a quick 30-minute check-in while you’re enjoying your morning coffee will allow you to relax and enjoy the rest of the day away from your computer, give that time to yourself freely!
- If a quick before-bed review of what went down during the day will help you sleep better at night, do it!
You’re the boss of your business and you call the shots. You get to define when you work, how you work, and how much you work, and you are the one who must set and hold your boundaries!
Vacation Is A Requirement For Sustainable 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.
Today, I take a lot of vacation but I didn’t get to that point overnight. It took a long time to get there! At first, simply taking an entire weekend off was a big deal. 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.
Believe in yourself and get the right systems and support in place to make it happen. And, if you follow these simple tips the next time you plan a vacation, you’ll be able to leave your freelance business behind and relax, stress-free, worry-free, and totally freak out-free.
Want More Help Building Your Freelance Business?
Check out Profitable Project Plan — a web design business course, pro community, and mentorship program for web designers, web developers, and people selling websites. It’s basically my web design business and my systems, processes, scripts, emails, tools, and resources packaged up with in-depth training and live Q&A and mentorship opportunities. And it’s changing members’ lives.
PPP has helped several members get the right systems in place to finally take their first work-free vacations ever! Their stories of vacations, quality family time, better health, and less stress and worry are the absolute best part of running Profitable Project Plan. And hearing that they’re closing their largest deals ever, closing deals faster, and making more money isn’t bad either!
