How to plan for time off in your creative business

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Erin Flynn:

Hey there, Erin here, and I know that as an entrepreneur, it can be really difficult to step away from your computer. I was even checking emails at my wedding, so I definitely know how hard it can be to go on vacation or take a break and not be glued to your computer or your phone 24/7. Today, I wanted to talk to our experts about how they plan for time off in their business, so for things like vacations, maternity leave, weddings, whatever, how they plan for that so that they are able to fully, or at least mostly, unplug and actually relax. Let’s hear what they have to say.

Jordan Gill:

Hi, I’m Jordan Gill from Systems Saved Me. When we’re able to go back and travel, I definitely plan to travel a ton. I was really blessed in 2019 to have traveled a lot. I’ve traveled a lot in my business, generally speaking, but in 2019, I was able to take quite a few vacations and opportunities abroad like Europe, so Italy, Spain, Poland, Portugal. We went to New York, we went to Mexico. I’ve gone to quite a few places and been able to really enjoy the cultures and experience new places and how I plan for them, it looked a lot different back then. I only had one team member. Now when I take time off my business… There’s been quite a few times that I’ve had to take, with short notice, some time off for a variety of reasons and I was able to do so because my team can pick it up.

Again, we don’t run a very complicated business. So again, it’s very synchronistic that I’m on the Successfully Simple Podcast talking to you about this, but there’s really, we get so ahead on content. We’re about a month or two ahead on all content at all times. So, if I have to take a week off or somebody on our team has to take a week off, it doesn’t really rock the boat very much. And then as far as our program, I have a coach inside who is able to still support our clients and make sure that they have what they need at any given time. I have pretty much all bases covered to keep things rocking and rolling, which I’m very blessed with.

This is pretty much our core team that we’re going to be riding with for a while, and at any given time, I can say in Slack, “Hey, I’m taking a day off,” or someone can say, “Hey, I’m taking a mental health day,” and again, our business works so far ahead that unless we’re going right into a launch, then there really is no reason for the wheels to fall off of our business, which is actually pretty nice. If you want to connect or find more resources, you can go to or find me on Instagram at systemssavedme.

Jordan Gil

Jordan Gill, operations consultant and founder of Systems Saved Me, helps overworked one-woman shows become streamlined solopreneurs. Her jam is creating a cohesive operating system for managing your tasks, files and inbox. She’s been on podcasts like What Works and CEO Vibes sharing her love of replacing monthly retainers with one day virtual intensives. She currently lives in Dallas TX with her cavapoo Vivienne and collection of 1,000 piece jigsaw puzzles.

Visit Jordan: Website | Instagram | Facebook

Katelyn Hamilton:

Hi, this is Katelyn Hamilton, and I’m an online business manager helping you get organized and create efficiencies in your business. Creating a plan for time off in your business is really hard when you’re a solo preneur. It is something that I have struggled with personally, but if you take the time to plan ahead, that is key, plan ahead, plan ahead, plan ahead. I will say that over and over again, it can be done and it can feel good as well. And you can feel supported, your clients can feel supported and you don’t have to miss a beat. It is something that I think as a solopreneur, we all can have a hard time with because your business is your baby, and especially if you’re very type A like me, letting go of some of that control sometimes can be tough, but I’ve learned that vacations and time away is really critical to allow you to decompress and be creative and come back with a fresh, clear mindset. It’s self-care. It’s necessary.

And to me, planning ahead is planning ahead with my clients, letting them know with plenty of notice when I will be out and making sure that they feel supported. I can get some stuff done ahead of time. Occasionally for me, that means working more maybe the week before I go out of town to make sure that all the ducks are in a row, but usually the clients are really great about giving me that time away, too, and knowing that they don’t have support for me during that week one gone, but the other thing is having a team to support you. There’s plenty of things that my team does while I’m out, that they can manage or take over and support me. And that keeps both my business running and my client’s businesses running because I have the support of those things happening while I’m gone. So, I don’t always have to be on 24 seven, knowing that I have a really awesome team that is supporting me and supporting them to still get stuff done without having to stress or worry about those things while I’m gone.

For example, also currently planning for maternity leave, I think creating specific videos on tasks that you do and just creating a block, or I should say, a reserve, of those things so that your team can see and reference exactly how you do things when you’re out is important. And I have been working on this for months now, as I plan to take time off for my baby, to just have that all there, so they don’t have to ping me with a ton of questions while I’m out. Also, creating really detailed SOPs, so your standard operating procedures. If it has more than two to three steps to it, document it. That way, people know where to find things, how to do things, especially if you want it done in a particular way. This gives them the exact steps to do so and there should be no questions asked.

Sometimes it’s hard to prepare for everything, but at least planning ahead gives you the ability to anticipate needs, anticipate things that are going to come up, and gives you the ability to relax and know that things are being taken care of. If you want to stay connected with me, you can follow me on Instagram at Katelyn, K-A-T-E-L-Y-N-E, Hamilton, or go to my website at

Katelyn Hamilton

Katelyn began her career in marketing and public relations in Nashville, Tennessee. After working in the agency world for six years, she decided to pursue the entrepreneurship route to create more freedom and flexibility in her life. Now, Katelyn works as an Online Business Manager where she helps entrepreneurs organize, strategize and prioritize the backend of their business to go from overwhelmed to out-in-front. A Georgia grad, she bleeds red and black and is a diehard Georgia football fan, dog mom and outdoor enthusiast.

Visit Katelyn: Website | Instagram

Megan Minns:

Hey there. This is Megan from and I help online course creators, coaches, and service providers learn how to run their business in a way that is strategic, scalable, sustainable, and enjoyable, most importantly. When it comes to taking time off in my business, I do things slightly differently. If it’s just a one or a two week vacation, it doesn’t really take a lot of planning for me to do this. I just make sure my team knows well in advance, and we have a process in place to make sure our clients know in advance. Depending on what we’re talking about within my business, sometimes nothing changes for the client. Coaching calls continue as usual and other times, we do decide to fully close our office and cancel a coaching call. So either way, we’re just making sure we communicate in advance, and that’s something that my team really oversees and handles, but not a lot has to change for me to take a one or a two week vacation.

Now, when it comes to taking time off in a more substantial way like maternity leave, this is something that’s very personal for me and a longer break like that is absolutely requiring a lot more upfront planning. I can’t fully speak from a place of expertise on this yet. I’m sure we’ll learn a lot as we get closer to maternity leave and during maternity leave, but my plan is to make sure that my clients are going to be taken care of. I run a high level group coaching program called Empowered CEO, where I have a team of coaches, including myself, who are supporting and coaching our clients as they grow their business. I am making sure right now we are doing a lot behind the scenes to get my team fully trained. And we are having a lot of meetings, a lot of conversations, a lot of internal trainings so that they can be answering questions like I would, but also how they will, because they all have their own expertise and experiences that they’re bringing to the table as well.

We are actively working on training my team and then also hiring new team members to make sure that our clients feel fully supported while I am recovering from having a baby and adjusting to being a first time parent. So, that is the biggest thing we’re doing is hiring and training team members. Now, we are also doing some prerecording of content. I do a weekly live show, so I am batching and prerecording content for that. So that, even while I am resting, we can still have content going out to our communities so that they can still be learning and growing and hearing from me, even though I may not be going live right then. We’re also making sure to communicate to clients in advance as things affect them, but the most important thing truly for us is making sure that our clients have full trust in my team and my coaches and that my team and coaches feel confident and know exactly what their systems and processes are, know how to handle things, and they feel the trust that I’m installing in them as well.

So, planning for maternity leave is a big up level and mindset shift for me. It’s been really helpful for me to reframe my decision-making because there is this period of time where I want to be offline. And so, it is helping me really view things through a different lens. Like I said, I have not actually done the maternity leave yet. I haven’t had a vacation as long as a maternity leave before, so this is definitely a new experience for me, but I think the core takeaways for you would be, if you want to take some time off, you want to make sure that there’s someone else in your business who can take care of your clients and customers while you’re gone, and if you don’t have that yet, that’s something I would encourage you to start doing, is to start looking at how you can hire even a contractor to help support your clients and customers while you are taking a vacation or maternity leave.

It’s absolutely about having the right team in place, having them feel fully confident, and then having your clients and customers already have full trust in those team members before the transition happens. So for you, I’d make sure you start working on building your team, documenting your processes, and doing what you need to get those ultimate end goals accomplished. I hope you do have a little trip planned soon, and if you want to know more about how much your indie leave actually goes for me, then follow me on Instagram at Megan_Minns, where I’m sure I’ll be sharing more as it’s happening, with what I learned, what went well and what lessons I learned along the way. So, hopefully I’ll see you there.

Megan Minns

Megan is a Life and Business Coach that specializes in helping online course creators, coaches, and service providers build a scalable, sustainable, and enjoyable business… without sacrificing their personal life!
She does this through her coaching program, Empowered CEO™, and her weekly live show, The Productive Life.
Megan has a Master’s Degree in Organizational and Human Resource Development, corporate Human Resources and Recruiting experience, and has been helping online business owners streamline and systemize their businesses since 2015.

Visit Megan: Website | Empowered CEO |Facebook Group

Quinn Tempest:

Hello everyone. This is Quinn Tempest. I help female founders create more purpose and profit in their businesses without burning out. So, how do I plan for time off in my business like vacations, et cetera? Well, this is probably something I need to get better at, but typically I tend to follow my husband’s schedule.

He has a full-time job. He has a set number of days off. And so, we try to plan together around when he can take time off based on his accrual and what works in seasons of my business. Typically, I look at things in terms of seasons, so if I have a big launch coming up, I love to schedule something right after that, even if it’s just a weekend away because I just need that time to relax and reset after putting myself out there during the launch. So, a lot of our little trips tend to happen after a busy season in my business, as long as it works for him. For longer things, I will be honest and say, I have not taken a longer trip in gosh, almost three years. So, this is something that I’m working on because I was really just in business building mode.

And of course, we would do a long weekend or a week, but I haven’t done really anything super long, two weeks or longer, in many years. It’s definitely a goal, and before COVID we were planning a two month trip and I would have loved to answer this question then, because I think I would have known a little bit better way to plan things out. So really for me, it’s typically following my husband’s schedule and thinking through the busy seasons of my own business. And then also, just getting away once in a while just to reset the brain. That’s really it. If you want to connect on this more, feel free to DM me. I am at Instagram at quinn.tempest, and I’d love to connect with you there.

Quinn Tempest

Quinn Tempest is a business strategist and coach who helps females founders create more purpose + profit in their business *without* burning out. She’s the founder of Create Your Purpose®, a community of global entrepreneurs dedicated to building impactful businesses with intention. Her professional expertise is in branding and holistic digital marketing strategy and she is a frequent speaker at events and organizations around the country.

Visit Quinn: Website | Instagram

Alisha Robertson:

I’m Alisha Robertson, founder of and when it comes to planning out vacation days or holidays or taking time off from my business, I’ll admit I haven’t always been the best at doing this. One, because I am a recovering workaholic who absolutely loves what she does. And two, I also have this fear that if I take a day off, everything is going to fall apart, which is absolutely not true. I have systems in place that will cover everything if I’m away, but it’s something that I have been working on. I am actually really proud of myself though, because when I had my daughter about a year ago or over a year ago, I planned out taking maternity leave a few months before she was actually set to arrive. So for me, that looked like wrapping up clients that I may have had, or wrapping up any work that I would have had that I wouldn’t be tempted to peak onto my laptop after my daughter was born. I also made sure that I had podcast episodes prerecorded, and ready to go. So that, that would last me through a few weeks after she was born.

And then I actually went into like a little mini podcast break after a while. And then also, I asked for help from my friends. I knew that I couldn’t record all those podcasts episodes myself. Outside of doing solo episodes and recording podcast interviews, I also asked a few friends to come on and do their own little solo episode on my show, which was super helpful for me and also helpful for them because it exposed them to a new audience. So for me, when it comes to taking time off, I really do try my best to plan as much in advance as I can. So, that may look like wrapping up projects, wrapping up with clients, recording podcast episodes or prerecording or pre-writing newsletters and getting those scheduled to go out on a specific date. So really planning in advance-

One of the things I am focusing on moving forward though, is putting on my calendar for the year, so when I sit down in January to plan out my year, putting it on the calendar of the days I’m going to be away or the time that I’m going to take off or like the holidays. And the time that I know my daughter won’t be in daycare. Going into the year with already knowing what time I need to take off is really going to be helpful for me with how I schedule out all the other tasks. So, if I’m getting ready to go on vacation, then I know I shouldn’t prepare a launch so close to vacation time or around the same time I’m going on vacation, or if I am completing a cohort with accelerator clients, making sure that cohort is done before the holidays begin or making sure I’m not launching anything right during holiday time when I know that I want to take off. Just planning in advance for taking those breaks helps me a lot.

Again, I’m not always the best at it. I’ll say that I’m on vacation or I’m on break and I’ll still end up popping in to look at my phone or look at my email or check in with my clients or my community, and I think to a certain extent that’s okay, but at least I know while I’m in vacation mode that my entire business won’t just completely burn to the ground, while I am trying to take time off. Biggest takeaway is to definitely just plan in advance for these things. Go ahead and put your time off on your calendar for the year, at the beginning of the year, and then working the rest of your business tasks around that. All right, you guys, I’m Alisha Robertson. If you would love to connect with me and learn more about what I do, you can head over to

Alisha Robertson

Alisha Robertson is an author, business coach and the founder of Living Over Existing; a podcast, newsletter and community for women entrepreneurs who want to run a successful business without sacrificing the life she desires.

After experiencing severe burnout, Alisha tore down everything she thought she knew about becoming a successful entrepreneur and decided to build a brand that helped women to focus on building their business and life with intention. Through her work, Alisha strives to not only help women entrepreneurs to launch, grow and scale their brands but also help them to prioritize themselves in the process.

Visit Alisha: Website | LOE Collective | LOE Instagram 

Erin Flynn:

Hey there. It’s Erin again, and before we wrap up this episode, I wanted to talk about how I plan for time off in my business, because I took a lot of time off. Well, a fair amount of time off considering that I live in America and we don’t really do maternity leave here like they do in other countries. Most employers will maybe give six weeks, if you’re lucky, then if you’re self-employed, tough, you basically get nothing, unless you set it all up. When I took my maternity leave last year, I hired a VA to handle client projects and my inbox and things like that. And I bulk scheduled my social media, my podcast episodes and all of that kind of stuff. Content was still going out. It was still sending people to my products. I did not take on any new clients during that time, but I did have my VA who is amazing.

She was able to handle client inquiries for things like WordPress and things like that. I felt fully covered and supported, but I definitely had to plan ahead because I knew that I wanted to take at least three months off and fully off, and then have a month of buffer, some time before and some time after. Knowing that I wanted that, I just really worked my booty off beforehand to get things scheduled and ready to go out. So that I would have some quote unquote, passive income coming in during my maternity leave, and that worked really, really well for me. Now, my business is very simple. I didn’t have coaching clients or anything to support in that way. Although, I did have a group program going at the time, but I just made it clear when I launched it, that I was going to be on maternity leave.

And so, it was the beta round and if anybody was going to have a problem with that, I told them, don’t join this round because I will be taking time off during that time. You can support each other and I may pop in occasionally, but I may not, and that worked out fine because that group was just an incredible group of people and they were able to go through the course material and everything while I was gone and then save their questions for when I was back, and it ended up working out really, really well, but that’s because I was very, very upfront that I was going to be on maternity leave. I think if I had surprised them with that, there would have been potentially some disappointment or questioning, why did I just join this thing where the person’s leaving?

I think having those expectations set at the beginning was really great, and having a VA who can handle clients and who you give the autonomy to, and the ability to make decisions within certain parameters, so if it’s a refund request up to a certain amount, just make it happen. Use your judgment in these areas. If you can have a VA who can do things like that, it takes so much work and so much stress off of your plate, and when I’ve traveled before, I’ve actually gone away for entire months at a time to do safaris in Africa. I went to Ecuador and the Galapagos Islands, I’ve been away for long periods of time and I’ve had VAs steps and I’ve just always found people who I trust enough to make decisions, and I think that is really, really key to not having to be stressed out because if they have to come back to you for every single decision, then it’s not going to be a relaxing vacation or maternity leave.

I highly recommend if you are going to hire a VA, find someone who will make decisions and who you can trust to do the best things for your customers or your clients and your business. All right. Now, I want to hear from you. Have you taken a vacation? Have you gone on maternity leave or paternity leave? Have you stepped away from your business for a decently long period of time and how have you made that happen? How did you plan and did it go according to plan? Let me know on Instagram at Successfully Simple, and I’ll see you over there.

Erin Flynn

Erin Flynn helps creative entrepreneurs design profitable and sustainable businesses that are simple and streamlined so that they can work less and live more. She’s the founder of Successfully Simple™ and is on a mission to help other creatives slash their work hours, earn more, and enjoy their lives.

Visit Erin: Website | Instagram | Shortcut

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