The 5 Essentials Every Entrepreneur Needs for an Unplugged Vacation

You are SO ready for summer. But is your business as beach-ready as you are?

Picture this… you’re on vacation, laying beach-side, with your feet up and a margarita in hand. 

Not a worry on your mind besides remembering to reapply SPF every 30 minutes and checking Yelp reviews to decide which fabulous restaurant you’ll visit for dinner. 

You don’t have a SINGLE concern about your business. 

And no, in this dream world you have not inherited millions from some distant relative and left your business behind. In this reality, you are still running the kick-ass business of your dreams, serving your clients, and, most importantly, serving yourself.


  • waking up with no alarm (unless you’re like me with two young kids in which case…HA funny!)
  • all of your projects and deliverables were done weeks ago
  • no clients reaching out because they are already completely taken care of

This dream doesn’t have to be out of reach. Intentionally putting the right systems in place ahead of time will let you step away from your business without worrying that everything might burn to the ground!

But taking a vacation without setting your own boundaries will usually leave you disappointed. If you don’t plan for the time away that YOU want, you’ll likely have to confront the fact that your R&R is going to look more like a working business trip than an actual vacation. 

The True Value of Rest

We very much live in a “grind” culture. Rest tends to be associated with laziness and a lack of productivity. We think that taking time off means less will get done when in fact the opposite is true. 

It feels counter-intuitive, but taking time to press pause on your day-to-day tasks can actually create space. You may find it inspires your creativity or helps you problem solve with a fresh perspective.

Repeat after me, “rest IS productive.”

This goes against everything the hustle mindset teaches us about work-ethic and even self-worth. But, unlearning that rest is unproductive can be a game changer in your business. 

This mindset shift made all the difference for one of my clients. This entrepreneur struggled to slow down and take time for herself outside of her business. I encouraged her to really commit to this phrase by writing the quote on a post-it note and sticking it on her bathroom mirror. 

Writing down your intentions makes them tangible. Hanging them up somewhere visible helps to keep this goal top of mind.

The quote has become a new mantra for her. Something to come back to again and again as a reminder that it is okay to relax her mind and slow down her pace. She is finding it easier and easier to take time to rest. She is finally prioritizing rest for the well-being of herself and her business.

“Attempted Vacations” 

So many entrepreneurs are afraid to take time away from their businesses. They feel like they’re the thread holding everything together. This pressure to be everything, for everyone, all the time leaves them feeling stuck. 

Others are jaded by past experiences. They have flashbacks of “attempted vacations” where they had expected to enjoy time to rest and turn off their CEO brain for a few days. Instead they found themselves responding to emails, answering frantic calls from team members, and even taking meetings! 

Before working with me, most of my clients admit that skipping out on the vacation sounds less stressful than GOING on the vacation!

The thing is, there’s a better way. My clients have experienced sheer relief, time and again. By implementing these essentials, you will be able to put the right systems in motion and seamlessly step away for a true vacation!

Babysitting List

I like to think of planning ahead for a vacation like planning to leave a child with a babysitter. You can literally create a “business babysitting list”. 

As a teenager I babysat for families in my neighborhood. I remember the pages-long lists that worried moms handed over to me to ensure I knew all the ins and outs of their child’s needs.  

They reviewed each and every line with care, as if giving instructions to disable a bomb. 

As a new mom, I was totally guilty of this as well!

It’s hard to give up control and security, both as a mom and as a business owner. You worry. It’s natural. 

As that babysitter, I remember (internally) rolling my eyes at the list of, “if this, then that” scenarios. A phone number was handy for literally every possible scenario. 

Sally gets sick? Here’s her pediatrician’s number. 

The power goes out? Here’s how to get in touch with the neighbor and the electric company. OH and the flashlights are under the sink in the cabinet to the left.

Basically… Moms know what they’re doing! Your business “babysitting” list should look similar. 

Let them roll their eyes, they’ll be thanking you later. 

Instead of sharing the number for the soccer coach or the Poison Control Center, make sure your team and your clients have the following information and systems in place. Taking the time to prepare the details upfront and anticipate client needs will leave them feeling taken care of and you feeling ready to kick your feet up. 

Here are the 5 essentials YOU need for your business to enjoy an unplugged vacation.

5 Vacation Essentials for your Business 

# 1 Decide

Making DECISIONS will help you plan for the trip that you envision. Because, not all vacations are created equal. You may want a completely “off-the-grid” trip. OR you might be okay with working a bit here and there. That’s totally okay! You just need to get real with your own expectations and boundaries so that you can set yourself, your team, and your clients up for success. 

Most vacations fall into three categories for entrepreneurs:

  1. Work with a View
  2. Limited Hours
  3. Off The Grid

Understanding each of these options is helpful as you define what your next vacation should look and feel like.

Work with a View

Work with a view means you don’t plan to skip a beat. You will continue to do all of your normal tasks, but your CEO hat may look like a sun hat for a few days. In this scenario, your clients and audience may not even need to know you’re away! Bonus: your audience will LOVE getting sneak peeks into your “work from the beach” days and the beautiful sights you see! 

Caution: choose this vacation type wisely. Level with yourself and know that this is not really a vacation, it’s just a change of scenery. Be sure that your hotel has the wifi you need and that you have all of your devices and chargers. Lastly, pay attention to time zones so you don’t accidentally show up to your weekly meeting an hour late!

Limited Availability

This is a great middle-of-the-road option, but only if done strategically. This will require you to set clear work time boundaries for yourself, your clients, and even your family! In the following sections I’ll outline helpful boundaries to consider around email and phone communications as well as ways to reduce hands on tasks through automation.

Caution: Setting limited hours for work can be a slippery slope. If you SAY you’ll only respond to emails at specific times, but end up replying to several communications while waiting for your dinner to be served, you’re not only communicating to your clients that you don’t mean what you say, but you’re also letting yourself down. Asking someone you’re traveling with to hold you accountable can ensure you don’t get sucked back into work when you’re trying to unplug and recharge. 

Off The Grid

Good. For. You.

If you are planning a totally “out of office” vacation, you will quite literally be unreachable for your full vacation. This is possible with the help of two good friends: automation and delegation. 

I work with my clients to help them establish vacation goals, set realistic expectations, and finally create and implement a plan so they can step away from their business confident and worry-free.

#2 Give Plenty of Notice

No one likes to be caught off guard. Let your team and clients know about your vacation plans well in advance. Have discussions early and often. Remind them multiple times and be especially clear in the days leading up to your departure. 

Pro Tip: I am intentional about letting new clients know about my vacation plans before the onboarding process so there aren’t any surprises. Being upfront about your availability before the contract is signed will help them manage their expectations. Honestly sharing your availability will kick-off your working relationship with transparency and solid communication.

 #3 Set Clear Boundaries 

Setting healthy boundaries is crucial to any successful, sustainable business. Boundaries are even more important when you are planning to be on vacation. Take time to identify and name which boundaries matter most to you.

So many entrepreneurs share with me that they just hadn’t considered the details of their vacation ahead of time. Sometimes life gets hectic and next thing you know you’re racing to the airport to catch your flight! Once you arrive at your destination, you realize that expectations were not set. This leaves you being reactive rather than proactive. Don’t let this happen to you and potentially spoil your R&R time!

Here are some questions to ask yourself as you set healthy vacation boundaries:

  1. Phone Calls: Will you take calls? If you will, are there specific hours you are available? If not, what are the exceptions? What about emergencies? Is there a person on your team that clients can be directed to reach out to in your absence? Make this clear and easy to implement.
  2. Email: Will you check your email and if so, when? Name it upfront. Make sure your clients know when to expect to hear back from you. 24 hours? 48 hours? On a specific return date? This will ease their minds and help you enforce your needs while you are away.
  3. Meetings: Do you plan to attend any regularly scheduled meetings? Can they be rescheduled or postponed? Be sure to make these requests ahead of time so that everyone involved can update their calendars. If you have a scheduler like Calendly, make sure to block off your vacation time so clients cannot schedule calls on the days you are away.

#4 Automation is Your Friend

Automating anything you can will make your vacation seamless. You can even make it appear that you are active and present on social media and email without anyone noticing that you’re actually jet-setting for a long weekend. Create content beforehand. Then, pre-schedule your social media posts and emails at least a week before your departure.

Here are some key pieces to automate in your business:

E-mail Autoresponder → be sure to include contact information if there is someone on your team they can reach out to instead. Also include the dates you’re out of office and when your clients or potential clients can expect to hear back from you. And if you’re constantly getting the same questions, go ahead and include a short FAQ section right there in your auto-response – if it helps even one person move ahead while you’re away, it’s well worth it!

Email Marketing Systems → platforms such as Flodesk, ConvertKit, and Active Campaign allow you to keep in touch with your audience and your clients while you’re away. Pre-schedule emails to go to your whole list, or just specific segments you want to nurture, so you can keep showing up and serving your people, even while you’re OOO.

Social Media Posts → You can schedule your posts with apps like Plann, CoSchedule, and Buzzsado. This will let you continue to nurture your audience and provide them with valuable content even while you’re away.

New Clients → Have workflows in place to capture and nurture new business. While you’re away, you will still want to welcome newcomers into your community. You can do this within a Customer Relationship Manager (CRM) like Dubsado or Honeybook to capture their contact information, create preset workflows to automate emails, and keep them engaged with your brand. You can even include a link to your scheduler so you return from vacation with sales calls lined up without ever needing to lift a finger.

Payments → using a CRM like Dubsado or Honeybook can also make automatic payments and email reminders streamlined. Check out this blog post where I break down the benefits of each CRM so that you can choose the system that will work best for your business needs.

# 5 Delegate Tasks

If you have a team, delegate, delegate, delegate

Be sure to take inventory of all the tasks you are responsible for and make sure that clear systems and procedures are in place. This will likely require some training upfront, so don’t put this off until the last minute. Carve out time to show your team the ropes so that when it is time to step away they will feel capable and you will feel confident that everything is under control.

You will want to appoint a specific person as the emergency contact. If there are specific deliverables that need to be completed and sent to clients while you’re away, make sure both the team member and the client know who is taking this on in your absence.

If you’re ready to…

→ genuinely BE on vacation

→ never miss a “hey, Mom watch this!” moment again

→ stay for another margarita instead of rushing back to your hotel wifi 

…then you need to take the time to set up systems proactively instead of reactively. Give plenty of notice, name and set clear boundaries for your time away, and finally automate or delegate tasks.

This is something I work on with my clients as COO to help them build businesses with space, time, and freedom. It takes some front-end planning and implementation, but your future self will thank you for making these systems a priority. 

Want support as you prep for that first big vacation away from your business? This is the kind of back-end designing I work on with my clients ALL the time! Reach out to set up a consultation and learn about my 1:1 Coaching Support.

Instead of coming home from your trip needing “a vacation from the vacation”, you’ll come back feeling refreshed. Pressing the pause button on your entrepreneurial checklist can actually help create the time and space for new ideas to flow. You’ll be ready to jump right back into building your business with fresh eyes, inspiration, and maybe even a tan!

  1. […] CEO Time can look however you choose. It can be as simple as one day or even as long as a week. If you’d like to learn more about what CEO Time is and how to set yourself up for some successful, unplugged time away from your business, check out this blog post about taking time off in your business.  […]

  2. […] you feel like you are on autopilot, take some CEO time to pause and reflect. Reconnect with the Vision and Core Values of your […]

  3. […] The last and perhaps most important thing – I urge all of my clients to prioritize rest during this time of year and carve out unplugged time away from their businesses! […]

  4. […] CEO Time is time to work ON your business instead of IN your business. It’s the time you prioritize away from the day-to-day tasks to TRULY wear your CEO hat (AKA this is not time off or vacation time). CEO Time is different from taking a few days to relax at the beach or visit family (although time off for YOU is equally as important!).  […]

  5. […] empowered to FINALLY take some time off in your business without worrying about the bottom […]

  6. […] CEO Time is time to work ON your business instead of IN your business. It means you carve out time away from the day-to-day tasks to TRULY wear your CEO hat (AKA it’s not time off or a vacation…although time off for YOU is equally as important).  […]

Let's Connect!
Follow Me  @erincantwellco