How to Prepare to Take Time Off From Your Business

Preparing to take time off as a freelancer is a LOT different than preparing for time out of office when you’re working a traditional 9-5, because, well, you ARE the office.

As I’m sure you’re well aware, there’s no other “you” to take care of tasks that have to happen on the regular; no receptionist to take your calls, so to speak.

…but ur gurl still wants to enjoy her time away from the blue light, right?!

For the last few summers, I don’t exist in July. Meaning I fully disappear from the Internet to enjoy Cape Cod summers on the beach, iced blueberry chai in hand, with my current read, making sick-ass sandcastles with my 7-year-old.

And before you start throwing tomatoes: No, I was not born this way.

I used to be deeply, spiritually, unwell about work.

At one point, I literally had to: block Gmail on Safari, remove email from my phone, and BRICK Stripe because I was addicted to checking my revenue.

If you just gasped and whispered, “oh my god, that’s me,” …welcome, squirrel.

This is how I do my best to prepare for an extended period of time off from work.

But first, a reality check.

Your business is not going to die because you didn’t check on it for six hours, and it is not sitting in the corner crying because you skipped Instagram Stories on Saturday.

And yet…

You’d think our businesses required around-the-clock medical supervision.

You are actually allowed to go outside.

People are not sitting around wondering where you are, and they’re not refreshing your Instagram waiting for your next carousel.

During the summer, they’re at Costco. They’re trying to remember why they walked into the kitchen. They’re scrolling Zillow, looking at houses they can’t afford. They’re texting their group chat.

They’re living their own lives.

So the amount of pressure we put on ourselves to remain constantly visible online is honestly exhausting and unnecessary.

Most of it stems from the belief that if we disappear for five minutes, all our momentum disappears too, but the strongest businesses don’t rely on constant visibility.

They rely on strong foundations.

The problem is that foundations are boring.

Everybody wants:

• Viral content
• Quick wins
• Explosive growth
• Immediate results

But the strongest businesses aren’t built on constant activity—they’re built on assets.

Things that keep introducing people to you long after you’ve finished creating them.

How to Go OFFline When Your Business is ONline

I think a lot of people hear: “Take time off!” and imagine disappearing into the woods for 14 days while their business burns to the ground behind them.

To be clear, that’s not what I’m talking about.

Being offline IS:

• Planning ahead
• Communicating clearly
• Creating systems
• Setting expectations
• And realizing you do not need to be emotionally supported, refreshing your inbox from the beach chair.

Listen to my 70-minute pep talk about taking time off here:

Here’s how you can afford to go offline this summer without worrying about losing momentum:

#1 — Inform clients in advance & clearly communicate when you will and will not be available.

The reason I chose to kick the list off with this particular task is that it starts way before the actual time off does; it typically starts when I’m booking client projects in the first place.

Being overly communicative about when I will and will not be available helps me feel better about leaving, because I can be certain no one is expecting anything from me. 

They’re well aware when I’m gone, and when I’ll be back, and where their project / deliverables / expectations fit into the mix.  

#2 — Be realistic about what you can and cannot take on right before and right after vacation.

A few years ago, when I took my first vacation from work, I found that I drastically over-committed myself (shocker!) and my pre-vaca to-do list was unbearable.

Since then, I’ve learned to:

• Stop being a yes man.
• Stop beating myself up about needing a day or two to recover from time off.
• Figure out what I realistically can and cannot handle.

Sanity > bank account, always.

#3 — Use your email OOO message generously.

I often put my “out of office” email auto-responder up a few days before I’m actually OOO to prepare to take time off, and a few days after the fact to catch up, too.

This is the best life hack if you, like me, feel stressed about responding to everyone, all the time, immediately, and feel bad / anxious when you don’t.

(I also do this whenever I feel overwhelmed and need to focus on client work, with a message that says something to the effect of “I’m busy surviving as a human rn, ttyl when I can finally exist again” — because, let’s be real, I’m nothing if not aggressively honest.)

#4 — Make sure you have enough $$$ in my business account for auto bills.

Even the .04 seconds it would take me to transfer money is a task I don’t want to be doing when I’m gone.

I want to be present with my family, not worry about whether or not I’m gonna have a bank issue.

#5 — Write and schedule any content your audience is expecting.

For me, of course, that’s my Tuesday Table of Contents newsletter.

Every single Tuesday morning, you’ve invited me to your inbox. I’m not going to miss that date just because I happen to be eating a blueberry scone on the beach at the time I usually show up for you.

Normally, when I’m going to be out of the office, I try to write and schedule the newsletter for the week before, the time I’m gone, and the week after, just to be safe and take a task off of my plate when I’m preparing for / recovering from time off.

For you, that might be prepping your:

• Blog posts
• Threads
• Instagram posts
• Podcast episodes

#6 — Finish all client work before leaving OR get all client work to a good “pick up” spot for when you get back.

I try to plan my projects so they’ll be finalized before I leave, but sometimes things just don’t work out that way.

So, instead, I’ll ensure they’re at a good pickup point before leaving.

For me, that looks like:

• Finalizing a brand messaging book, so I can start on website copy when I return.
• Letting a client’s designer know that the web copy has been finalized, so they can start on design.
• Sending the first draft of a website copy project, with the review call scheduled for when I get back.
• Editing blog posts, with a message to the client letting them know the final drafts are ready for their review.

Of course, depending on what you do for work, this may look different, but the point is: don’t leave anything feeling open-ended / unfinished before you leave.

You’ll feel better while you’re gone if there isn’t an undone task waiting at your desk, nagging at your brain the whole time.

#7 — Make your website your 100% online employee.

Shocker! Website Girl is about to talk about websites!

But seriously, your website should be doing several jobs at once:

• It should answer questions.
• It should help people understand what you do.
• It should communicate your personality.
• It should build trust.
• It should tell people how to work with you.
• It should move people toward the next step.

All without you lifting a finger.

Good website copy keeps working after you’ve walked away.

And SEO is the underrated employee who keeps bringing people in while you’re out.

While social media is constantly demanding your attention, SEO is quietly introducing people to your business behind the scenes.

People search, and Google sends them to you.

They find answers, AND they discover your offers.

All while you’re doing literally anything else.

That’s what people actually mean when they say: “Your business works for you.”

​Not magic. Not passive income fairy dust.

​Just marketing assets doing their jobs.

#8 — Decide if you’re going to succumb to the urge to post “OOO🤪” on Instagram.

No one would notice if I didn’t post on Instagram for months, let alone one week. But maybe I just wanted an excuse to post a beach picture on my feed.

If you see an OOO post on my Instagram, mind your business.

If you don’t, I took the high road. Be proud of me.

#9 — Delete email off your phone and BE PRESENT! YOU MOFO!

That last part was a message to me. I’m the mofo.

I will literally log into my email on Safari if I delete the Gmail app.

So, I deleted Safari, too.

My new motto is: if I paid for this vacation, I’m going to be present on this vacation.

And if that motto doesn’t work — because, I can already tell, it’s not going to — I’ll just remind myself that I only have so many days where Woo will even want to go on a trip and play in the sand and water with me. That’ll work.

If all of this is starting to make you feel guilty about taking time off…

Here’s the thing nobody wants to admit: Sometimes the guilt is just your ego wearing business casual.

OOP.

Don’t lie, a tiny part of you LIKES feeling needed and wanted and important in your business.

So when we finally unplug, we realize: “Oh… the world did not collapse because I didn’t answer an email for four hours.”

​Humbling!

​Also, sometimes being busy just feels familiar.

​A lot of us started businesses because we wanted freedom, flexibility, and a life outside of work…

​…and then accidentally rebuilt a corporate prison but with prettier fonts.

​Your business works for you when you’ve built it on a foundation that doesn’t need you online 24/7 to keep running.

​If you want more practical tips on how to take time off—whether that’s for a much-deserved vacation, maternity leave, or because you need a damn break—take my workshop on vacation-proofing your business. You’ll learn everything you need to know about how to build the business foundation necessary to ensure your marketing works FOR you, even when you are offline.  

Now I gotta go finish packing for my Cape Cod summer and you will NOT be hearing from me (except every Tuesday in my newsletter and every Sunday on my Substack).