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How to put your creative business on autopilot for creative entrepreneurs by creative copywriter Ashlyn Carter


last updated:
June 8, 2017


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Let's get you a message so tight you can bounce a quarter off of it. Around here, we serve up science-based storytelling strategies the creative set.  Even while raking in more than 1.26M in agency work since I've been at it, I firmly believe working from a place of rest (not hustle) IS possible—and I want the same for you. Words matter. Best be sure they work (and oui, with math) ... and know how to party while they're at it. 

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Reading time: 6 min.


As an entrepreneur, my creative small business needs to run on autopilot while I’m out-of-office.

How do I take vacation days wisely?

A creativepreneur will quit working 40 hours for someone to work 80 hours for themselves (wink), so I’m the first to admit it’s hard for me to take off work.

But, here’s the thing.

Magic happens in the extremes.

[bctt tweet=”Magic happens in the extremes.” username=”via AshlynSCarter”]

 I’ve written entire email newsletters about how I don’t believe in the term “work-life balance.” Counterbalance is how to do entrepreneurship well, if you ask me.

And as Mary Oliver says, “Are you just breathing in and out and calling it a life?”

Settling into the rhythms of freelance and work-from-home life at first was sweet for certain: my husband works for Delta, which scored him points during the husband-hunting interview process (just kiddin’)–technically, we could vacation anywhere.

How to put your creative business on autopilot for creative entrepreneurs

How to put your creative business on autopilot for creative entrepreneurs



From our first trip together to Europe to mini-trips to Orange Beach, Ala. to dip our toes in the sand, Wes and I love to travel–which means I need to put things on auto-pilot in my business when we head out.

Further, Wes is the Type B to my keyed up Type A, I need to coax myself into the thought of 7 days with nary a Mac cord insight.

 Read on for the 5 tools (and downloadable workflow checklist!) I use to do so!  ????????

*Now, this post is chock-full-of affiliate links, which means yes, I get a kick-back if you decide you like the tool so much you want to use it in your own business. But I wouldn’t tell you to use anything I didn’t use in my business: consider me your guinea pig–I’ll only tell you the tools I’ve invested in that actually help me in my business … you have my word.

1 | Use Gmail ninja hacks.

I think the first thing anyone thinks of when you see a washi-taped week on the calendar is your autoresponder, so we’ll just start there. Not everyone loves an auto-responder, but I’ll be honest. I’m a fan.

So, first, I make sure I have an autoresponder up (and I also use one all the time). Here’s what one of my first autoresponders looked like:

Make sure you include a brief note to current clients, interested clients, and anyone who may be in another bucket of your biz (ex. partnerships).

But here’s where the Gmail magic comes in. My two favorite out-of-office Gmail tools are actually:

  1. Folders
  2. Boomerang

I *hate* waltzing back from vacation to 234,291 emails, so I set up folders and rules. That way, all my newsletters I’m signed up for go to one folder, all the emails from programs I’m in go to another folder, client inquiries go to another folder, receipts to another subfolder of a folder … you get the gist. I just counted and I have 91 email folders set up in Gmail (remember I write email copy though, so that’s a lot of files and funnels I need to organize!), and I find it so much easier to see a little more white space in my inbox … but have the info at my fingertips when I need it after vacation.

Here’s a quick video on how to do that:

But what if I get an email while we’re out, and it’s 11 p.m. where I am, 3 a.m. where they are, and I’m technically “on vacation?” Boomerang is a plugin that lets you tee up an email to send at the timestamp of your choosing.

Want that email to go out at 8 a.m., not 11 p.m.?


Or you’re working on Saturday, getting everything ready for a week out of the office, and need it to send out on Monday?


Click here to grab the free tool–you’ll love it if you don’t already use it!


2 | Schedule most of your social media posts.

I want my social media accounts to continue to churn out helpful content for my followers, so I tee up MOST of my posts in a tool–I like MeetEdgar now, but I used  CoSchedule for a while, too!

Here’s how my MeetEdgar dashboard looks, and the types of libraries I keep:

MeetEdgar library ideas Ashlyn Writes

Facebook honors native posts, so I typically schedule those ahead of time in Facebook, and I pre-draft a few Instagram posts in something like Plann. Y’all know me, and I’m still learning to *love* Instagram (????), so mostly, I just post Instagrams on the fly.

Read more about how I schedule my posts in CoSchedule here, and to start your own free two-week trial, click here! It’s a little more cost-effective than MeetEdgar, which I pay around $600 a year for. 🙂

3 | Set up Boardbooster to keep your website traffic up.

Popping Pinterest over here, because to me, Pinterest is like YouTube: it’s not social media, it’s a search engine.

It’s also the #1 driver of website traffic for me … so, it’s something I want to be rocking when I’m out-of-office.

Boardbooster is a sweet tool that pins FOR me. As creative small business owners and bloggers (many of whom grew up on the website, since we were coming of age when it got hot!), we know that Pinterest looks for accounts that are active and healthy, with accurate links.

So how do you make sure your content bubbles up to the top? Boardbooster! The tool pins up to 100 times for free each month, and at $5 a month to pin 500 pins a month for you, it’s a fairly cost-effective traffic driver. Now that, that is out-sourcing, my friends.

Click here to make a Boardbooster account for free.


4 | Schedule weekly email(s) in ConvertKit.

People are 2x likely to sign up for an email list than interacting with your Facebook page, according to a recent report from Forrester. They’re 90% more likely to see an email from you than your last Instagram post, 61% of people say they enjoy getting promotional emails from brands.

Plus, every $1 spent on email marketing typically makes back $45, when used correctly.

That’s not an opportunity I’m going to miss out on just because I’m sipping wine in Napa for a week!

I need my weekly newsletter to go out, and also, emails to be dropped to students that are in my free course or my Copywriting for Creatives course. My email funnels are already going (click here to learn how to write your first sales funnel and set it up), but as per my weekly newsletter and the segments that get that, I write it a week out, and tee it up.

Email marketing can move the needle in your creative business.

Still not sure how to get started with email marketing?

My friends at ConvertKit have a great FREE 74-page ebook called The Complete Guide to Email Marketing, where they explain exactly how to get started with email marketing, and–as they say–do it in a “human” way, and create a living. It’s a great place to start!

Click here to grab your copy, and click here to listen to Being Boss’s podcast on email marketing … it’s the first podcast I listened to where email marketing really clicked for me, and I was sold!

 5 | Go through your client list and send a personalized note to each client.

My go-to tool here is HoneyBook. This is my client automation software, and I’m able to see all of my client’s workspaces in one page, like this sample:

All I do is click on each name, copy/paste a note about my absence, personalize it, and hit send!

Good ol’ HoneyBook … there’s no way I’d be able to keep up with all my client workflows and workspaces in Gmail, so I rely on this tool like gangbusters.

Interested in HoneyBook? I wrote a post right here about exactly HOW I use it to manage client workflows, and you can grab yourself a free trial and 20% off membership by clicking here.

That’s it! That’s how I manage my business to keep running, so I can take a week off of work–and not feel bad about it.

There’s beaches to sleep on, art history to explore, and wine to drink: The older I get, I see the psychological benefits in giving myself true time to Sabbath and recharge my batteries. Being able to employ tools like these–and pay for some of them–is worth all the set-up.

Since doing this a few times, I’ve created an out-of-office workflow checklist: grab it below, and use it for the next time you head out of town!

Reading Time: 7 Minutes

We’re taking a vacation from work to go to Europe this week, but as an entrepreneur, my creative small business needs to run on autopilot while I’m out-of-office. How do I take vacation days wisely? Read on to find out!


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