You became your own boss because you wanted to call your own shots.

One of the big reasons you wanted to call your own shots? Time freedom! A huge advantage of being your own boss means that nobody is imposing a timetable on you, your schedule is entirely up to you and you may even have the luxury of choosing where exactly you want to work from.

Until you don’t! 😵 Let’s be honest :: you put in way more hours than most of your employed friends, you’re often plagued by the feeling of not having much security or safety net, and when it comes to vacation time, you kinda-sorta-totally envy your corporate counterparts for being able to submit their two week’s vacation whenever they damned well choose.

Here’s a little secret for the self-employed :: you can totally do the same to score your own much-needed + well-deserved vacation time.

And before we get into the “how”, I wanna address the big fat “but” that I know is sitting in your mind.

“But, Lanie, if I log off for a whole week, my prospective clients are just going to go ahead + book with someone else who got back to them right away.”

To this, yes, I agree 100%. However, that’s exactly what this post is all about :: setting up the necessary systems to make your people feel like they’re getting the red carpet treatment + to keep those sales rolling in for your service-based business, even if you’re hanging out on a beach that’s so far off the grid you can actually hear the sigh of relief coming from your smartphone.


Auto-responders are great. 👉 For the uninitiated, auto-responders are emails that are set up to automatically respond to anyone who sends you an email to let them know that you’re out of the office or that they can anticipate 2-4 days before getting a reply. They’re a lot like an answering machine, for the digital age, explaining that you’re out + when you’ll get back to them.

Since MacGuyver is my spirit animal, I’m a big fan of taking existing technology to make it serve my own uses + interests. In this case, I suggest that instead of using auto-responders to say you’re not available, use them to direct those prospective clients like air traffic control TOWARDS GIVING YOU THE SALE. I mean, these people didn’t write you to find out if you’re in the office, did they? Nope! They wrote to you because they’re interested in what you’re selling + it’s your job to make that as easy for them to do as humanly + professionally possible.

Let’s see how that works.
If you’ve been in business for any length of time, you’re all-too-familiar with the Frequently Asked Questions that people have for you before they hit the BUY NOW button. Feel free to address those at the hop or, if there are just too many to cover in an email, you should provide a link that invites prospective clients to visit your FAQs page where the most common questions about your services are addressed.

Likewise, make sure to include an option for people to sign up right away. If someone is ready to buy, it’s your job to make it easy for them to do so by funneling them towards the sale. Have you ever been on a website where you want to buy something + they make it difficult for you to complete the purchase by not making their buying options easy enough to identify or worse, they make you jump through a bunch of hoops before you can give them your money? Don’t be that person! Just because you aren’t there doesn’t mean you shouldn’t provide a way for people who want to pay you to do so.

This begs the question :: “how do you include the sales pitch in a cold email without looking pushy?”
I put together an example of how you can use an auto-responder that isn’t icky or sales-y, but rather acts as a welcome mat to people who like you + what you do enough to be reaching out to potentially hire you.

       Hi there!
I’m currently enjoying some much-deserved beach time with the family – {insert link} check out my Instagram for splashy updates!
At the time of my departure, I was booking for {insert when your first available appointments would be} and I am still allowing clients to pick up their desired spots during my absence. Note that availability is on a first come, first serve basis and unless you have secured your spot with me, I can’t guarantee these earlier spots will still be available when I return. To secure your spot in my queue, you can {insert link} make sure we are confirmed by booking here.
If you have any questions about my services, please {insert link} visit my Frequently Asked Questions. For anything that isn’t addressed here, I will happy to help you when I’m back and refreshed at work on {insert return date}.
      Thanks for reaching out and I hope you’re enjoying your summer as much as I am!

See? You can be personable, informative + sell, all at once. The key is to writing an email like this is to be human about it. Make it clear that you value that they’ve connected with you + that even when you’re away, you have something to offer them + won’t leave them hanging. You’re a professional, goddamnit, and you act like one. Even when you’re on vacay!


You’ll notice that the above sample auto-responder included a link for people to book with you. Providing an easy method for people to book with you is one of the steps towards hiring you to perform a service. When you line all those steps that go into seeing a service through – from beginning to end – you have what is called a WORKFLOW.
A workflow acts as a kind of checklist for all the items that go into each + every project you perform + establishing those steps is the first step towards doing yourself the biggest favor any service provider can make because not only does it save your sanity but you can also save yourself a heckload of time once you automate your workflow (which we will talk about a little later.)

First, let’s look at what a simplified workflow may look like for a photographer ::


Meanwhile, another photographer may prefer to work like this ::


There is no right or wrong answer when it comes to workflows + there is no cookie-cutter formula; each workflow is as individual as the service provider it is designed to serve.

However, in order to automate the way you work so that you can keep accepting clients – even if you’re off somewhere sipping on pina coladas! – you have to start by establishing this series of steps that each + every project will go through. Not only will this save you the time that goes into doing this on repeat, but you’ll wonder how you ever managed constantly having to second-guess whether you remembered to send out that email + you can rest assured that every client is getting the same gold-star treatment, without missing a beat, because you set it up that way.
Because you created a workflow designed to roll out the red carpet in the same manner, each + every time.



Once you’ve settled on a workflow that reflects the way you want to work, it’s time to make that workflow work (hella hard!) for you. With the help of technology, you can easily set up each step of your workflow to move into the next step like a set of perfectly lined-up dominoes.

Here’s how it works, using our first photography example ::
📆 The Client books appointment online 💪 an email is automagically sent to the client with a link to make a deposit in order to secure the desired appointment time
💰The Client makes a deposit 💪  another email is sent including the contract that the client must sign electronically prior to the shoot
📃 The Client signs the contract 💪  an email is sent 48 hours prior to the appointment time reminding them of their shoot and the details such as where to show up, what to bring, etc.
📷 The Client pays in full at the photo shoot 💪  an email is sent a week later with a link to their photo gallery

You have to write these emails exactly once – not every time, individualized every time you have a new client but once + only once! – because you will use automations to set-it-and-forget-it. That’s right, after you have all your scripts down, you can walk away from these emails like it’s a burning car in a Quentin Tarantino movie – in slow motion, looking fiiiiiine – because you’ll never have to write or remember to send those emails again.

How? By using a CRM, or what is called a Client Relationship Manager. This is the tool/technology that will take care of your workflow + give you the space you need to focus on more important things, like doing actual client work or perhaps ordering another mai-tai. Whatever you’re into.

Most CRMs are so freaking smart that you can even embed “what if” situations for your workflow to send different emails, based on your client’s response (or lack thereof!). For instance, if the client didn’t make the deposit required to secure the appointment time they booked, your CRM can be set up in a way that it will auto-magically send an email a week later reminding the client that their desired time can’t be secured until the initial deposit is made. You don’t have to think about it, you don’t have to look up who has put money down, it all just gets done for you so that you can skip having to waste your time writing awkward emails about payments past due or making sugar-coated phone calls to follow up on the status of a contract. Everything you need to know about the status of each + every project is quickly visible at a glance, and all the “gotta remember” moments that clutters your mind is a thing of the past.
There are plenty of CRMs to choose from, depending on your own needs, and I personally use Dubsado* as my CRM. Others you may be interested in checking out + I recommend include Streak for Gmail, 17hats, and SatoriApp.

CRMs make it feel like you’re working with magic. Only it’s not. It’s being organized AF about how you’re operating + smart as all hell about how you’re using your time.


If you’re feeling like you can’t take a break or that automations will make your business impersonal, realize that this is a self-imposed limitation. Burnt out freelancers aren’t doing anyone any above-and-beyond favors + if we’re being honest, your personality is always the same so how different are your emails from client to client, really? Try getting out of your own way – things will still be done exactly the way you would have done it, except better, faster + more reliably than you ever could.

As far as vacay goes, clients who are told ahead of time that “hey! heads up that I’ll be taking a week off of project work at the end of next month” aren’t generally offended. Nobody thinks it’s a big deal or a deal-breaker to doing business with someone. In fact, they’ll appreciate that you were straight-forward about it, they’ll respect that you had this planned + you can probably expect questions + small talk about whether you’re doing anything special!
Meanwhile, prospective clients aren’t turned off of your services just because you’re out of the office. Quite to the contrary, someone who is as prepared as a Boy Scout to anticipate what you want + need from them – even when they’re not there! – will come off as being a boss who has their freaking act together!

And even if you aren’t headed for a big ole vacay, having a system in place to handle the “business as usual” BS for you to have more downtime in your day-to-day life is a move your future self will thank you for!

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Author: Lanie

Lanie Lamarre is the headmistress at Miss #GSD, where feisty biz ladies like you come to flip their To Do lists into DONE! Overwhelmed much? Drop her a line — all you have to lose is your gigantor workload!