Yes, You Can Take Time Off as a Solo Entrepreneur

Your eye’s on the prize: that week-long trip with your favorite person and/or bingeworthy Netflix show. You’re ready to relax, put your feet up, and stop thinking about work for a few days.

And then you panic.

Friends Janice Hyperventilating

Because with no one looking after your business, you’re pretty certain you will:

a) lose all of your clients immediately
b) not have any money in the bank when you return
c) have to start your whole business over and why even bother at that point and now you’re headed back to that corporate cubicle you swore you’d never go back to

Hang on a second.

Reality check time: with a simple plan in place, your vacay dreams aren’t actually that unattainable – even if you’re the only person managing your business. (Or one of the only people.)

Getting your business set up for a little time off takes effort, but it’s more doable than it sounds – so where do you start?

You’ve got two options

Say you’re a solopreneur.

(Well, don’t literally say it. We can’t hear you!)

You do it all – from client work to marketing to accounting and beyond. You’re living your dream…you just didn’t know you’d feel like you can never step away.

You can, though, and you have two ways to do it:

Option 1: increase your working hours leading up to your vacation, so everything is done ahead of time
Option 2: find ways to replace yourself while you’re gone

While Option 1 might sound like a great idea now, you’ll never need that vacay more than after you’ve worked two 60-hour work weeks in a row.

Chris Traeger anxiety quote

So, Option 2 it is!

Here’s how to make it happen:

Find your people

In order to step away from your business for a bit, you’re going to need to know what exactly you do every day, so you can find the right people to support you while you’re away.

Sounds simple enough – but most people don’t actually have a clear idea of what they do every day!

Here’s how to break it down.

1) Make a list of all of the things you do every day. Include tasks and the approximate number of hours you spend doing those tasks.

(Tip: don’t just try to do it all at once, from memory. Keep track for a week or two – a tool like Toggl is perfect for this sort of thing!)

2) Decide what can be done ahead of time and/or automated. Do you write your social media posts every day? Schedule them in advance with a social media scheduling tool! The more you can do ahead of time (without running yourself ragged), the more you can relax while you step away. For the rest, move on to Step #3.

3) Seek out groups of people who do what you do. If you aren’t networking in this way already, Facebook Groups and LinkedIn Groups are some of the most active communities of entrepreneurs ready to help you out.

4) Use those groups to send out feelers for freelancers and virtual assistants (so long as that doesn’t break any of the groups’ rules).  Be super specific about what you want, as these posts tend to get big responses. Here’s a quick sample script to get you going:

My team is growing! I’m looking for part time experts in: customer service (phone and email), social media (creating graphics and content), and any WordPress experts. Please email me by this Friday at with the subject line “team member search” and include your specialty, your rates, and how many hours you have available each week. Thanks!

Also specify how long you’re going to be away – that is, the duration of the gig. (Pretty much everyone who contacts you is going to ask, so you might as well nip that in the bud.)

5) Look through those email responses and set up interviews with those that seem like a good fit! There’s a freelancer and a VA for practically every need and occasion – not just in terms of specialties, but in terms of the gig’s length. (Some prefer long-term commitments, while others specialize in short assignments.)

Basic training

Training someone to take over for you – even on a very short-term basis – sounds time-consuming.

That’s because you have to do it to scale.

Think of it this way: if you hire someone different to take the reins every time, and you personally train each and every one of them, that’s a ton of time and energy.

You can’t be expected to do things that way – it’s just not sustainable.

Bart throws up his hat

If you put a little time into creating a training and resource kit, though – something you can send to anyone you hire for a short-term gig – you’re only doing that work once.

One of the easiest ways to train someone like this is to create a screencast video. Turn on your video recording tool, describe the steps to each task as you do them, and voila – instant training tool!

(Tip: don’t like recordings? You could also create a PDF, or share a guide via Google Docs.)

Go back to that list of tasks you need covered, and start recording screencasts of you doing the ones that can’t be automated. (One way to tackle this is to start on Monday, and for an entire week, record a screencast any time you do a new task.) Check each one off as you go, and re-record any that might need it.

Want to make your recordings shine? Here are a few tips:

  • Go slowly – this is true of your actions on the screen and your words. Remember, your new team member has never done this for you before, so slow and methodical walkthroughs will help them learn. If it seems too slow, it’s probably the right pace!
  • Use a headset to get clear sound quality. If your computer has an integrated microphone, you can certainly use it, but a set of headphones will make the recording so much more clear – and help prevent miscommunications.
  • Don’t use your team member’s name when you record. If you say, “Hi, Cornelius, here’s how you download the report and share it at the end of the week,” you’ll have to re-record it if/when you hire someone different next time! (Not that we don’t have faith in Cornelius.) Do your future self a favor, and keep names out of the recording.

Training Pro Tip: Once your screencasts are done, send them on to your new team member and have them create a checklist based off of the video – watch-and-learn style. By reviewing the checklist they create, you’ll find out what wasn’t clear in the video, and they’ll have a better handle on what questions they actually have for you!

Now that the video is in hand and reviewed with a checklist created by your new assistant, set up a brief training call so you can answer any questions they might have.

Put it all to work

So here’s a little secret – the absolute key to stepping away and letting your team run things for you is this:

Actually step away and let your team run things for you.

When it comes down to it, it’s as simple – and as hard – as that.

Because it’s tempting to keep checking in (and checking in, and checking in), but it isn’t necessarily useful. Making yourself available in case of emergencies is one thing, but if you’re paying someone to handle things for you, let them handle things for you!

What are YOUR solopreneur tips for taking time off?

Do you have someone you work with to cover for you, or do you use someone new each time?

Are you an extensive planner, or do you wing it?

Tell us in the comments below how you get your small biz ready when you’re planning an absence!