How to Take Time Off As An Entrepreneur


To those of you who work a 9-5, the concept of not being able to take time off may sound outrageous.  Most people cash in on their vacation time as soon as they can, and some are even fortunate enough to not have to think or worry about work while they’re gone (When you meet a person like that, shake their hand.  They’re a rare breed these days.).  Entrepreneurs, however, have a tendency to work long hours during the week and have trouble taking time off from their work.  This is especially true in the service-based industry because long hours are spent working on work for clients, and then even more time has to be put into marketing, networking, and working on the business.

While this may sound admirable (it is but…), it’s not altogether healthy.  There has to be a balance, and even though the old “work-life balance” adage might not be entirely realistic because if you dedicated the same amount of time to your family as you did to your business, you a. probably wouldn’t have much of a business going b. wouldn’t be able to sleep at all or c. not be able to make enough money to support your family.  Even in the higher paying service careers, long hours are spent up day and night on customer service, the service itself, and all of the things required for your business.

Entrepreneurs, especially solopreneurs and those without employees or sub-contractors under them, tend to find that taking time off work is less of a break and more of a headache.  This is because taking time off usually means pushing back work or not answering clients for a few days, and this can be detrimental to projects and usually leads to more work when you get back.

So, as an entrepreneur, how do you avoid working 365 days a year?  How can you get to go on a week-long vacation with your family or even do something seemingly crazy like take off a couple hours to take your kid to the pool in the middle of the day (yes, it IS possible)?  Follow my steps, and you’ll have yourself a little break on your hands–but first, catch up on all your work.  Don’t come to me when clients get mad because you didn’t make your deadlines; I don’t condone that.

delegate business tasks

  1. Take a step back – Look at your business from the outside.  Are you maybe a little biased when it comes to certain things you’re doing, assuming that you’re the only one who could do them?  Are you prioritizing things correctly?  Are you using your time well?  It may seem like you are, but rather than being able to take large breaks, you take small breaks throughout the day or throughout the week, taking up the time that could be put into bigger chunks of time off that could help you rejuvenate (and even improve your work when you come back fresh)!
  2. Prioritize – If you don’t already, sit down and make a list of all the things you have to do and their deadlines.  If you just finished the release of a big software update and know you’ll have service calls for a couple weeks following, this probably isn’t the best time to take off.  Writing everything down and putting your priorities and deadlines on a calendar will help you visualize when you can step away without harming your business or any work that needs to be done.
  3. Get Things Organized – Leaving your business alone for a few days or a week at a time can be incredibly stressful, especially if things aren’t organized.  Make sure you know where each project and customer is at, get anything done ahead of time that you can (if you do social media management for a living, schedule out your pre-scheduled posts ahead of time so you don’t have to worry about them), make sure all your clients know the dates during which you’ll be gone, get substitutes for any networking meetings you’re in (or am I the only one in multiple networking meetings per week?), and clean up your desk and e-mail.  The more organized your workspace is when you come back, the easier the transition back to work will be, and the simpler it will be to leave next time.
  4. Delegate – It’s time for another list.  Make a list of all the tasks you do that could probably be completed by someone else.  You might have to do some minor training that is company-specific or software-specific (remember that if you’re bringing on a sub-contractor, you can’t train them in the job itself if you want to avoid treating them like an employee!).  Bring on a sub-contractor who knows what they’re doing.  If they don’t have an agreement of their own, make sure you get one going.  Tasks that are easily delegated are customer service (taking phone calls and having phones forwarded while you’re gone, following up on phone calls, responding to e-mails, etc), social media management (make sure you’re hiring a professional so they stay true to your brand), client management so that your client has someone to hear their concerns wile you’re gone, and even scheduling appointments for when you come back.  Data entry, document creation, sending out follow-up packets to individuals, etc., are other things that are often delegated.  It’s important to find a person who understands you and your brand, knows what they’re doing, and to whom you feel comfortable handing things for your time off.  Who knows, you may even find that having someone there to help with these tasks is a good long-term solution.
  5. Unplug – Yes, I know it’s hard.  No, don’t cry.  You can do it!  I know, I’m telling you to stay away from your e-mail, computer, text messages, phone calls…anything that takes you away from enjoying your wonderful vacation or time off with your family or dog walk in the park.  Whatever you’ve chosen to do with your time off, you need to be there and in the moment, or your mind won’t fully be able to re-fuel, and you won’t be able to come back rested and ready to get back to work.  What I typically do for vacations is have some set time in the early morning or evening when there’s downtime to check e-mails, texts, and phone calls and follow-up.  Make sure whomever you have filling in for you knows to tell customers that you will get back to them within 24 hours, and set an auto-response on e-mail if you don’t have someone managing your e-mail for you.  If you have a situation where you absolutely have to be near the phone in case of a client emergency, only take those calls–NO OTHERS!

vacationThe problem is, it’s really hard to enjoy time off when all you’re thinking about is what should be getting done with your work.  Understand that if you’ve gotten all your necessary work done and notified your clients with enough notice, people do understand that you need a little bit of time off from time to time.  If you’ve delegated your management tasks to a Virtual Assistant or marketer you trust while you’re gone, you won’t have to worry about anything at all.  Make sure everything is in order beforehand, get your assistant (whether he/she is long-term or temporary just for the vacation) ready to handle possible scenarios, and put your feet up and relax.

If you’re looking to delegate some of your tasks or need someone to “man the fort” while you’re taking time off, contact me at Pro-Assist, LLC, to see how I can help you with Virtual Assisting and marketing management while you’re gone!

64 thoughts on “How to Take Time Off As An Entrepreneur”

    1. Thank you! I have trouble with it, too. I know it’s really common among all the entrepreneurs I know!

  1. Great Blog with great advice. As someone as a solo-entrepreneur for 17 years and someone who taught people how to add some balance. I so get this on so many levels.

    1. Thanks! Yeah, I think balance is so important. You as a stress coach would probably have some very beneficial input on this topic too and trying to make having a business less stressful than it needs to be!

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