You would think it might be easy for an Executive in Sweatpants to sneak off and take a vacation.  Since I work from home and how to work on vacationdon’t have to drive to an office each day, it’s easy to understand why someone might make this assumption.  Here’s the problem:  your clients do not go on vacation the same time you do.  This means that a week in paradise can quickly dig a hole that you may never get out of.  In this article, I’ll give you a few tips for balancing your clients’ expectations with your desire to sit on the beach.

Set Clear Expectations Upfront

Don’t wait until the day before you leave to tell your clients about your vacation.  I might go overboard here, but I typically lay the groundwork at least two weeks in advance.  This gives everyone time to make plans for your absence.  It also gives you time to shuffle calendars and avoid scheduling time-sensitive activities during your vacation.  Let me give you an example.  My family recently visited the Portofino Island Resort in Pensacola Beach, Florida (highly recommended, by the way!).  One of my clients was preparing to “go live” with a new website.  Unfortunately, they had some technical issues with their hosting that prevented us from going live before my departure.  I made the recommendation that if we could not go live before I left that we wait until after I return from my trip.  We agreed to this and everything worked out fine.  Clients just want open communication.  Working together to develop a plan is much better than waiting to the last minute and popping a surprise on the client.

Find Time to Do Some Work

Going into my recent vacation, I knew that it would be impossible for me to totally avoid working.  With nearly a dozen clients and many different projects, I understand that completely “unplugging” is virtually impossible.  The week before I left, I took a look at my weekly hour tracking sheet and determined I would need to work about 14 hours while on vacation.  Once I set my hour budget for the week, I realized that working about three hours per weekday would allow me to achieve this goal.  I was able to sit on the balcony (pictured above) of my room and hammer out a couple hours in the morning before everyone else awoke.  Then, in the afternoon, I was able to pick up another hour or so while the kiddos were napping.  It worked out great for me and for my clients.  I recommend you set an hour goal (based on client needs) and implement a plan to achieve the goal.

Clients Might Think You’re Crazy

One thing to keep in mind:  some clients may think you are crazy for working while on vacation.  I had one client respond to an email I had sent in the following way:  “Is this how you relax on vacation?”.  Don’t be distracted by these types of comments.  In reality, as an Executive in Sweatpants you are selling reliability and trust to your clients.  Accessibility is an important factor in building and maintaining these two virtues.  Making yourself at least somewhat available while on vacation is a great way to solidify this attribute.

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Matt Keener is the original "Executive in Sweatpants," having built a successful online consulting business (from home). His best-selling book offers tips for capitalizing on outsourcing and freelancing. Matt holds an MBA and has been featured by many recognizable brands, including Upwork (formerly oDesk), Elance, Insightly, the Dave Ramsey Show, and


  1. Matt, you make some very good points in your article. Your clients need to know when you are going to be out of pocket, as they rely heavily on your expertise, and have become accustomed to your accessibility. Glad you were able to enjoy your vacation, and still have some time to service your clients!

  2. Ruth Carrell Reply

    Good article, Matt. You hit the nail on the head in your first paragraph “Open Communication”. It’s key in any relationship whether it’s at work or at home. If only everyone to do that though.

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