Taking a vacation when you own a business…

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by Tom Watson on November 29, 2015

Getting away on vacation when you are a business owner can be a challenge. You have jobs, deadlines and employees to worry about.

From there you have to worry about who’s in charge, what happens to any money that is collected and the list goers on and on. It sounds pretty daunting. And to a certain extent, it is!

In my career, preparing for a vacation was always one of my more stressful times. I had so much to do to in preparation for vacation, plus it always seemed like my world fell apart the week or two before vacation started. One thing or another would happen and just drove me nuts.

It always seemed like I would get hired for a big new job and my start date would happen while I was away. Admittedly that was a good problem, but still a problem nonetheless. Other times I would have employees leave just before I went away, leaving me short handed.

I even had one of my key employees “go on strike” as they put it because they wanted to extort more pay out of me. This happened the day I was supposed to go to Vegas. The limo was at my door (true story) when my largest customer called me and wanted to know why their facility wasn’t clean.

My employee never showed up the night before, the place didn’t get cleaned and now the big boss wanted to know WHY. I didn’t have any answers at that moment. So I had to cancel my vacation right then and there. It stunk! I had friends waiting for us plus a gorgeous suite in a fine hotel. That’s life as they say.

Another time I had a big customer call me and want all their newly laid floors waxed on Friday night after 7 PM. They had a grand re-opening scheduled for Monday. The only problem was I was getting on a plane to Aruba at 6 AM Saturday morning. The timing would be tight, as I wasn’t sure it could be done.

Just to make the flight it meant I had to be at the airport by 4 AM because it was an international flight. And the airport was an hour away, so this meant I had to leave at 3 AM, which meant I needed to wake up at 2:30 AM to get ready. Needless to say this was a job I didn’t want to do.

But after thinking about it I did take the job. This was a very profitable customer, and I always wanted to make her as happy as can be. I was a little nervous to be honest because I needed everything to go perfectly to get done.

While performing the work I motivated myself by saying over and over that this job was basically paying for a good portion of my trip, so BE HAPPY. All went well and I got home just in time to catch an hours sleep. I can still clearly remember how tired I was!

With all that said, taking regular vacations is a something we all must do. They are something you must work hard for. They recharge the batteries and make life worth living. I never once in all my life went away on vacation and regretted it and I don’t think you will either.

So my advice to you is to MAKE IT HAPPEN. Even if it’s just a small trip, plan it and take it! So many business owners think it’s too hard, but it’s not. It may be a pain in the butt, but owning a business that you can’t leave isn’t freedom. It’s prison! Think about that for a moment.


{ 4 comments… read them below or add one }

1 Christiane November 29, 2015 at 6:30 pm

Hi so I read your site all the time you say so much informational stuff. I to have a cleaning business I’m insured & bonded I do residential and commercial properties in the summer time my business is very busy I’m at a point right now we’re I am so slow I barely being able to make it I run ads after ads but don’t seem to be getting the customer I need is there any helpful advice you can give to me it sounds like you’ve been through it all please help

2 Tom Watson December 1, 2015 at 9:53 am

Hi Christiane! Maybe it’s the ads that are not all that good. Try something different. You can’t just have one method of getting accounts. You need it to be versatile. Go to real estate offices (I’ve wrote about that A TON). Advertise on Craigslist (it’s FREE). Join networking groups, hand out some flyers. You need to mix it up.

3 James January 16, 2016 at 8:09 pm

Hi Tom,

I want to visit my girlfriend in a different city in the near future. However, I can’t leave my business because it would be a waste of my past effort to build my business. What advice can you give me to make this happen? How important is setting up your business ‘the right way’ from the moment you start it? Is it possible to take a leave of absence and run your business from miles away? I was thinking that maybe I could take time off during slower periods throughout the year, but when your business is already slow, every moment is an opportunity to change that.

How shall I approach this?



4 Tom Watson January 17, 2016 at 1:44 pm

Hi James! You need one or more people that you can depend on to carry the load while you are away. It all comes down to who you hire. The business will run just fine while you are away with the right people there.

This doesn’t mean you can take months on end and neglect things, but one or two weeks should be pretty easy to pull off. I used to go away several times per year without incident.

And this doesn’t have to be from day one… you can start getting people in place now. We all learn and mold our business into what we want. Very few people get it right from the start. It’s a process.

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