Self-Employed? Kiss Your Vacations Goodbye

03/10/2015 08:47 am ET | Updated May 10, 2015

If you're self-employed, you'll never get a real vacation again.

I read an article on the truths of self-employment recently. I'm in complete agreement that you can kiss your real vacations goodbye.

I've been self-employed for the majority of my 22 years in financial services. And I really wouldn't have it any other way. But once you leave working for someone else, you no longer get those paid sick days or vacation days.

Even when you do take time off, you are still working: checking email, making calls and checking in on things.

I've always been a real advocate of the self-employed getting at least one week totally away from the business.

"But David," you ask, "how in the world will I make up the lost income and time away for vacation?"

Well there are a couple of things I've done during my self-employment years to try to take a real vacation:

1. Save for the vacation. Yep. Don't use that stupid plastic thing in your pocket. A lot of us think that we'll pay off that credit card at some point, but that money just racks up. Set aside money in a dedicated savings account. You don't have to look for anything paying a lot of interest; that's not the point. Decide how much you are going to spend, divide by 12, and put that away every month.

2. Save for the lost income. Huh? That's right, Sparky, you don't get a paid vacation in the Caribbean. So take last year's income, divide by 52, and save that amount for the next 12 months. That way you have that lost income as well as the vacation covered. Unfortunately, this is just one of the many things the self-employed have to overthink.

3. Take a staycation. This isn't my favorite option. I just like to get a change of scenery and leave town. But if it's completely impossible to leave, you could just take the week off and do some things at home or take a mini-vacation. Work on fun home projects, go camping nearby or just do a weekend at a nice hotel with room service and all the amenities.

How do I get the real vacation experience even with owning my business?

  • For Pete's sake, turn off voicemail and email if your want any sort of vacation!
  • Set up an auto responder on your email.
  • Send business calls to voicemail with instructions that you are just out.

The issues and the problems will be there in a week. If you don't stop and recharge your business-owner battery, you'll have more stress, and it could affect your health. So sip that margarita and take a nap on the beach. Just try to take some time off. It's one week I really look forward to.

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