How to Take a Vacation When You Work for Yourself

how to take a vacation when you work for yourself

How to Take a Vacation When You Work for Yourself

It’s great to be the boss. When you run your own business, it can feel really fulfilling to be only accountable to yourself. No one playing politics with your career, no dreaded annual reviews, no painful holiday party. But…also…no risk, no excuses, and . . . no days off. If you want to take a vacation when you work for yourself, it gets tricky to find the time and the money. Whether you’re a solopreneur, or managing  a hundred employees, it’s not as easy as just putting on the out of office.

how to take a vacation when you work for yourself

You can (and should) take a vacation when you work for yourself :

Plan ahead. . . .way, way ahead. Remember when your biggest problem was figuring out how to enter vacation days into the timekeeping system? Now you have to manage leaving in the lurch customers, employees and vendors. There’s no point in going on vacation if it’s going to all be spent on the phone, putting out fires and worrying. If you plan ahead (at least a month, preferably two), you have some time up front to get ahead of the curve.

Team spirit. Meet with your team far in advance to let them know the dates that you will be gone, and explain in general terms who will be covering what. This way, everyone knows who is taking care of which accounts, or signing checks, or whatever else has to happen while you are gone.

Then, follow that up with a specific directive to each person — ideally, meet one on one with a specific list of what they need to do, who to call for what, and when it should be done. Equally important — what not to do — move forward on that account, but don’t negotiate the sales agreement.

Two steps forward, two steps back. Take a hard look at what really has to happen while you’re away. Part of the reason that it’s so difficult to take a vacation when you work for yourself is that it’s easy to overestimate how vital every activity is, and you are.

You can pay bills ahead of time but post date the check, or set an an auto-pay in the future. Push out non-essential meetings, and try to pull forward essential ones (don’t push out really important meetings or you’ll spend the whole vacation peeking at your presentation or spreadsheet).

And get vacation insurance. Well, stuff happens, so maybe you should actually get vacation insurance. But even better — try to plan something that if you do have to cut it short, or arrive a day early it’s not a disaster.

And be realistic — that yoga retreat on the mountain top sounds amazing, but if you’re going to lose your mind if you have to go a week without a signal . . .maybe a spa just outside the city is more appropriate. Likewise, leave the cruise for retirement.

You have to work hard to take a vacation when you work for yourself.

It’s actually not very easy in the digital age to unplug. And while it’s tempting to say don’t cheat, be realistic. Some say you need a full week — or longer — to really decompress. If it will make it easier to set up one call during the halfway mark, well, know thyself. But if you find you’re on your phone more than your beach towel . . . it’s time to have a word with the boss.