How To Plan Vacations For Solopreneurs

The holidays are upon us! Would you like to take a week or two off but are, in effect, afraid that it will destroy your new business?

The Solopreneur Paradox

As you know, one of the pleasures of being a solopreneur is the power you have to set your own schedule on a daily and weekly basis.

On the other hand, one of the pains of being a solopreneur is that it is difficult to take extended periods of time off and “get away from it all.”

As the holidays arrive, or especially around summertime, you might begin to feel a little envious of your corporate friends. They are leaving the country–and getting paid!

Meanwhile, you are going full throttle and feeling stressed out.

You Deserve a Vacation

Or do you?

Did you know that vacation is a relatively new invention? In the US, it resulted from changing conditions in the 19th Century. These included:

  • Disposable income
  • Infrastructure such as railroads

Retirement is also a pretty new concept invented at about the same time as social security. If you are in a field that is destroying your body, mind or spirit, you really do need to retire, and as quickly as possible.

What if, however, you are engaged in work you truly love? If you do something because you truly love it, why would you quit? Artists such as Picasso, Beethoven and Marguerite Duras and countless thousands of others work right up to their deaths because, in fact, they don’t view their work as separate from their lives and who they are.

As solopreneurs, we are in the business of doing work we love. If you passionately love something, at least in theory, you don’t need to “get away” from it.

Rethinking Vacation

This, of course, does not mean you don’t need breaks to replenish. And, certainly, it is true, that the average American today works more hours per week than an agricultural worker in the Middle Ages.

In other words, the way we work has changed dramatically in the past 500 years and the changes in the last 25 have been nothing short of revolutionary.

So why not rethink vacation?

Here are some options:

Be patient. As you build your business as a solopreneur, you may not be able to take much vacation, let alone extended vacation, for perhaps several years.

This may be hard. Will it be worth it? Only you can decide. For COLIBRI the choice is clear. She is investing time and energy up front to create a workstyle that she can sustain.

Combine business with pleasure. This is COLIBRI’s personal favorite. COLIBRI decided early on to “go mobile” so she could travel. Right now she’s considering her options for taking the kids for a couple of weeks to Mexico or Hawaii. She is already planning to take the kids to France for a month (as she has for the past two summers).

However. These are working travel trips. COLIBRI works with clients when she goes and balances that with full time parenting. Sometimes it’s stressful. Is it worth it? COLIBRI thinks so.

Take regular, small doses. Since COLIBRI realized she will not be able to take a month off and lie on the beach doing nothing any time soon, she has committed to taking Sundays off.

If you are not able, even temporarily, to take extended time off, make sure you get small amounts of regular time off from work. It’s not optional, people. You need breaks to recharge in order to be effective.

Understand the importance of breaks. Although you may accept that you have to defer vacation for awhile, you must also understand how important time away from work is. Don’t, for example, let five years pass without a real change of pace.

Commit to rewarding yourself with a vacation and start planning it now.

Effective Vacation Planning for Solopreneurs

Here are some things you can do to make vacations fun, relaxing and doable:

Mark your calendar. The act of scheduling signals your commitment. If you have a smart phone, you can schedule Greece for December of 2014. Or whatever strikes your fancy–this you will have to decide without COLIBRI.

By the time your vacation is getting near, you will have accepted it as a fact. Taking time off can be hard for the Type A’s among us, which is another reason why scheduling is important.

Organize your finances. Start a vacation fund. That way, when the time comes, you will feel financially free to vacation.

Organize your time. Let your clients know at least three months in advance when you are planning to take time off.

Wrap up projects. Since you have planned in advance, time your projects to reach stopping points before you leave.

Get backup. Start networking now and find a trusted vacation buddy. No, COLIBRI doesn’t mean someone with whom you can vacation. She means someone who can attend to emergencies while you are gone should they arise. Naturally, you will do the same for them.

Reality check. Even the most disciplined among you will probably check email or tweet a time or two. Fine. But keep it to a minimum and get back on vacation track.

Choose wisely. Before you had your business, it was probably fun to vacation in the off season. But now it’s better for you to vacation when work is likely to be scarce. For most industries, this means the winter and summer holidays.

Have a re-entry plan. Line up work and projects for when you get back. At the very least, clean off your desk, put things in order, and write a detailed note for yourself about where you left off and what you need to do to get back in the flow. The longer the vacation, the more disorienting the re-entry, COLIBRI has found.

Your Turn

Please share your solopreneur vacation and travel trips in the comments below. As you know, must of us can use advice and encouragement about how to take breaks and thrive.


Cowan, Katy. How to go on holiday and relax when freelancing. Creative Boom. March 22, 2012.

Norris, Michelle. The History of the Vacation Examined. All Things Considered (NPR). June 17, 2009.

Wasson, Tim. How to Plan For a Long Vacation From Your Freelancing Business. Freelance Folder. June 3, 2010.


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