December 10, 2011. By Adelaide Lancaster contributed to Forbes.com
The idea of taking time off seems preposterous for a lot of entrepreneurs. I
know many who can barely spare themselves a week, much less an extended
vacation. Paranoid that everything will go down in flames just as soon as their
phone is turned off, many entrepreneurs maintain a state of hyper-vigilance for
a very, very long time.
If this sounds like you, it might be time to rethink things. Not only does
this behavior burnout, but it does us great disservice by falsely tethering us to
the daily grind and inflating our own sense of importance. After all, how strong
can our business be if being unavailable is such a tremendous liability? More
importantly, what important opportunities are we sacrificing by thinking that
time off is just not possible?
Taking time off from a business is also a necessity sometimes—for maternity
leave, medical leave, or time working the fundraising circuit (and no, that’s
not really time off, but it is time away from your regular responsibilities).
Learning how to temporarily disentangle yourself from your day-to-day duties
can be tough, but it’s also crucial. Here are nine strategies to help you do just that.
Behind-the-Scenes Planning
1. Determine the Right Level of Hummm
Perhaps the most challenging task when preparing for a vacation is
determining the right level of hum for the business—there’s a large middle
ground between operating a full tilt and completely closing up shop. So think
ahead of time about what you’re comfortable with: Do you want to be able to
field new business? Maintain current accounts? Will you continue your regular
online presence or dial things back a bit?
Tip: Don’t concern yourself (yet) with how things will get done. Setting strong expectations for the business doesn’t mean that you will be doing all of the work.
2. Reprioritize
After you determine the general operational level for your business, you need
to spend some time evaluating your current efforts. With your desired level of
hum in mind, make three lists: the things that MUST get done, the things that
would be NICE to get done, and the things that are UNNECESSARY to do. (This
framework was suggested by Diane Costigan, Executive, Career and Life Coach.)
Make your primary focus the things that MUST get done. You will need to give
yourself time to think about who should do them and what preparation they need
in order to do them well (enough). As your leave date gets closer, you can
revisit the NICE to get done list—if time allows. And scrap the UNNECESSARY
tasks altogether.
Tip: Things become even more manageable if you can divide the things that MUST get done into two categories—things that can be done in advance and things that need to be done while you’re gone.
3. Reallocate Responsibilities
The next step is to determine who will do the things that MUST get done. With
only those items in mind, make another list: Things that MUST be done by you and
things that are UNNECESSARY for you to do.
For things that MUST be done by you, commit to finding a specific, efficient,
time-bound way for you to do these tasks. For example, “each Friday morning, I
will spend two hours preparing the bills for the past week.” For the list that’s
UNNECESSARY for you to do, the goal becomes identifying the best person to do
these tasks. (And before you protest let me say that yes, this person
does exist and yes, you can afford it.) Be creative. The solution may be a temporary virtual assistant, hiring another entrepreneurial friend who runs a similar business (or maybe trading her for coverage on her time off), a student, an intern, a part-time employee, or perhaps a combination of these people.
Tip: Be discerning about what goes where. Most people overestimate the amount of work that they can (or will want!) to do while on leave.
4. Set Your Boundaries
After you develop your plan, let people know what they can and can’t expect
from you. Will you have a short weekly check-in call? Or are you just a lifeline
in the case of an emergency? Will you be referring your clients elsewhere in
your absence, or are you asking them to wait until your return? It doesn’t
matter what your boundaries are, only that your staff and clients are
well-prepared to honor them.
Tip: Be conservative. It’s better to underestimate your availability than overestimate.
Share Your Plan
5. Practice Your Pitch
It’s essential that you demonstrate that you’re confident and comfortable
with all parts of your plan—the transition, terms, and team. Clients and staff
don’t want to be left in a lurch. Make a list of anticipated frequently asked
questions and take the time to prepare strong answers. For example, “in that
event, you can expect to hear from [this person] right away.”
Tip: Be confident. People will take their cues from you. If you leave no room for second-guessing how things will go while you’re gone, they won’t either.
6. Craft a Cohesive Communication Strategy
There are lots of ways to let people know about an upcoming leave—you could
send an email, include a snippet in your newsletter, or even write a dedicated
blog post about it. Depending on the size of your business, you could even call
clients to let them know what’s coming up. In any case, make sure that your
messaging is honest and reinforces the contingency plan you’ve designed. Don’t
tell people that they won’t even realize you’re gone if they’ll really be in
touch with people replacing you. Instead, assure them that they’re in good hands
and that you look forward to picking up with them when you return.
Tip: No one likes to be surprised, so don’t hope your leave goes unnoticed. Instead, be proactive and straight with people about how your plans may impact them.
Secure Peace of Mind
7. Adjust Your Tech Settings
Technology is your friend, as long as you make use of all the settings. Make
sure to adjust your gadgets to reflect your desired boundaries. Change your
outgoing voice mail to indicate your absence and who can be contacted in the
meantime, disable your email on your smartphone and rely on texting instead, and
create a painfully specific out-of-office message for your email detailing what
people should do while you’re gone.
Tip: During the month before you leave, take a minute to deal with your unwanted emails as soon as they come in. Unsubcribe to as much as possible and redirect things to junk mail or other folders.
8. Set Up Online Bill Pay
If you’re the one who pays the bills, make sure to set up online bill pay
through your bank rather than the provider’s site, so it’s in one centralized
place. That way you can easily and effortlessly pay your bills all at once—and
from anywhere. You can also pre-schedule payments for a little bit more than
your average bill for any period of time that you’ll be completely unavailable.
(Of course, you can also hire someone to pay the bills in your absence.)
Tip: Be thorough. It pays (literally) to be very organized financially. A spreadsheet of due dates for all your bills will help you plan the fewest number of payment sessions.
9. Establish an Emergency Response System
Select someone to check your email once a day. She doesn’t need to read
everything, but should look out for anything alarming or urgent. Direct her to
call you if she sees something troubling or that needs immediate attention. That
way, you can rest assured that nothing emergent is going overlooked. You can
also assume that no news is good news, and not be interrupted from what you’re
supposed to be doing—enjoying your time off.
Tip: Challenge yourself to let go! You’re actually the person who is most likely to sabotage your own planning and vacation. Trust your planning and your business—your thoughtful preparation will pay off, if you let it work the way it should!

