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Planning a Vacation – the Five-Week Plan

Intro by Skip Cohen

One of the biggest challenges of being a business owner is taking time off. All of us at some point wind up in the same boat – believing we just can’t take a vacation. I’m not talking about a long weekend or one day here and there, but a true uninterrupted-don’t-think-about-work vacation of a week or more.

Regardless of how good or bad your business might be doing, without taking a true break, you’ll never get a chance to fully recharge your battery. Plus, you’re doing yourself a huge disservice because creativity can’t be forced. Sooner or later, working too hard without a solid break will eat away at the spirit and passion that brought you into photography in the first place.

While this post is a little longer than usual, my good buddy Bryan Caporicci does an outstanding job of helping you lay out a timeline for a true vacation. He’s giving you all the steps you need to follow so you can walk away from the business and simply have fun.

Remember “fun?” It’s one of those incredibly simple words too often lost under the baggage of stress and working to build your business. For so many of you, even though you love the craft and your life as an artist, a good vacation might be just what you need to elevate your skills and business even more!

By Bryan Capporicci

One of the greatest freedoms being an entrepreneur allows for is the ability to be your own boss and create your own schedule. You may remember a time when vacation days were limited to what your work allowed, or when days off were chosen in order of seniority. But, as a photographer, you are on the top of the seniority list and you have the flexibility to do what you want and when you want.

As much as you love to go away on vacation, you probably also know the stress of planning to be out of the office for an extended period of time, and you likely can also relate to the feeling of coming back from vacation, feeling behind and overwhelmed with work.

Today, I am going to give you a step-by-step process to plan a stress-free period out of the office that will allow you to:

  1. Leave for vacation feeling confident and comfortable.
  2. Be on vacation and truly be relaxed and at ease.
  3. Come back from vacation and not feel overwhelmed and behind.

Although I’ll be discussing many principles today in the context of going away on vacation, they can be applied anytime you’re planning to be out of the office, such as:

  • Longer sabbaticals
  • Holidays
  • Stay-vacations
  • Working vacations
  • Conventions/Conferences
  • Weekends

The 5-Week Plan

In order to enjoy your vacation and not feel stressed about it, you’ll need to do a bit of planning. The saying goes “failure to plan is a plan to fail”, and it’s true, so a bit of organization can go a long way.

In order to have a relaxing vacation and not feel stressed about work or overwhelmed upon your return, the key is a 5-week plan, broken down as such:

  • The 3 weeks leading up to vacation
  • The week before vacation
  • The 2 days before vacation
  • The week of vacation
  • The 2 days upon returning from vacation

In researching for this article, I came across many blog posts that gave suggestions for entrepreneurs as to how to go on vacation. Many of them suggested going away in the “off” season, answering emails only once a day while away and screening your phone calls while out of the office. Personally, I don’t see that as a vacation, though; it just seems like a limited work-week. I believe that as entrepreneurs, we should be able to enjoy the freedom of a vacation whenever we want, and we should be able to do so while not worrying about work at all. This isn’t to say that you have to go completely unplugged (although you should try it), but instead, the key here is that you have the choice. My suggestions in this article will not be about how you balance yourself while on vacation, nor will it be about when you should go on vacation. These choices are yours, and that ability to choose is the ultimate luxury of being an entrepreneur.

3 Weeks Before Vacation

You wouldn’t start planning your vacation the day before you leave, and so similarly, you should take the time to plan your time out of the office so that you can ensure that you don’t get stressed, feel anxious or come back to a pile of work.

My suggestion is to start planning for your being out of the office 3 weeks before you actually leave. You can start by letting those you’re having ongoing discussions with know that you’ll be going away. Set the expectation as to what days you’ll be out of the office and when you’ll be back. Note: I suggest setting those “out” and “return” dates to be 2 days before you leave and 2 days after you return, respectively. More on that in a bit.

Set hard cutoff dates for sessions and all the kinds of appointments you have. As you know, each session and appointment have its own set of tasks that need to be done afterward, for example:

  • After a portrait session, you have to cull, edit, set up viewing appointments, etc.
  • After a viewing appointment, you have to process the order, retouch the images, order the prints, etc.
  • After a meet-and-greet, you have to follow-up with the potential client.

The point here is to set your cutoff dates in such a way that you can get these associated tasks done before you leave. The goal is to leave for vacation without any outstanding work to be done.

Furthermore, my suggestion is to not book any appointments the week before your vacation that will potentially add more tasks to your list and give yourself that buffer week to get caught up and prepare for being away.

Week Before Vacation

The week before you leave for vacation is when you should exclusively focus to getting completely caught up. You want to get all projects, deliverables and tasks off your plate, which means either just getting them done or deferring them. Tasks for this week should include:

  • Order all outstanding prints and books.
  • Book any viewing/ordering appointments that haven’t been booked yet (for when you return).
  • Send all outstanding galleries to clients.
  • Arrange pick-ups for all packaged orders.
  • Complete any other tasks on your to-do list.

Quick note: sometimes we have ongoing tasks on our list that aren’t necessarily time-sensitive, such as “update website” or “look into XYZ new product” or “download course on CreativeLive”. My suggestion is to carefully look at your task list the week before you leave for vacation and defer any tasks that aren’t time sensitive to be done when you get back instead of before you leave. The week before you leave is all about getting things off your plate; you’re in productivity mode now and don’t have the time to peruse around and waste time.

2 Days Before Vacation

The 2 days before you leave for vacation should be focused on getting last-minute things done and getting your office prepared for being away. Don’t take any appointments at all during these 2 days.

Some tasks to do in those last 2 days include:

  • Empty your email inbox.
  • Return all phone messages.
  • Clean-up and tidy your office.
  • Make sure that your backup hard drives are completely up-to-date.
  • Bring a backup of your hard drives offsite.
  • Set up vacation email auto responder.
  • Change voicemail message to let clients know that you’re out-of-the-office.
  • Schedule social media messages.
  • Give your cell number or contact info while away only to a select few; those who really might need it.
  • Remind all “ongoing project” partners and current conversations that you’ll be away.
  • Gather up a couple of books or audio books to enjoy while away.

Sample out-of-office email and voicemail messages

I like a real simple out of office email auto-responder, and here’s what I might suggest:

Thanks for getting in touch.

We are currently out of the office on holidays and will be returning on XYZ date. We’ll be getting back to all emails and phone calls as well as we’re back.

Thanks for your patience.

Your Name

Similarly, here’s what I might suggest using as your voicemail message:

Thanks for calling the studio of Your Business Name. We are currently out of the office on holidays and will be returning on XYZ date. We’ll be returning all phone messages as soon as we’re back. Thanks for your patience. Have a great day.

Week of Vacation

The whole point of being on vacation is to be on vacation! Enjoy your time; rest, relax and have fun! Be assured knowing that your work is completely caught up and that you have a plan to tackle any outstanding tasks upon your return. You may want to consider going completely unplugged for an ultimate stress-free time away.

2 Days After Vacation

Just like the 2 days before you left were reserved for getting caught up, my suggestion is to plan on having a couple of “catch-up” days when you get back as well. Don’t schedule any appointments or sessions in those days, just take your time to return all phone calls, emails and messages.

Making a Plan

Going on vacation doesn’t have to be a stressful event; it is intended to be the opposite, in fact. When you take the time to prepare and plan for being out of the office, you can “shut off” work and enjoy some rest and relaxation.

Next time you’re planning to go away, implement the strategies discussed here. My suggestion would be to print out this article and keep it nearby so that next time you are planning a vacation, you’ve got the information ready-to-go.


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