How to Talk to Your Boss About Taking Time Off To Travel: An Expert’s Advice

Crossroads - Photo by David Yu

Photo on Flickr by David Uy

Pinterest board of all the places you dream about: Pinned, shared, and followed. Lonely Planets – stacked on the shelf, organized by region. Travel magazines AFAR, Condé Nast Traveler, National Geographic Traveler– torn up and dog-eared, a page or two tacked to a board or on the fridge. Screen saver – a beach. Jealousy reaching new heights when you see your European friend posting all over South America on her 6-month trip – check.Wanderlust – itching like a rash.  You’re ready to travel. You are ready to take off and see the world for a while. Like more-than-10-days-PTO-while.

And yet… You like your job. You’re boss is great and your team does things like decorate your desk for your birthday and you have inside jokes over messenger. Your work is interesting and challenging, you know what you’re doing and sometimes (gasp!) you get excited about what you’re working on. That’s why you can’t really see leaving your job to travel. You don’t want to quit and take off.

It’s Ok to admit it. You want to travel for a few months and then come back to your job. You want to take a sabbatical to travel. And you think that this particular American dream cannot be achieved, especially in the world of projects that come in tumbling one after another and “lean” teams and two weeks PTO that includes sick days and all the endless reasons why taking time off would be terrible for you and your career. You dream, what seems like, a very impossible dream.

I’m here to tell you: It’s not impossible. It’s actually quite possible. You can take time off from your job to travel and return to it, career intact.  It’s a matter of some planning, preparation, and a thoughtful conversation with your boss.

At speaking events and through this blog, I receive many questions about how a person can talk to their boss about taking time off to travel. I have gotten some advice from managers and have seen commentary on message boards, but every situation is different because our career paths are unique. I needed to find common guidelines and advice that could span many situations and not unique anecdotes.

To answer the question, I went to the Society of Human Resource Management (SHRM) and they connected me with SHRM expert Sharlyn Lauby, president of ITM Group  and author of the blog HR Bartender. She offered excellent advice and tactics to help travelers prepare for this important decision and discussion about a travel sabbatical.

The First Step Is To Plan

A SHRM study shows that 12% of organizations offer unpaid sabbatical programs and 3% offer paid sabbatical programs. For the 88%, who don’t have sabbatical programs, how can they approach a sabbatical to travel with their manager/boss?

“Planning – Think through how long want to be gone and have a dialogue with your manager, but don’t view as a long vacation. You’ll have the least success if you say ‘I want to go in two weeks.’ If you want to come back to your place in the organization, think about how best to plan it out.”

In planning, she recommends thinking through a few things:

  • Work: How will it get done in my absence? Does anyone need to be trained or hired to fill my spot? Sharlyn describes, “If one of my employees came to me and asked for a leave, I would ask, do you think your work can be spread among several people or do we need to hire a new person?”
  • The Timing: Organizations that have “down time,” may be more amenable to sabbaticals. If there is a clear time in the company where it may be slow, it will be easier to take time off during that cycle. Plan to come back when a project will be ramping up, because there will be a need for a hardworking employee to step right in.
  • The Leave: If you are a full-time employee, what does it mean to my pay and benefits? She clarifies, “It’s possible that an organization might have a generous personal leave policy that would cover a sabbatical. An employee can speak with human resources to see if their situation fits the criteria. “
  • Attitude: If there’s no program in place, you are volunteering to be the guinea pig. Go in with the spirit of working with the company in case someone else wants to do it. You could be forging a new path for the company and there will be hiccups along the way.

Decide the Best Time to Take the Sabbatical

For timing, Sharlyn recommends finding time to discuss the possibilities with your supervisor. You could have the conversation during a one-on-one meeting or, if the opportunity presents itself, during the annual performance review. The important part is to have the attitude to work with your manager to make it a success.

I asked Sharlyn if there’s a best time one’s career to take the sabbatical. I had a theory that it’s before or after a promotion, but that wasn’t her experience. She’s “seen employees take extended time off at all levels.” It’s difficult when “there’s only one of you” for a skill or a role. “It may be a challenge, but you have to talk about how to make it happen.”

Sharlyn explained that there are many opportunities in one’s career. To make the decision to take one of those opportunities or go travel, she said to review the decision from the point of view of a “once in a lifetime opportunity.” If the long-term travel is only going to happen once, then go for it. It’s the same thought process with any career decision.

Make a Plan and Then Talk to Your Boss

Sharlyn talked me though this specific T-chart exercise to prepare for the discussion with your boss. Personally, I think this is genius because it helps you plan for all scenarios and objections. After doing this exercise, you can go into the discussion with your boss feeling prepared because you’ve thought through many possible discussion points and objections.

  1. Draw a T on a piece of paper.
  2. On the left side, list all the pros and on the right side, list all the cons. In your mind, what are the pros and cons for taking the sabbatical?
  3. Go through the list again and think about the pros/cons from the company’s perspective. You won’t be successful if you don’t. Think through these benefits to the company:
    1. If the sabbatical were planned around a slow time, this would create a win-win for payroll. This means there’s one less employee to pay at a time when the company needs to be lean.
    2. It’s a strong case for employee mental health. You’ll go somewhere, have rest and relaxation, and come back refreshed and ready to work.
    3. Upon the return, there’s going to be an employee who’s going to give 200% because the company just let them have a sabbatical.
  4. Bounce the list off of family and friends – did I think of everything?

“This is an important conversation about you and your career. The way you tee it up is important. Take the pause and make sure all your bases are covered. It’s easy for people to throw you off and end the conversation, so you can have a response to deal with each possible objections.”

Your Boss Says Yes! Now What?

Go out and celebrate! Do that and these official things for you to move forward in a graceful and professional way.

  • Get the approval in writing: Sharlyn recommends having a memo drafted and placed in your employee file that details two things – what you will do and what the company will do in terms of the sabbatical. This includes all the planning points around timing, coverage, pay, and benefits. Not only does this place the terms in writing, but also if someone else wants to do it, the company can always go back and see what had been set up for you.
  • Ask your boss how to talk about it to others: You want to be respectful to the company, especially if the sabbatical program doesn’t have a formal policy. Communicate it in the right way – the way that you and your boss discussed – so anyone else won’t be caught off guard.

Make Sure Re-Entry Goes OK

Sharlyn outlined a three great things you can do during the trip to make sure re-entry goes well for you and the company.

  1. Send your manager and teammates a postcard letting them know you are having a good time and that you are looking forward to coming back.
  2. Come back when you’re supposed to come back. It may be easy to say, “I’ll stay another week,” but you made an agreement with the company and you need to honor it. Come back when supposed to come back. That goes for early and late. The company made promises to people and there may be a hiccup if you come back early.
  3. Thank your manager and coworkers who picked up the slack when you were gone. Personally, I would add them to your souvenir shopping list.

Final Advice

“Do well because it’s a reflection on you. If you leave a mess, that’s what people remember. When you come back, you don’t want to come back to a mess.”

In other words, you want to come back to a desk decorated with streamers and a “Welcome Back!” poster.

Next Steps

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5 Responses to “How to Talk to Your Boss About Taking Time Off To Travel: An Expert’s Advice”

  1. September 22, 2014 at 9:02 pm #

    Kristin, this is great stuff. Thanks for putting all this out there. 😀

    • Kristin
      September 23, 2014 at 9:49 am #

      Thanks Dave!

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