8 Tips For Preparing To Leave on a Career Break 

One can desire to take a career break, but often the act of actually beginning the process can undermine those dreams. I say, “Put one foot in front of the other, and soon you’ll be walking out the door!

What makes one want to take a career break? Is it disinterest in your current career? A personal life change? Or a desire to shake things up as you enter a new phase of your life?

Want planning help?
Want planning help?
Take our free planning e-course

For me, it was all three. I had an interior decorating business that wasn’t exciting me anymore, my mother had recently passed away from an aggressive cancer, and I had stepped over the that magic age of 50. I wasn’t getting any younger, and the realization that we can all “go” at any moment propelled me to seek change. It was time to take matters into my own hands. It began as a question: Could I get away with checking out of my complex life for a few months?

While trolling the internet, I happened upon Meet Plan Go and realized at that moment that I was not alone in this quest. I scoured the website for every tidbit of information on how others had made their career break a reality, and then I began to envision my own journey.

Tackle the career break process one step at a time.

Anyone with an established life in their own town or city knows it is not possible to just wake up one morning and announce that they are chucking it all and heading off to the airport.  Sure, we’ve all had that “Calgon take me away” moment, but honestly can we act on it? I have two children, a home, a small business, and a life rich with friends. I needed to go slow, be methodical, and break it down into manageable pieces so even I could process the concept of upheaving every aspect of my life.

So, I addressed each of these areas one at a time.

1. Budget planning

First things first, with little savings to speak of or a winning lottery ticket in my pocket, in order to finance the bulk of the trip, it was clear that I would have to put my one asset to work: rent out my house.

I contacted a real estate agent friend of mine who educated me on the rental market. Then armed with that information, I slept on it…for weeks! I mulled over it and chewed on it and debated the possibility of being able to travel long term. It took me about 4 months to get the courage to take this step forward.

In anticipation of making the leap, I also began to be more mindful of how I spent my money and seriously cut back on unnecessary expenditures, so I could pay down debt instead.

2. Downsizing

Start purging NOW! – closets first then paring back your living areas.

The nervous excitement I felt while arriving at my decision I put to good use. I began to clear out closets…I figured even if I couldn’t make the break, I would have clean closets, and if it did happen, I would have less to deal with as moving day drew near.

Downsizing our stuff is no small task when living in a society that encourages acquisition. As I cleaned out each cupboard and closet, I asked these questions:

  • Have I used it in the last 2 years?
  • Do I like it?
  • Can I take it on the trip (that was almost always a no!)?
  • Do I want to see and deal with it when I come back?

If the item in question didn’t have a yes attached to it, I jettisoned it. (See, even my stuff got to take a trip!) Craig’s List, friends, Goodwill, and the local recycling center were all great places to relieve me of my things. Be ruthless in this process, you will be happy you did later.

Once I had finally decided to rent out the house, I had to make it “viewing” ready for prospective tenants. Real estate agents prefer showing a house devoid of personal items, so in preparation for the open house, I packed up photos and artwork and pared down the furnishings. Within 3 days of the open house, I had a tenant. Yikes! Now I really needed to get in gear. I had six weeks to completely pack up and vacate…better get organized.

3. Make a to-do list and revise it regularly

I love To-Do lists. In my work life they have always been effective in aiding me in getting the job done. I prefer using a legal pad when I am making major lists. Each page has a topic and I begin by organizing the seemingly endless tasks onto those pages. Each item – large and small – gets a neat little checkable box next to it. When the task is completed, I check it off – at the end of the day I can see the progress I made (or didn’t make).

For preparing my career break, I did a “data dump” almost daily and revised these lists often, and gradually the To-Do’s began to shrink. As moving approached, these lists gave me a sense of control and helped keep me focused on my end goal of taking off on my solo journey.

I was lucky enough to be able to store my things in half of my basement. I could move things down there as I packed them up, which gave me a real sense of accomplishment as well.

4. Keep your loved ones informed before and after you go

Concurrent with packing up, I regularly discussed my career break with my children to help prepare them for my absence. My daughter would be away at college during the period I had allotted, and my son would be taking a semester at a boarding school. I could be available anytime to them with FaceTime and Skype, and I would have a SIM card for my phone so I wouldn’t have to rely on crappy wifi. It was important to me that they did not feel that I had fallen off the face of the earth. Facebook was perfect for staying in touch with old friends and new ones that I met on the road.

5. Pay down your debt

I was extremely attached to my home, and what it represented in my life. To move out was one of the bigger decisions I have grappled with in recent years. I knew that if I jumped on a plane the day I handed over the keys, I would not enjoy the first few weeks on the road as I would still be “letting go” of my old life.

Therefore, to make the initial departure easier, I decamped for a few weeks to a friend’s home in my old hometown and took a breather before I began working on the next phase of my career break planning. I wanted to be mostly debt free when I began the journey, so I further curbed my spending and put every cent I made into paying off credit cards. Suddenly, my goals were actually becoming attainable..

Putting the final part of the plan together

After that little period of adjustment, I went back to Brooklyn, rented two rooms from a friend of mine and spent four months completing my decorating projects. Thanks to a couple of last minute jobs, I cleared my credit card debt, too.

6. Know yourself and what makes you comfortable to go

Planning a solo trip is like being a kid in a candy shop; I could go anywhere I wanted to because this was solely my trip!

When you unburden yourself of your possessions, free yourself of debt, and open your eyes to a world of possibility, there is no looking back, and suddenly what you want becomes quite clear.

For me it was, “Who am I? and What do I really want out of the next phase of my life?” Those were the driving force in my pre-trip planning.

I created a framework for where I wanted to go, but also kept things loose enough to be open to any fun opportunity that might arise. Ultimately, other than a fully planned 5 weeks in Africa and my first 3 nights in Bali, I was open to where the journey would take me.

7. Plan your departure during a quiet time of year

I waited to depart just after the holidays. That way I didn’t miss out on the usual end of year celebrations with family and friends, and I had something to look forward to in the new year. I would be leaving for Africa just as the cold of winter settled onto the city.

8. Say YES!

I traveled with an open mind and an open heart, and in so doing I had countless experiences that I never dreamed of during the whole planning process. Among many experiences, by saying “Yes!” I found myself on a surf charter boat in Sumatra for 13 days making wonderful friends and experiencing a part of the world that is rarely seen by humans.

I ate foods I had never heard of, but when coaxed by a local, you most certainly cannot say no!  I saw temples and world heritage sites I would have skipped save for a great recommendation by fellow travelers.

I met so many wonderful people along the way, and the best thing through all of it was that I felt truly alive and present in my surroundings.

Going slow and preparing in a thoughtful manner enabled me to get the most out of my career break. The experiences were plentiful, the memories are abundant, and my life is richer now than I could have ever imagined.  So, what are you waiting for?

Tamara made the career break leap this past January (2014) and has just returned to New York City after having the opportunity to visit 15 countries, experiencing the wilds of Africa, the tropical landscapes of Indonesia, the rolling hills of Tuscany, the beautiful coastline of Cornwall, and the archipelago of Sweden. Traveling solo for most of the adventure gave Tamara an excellent opportunity to spend time with herself and to really think about and shape the next chapter in her life as she re-enters the work force. You can connect with Tamara through her website and on Twitter.

Photo credits: Thinglass, trekandshoot, Jenn Hulls, Lisa S., Marin Veraja, elephant photo courtesy of the author and may not be used without permission.

Career Break Guide Table of Contents

Meet Plan Go