4 Things to Consider Before Taking Time Off of Work

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Updated on Wednesday, May 11, 2016


There are a myriad of reasons why someone might decide to try to take time off of work. Whether it’s simply to take a break, to travel, for medical reasons or for something else entirely, most working people have probably considered what a break from work would look like for them.

Of course the reason for your leave of absence will probably dictate how much flexibility you have in terms of how long you can take off and what rights you have with your current job for that leave. Medical reasons, for example, will most likely allow you more wiggle room with your job than if you wanted to take time off to, say, use a month to drive across the country.

No matter your reason for taking some time, though, here are a few things you might want to think about before approaching your boss with your request or before quitting.

Consideration No. 1: How much time will you take, and how flexible are you willing to be?

Unless you’ll be flat-out leaving your job, you’ll need to have at least a pretty solid idea of how much time you want to take off before approaching your boss with your request. If you plan far enough ahead of time, you can work with your employer to make the best use of your vacation, sick and other paid days off, as well as try to pick a timeframe that will least affect the company. For Kurtis Weins, when his 50-hour a week engineering job got to be too much in 2014, he decided to approach his boss with a request.

“Weeks were disappearing before my eyes,” Weins said. “Still in my mid 20s, I thought if I had any time to quit and travel, it was then. First I asked my employer for six months of unpaid leave while holding my letter of resignation in my hand, already knowing the likely answer. I quit in July and started my 20 month ‘funemployed’ adventure.”

If your employer won’t work with you for the time you need or want, and quitting outright just isn’t a possibility, you might consider asking to switch to part-time.

For Rick Lauber, taking some time off work was more of a necessity than a luxury when he decided it was time to provide care and support for his aging parents. Since leaving his job completely wouldn’t be an option — especially with two sick parents to look after — Lauber managed to work with his employer and reduce his working hours to part-time.

“This wasn’t an easy decision to make as my income was obviously affected; however, my priority then was helping my mother and father with their health needs, and I needed more time and scheduling flexibility to do so,” he said. “Working part-time proved to be a good answer as it continued to provide me a modest income and I kept my foot in the door with my employer.”

Consideration No. 2: How will you afford it?

Again depending on your situation, you may be able to work out a deal with your employer where you are paid at least part of your salary (potentially if your leave is medical related), but if you’re pretty sure you won’t be making any money during your time away, that will require some planning on your part. Weins admits that despite having a reasonable amount in savings, he did have to cash out his retirement fund when he left his country of employment to travel (not something we would necessarily recommend doing). He also received some lucrative tax returns and kept his expenses way down while traveling to cover his costs.

Holly Shulman, on the other hand, always knew she wanted to take some time off and travel for a number of months, but she knew that the only way she could effectively do so was to quit her current job and transition into a freelance role that was more flexible and would allow her to still accrue some income while traveling. “So I left my job at the DNC a few months ago and transitioned to running my own business — freelance PR with the idea that I can continue to work occasionally if I want to supplement my savings for the trip,” she said. “I also will be renting my home while I travel, which will help fund the trip.”

Consideration No. 3: What will you do about health insurance?

If you’re not fully leaving your job but rather taking some time off, you should be able to stay on the health insurance plan you currently have through your employer (though you should double check). If you’ll be leaving your job completely, though, you’ll need to figure out how you’ll cover yourself. For example, when Tara Tiger was laid off in 2010 during her maternity leave and she and her husband decided to use that as impetus to travel, she was able to get Cobra for part of the year, and then afterwards had to get private health insurance. If you’ll be leaving your job completely, check with your employer to see if you qualify for (and can afford) the Cobra option to continue your current health insurance plan for a while, or else check out HealthCare.gov to see what your other healthcare options are.

Consideration No. 4: What will your plan be for after your break?

While it might not be most fun to think about your future while you’re gearing up to take a break, it is the smart thing to do. Consider what that gap in your resume will look like to future potential employers, and think about whether or not picking up some side work during your hiatus to keep your foot in the door is something you’ll want to look into. For example, once Shulman decided she was definitely going to leave her job, she gave her old employer about eight weeks notice (which left her in good standing) and transitioned into freelancing leading up to the trip. “This gave me the flexible schedule I needed to work on trip logistics (like Visas, finding tenants, finding a temporary home for my piano), some extra income (I actually make more now than at my previous job), short-term job opportunities and also potential work while on the trip if I want,” she said.

As far as Weins goes, he admits that since returning from his time off he’s returned to work, but at a lower level position than when he left. “I knew in taking my time off that I would affect my career,” he said, “but I figured I’d rather be happy and poor in my 20s than rich and grumpy in my 30s.”

You’ll have to determine if you’re willing to potentially take a step back once returning to the workforce for yourself.