How to Negotiate The Ultimate Vacation with your Employer

In many areas of the world, work is only a part of life with enough time off to actually enjoy the money you earn. In fact, Europeans are among the least-deprived vacationers with some nations across the pond offering up to 30 days off. T-H-I-R-T-Y! Meanwhile here in the US, the average worker gets 15 days and most use only 11 days – leaving around 500 million vacation days unused.

Why don’t we take vacation we’re owed? Reasons often include busy work schedules, feelings of guilt about being away, money, or fear of a negative perception from one’s boss. To this I say, no more! We deserve more time off! Various reports prove a healthy-work life balance not only leaves employees feeling recharged and motivated once they return to work, ultimately creating a more productive worker bee but also reduces stress, absenteeism and expenses.

So, this is a story about how to negotiate the ultimate vacation – a sabbatical – specifically if you haven’t had a life changing event like giving birth or hitting a 10-year work anniversary, often a requirement for most US employers. About 2 years ago, I was at a crossroads.

I felt I was done working in the ad agency world, tired of NYC, ready for warmer weather year round (Hello LA) and thought a major shift, like a move across country, could afford me some time off for traveling abroad. But then something happened. Changes at the company provided me room to flourish and lead projects for the biggest and highest profile clients in the agency.

I produced 4 TV spots in 5 months, got promoted and was working the way I saw fit. I realized this job is what I make of it. And I decided to make it mine. However, I couldn’t shake the insatiable itch to explore unknown lands so, after feeling extra inspired by a few glasses of wine, I decided to ask my company for three months to travel. Here’s how I did it: Find the right time. This is crucial. Is there a period during the year that’s particularly slow at work? This is the ideal time to go.

I was able to determine that October through the beginning of the year would be slow – I had finished all my major projects and one of my clients was going to be on maternity leave during this time. Plus, the holidays and New Year create a slower-than-usual pace at the office, making it easier to digest. Express love for your job. I wasn’t interested in quitting, coming back, having to find a new job and proving myself all over again.

Up until this crossroads moment, I didn’t think it was possible but I had learned to love my job and the people I work with. I made sure to express this sincerely to the powers that be and worked with my team to garner support and develop a coverage plan while I was gone. Also, I’m pretty sure the fact that I wanted to come back sounded like music to my company’s ears given the extreme turnover in agencies in NYC. Make the case: it’s a win-win. Once you’ve found the right time to go, for how long and expressed you want to come back, think and focus on what the benefits are.

They get a happy-as-a-clam employee who will probably be more loyal than they could ever imagine and they wont have to go through the horrendous process of interviewing, finding your replacement and getting them up to speed quickly. In the grand scheme of things, a few months isn’t that long of a time away and you’ll return refreshed, motivated, and ready to jump in the saddle when you get back.

So did it work? Yes! Yes it did! I negotiated the terms of my leave of absence (3 months, unpaid) and left for my stint in Southeast Asia which was the inspiration for my blog: Out of Office, Gone Living. To anyone who is thinking about doing that backpacking trip for an extended period of time, I say go for it. Or, at least try to figure out a way you can make it work if your job is of concern – you might be surprised. The answer is always no unless you ask.


Ola Abayomi is a blogger living in New York City. In 2015, she was lucky enough to spend 3 glorious months backpacking through Southeast Asia. That sabbatical inspired her blog Out of Office: Gone Living.  Follow Ola’s adventures on IG @ola_ola_ayy.


Leave a Reply

Latest from All Posts