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Dear Sir: thank you for letting me travel for 3 months and still keep my job

You might be wondering: “is it possible to travel and still keep my job? That’s insane!”

Apparently, it is. I’ve been writing about my friend’s story (Pamela) since February and if you have been following, you will know about this: how one girl tenaciously went after her dreams by viciously asking for a 3-month leave and still keep her job.

It took 6 months of brainstorming, compromising, paperwork and endless e-mail exchange but in the end, the leave was approved.

Here’s the timeline and related articles:

November 2015

Pamela told me she already gave subliminal messages to the boss about the sabbatical leave. There were no agreements or disagreements between them. But there was a positive vibe about the possibility.

February 2016

She just needed more convincing on why and how is it worth it. With that, I wrote: Why travelers make the best employees and she used this material to lure the boss. This post also ended up in the Huffington Post!

April 2016

The leagues of bosses were slowly deliberating everything. She was asked to draft a sabbatical letter (yes, that exists!) so I helped her do it.

Pamela did not submit this letter as it is. She wanted to submit something in her own words. This was just a guide. You can read the letter here.

And today, 03 May 2016, while in line at the office cafeteria for lunch, the boss saw Pamela and said, “your sabbatical leave has been approved.”

Just like that, her world seemed to be different again. Her journey will start in July until September. Where? She hasn’t planned it yet but I am pretty sure it won’t be boring.

By the end of the trip, she has a job to go back to as a different person — more passionate, enthusiastic, full of life, compassionate and every good adjective you can think of.


Dear Sir,

Thank you so much for approving my leave. I promise you won’t regret this!



Info: Pamela is a Filipina working in a non-travel related company in Singapore. This is not a paid leave but she will still be employed when she comes back from the trip. How awesome is that?

Sabbatical leaves like this are not allowed in most companies and even if she knew there was no way it will be possible, she still took a leap and tried it.

I’ve never had a full-time job in years so I don’t really know how the office setting operates now but let me tell you this: until you try, you will never know.

Here are some tips if you want to take a step in asking for more leaves than usual:

Build your credibility

Are you one of a kind? Are you someone that your boss will think twice before firing? Are you the person who they beg to stay even if you want to resign?

At least try

Six months before your anticipated sabbatical leave, start bringing it up casually to your employer. It doesn’t have to be formal.

It can be while in line at the cafeteria, as you pass by his office, as you see him/her making coffee. TRY. There is no harm in trying.

“Hey sir, I was just thinking if there’s a possibility for me to request a 3-month leave? I want to travel the world.”

Leave it with that. Be simple. Be straight to the point. You will be surprised how employers react to employees who say “I want to travel the world.” It’s something powerful and appealing to them.

Express your thoughts

Your employer cares for you more than you think. They are willing to be a part of your growth and success in their company. What you say matters.

Tell them how traveling will help you become a more competent employer which will be beneficial to their company.

Always remember to be clear with your intentions. You can get more tips from the sample letter I wrote here.

Be confident

Don’t be shy. Don’t be intimidated. You are actually bringing something different on the table. Believe in what you say.

Do not write a script on how to approach your boss. Most employers love confidence. It makes you more eligible for promotion and it can surely be your ticket to a 90 day leave.

Follow through

Don’t just leave it there. Don’t give up until the boss says it’s possible. Email them once a week asking for developments.

Show them more credentials if needed. Your tenacity will be a crucial factor if they will approve the leave or not.

Once they see your enthusiasm fading, they will definitely think you are not ready for this kind of sabbatical. They will also change the way they look at you as an asset to the company.

Lastly, believe in yourself. You matter. Convince them that you need this and they will never regret it if they say yes.

It’s not about your words. It’s about the strong feeling you have towards it that will make this kind of endeavour successful.

So good luck and may the force be with you!

Have you tried asking your employer for a 3-month leave and still keep your job? How did it go? I would like to hear your thoughts! Share it on the comment box below.

cebu safari

Tuesday 4th of December 2018

Great post Trisha! Great story and really helpful for those who want to travel more, but keep their day jobs. I switched to freelancing a long time ago, but for different reasons. This is really an amazing article worth of reading!

Regards, Zane

Agness of aTukTuk

Monday 12th of June 2017

It seems like you had lots of luck and amazing experience! Keep up the great work!


Thursday 25th of August 2016

3 months ago I told my boss that I am resigning from my HR job of 3 years because I wanted to see Dubai and yes, to visit other countries near Asia-Europe/Africa border. What she offered me surprised me! She said I can go for a 1- month leave and if along the way I still like to stay in Dubai I can just send her my final exit letter OR if I won't like Dubai, I can go back to Cebu and still have my old job back. It's a win-win scenario! Currently, I'm in Dubai (after stopping in Singapore for 10 days) and so far I like everything! I still have less than 2 weeks to figure out if I'm going back home or if I will continue this awesome solo journey! :)


Thursday 19th of May 2016

Surely got baffled by the tenacity of your dear friend. Now I'm having the answers falling like snow on a summer day! Thanks for motivating me in a guided format to having your boss say yes!


Tuesday 17th of May 2016

More employers should do this as employees come back renewed, refreshed and recommitted to their job. Great read!