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.

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  1. That’s a great story! I (Gian) am also lucky to be employed in a company that is managed by bosses who are adventurers and travelers themselves! So if I ask for a leave or two to climb a mountain, scuba dive, etc., they readily approve my leaves as long as I did my tasks. Actually, they encourage their employees to take such leaves.

  2. More than 2 years ago, I asked my manager if I’m allowed a 3 months sabbatical leave and what he said still stuck in my head.
    “I won’t approve your leave but you can come back anytime. Go out and wander. The world is the place where you can learn far more than just sitting in front of the computer. Once you feel like you want to come back and work with me, just give me a call, you know where to find me.”
    As of now, I’m still stuck in paradise. Not sure if I’ll head back to the old job as of now I’m a much happier person.

  3. I love your idea about being unique. I think that if your employers believe that you are one of a kind and you are a hard worker then they will want you back regardless. I can imagine that the big thing for employers is to have employees come and go a lot. But, that can also depend on the job as well. Personally, I have just looked for jobs in different countries around the world. So, I could live there and make money at the same time.

  4. I think more and more employers are realizing that employees who have experienced different cultures and people make better workers. Not to say every employer is open to such an agreement but as you proved, if crafted right and you can show how it will benefit the company, you have a good chance of getting approved.

  5. Unfortunately being in the US that definitely would not fly at my company. I’m sure Pamela will have the trip of a lifetime!

  6. I’m so please it all worked out for your friend. I have currently put in a request for 3 months leave – and my employer has known about it for 18 months – but it is yet to be approved. Its a nail-biting time but I’m keeping my fingers crossed.

  7. I think it’s wonderful that this company supported Pamela’s request for some time off – I think every company should do this! Australia have this wonderful system whereby if you’ve worked for a company for 10 years (I think!), they give you an extended period of time off. If only other countries and companies would follow suit!

  8. This is fantastic. Congrats to Pamela for her determination and ultimately achieving her goal of having her sabbatical approved. I’d love to know where she decides to travel. I think more employers should consider offering sabbaticals: less turnover and happy employees- a win-win!

  9. I’ve wondered what my boss would say if I asked for that much non-paid leave. I think he would be ok with it, but it’s the higher ups that always seem to be the problem. I’m so happy that it worked out for your friend though!

  10. I think it’s fantastic that more and more employers are starting to be open to sabbaticals for travel. I’ve never been in that situation because I’ve only held jobs at places like Subway where it’s no big deal to say that you’re going to be gone for a while and come home to a job.

  11. Lovely story and brave girl. Smart girl (!) Planning it is really the key. I spent several years planning how I’d leave/take sabbatical from my job (ex lawyer). Turns out it was leaving permanently and not looked back since. My employer was (still is) a diamond and we maintain an excellent relationship. If you manage it carefully there’s no reason why a reasonable employer would not allow such a sabbatical.

  12. Great story and really helpful for those who want to travel more, but keep their day jobs. I switched o freelancing a long time ago, but for different reasons. The longest vacation I took was three weeks after about three years with no real break. I would have loved to be able to go for a longer period back then.

  13. All bosses and companies should be this flexible. I have such a boss also lat year i had 9 weeks off to travel Europe this year between November 2016 and January 2017 i am having 10 weeks off to travel. the thing is no one is that irreplaceable. If the leave is unpaid there is no reason they should say no.

  14. Great post. Thank you! Well I am a bit different. I quit my job to travel around the world for the last 13 months. Now we are back home and getting back to our normal life. Still we try to travel more and now I do freelancing, teach yoga and hope to be able to have a great balance between daily life and traveling. I actually like to have a home base. Great post though for anyone who just wants to travel for a few months. Do it! You’ll never regret it.

  15. Awesome! It must be a great feeling to know you can come back to your job after you’ve gone on such a big adventure. I’ve tried to take extended leave a few times just to get laughed at in the end. Hopefully more companies will take this approach.

  16. Unfortunately, my old employer would have laughed at the thought of me taking a three-month break. I have met many people while traveling (particularly Americans) that have managed to do this. As a traveler, I think it is great for employee morale!

  17. How exciting for your friend! Like you said, you’ll never know if it’s possible until you try. Hopefully more employers will see the benefits of having employees who want to travel! The confidence, problem solving abilities, and learning that happens through travel can’t be taught in any book or office.

  18. I fully plan on doing this at some point. I plan on asking for a year with the either approve it or I quit. I don’t have enough vacation to see the world so I plan on taking a year to do it.

  19. This is a great empowering article for everyone! I’ve always stood by that act of courage to tell your superiors what you want in a simple, straight manner and yes, it does work. While I’m happy and content that I can already travel as I please, surely I wouldn’t mind other people getting into our positions. The world is a big place full of hopes and discoveries!

  20. Funny I came by this article – I had literally just dropped the first hints to my boss, and while he seemed taken aback, he didn’t really say anything discouraging. Let’s see how this goes.

  21. 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!

  22. 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! 🙂

  23. 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!


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