Terry sat in silence as I laid out my plans to take my leave of absence. I laid it out pretty good.. needed a year off to go travel, see the world and experience life.. to rejuvenate and de-stress. As I finished he seemed to get madder by the second and started yelling about the economy and taking time off.. it was such a bad idea… After a couple minutes I had enough, threw some papers in the air and stormed out of his office and hit the road…
That was my worst case scenario going through my head as I drove to head office in the morning,
I really wasn’t sure how this meeting was going to go. It could go either very good or very bad, and I really hoped it wouldn’t be the crazy story I had just envisioned. I’ve worked for my company for almost 10 years and really needed a break, so as I told my boss Terry my request he seemed a little shocked at first. He then broke out into a huge smile and said “I think it’s a fantastic idea, your going to have a great time!” Terry went on to say he had taken a similar trip before he was married, and it taught him a “university education of the world”. That you’ll learn more about yourself and other cultures than you ever thought possible. We ended up talking about traveling for 30 minutes. We needed to get the business of moving Alex into my position, transferring my residuals to Alex, keeping my medical and having my job when I get back with my residuals and client base. A tall order but in the end everything was agreed on.
I have to say it was far less dramatic than I envisioned, and a fantastic experience. It’s a great relief to break the news to the boss and have him be enthusiastic about your adventures. A couple tips if your going to ask for a long term sabatical or leave of absense:
- Give your company lots of notice. We felt that 45 days was cutting it a bit short.
- Talk to your boss before anyone else, they deserve to hear it from you in person and not over an email or phone call.
- If your going to ask for your job back or some special circumstance, be prepared to sell your self a bit. Put together an elevator pitch – a 60-120 second commercial about yourself. When you first sit down give them the pitch – how long you’ve been with the company, some of your achievements, mention positive reviews, etc. Your goal is to get your manager to remember instantly all the positives of why he’s going to help you out.
- Spill the beans, say your taking a leave and give your asks. Be honest and lay it all out, trying to be as clear and specific as possible. In my case I wanted to have my friend Alex who works with me promoted to a full outbound rep, get my residual payments transferred to him and then returned when I came back and my position will be here for me.
- Because your prepared, your more likely to get it all. Please note this list is my formula and is only guaranteed to work on every third person.
Have you taken a long leave of absence from your work? How did you and your boss handle it? We’d love to hear, just write a comment below!


My bos was also fabulous. I’d had a ‘puppet show’ going on in my head about how it would go and I was more than pleasantly surprised. In fact, we have never had a negative response to our plans – everyone is so supportive and excited for us. The key, for us I think, is giving people plenty of time to get used to the idea and to answer all their questions to show that, yes, we’ve done our homework. Congrats on getting the leave!!
Good job guys!! I am so excited for you and I’m glad that both of your bosses took it so well!! Talk to you guys soon!!
Man Scott – you had my heart pounding in your first paragraph – I could totally envision the whole scene – including the eyes, red face and shouting!
So happy for you that it went well. This must be a fantastic relief for this portion of trip planning… I know there is one major speed bump in your way… it all seems to be falling into place so move forward, do what you need to do and before you know it you will ne moving forward really fast… and upward and the hell out of here!
Much love and respect for your challenges to make it come true.
It’s a huge relief to have the company know, and I’m so glad Terry responded so positively to my request! This was one of the bigger things that was looming over our heads so now that we’ve both told our work we can start finalizing our next steps!
Though I still wonder if it’s ever gone as bad as I had imagined?
My boss took it well. Given we are only going for 2 months rather than a year. I basically wanted her to hear from me. Not from any rumors that can travel around an office.
I couldnt agree more that giving time is the best way to save face and have things go accordingly.
Steve gave almost 8 months, he wanted to know that would be ok and he would be able to return to his job before we even started really planning for the trip.
Congrats on one more thing crossed off your list!
I’m in a similar boat as you Scott, I am planning on leaving my job for an extended period of time but still haven’t told my boss. Honestly I don’t think he is going to take it very well so I was thinking about sending him an e-mail once he goes on vacation.
that is a big step. glad to hear it went positively rather than red faces and screaming.
sweet… that is super exciting that you are one step closer to globetrotting!