I’ve known for a few years now that I’d have to have the conversation I had with my boss last week about our trip, but I honestly had no idea how he would react.  I’ve worked on a project with him for the last three years and I’ve known him for longer than that.  He’s been a great boss, as evident in how he took the news that I’d be quitting to travel the world.

I had asked him to schedule a meeting with me, which I never do.  If we need to talk, we just talk or message each other.  There’s never really been a reason to have a sit down meeting like I was requesting and it made him nervous.  I scheduled it for Monday and he later told me he was wondering what I wanted to talk about the entire weekend.  When I first got into work that morning, he asked me when I wanted to meet so I set it up for after lunch.  When I got back from lunch, I had a message waiting from him asking me to tell him when I got back from lunch.  He was ready to find out what was going on.

So we went into a meeting room and sat down.  “What’s going on man?” he asked.  I was sweating, so I took off my jacket.  I started to speak when I realized I was still standing up, so I sat down.  I felt my voice crack and I tried to compose myself.  “Michael, we’ve been saving up for a trip that we’re about to take next month.”  I explained what our trip was all about and where we were going and that I’d be leaving the company.   The first thing he said was, “Well good for you guys.”  He knows we don’t have kids or pets or a house for that matter and was really supportive.  I told him we wanted to do it now, when we are still (relatively) young and our parents are in good health.  “Absolutely man…If that’s something you guys want to do, you should do it.”  He was actually relieved that I wasn’t going to demand a raise or a promotion, or tell him I didn’t want to work on this project with him anymore.

Phew.

He’s asked a few questions since then and I’ve answered them, which made me realize how long we’ve been planning for this trip.

But it was what he did next that made me realize how great of a guy I’ve been working for the last few years.  I asked about my vacation for next year, fully expecting that I’d have to get a small payout of what I had available to me next year, but no.  No, He’s going to let me schedule all my vacation time that I was going to have coming to me next year for all of January and into February.  For the first month of our trip, I’ll still be getting paid.  Which is nice!  Plus, if we get to Guatemala and we realize that this trip is for the birds, I’ll still have a job to come back to.  (That’s not going to happen though).

Mandy told her boss last week and aside from a few tears, it went well too. Her boss kept saying, “Wow…..Wow!…..Wow!!”  over and over again every time Mandy would give more details about our trip.  She had some questions too, like “What if you get sick?”  Travel insurance, Val.  We’ll be fine.

So, our bosses know and last night we bought our travel insurance.  So I guess we kinda have to go on this trip now.

(Kudos to you if you got that the title of this post is also the name of the episode of The Office where Michael Scott leaves Dunder Mifflin)