How to break the news (of my leaving) to my boss

I know this sounds odd, but I'm having a hard time facing the fact that when (if) my Settlement Visa gets accepted, I'm going to have to walk into my boss's office and tell him I'm leaving the company.

I've been working for this tiny company for over 14 years. They comforted me through my divorce, came and cheered me at my second wedding (to a UK citizen), celebrated the birth of my son, cheered when my UK husband finally got his US citizenship. etc...

They're like my family, albeit with the power to fire me

I love my boss. He and I worked tirelessly through the years to create and evolve my very unique position in this company.

Now I'm having all this guilt. No one knows how to do my job. It's partially that I worked with the IT guy to build a complex database that only I use, it's partially that over the years I've built up a network of contacts and shortcuts and stuff, so that I do my job efficiently and well. I'm honestly not bragging, it's killing me that when I go, they're going to be horribly thrown into a bind. And yet, it's a catch-22. I can't tell them I'm leaving until I get my Visa approved (because what if it doesn't, and I end up not going anywhere?). And yet, I need to start prepping so that someone else can learn my job.

I've already taken some steps. I've created an instruction manual, along with an extensive annotated contact list.

I guess I'm just venting, and I feel sad. It's like leaving my family (oddly enough, the thought of leaving my extended family isn't causing me as much grief).

How did other people handle this? What did you say? any other suggestions for what I can do?

I had a job that I loved that I had to give up for my rtw.   I hadn’t been there as long as you, but I had really made the position my own and had also just gotten a great promotion and a lot of fabulous projects.  I just went to my boss and told her how much I liked working there and that I wouldn’t leave if it weren’t for my desire to travel.  She understood and we are still in touch.  Perhaps you could offer to answer question or even work remotely for a while after you’ve left the country.

It is nerve-racking to leave a job.  I’ll be giving my notice in about 6 weeks.  While I really HATE my job and am excited about leaving, the actual act of giving my notice is not on my fun things to do list. 

I had a job that I loved that I had to give up for my rtw.   I hadn’t been there as long as you, but I had really made the position my own and had also just gotten a great promotion and a lot of fabulous projects.  I just went to my boss and told her how much I liked working there and that I wouldn’t leave if it weren’t for my desire to travel.  She understood and we are still in touch.  Perhaps you could offer to answer question or even work remotely for a while after you’ve left the country.

It is nerve-racking to leave a job.  I’ll be giving my notice in about 6 weeks.  While I really HATE my job and am excited about leaving, the actual act of giving my notice is not on my fun things to do list. 

That's an EXCELLENT idea! Thank you very much for your advice, I hope I can carry myself as well as it sounds you did!

That's an EXCELLENT idea! Thank you very much for your advice, I hope I can carry myself as well as it sounds you did!

I was a little teary eyed.  It was hard!

Scarllet's advice is good.  I just wanted to say I know how you feel because I was also at my job for 14 years and my bosses and co-workers were just as important to me personally as my friends.

They will be happy for you, I'm sure!

I also know how you feel, my boss had treated me so well and I hated the idea of making plans and not letting them know. In the end I decided to have a quiet word with my boss letting her know my plans, but also being honest and letting her know I wouldn't be submitting my formal resignation until I had my visa approved. She was great with it- and it gave her more notice to informally plan for my leaving. Not sure if you feel this would work at your place, but I figured they couldn't force me to leave if I had not resigned ;-)...in the end it worked well. I had my visa approved and then could easily hand my formal letter of resignation without a big shock.

Your situation is different than mine, in that it is a small company and your job would require special training for your replacement. I was managing a Subway, so a replacement would require training for the food order, weekly paperwork, managing employees, etc... but restaurant/fast food managers are a dime a dozen. It was still hard for me because I took pride in my job and had the place running more efficiently and profitably that it had in all the years they'd owned it and they were comfortable with not needing to check in for weeks at a time if they needed or wanted to be out of town. The owners knew there was always a chance we'd move to hubby's hometown in the UK, and asked for a bit of advance notice. When we made the decision, I was able to give him about four months notice before hubby moved here and I came for a six month visit before going back to apply for my visa.

I would have a talk with your boss and let him know it is a distinct possibility that you will be leaving and you are willing to help train someone when the time comes, but that you wish to stay as long as you can/stay on if something would go wrong with the visa process (although I don't imagine there would be a problem). Keeping the ties and being up front with him will go a long way toward getting your job back should you ever decide it is a step you want to take (you and hubby decide in the future to move back there).

An update:

I followed a lot of good advice here, spoke privately with my boss, and when my visa was approved, formally gave my resignation. I'll work with my replacements for the next month, helping them to ease into my position (yes, my boss felt it took TWO people to replace me!).

He also said, "While we can find other people to do your job, we can never replace you, and no one will be able to do as well as you've done." There are many tears and hugs going around. Everyone is happy for me.

That's great!  I'm sure that they'd give you a great recomendation in the future as well!

He also said, "While we can find other people to do your job, we can never replace you, and no one will be able to do as well as you've done." There are many tears and hugs going around. Everyone is happy for me.

Awww, its bittersweet, isn't it? 

Glad to hear it all worked out for you