Timing of retirement discussion with boss

[travelover]

I say talk to your boss now. If you do the big trip then leave your legacy will be the a-hole who took the big trip and left us high and dry. I would think if you express your commitment to help keep critical initiatives moving forward during your final months it will be greatly appreciated. Maybe your boss will send you on the trip anyway. But don’t burn bridges.

Legacy? Unless you are Jack (the Klepto) Welsh, you are not going to have a legacy except with a very few people that might remember you for a couple of years. I'm fully in the wait until stock is vested, check clears, then bye, bye. Right now Mega is your world, once you retire, it is like last week's newspaper.

 

[Unpaintedhuffhines]

Well, quick update: I went on one of the two trips (Europe, not Asia). On the last day of our conference , I resigned. Boss was actually very cordial, wished me the best, etc. We agreed on 2 weeks notice, so my final countdown has started! No mention of the trip expenses, but I do not expect any issues at all.

Told my team this afternoon. They will miss me but they’ll get over it.

Kind of stunned that this is happening. I made the right choice.

 

[TripleLindy]

Congrats! I had my conversation with my boss about this time of year 5 years ago. He asked me to stay on for about 6 more weeks, which I did, but on the condition of no travel. It was odd. I’d attend meetings remotely but everyone knew I was leaving, so there was no need for input from me. I mostly played golf the last 4 weeks. And I was able to get my equity out of the company from our private equity partner. My successor wasn’t as fortunate, as he left about a year later and still hasn’t seen his equity.

 

[caninelover]

Congrats! I had my conversation with my boss about this time of year 5 years ago. He asked me to stay on for about 6 more weeks, which I did, but on the condition of no travel. It was odd. I’d attend meetings remotely but everyone knew I was leaving, so there was no need for input from me. I mostly played golf the last 4 weeks. And I was able to get my equity out of the company from our private equity partner. My successor wasn’t as fortunate, as he left about a year later and still hasn’t seen his equity.

I had my conversation with my boss the Friday before labor day, and targeted year end to leave to allow them time to hire a replacement. They found someone and my boss asked me to stay a bit longer through January to help train the new person.

It felt right to me to give advance notice. My boss and I had a great relationship so I wasn't worried about retaliation and I was right. My boss was grateful as well, so I left in a high note.

Every situation is different. Glad OP took the trip and will be done soon.

 

[big-papa]

I had my conversation with my boss the Friday before labor day, and targeted year end to leave to allow them time to hire a replacement. They found someone and my boss asked me to stay a bit longer through January to help train the new person.

It felt right to me to give advance notice. My boss and I had a great relationship so I wasn't worried about retaliation and I was right. My boss was grateful as well, so I left in a high note.

Every situation is different. Glad OP took the trip and will be done soon.

Indeed - your experience is also similar to the one I described upthread as what's happening to me. No replacement yet, but down to two candidates. Should know soon. I'll be here at least through EOY, but I'm starting to discuss going into Q1 since that's when corp bonus pays out and I have some RSU's in Q1 vesting. Would be a shame to be that close and miss out - especially in a down market.