Vacation issue with boss

Go. Absolutely. Life is about adventuring outside, not answering to a boss who wouldn’t even given your requests for time off the time of day. Especially since you’re going with your dad.

At the end of the day, while your new boss may think differently of you, the rest of your time likely knows how valuable to the company, and if the worst case scenario happens, you can always go somewhere where your superiors will value you enough to respect your use of vacation.

Enjoy Kenya/Tanzania!

You've been there 5 years. Strong track record, obviously well-liked there. Seems like if you did die on this hill and you did get axed (seems unlikely), explanation to new employers is "I did everything above board -- gave 4 months' advance notice, reminded him two weeks before, scheduled for slow time... it was a once-in-a-lifetime thing with my dad, and while I'm team player and more than willing to change/cancel plans when necessary, if this is the place where I'll have to cancel my first vacation in two years over something that's not essential, maybe I'm not your guy."  

I think in a lot of cases, these things should be handled elegantly and with some finesse. However, given your situation, having been at the company for 5 years with a strong track record, this is not one of those cases. Legitimately tell your boss to go fuck himself. He hasn’t even been there 6 months - you are way more apart of this group than he is. This is a once in a lifetime opportunity with your dad that you will never get back. Think of how it will be if you don’t go: you’ll be miserable, and your boss isn’t going to respect you any more than he already does. What an asshole

Your boss is being ridiculous. Go on your trip. Nothing can be that important, the firm isn’t going bankrupt because of your trip. 

I read title as vaccination issue and was confused 

Your boss sucks - lateral out

I would not. Work is very important and should always take priority over some trip - otherwise your bonus will get dinged

I got pissed just reading this lol so can’t imagine how you feel.

Maybe don’t tell him to go fuck himself, but 100% go.

In this tight labor market go on the trip. If you get blow back in comp or rating just peace out 

This is how you deal with your boss in this situation: 

I would approach like a negotiation. Very politely - "Trip is expensive and non-refundable, last chance to go with my old man. Can't do it. Sorry". Let him come back and counter.

If he is "suggesting" and has let it sit in his inbox for 4 months, onus is on him. You have your 5 years at the company and track record to stand on.

Would def die on this hill if I were you. Enjoy the trip! Had a friend climb Kili and said it was amazing.

If you gave all the proper notice you say you did, then your boss can go to hell. I'm also going to go on a limb and guess that he is the kind of boss who passes literally everything on to you and doesn't do shit himself...

That being said, in reality, remind him you told him 4 months ago and reminded him 2 weeks ago. He has no ground to push back on work which may "potentially" come across your desk. Tell him you'll send a postcard from Kili.

No competent manager would spring this kind of shit on you after you've provided a ton of forewarning. If he's managing a team and you actually submitted time off then it's part of his job to open those emails and approve/have a discussion around rescheduling when submitted.

As you may tell I feel very strongly about this as I had an extremely toxic and controlling director in PE who I told I would be going to a taping of Colbert from 4-onwards a couple weeks in advance. The day of he says "hey may need your help around 6 or so so you need to skip the colbert taping". I ended up sitting around and filing my own emails waiting for this non-existent work to come in. So angry and worse I flaked on my friend the day of who had been trying to get tickets for ages

In my experience with bosses who do things like this (sitting on email notification then trying to suggest the facts were otherwise), they do not respect you or your time. They will not grow to respect you or your time until you curb their transparent behavior. Of course you must do it diplomatically so that they can’t take issue with you or your approach, and remain on good terms with you. But if you just let their BS slide, they will only continue to treat you that way.

Sounds like your boss is still in hardo, try hard mode as they have only been there for six months. Maybe they're thinking senior folks won't like it as a managerial decision? 

Hopefully he/she isn't that terrible going fwd.

100% die on this hill. This post speaks to everything that is wrong with the broader finance world in general, and you will absolutely regret any course of action that does not end with you on top of Kilimanjaro!

1000% go on the trip, like don't even second guess this. You're going to have a blast and create an awesome memory for life.  I'd just suggest not using the phrase "die on this hill" when about to climb a mountain lmao. 

You work in CorpDev rather than banking (to be clear - not meant to be a jab), so there is an expectation of appropriate work / life balance. I would 100% go on the trip and, if there is pushback, draft your resignation letter and hand it in. Say you would be happy to sign it when you get back if your boss feels so strongly. 

Employees' market - capitalize on market conditions.

"Secondly, I am going with my dad and this is likely the last opportunity I'll have while he is still in decent enough health/shape."

You answered your own question. Tell your boss to kick the dust. There will be other jobs if he feels so strongly. This is your shot at this trip. On your death bed you are gonna remember the trip, not another 2 weeks of malaise. 

An aside, the lack of empathy or consideration from your boss for someone planning to accomplish such a feat as you're contemplating is shocking, some psychopathic shit. I'd take this into consideration after returning irrespective of whether they begrudgingly cede your request. 

Absolutely go, fuck your boss.

Guy is just projecting that he has never done anything like this.

Enjoy the trip and update your resume on the flight, he will hold onto this and fuck you in the future.

I can smell your boss’ insecurity from here.

Go! Your boss sucks. He could have denied your request 4 months ago and didn’t. This is a hill worth dying on. Would also lateral and when asked say you were there 5 years and it’s time to move on. Maybe share what you wrote above and call it a day.  

Go on the trip. You followed the process. Not many chances in adulthood to hang out with our parents outside of holidays. If you've had your seat for five years there are other companies in your space that would take you if your boss even fires you for this. I think he'll be a little pissed but if it really isn't busy like you expect there shouldn't be an issue. I don't know your office dynamic but I think at six months in he might realize he can't do some of your responsibilities and he's trying to make sure he can still lean on you during these weeks.

I would of just hung up the phone on your boss…enjoy your trip. It’s well deserved at this point

He suggested you not go 2 Days before your trip. Clearly, he was aware of the trip. 2 Days before, there's nothing you can do. Hell, even 2 weeks before, there's nothing you can do. He's an asshole and he'll have to make do. Just be aware though, as good of a track record as you have, you'll now have a target on your back and need to be on point no matter what for the next year. This is what a shmuck like that does - he'll try to use it against you, so be aware of it. 

In addition to what everyone else said - please don't take your phone or laptop with you either. 100% this insecure asshole will try and email and call you all the time during the trip. Set an OOF and go enjoy the trip! Please make sure to follow up here in a few weeks with an update!!

Fuck him. Spending quality time with your father while he's still healthy takes precedence over all. 

Please go man. Please go. Just to echo what everyone else has said. Your boss can absolutely go fuck himself. My dad means everything to me - take that trip and please do not spend a single fucking minute thinking about your dumb ass boss. Good luck on the climb 💪🏼

You should go and not leave any regrets on the table. Years of long hours in IB made me realize that family and friends are what make you happy; it's not the career but rather your family, friends, and significant others. I realized this too late and completely regret (to an extent) the decisions I have made. If I were to redo my career, I would have chosen my family, friends, etc. over the needs of my "unresponsive" boss who clearly has no respect for your time.