It's only $500. You could play it by ear and eat the cost if you have to. Such small dollars - it's not worth causing a stir.

Another alternative is to talk to the partner on the deal outlining your situation. You can even claim to be available / accessible and work remotely if its required. You run the risk of getting booted off the deal and replaced by the other Associate.

 

Might not hold true at smaller firm, but I know a lot of places will reimburse the costs you've incurred if forced to cancel vacation for work. Would still suck for your friend (maybe split the cost?) and you miss out on the discount deal, but, hey, the good work might be rewarded with a bonus that more than makes up for it.

If culture is relaxed as you said, though, I doubt there would be too many qualms about taking a vacation that you gave a heads up for months in advance. Might mean more work for the rest of the firm, but I'm sure they can understand and realize that you've probably picked up for their slack in the past.

 

I know not necessarily my position to talk about this since I am much lower ranked than you in the finance world, however, I thought I'd share my two cents. I'd personally stay on the deal and then book a flight when you know it's been completed for some time off.

I'd personally see it to be much more worthwhile vacationing after you know you busted your ass to work on the deal and you will be rewarded for it, rather than taking a vacation during the deal because you'll be worrying on your vacation about missing out on the deal only to come home and stress out, even more, to catch up. I'd rather not have any worries or added stress.

If the vacation price is an issue, I can try and hook you up. I'm a private pilot who has some research knowledge/contacts in the aviation biz so I'd be happy to find you a reasonable fare (not guaranteed, might be the same fare). PM me if you're interested. Prices to asia itself aren't super expensive after the first week of january, even if you book a flight with a day in advance.

 
Best Response

You are the best positioned to judge whether you should cancel, but I'll share my experiences to the extent you find them helpful.

In my (almost) 10 year career, I've had to cancel about 5 vacations, including an international one last week. It is usually a pretty bad feeling, the worst of which is letting your co-travelers down, particularly if it is just two of you going on the trip. The deal world is unpredictable, but I've found that almost no deal ever closes on the initial targeted close date. It could be something as minor as a customer consent, an environmental issue, who knows -- but it happens a lot. The only way I've found to combat it is to do one of two things: (1) Book around major holidays when there won't be much activity, or (2) Book trips on short notice when you have clear visibility into your workload (I'm talking 2-4 weeks out). This is obviously more costly and creates a whole host of other issues with organizing and planning, but it is the only foolproof way to ensure your trip goes as expected. Well, that or take shorter trips (long weekends in Europe can actually be quite fun).

As someone who manages associates, it can be quite painful to lose your junior resource towards the end of a deal. There is a lot of blocking and tackling that needs to be done -- the funds flow, investment committee materials, gathering wire instructions, collecting payoff letters, and a thousand other things. It will be VERY difficult for you to do this work from Asia, particularly if you have never done a deal before (you didn't say if this is your first). If you don't have a middle layer (VP-type) sitting between you and the partner, your partner is likely to be ill-equipped to prepare these materials. Substituting another associate in your place to 'cover' will present its own challenges.

I wish it were different, but there is a chance that the senior guys get frustrated if you take the vacation and things get messy, even if you absolutely crushed it on all aspects of the deal leading up to the trip. On the bright side, I've found that people are more willing to cover for and to forgive vacations of the folks that they think are high performers. Also, in a small firm, corporate policy can be a bit more flexible, and you may find that the partners are willing to cover your cancellation fees (particularly if they can expense them to the deal -- Disclaimer: I'm not recommending this!).

In the final analysis, I think you should sit down with the partner on the deal and just talk it out. Maybe I'm misreading your description, but it sounds like you booked the flights last night, but you also had an update call early this week (yesterday was Monday?) where you found out the deal was going to be pushed into January. I'm probably just not understanding the situation, but if you booked your flight after knowing the deal was getting pushed back, that's a different assessment.

Lastly, and this is more for WSO than your direct situation, but the concept of 'unlimited PTO' is actually not very employee friendly. Having unlimited PTO means the company does not need to accrue vacation time on its books. Additionally, when an employee leaves or is terminated, there is no obligation to pay out earned but unused vacation time. So in reality, this helps them, not you.

CompBanker’s Career Guidance Services: https://www.rossettiadvisors.com/
 

Thank you all for the insight, it's been very helpful as I thought through my options. To clarify the timing we received a signed LOI and had a initial planning call on the same day and determined at that point that the deal was likely to close by the end of the month. Usually I wouldn't book a trip without giving things a few days to settle, but the flight deal presented itself so I booked later that night. The following day is when we had another call and found out that due a variety of things that a end of year close was going to be difficult. So I booked under the assumption that I would be in the clear.

I spoke with the partner yesterday and while he didn't discourage it at all, the reception wasn't as warm as I would have liked. It wasn't "that sounds great, go for it, we'll cover for you etc" it was more "deals always move around, for all we know it could be earlier/later, keep the ticket and we'll see what happens".

I mulled it over and decided to cancel the trip.(free cancellation as I cancelled in under 24 hours)

I could have gone and it probably wouldn't have been a huge deal, but it would have reflected somewhat poorly on me, I think that I would have been anxious during my trip, and what would be the point of flying halfway around the world to have to work. To Compbanker's point, we're a small organization and it definitely would have put strain on the deal and on everyone else; there is no mid layer between Associates and Partners so I take care of nearly all the process.

Its a good learning experience for me overall and good insight into the long term PE lifestyle. Thanks again for the advice from everyone.

 

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