Career and Life Advice

Hi all. Long story short, I left NY for Chicago and have been at my fund for about 3 months now. I really enjoy the work, the people and think I can stay here long term. That being said, I miss NY and want to move back asap. My thought was to try and stay for a year then ask to WFH. One mid level did it for another Midwest state. Does anyone have any thoughts on this?

 

GTCR is a nice place but they generally don't let you stay on anyways so just do the 2 years. If its not GTCR it probably wasn't too good to pass up...

 

Honestly, you’re only three months in. You need to give yourself at least another 3-4 months to properly settle into the job and the city. I think if you make a drastic decision now you’ll likely regret it later. A new job and a new city is obviously a big change for anyone - give yourself time to get used to it and you may find it’s not so bad.

 

Following - curious at the VP level as well

 
Most Helpful

There are two parts to your post -- the enjoying Chicago part and the work remote part.

In terms of WFH out of NYC, it is very low likelihood as such a junior employee who has only recently joined the fund. The most important factors will be how indispensable you are to the team and their general willingness to support WFH. It sounds like they already accommodated a more senior employee, which is a least a good sign for the second factor. If that arrangement is working out it will help you -- if the mid-level employee is failing to perform, your chances of a similar arrangement go out the window. I assume you are a new associate based on your title? My gut reaction is that they will reject this, particularly if your rationale is that you want to go to NYC versus the other employee who probably wanted to be closer to family (pure guess here).

In terms of Chicago, I'll echo the other comments that you've only been there three months. I have moved cities a LOT, including moving to Richmond VA and Pittsburgh PA for jobs. I also did my MBA in Chicago, which is admittedly a different environment because you have a ready-made social network. Regardless, three months is definitely too short. All it takes is one girl, one good friend, or a really fun social activity (such as recreational sports) to completely change your opinion of a city. It almost sounds like you've given up on Chicago. I encourage you to put a very real effort in to meet people and get out more. Join a sports team, a gym, a book club ... take a guitar class ... whatever it is you're interested in, try to find it. Go to a foreign language meetup.com session ... go sit at a bar and talk to some strangers ... whatever it is, just do it. With a little bit and time and effort you'll significantly increase your odds of finding people with similar interests that will make the city more enjoyable. The truth is that Chicago is quite a big city with loads to do in terms of culture / sports / nightlife / restaurants / etc. While the vibe is very distinct from NYC, there is a little bit of everything. Besides, as the saying goes, if you can make it in NYC, you can make it anywhere!

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

If it is a 2 and out program there is very little chance they would entertain a remote working arrangement for the second year. That’s a big investment in an employee and you’re just there for a short time and quite easily replaceable. Unless you are the best associate they’ve ever had and they want to keep you on longer than two years, I don’t see them accommodating.
From a career perspective, you’d be doing yourself a disservice professionally to lateral after one year and would need to come up with a stronger rationale than not liking Chicago. It would raise suspicions and reflect poorly on you in interviews if you couldn’t stick out the two years in Chicago. Obviously your happiness is important and winters in Chicago are no joke, but you ought to be able to build a social circle and find activities you enjoy to sustain you until you fulfill the two years.

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

I highly doubt a regimented (2 and out) associate program would be willing to make accommodations like permanent WFH.  They can do so for a senior-level employee they really want to retain and who has tenure, but no firm wants to open up a can of worms with other associates asking for the same benefit.

Of course easier said than done, but echoing the others above me, I think the unfortunate best solution needs to either be (i) finding a way to enjoy Chicago more or (ii) just putting head down and toughing it out for the full two years, and if this place has a good brand name (which it sounds like it does because of the reason you noted for taking it in the first place), then it shouldn't be hard for you to lateral back over to NYC after the two years are up.

 

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