The 5 Most Over-Rated Cities to Visit for Work

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Last week, I wrote a blog about my top five favorite places to visit for work. The caveat being that these are best work destinations, and not necessarily my favorite de facto places to visit. I jokingly made a comment that someday I would come up with my five least favorite places to visit for work. Don’t worry – I am not going to commit professional suicide and write that blog. The last thing I want is a prospect or customer to remind me that they reside in one of my top five least favorite places to go (fortunately, my top five least favorite places to go are not places where potential or current clients exist anyway).


But the reaction to the blog was pretty fun. Many people cheered some of the choices, some people were really interested in checking out a new place based on reading the blog, and others were disappointed that other cities had not made it on the list. So what I thought might stir the pot even a little bit deeper was to come up with the five most over-rated cities to visit for work. Nota bene: these are not my least favorite places to go – nor are they places I necessarily do not enjoy – they are just over-rated. I have to say that so no one gets too upset.


So without further ado, let the complaining begin.



  1. Austin


Austin is honestly a really fun and great city to go to. If I find out I am going to Austin for a conference or a meeting, I get excited about it. I just don’t think that Austin realizes that Charleston has taken over as the new, en-vogue random city in America that everyone is fawning over.


Austin, your time in the sun was five years ago. You’re still pretty cool, you’re just not as cool as you think you are (any more). Also, you are no fun to travel to during the summer. Way too hot.



  1. Nashville


Nashville is a popular destination for bachelor and bachelorette parties, and I understand why. There are lots of bars and a great honky-tonk vibe around the Country Music Hall of Fame (and the history of country music in this city, along with all the accessible live music at every corner). I get it.


My thing with Nashville is that what more is there to do here when you have already been here once before? I feel like this is kind of a one-and-done place. Don’t @ me in the comments for feeling that way.


On a lesser note, why is it so cold here all the time? Isn’t Tennessee in the south? This is always confusing to me every time I go. I show up in shorts and a t-shirt and then the weather is colder than it is back in New York. Strange.


  1. Seattle


Ok, now we are heating up. I’m very passionate about Seattle being over-rated. And it really just stems down to one irrational and stubborn moment.


I had time to kill one evening and wanted to find a sports bar in downtown Seattle to watch a Celtics playoff game. Being from Boston, there is always a team of ours to cheer on and support. It is honestly like having a second job, the time commitment to watching all the superior athletic teams.
Anyway, I digress. I couldn’t find anything local or with character to really get into the Seattle spirit. I had to settle for a Buffalo Wild Wings. I found this surprising for a city with such self-aggrandizing fans (Seahawks fans call themselves the 12th man, after all), but it is what it is. Couple this with the fact that it’s always cold and rainy here, and that Starbucks was created here, and you have the perfect storm for an over-rated city.


  1. Any resort in the great outdoors


Hear me out on this one.


I love the outdoors. I like to go skiing, hiking, and even just breathing air that smells nice and not like the trash heap that is New York City. So I’m down with all this stuff. And I enjoy getting to go to the middle of nowhere in Colorado or Vermont to stay at one of these five star resorts for a conference, because it’s probably not something I am going to get to do on my own time.


Here’s the rub: I go to these conferences to work. Which means I am flying halfway across the country to stay in this really nice, fancy place just to sit in a conference room all day listening to someone speak or at a tradeshow booth having meetings. So basically I am just doing the same stuff I could do in my backyard.


So it’s all a tease. I don’t get to actually enjoy any of the outdoors. I am indoors all day. And I had to fly halfway across the country to be indoors all day, teased by how fun it might be to be outdoors. And yes, hopefully my employer is reading this and commending me for all of my hard work. Because I certainly do NOT have time to go to the spa, with all of the incredibly hard work I am doing.



  1. San Francisco


This is going to be controversial. Friendships might be broken because of this.

I used to go to San Francisco on average four times a year for work. I used to love San Francisco and I even thought about moving there permanently at one point in time. And don’t get me wrong, I still like San Francisco, I just feel that it is the most overrated city to go to for work.


Why is that? Well, let’s start with how expensive it is. What is even the point of going to Dreamforce or Oracle Open World when the price of a hotel is the cost of just flat out hiring another salesperson at your company? I’d prefer to just have another person on my staff than spend the money at a hotel for a three day conference. It is absolute highway robbery and people should be complaining about this more. It’s atrocious.


Second, this is a very dirty city. It baffles me that the joke is on NYC as the dirty, smelly city when San Francisco is objectively ten times worse. Like, in New York you can tell they are making an effort. In San Francisco, I’m not so sure.


I think most importantly, when you get down to it, SF has become fairly homogenous. Tech is critical – I work in a tech company that spent time in Silicon Valley and has deep ties to the area. I am grateful to be a part of the community. But one thing I like about living in New York City is that it seems like every different person I meet is truly different from the one I just met previously. In other words, not everyone is part of the same community. And I think with that, there is less of an element of social climbing. To be sure, there are people in NYC who are trying to outflash one another, but that exists within specific social hierarchies, not the dominant social hierarchy.


And I should be clear – I enjoy San Francisco, and I relish the opportunity to go there. So I don’t want anyone going too crazy on me for this. It would probably be in my top 10 or 15 cities in the US (period) to just go visit because of how much cool stuff there is to do there, the food, the weather, the proximity to Napa Valley, and so on. (As well as the best Mexican restaurant on the planet, Don Pistos, you should go try it). Just need San Francisco and Austin to have a conversation about whether they’re really in fashion these days.

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