Whenever I travel for a conference, trade show, or event for work (and I don’t go to a lot of them), I am asked the same question:  what are you going to do when you get there?  Or: what do you have planned?  Or: have fun, you should check out ‘X’ while there!.  They are fair questions and statements, and I don’t for one second blame or begrudge anyone for bringing them forward; I’ve done the same to others in the past and will likely do so again in the future.  The truth is, however, to answer the question of ‘what are you going to do when you get there?’ the answer is quite simple: I’ll be working.

Whether it’s as an attendee or a sponsor, I’ve never really enjoyed the conference going experience. Beyond the schmoozing, the handshakes and the ‘sales’ of it all – activities, all, which very much drain my energy – being at such an event is not what many people think it is.  Across the multiple days of whatever it happens to be recognizing or pitching, you are typically inside – usually in a hotel – and either fully on your feet or sitting strictly in a chair for 12-hours at a time, usually in poor lighting, freezing cold air, and finding little time to eat proper, healthy food.  At the end of a day just spent trying to either impress or learn, you’ll likely find yourself at at the hotel bar/restaurant, where all the same people you just spent so many hours with trying to buy or sell something, are now at least 4 gin and tonics deep and, well, wanting to continue that same conversation of either trying to buy or sell you something.  This, of course, is after you’ve spent many, many hours travelling via whichever means you’ve travelled, and slept in a not so great hotel room.  Beyond the trip from the airport shuttle into the hotel upon arrival, it’s likely you haven’t been outside or seen the sunlight, and you’re all the while trying to adjust the timezone you’re now immersed in, while at the same time trying to be on your A-game.  So – as much as it would be great to do ‘X’ while attending these things, the reality is, that sleep is much more likely.

These things in mind, I am me, I do try take on more than is likely capable, and so I of course make every effort to squeeze whatever adventure(s) I can into the few minutes that I have on these things, and a recent 4-day stint in Chicago was the most recent opportunity in which I had to spend those few precious hours exploring a city I’ve heard is worth exploring.  Stretching or pushing myself to find the fun on these work-related escapades helps to make it all worth while in the end.

To be transparent – about the only few things I know or knew about Chicago are that 1) there’s a giant mirrored bean.  2) they have deep dish pizza.  3) there was a fire that was started by a cow or something (a rumour which isn’t actually true).  Beyond those superficial topics, there’s not much I could have told you about the ‘Windy City’…to be honest, even after visiting it there’s still not much I could tell you about it.  Having said that, however, I did manage to venture down the blue line from the hotel and find myself face to face with said giant bean, I did find a deep dish pizza, and I was able to make it to the site of one of the only few buildings that managed to survive that great fire.  After receiving countless recommendations that I do so, I also managed to make it onto an architecture boat tour, which, despite my non-interest and lack of knowledge in architecture, was admittedly quite worth the time, even if for no other reason than to catch a breeze on a 39-degree day.  It’s not that I actively don’t appreciate architecture, but until that boat ride I suppose I have never had the company of someone who could open my mind and eye to the art that it beholds, or the nuances of why a building may be built the way that it is.  I’m not saying that I’m any Art Vandelay, but having a guide certainly opened my eyes to see a building beyond its purpose and look for all of the storeys it can tell (see what I did there?). For these reasons and more, I am now in the camp of: if you’re going to go to Chicago, you really do need to take one of these tours.

The rest of my limited time downtown brought me to The Magnificent Mile – a mix of shopping, food, and, yes, more architecture, that had me standing in front of things I mostly couldn’t afford and had no business even window shopping for.  I sent my wife a picture of the Tiffany’s window display, which is about as close as that’s ever going to get, I stood at the doorway of Louis Vuitton with my open-toe, $20, three-year old flip flops and my Old Navy shirt, and I saw the Coach sign from a distance.  Suffice to say, this area was more or less not in my wheel house.  There was, however, a Harry Potter store, a Lego shop, and I managed to get some of the famous Garrets, Chicago mix popcorn before I finally found myself a deep dish pizza at Lou Malnati’s  – a pizza style that, despite all the hype, I would best describe as ‘just fine’.  That’s a lot of crust and, frankly, not the part of a pizza that. care most about.  I know there was much more I could have done in that particular area (the ice cream museum sounded fun), but the reality was that I needed to get back to the hotel for at least a bit of sleep for my flight out in the morning.

Chicago, for all intents and purposes, is a place I would describe to others as ‘Toronto, but American’.  There are some cool sights to see, plenty of wonderful art installations and opportunities, lots of interesting smells, and a fine way to spend a day if big city sights are your thing.  I don’t mean to undercut it, but, well, ‘big city’ isn’t really a draw for me.   I will always make the most of it, always find the fun, and always seek out an adventure, but I feel satisfied with even the limited time that I found outside the hotel and its conference spaces, without the need to revisit it.  Unless its to dine at Alinea…that is definitely one place that as been on my bucket list for a very long time and I was so close to doing it this week, too; but something like that, in my mind, needs to be experienced with someone else.

I don’t know where the next ‘travel for work’ path is going to take me, but I promise you this: someone is going to ask me “Oh!  What are you going to do there?”  I’m going to roll my eyes and reply “I’ll be working”…but in the back of my mind, I’ll already be planning my every move.