“Travel isn’t always pretty. It isn’t always comfortable. Sometimes it hurts, it even breaks your heart. But that’s okay. The journey changes you; it should change you. It leaves marks on your memory, on your consciousness, on your heart, and on your body. You take something with you. Hopefully, you leave something good behind.” – Anthony Bourdain


So last week, I took my first business trip since March 2020. Venturing out in the brave new world to give a law practice management presentation to an industry group in Chicago. To be honest, I approached the event with excitement but not without a fair amount of fear and trepidation. I was not sure what to expect. And of course, even though I’m fully vaccinated, the threat of Covid still loomed large.

By way of disclosure, I was initially supposed to go to the International Legal Technology Association conference in Las Vegas and then go directly from there to Chicago. Like several others who planned to attend ILTA, I canceled Las Vegas. The notion of walking through casinos—you can’t get any place in Las Vegas without doing so–made me uneasy. Plus, going to ILTA would have made for a 7 day trip instead of a 3 day trip. 3 days in Chicago just felt safer than 4 days in Las Vegas and then 3 more days in Chicago. Plus, less wearing. Not to mention less stressful. I was already uneasy about travel anyway.


So how did it go with Chicago? In large part (and so far): invigorating. I forgot what live presenting and networking, and in-person learning does for your view of the world. For spurring you on to do more and better things. To get you excited about working again. To get the juices flowing.


I came back with renewed energy and outlook. Which I guess is why I always liked travel.

“Travel has a way of stretching the mind”  Ralph Crawshaw


A few things I had forgotten over the past 18 months of no travel. Never book a late afternoon flight in the summer. There is always the risk of bad weather, which of course, is what happened. Flight was canceled, and I had to go the following day at 6 am. (Yes, I know, it’s ironic that my first plane trip in over a year started with a cancellation and postponement of the journey till the next day).


I had forgotten how crappy early morning flights really are.


I had forgotten how to quickly pack. Used to be had everything ready, and packing took 5 minutes. Now it took hours. Had to find travel toiletries. Had to locate all my cables and chargers that I used to keep in one place. Over the past 18 months, I had pilfered my electronics bag so many times, so there was nothing left in it. Had to start from scratch.


I forgot I had the Clear pass, so I got to the airport way earlier than needed to. Forgot how waiting in an airport is not much fun, especially when you have to wear a mask the whole time.


What was new and different? Fewer people in airports. Less wait times for security. Everyone with masks on, at least in the airport and on the plane. I actually felt more secure in the airport than most other places since everyone always and everywhere was masked up.


More flight cancellations than I recall (many attendees of the seminar had the same problem I did. Either we all forgot about the potential for late afternoon flight issues in the summer, or there was a massive weather system. Or maybe more flights are being canceled these days).


Unlike the airports, the Chicago restaurants I went to were pretty crowded. In fact, it was the most unnerving part of the trip since most restaurant-goers did not wear masks at all (despite the local mask mandate). Most were eating and drinking like normal. Frequent loud and robust talking. People seated close to one another. Yes, I eat out some here at home. But I try to pick times and days that I know the places I go won’t be crowded. Hard to do that on the road. Plus, I couldn’t bring myself to order take-out food to my hotel room. Sounded pretty depressing; Covid be damned.


The number of people out and about in Chicago seemed surprisingly normal. It made me forget at times that Covid is still lurking. But lots of businesses shuttered, especially along Michigan Avenue. I wonder if the days of in-person shopping at stores in locales like this are numbered. (Yeah, I bought some stuff…doing my part for merchants. Plus, it’s always fun to buy something on a trip. Every time I see the item or wear it, I remember the trip).


I’ll also have to say boarding, disembarking and the time on the plane made me a little uneasy as well. Even though we all had masks on, I have not been in such close proximity to that many people since the pandemic started.


Taxis and Uber little scary too. I dutifully kept the window down and, of course, wore a mask. Thankful the drivers were also masked and the ones I had weren’t talkative.



As for the seminar: it was a practice management seminar. The attendees mainly were defense lawyers from small to mid-size firms. I was wondering what their view of the remote work world would be. The surprising thing, though, was the acceptance by the managing partners of the desire of younger lawyers to work more remotely.


Yes, many of the managing partners aren’t particular fans of remote work. Still, most realized the advantages of it and believe that it’s here to stay. Many even grudgingly embraced remote work and without hesitation admitted it works and works well for others. But most still themselves want to be back in the office.


More importantly, I got the feeling from the comments that there is a greater openness to change and innovation than before. The pandemic may have indeed opened some minds and changed attitudes. That new and different way of doing things—just like remote work—can work. That innovation and change can make work better. Many of the lawyers in the room experienced that something they never though possible was not only possible but better.Makes me think that as the pandemic and time march on, we may see more and more openness and innovation. Lawyers are actually getting more used to change…


The other big takeaway: we involved the attendees in the discussion. We sought their expertise instead of blathering on via lecture. The result confirmed for me once again: we all can learn from each other more than just a lecturer. It confirmed that the collective knowledge and insights of the group in a seminar setting are more than that of any individual.


As an aside, on a more general level, I also noticed that there was less and less mask-wearing as meetings and the conference went on. I guess it’s human nature to get more comfortable with risk as time goes on and you see others accepting a risk. Hope and pray none of us gets sick.


Yes, between eating out, being with others in meetings, and on planes, I’ll be watching my physical condition for the next few days. Always hard to know if a sniffle or sneeze is just that—a sniffle or a sneeze- or the opening Covid salvo. And now that I’m sensitive to the issue, I’m sure I’ll notice more would be symptoms.


“To travel is to live.” Hans Christian Andersen



So what’s my bottom line about the trip? Ask me in a few days. If I’m still Covid free, I will say it was all well worth it. If I get a little sick and am over it soon, I will say it was still probably worth it. But the big boogeyman is still out there lurking in the dark.


My advice for future travelers: balance the risks, and do what you are comfortable with.