It’s been a while since the last edition of the old Squirreling Gone Wild series, and a recent discussion with a former coworker – where we were recalling old stories – got me thinking of an episode of cheapskate behavior of one of our former colleagues. I thought I would share it as the 34th edition in the series, and get your thoughts on it.
In reality, the idea that this person would engage in cheapskate behavior wasn’t a total surprise. She is the person who was obsessed with free food in the office, to the point of claiming to spend only $100 per month on food due to taking leftovers from meetings and department lunches. It was something that she could eventually laugh at a bit, and really she took pride in it. Or, should I say, threw her pride out the window by hustling for free things more than she hustled to get work done. Hey, it was entertaining if nothing else!
The Frugal Co-worker on a Business Trip
Anyway, there was a point in time where a few of us had to travel to Philadelphia for a business trip. It would have been a fairly short trip, just one full day there, and two nights. We would get in the night before the meeting, have the meeting the next day, then stay that night and fly back in the morning.
So, we often collaborated on booking flights, to see if we could travel together. That part wasn’t really something I needed to do, and frankly I had no problem traveling alone, but the culture in the office was to have people travel together. No problem, I can do that. Three of us got on the same flight, but then this other person – let’s call her “Jane” – booked an earlier flight to Philadelphia on her own.
Then, the day of the meetings, we were all going to go out for dinner later in the evening. Jane tried to avoid the conversation, then said she was going to be busy. We thought maybe she knew people in town who she wanted to visit, or maybe she was just tired. Nope. Ultimately, she said that she only had a short period of time to go shopping, and had a lot to buy.
Why? She said that she could save on sales tax if she bought things in Philadelphia. Apparently, the sales tax on clothing there was much lower than it was in Illinois. So Jane felt that she had to maximize her time that evening to rush to stores to buy clothes and shoes. When our meetings ended that day, she literally packed her bags and rushed out the door without saying goodbye! She also took a different flight back the next morning, so we never saw her until being back at the office.
Now, I’m cool with people marching to the beat of a different drummer. Conforming can be overrated. That being said, when you’re dealing with people with whom you work – and the culture associated with that workplace – sometimes you have to be cognizant of “expectations”. In Jane’s case, she blew off those expectations and a dinner with coworkers just to save some money shopping.
Was the benefit of saving some money worth the cost of alienating coworkers? Again, not that I cared that much – and frankly, I smile when I think about it. It was funny at the time! Yet, in reality it was weird and it bothered the other people on the trip. I don’t think it could have been worth it for her to save a few bucks on clothes, in the bigger picture.
My Own Business Trip
I actually had a somewhat similar situation present itself to me a few years before that. I was on a trip to Boston, where a group of coworkers and I were at a conference. My boss was there as well, and all of us had dinner plans for that evening.
During the day, a supplier talked to me about sports, just making small talk. I had mentioned that I had always wanted to see a game at Fenway Park, and would have really liked to do so if I had time. At that point, the salesman in him pounced like a tiger – saying that he had tickets for that night’s Red Sox game, and that he could keep a ticket for me. FREE!
What to do? I enjoy seeing different ballparks, and especially appreciate historic venues. We have one here in Chicago (Wrigley Field), had another one a few decades ago – the old Comiskey Park - that I visited often as a kid before it was torn down in 1990. I made sure to visit the old Tiger Stadium in Detroit before it was shut down back in 1999. As you can see, I like the old parks, and Fenway is one that would be a treat to see.
But what about that dinner with the boss?
One might think I was shortsighted in my own way, but I actually turned the guy down. Instead, went out to dinner with my boss and coworkers. Sure, it was a really nice dinner. But I have to say, going to the ballgame would have been much more fun!
Of course, it would have looked very bad if I chose a great fun evening over dinner with the group. Perceptions matter, and ultimately our income matters more. I thought it would have been penny wise and pound foolish to go for the free tickets and the great memories, instead of prioritizing the norms of the workplace. I chose the latter, thinking of the bigger picture.
Besides, who’s to say that I couldn’t go to Fenway another time in the future?
My Questions for You
If you were that coworker, would you have taken advantage of the opportunity to save money shopping? Or, would you have given that up and conformed to the norms of the group and gone out to dinner with coworkers?
If you were me on the other trip, would you have taken advantage of the opportunity for a cool life experience on someone else’s expense? Or, would you have done what was expected on the job, and gone to dinner with the boss and coworkers?
Have you ever seen anyone lose respect by being cheap in any situation?



