Squirreling Gone Wild #34: The High Cost of Being Cheap

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?


  1. says

    The sales tax difference couldn’t have been more than 10%. You can save at least that much by buying things on sale or using coupons at many clothes stores… I’d say that definitely wasn’t the best move to make on a business trip.

  2. says

    That sales tax thing is so crazy I almost believe there was really something else going on–a boyfriend?–and she made up the shopping story.

    Like you, I probably would have skipped the Fenway opportunity in favor of dinner with colleagues. That the game would have been free wouldn’t have played a role in my choice–the main issue I think is that my colleagues may have felt disrespected if I’d gone to the game.

    • Squirrelers says

      Kurt – ah, good point there! Maybe there is more to the story! I’d say in this case, the lady was so obsessed with saving money on certain things (despite admitting to spending profusely on other things) that it’s actually quite believable that she tried to save on clothes.

  3. says

    Your co-worker was being truly disrespectful of the organization and it’s culture. Is she still working there? It was the COMPANY that paid for her to fly to Philly with the expectation that she is there to work. Work also includes networking and building relationships with colleagues, which she completely blew off. It is unreasonable for a company to expect an employee to not need some personal time on a business trip to take care of themselves (exercising, sleeping, etc.), but shopping is not reasonable personal care time!

    As for your dilemma, I have extended business trips when travel policy allowed it and fit in personal activities when they don’t interfere with meetings or other business activities, but it sounds like you weren’t in that situation. You made the right call.

    • Squirrelers says

      Linda – yeah, I thought it was odd. Have no idea if she’s still there, it was a prior job. I do think it’s okay to have some time for personal time, and if one chooses to shop instead of exercise (as an example) it’s all good. Maybe just don’t make a big deal, or be discreet. But to blow off coworkers blatantly is not too smart!

  4. says

    As a former CFO, I think I have seen many different approaches to business trips. Some companies pay per diem and you can save a lot by just pocketing the money and buy something from the supermarket. Other people go the other way and buy dinners that thye would never pay for if it were their money.

    Regarding the tickets, it depends on the dinner. If the dinner was simply to do something together vs, something more meaningful. I would told the boss about the tickets and feel him out whether I should go. Everything depends on the relationship and circumstances.

    • Squirrelers says

      krantcents – good points. In the case of my dinner, I really needed to forego the game at Fenway, despite being tempted. The boss wouldn’t have understood, and I believe in being cognizant of the ground rules so to speak, and acting accordingly.

  5. says

    Yeah, that sounds kinda cheesy. And last I checked, sales taxes in Phila aren’t all that cheap either – what’d they save, like 30 bucks? When I travel for work I try to do something cultural and/or with fellow co-workers when on the trip since it’s good to learn about other areas, see some sights, network a little, etc.

    • Squirrelers says

      Darwin – it was interesting, I’ll say that! I take the same approach as you it would seem, balance networking with taking in the sights in the area. For example, in case of Philly (where the trip in the post was), I’ve taken the time to have dinners on 2 trips with coworkers while on 2 other trips I explored. Learned that Philly can be a good city to visit if you do it right, in addition to the history there!

  6. says

    This reminds me of my public accounting days where it was “proper” and “expected” to travel together, eat together, drive together. I am inclined to believe there was something more to your colleagues trip than saving sales tax but I don’t see anything wrong with it.

    • Squirrelers says

      I know that type of culture, and this one wasn’t extreme like that. Most people were pretty reasonable, but there was a culture of doing some things with coworkers. You could be right about something more than shopping for her, but given her apparent obsession with saving and getting free things, I lean toward her actually trying to save on shopping :) Personally, I have no problem with people going off on their own for some “me” time, and I’ve done it too – and relished it! Just have to pick spots.

  7. says

    I think you made it clear what the culture of the workplace was – plans were made together, and everyone was expected to go along. I have attended lots of conferences where it was expected that you would attend evening sessions and have networking dinners, or at least not “abandon” a co-worker by leaving them alone in a different city. On the other hand, if no plans have been made and a co-worker asks you, “What are you going to do for dinner this evening?” and you say, “I have a ticket for a ball game,” then you haven’t broken any promises or expectations. I would not bail out of something already arranged.

    • Squirrelers says

      I think you’ve described it pretty well. In my case, I didn’t want to abandon the pre-arranged dinner – particularly considering the attendees!

  8. says

    Haha, I have actually gone shopping on a business trip myself to save on sales tax. BUT I did it on my own time over the weekend before going to the airport to fly back home. I spent the weekday evenings with my coworkers and that was totally worth it. We got to know each other better and share stories.

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