Do You Have Spending Guilt Or Frugality Disease?

Do You Have Spending Guilt Or Frugality Disease?

My parents taught me never to order a beverage other than tap water because prices were astronomically high compared to cost.  Til this day, I still have trouble ordering anything other than a glass of water with a lemon slice if I’m going out to eat.  I start rationalizing how water has zero calories, is plentiful, and good for me.  Meanwhile, I’m craving the $6 fresh young coconut juice to go with my chicken satay at my favorite Malaysian restaurant.

One of the best tricks I’ve devised to overcome spending guilt is to actually purchase what’s desired, marvel at it through the duration of the return policy, and return it!  If there was a 30 day return policy on cars, I would literally be the most hated customer in the area because I would have no shame buying a new one every other month and handing back the keys.  I’m addicted to cars and their new car smell, even though I’ve stayed “sober” with Moose for over 5 years now.


Look down upon me all you want, but I’m telling you I have a frugality problem which needs course correcting.  Over Thanksgiving weekend, I decided to create a challenge to only buy things with only the money I earned online during that 4-day weekend.  Who the hell works online during those four days?  It caused me to think more deeply and go seek business.  I concluded that practically everybody outside of America works on that Thursday and Friday, and so I pinged my Australian and English clients.

I managed to secure $1,100 in online income that weekend and felt relieved I could go spend some money on some socks and business shoes.  I mustered up the courage the first week in December to hunt for my favorite Tod’s loafers at Barney’s.  They usually run $485 a pair after tax and are never on sale.  Miraculously, I found one good enough for my liking for “only” $315 after tax.  I bought them immediately and brought them home to admire.

I’m keenly aware that $315 is still a ton of money to spend on shoes.  However, relative to the income generated during the same period, it’s not much.  If I hadn’t made any peripheral money in addition to my day job income, I would definitely not go ahead with the purchase.


It’s been over 10 days now and I still haven’t worn them outside!  Spending guilt has taken hold again, given these shoes are more than double what I spend normally.  I cannot fight the urge to return the shoes and go find some other sale for a third the price.  The kicker is that since Thanksgiving weekend, I’ve done much more online and still can’t manage to step outside and scuff the new soles!

By highlighting my monthly personal credit card expenses, I fear it’ll make me want to spend even less.  I even write posts expounding there’s no point making money if you don’t spend your money to will myself and others to stop being so frugal.  For the life of me, I can’t break free from my spending habits.

Related: The Best Things To Buy With Your Massive Investment Gains

I’m curious to whether any of you also have spending guilt and frugality disease when you can afford the items?  What are some of the things you do to make you spend a little and not feel guilty?  Why are we so conditioned to act the way we do?

Photo: Tod’s Shoes. Are these shoes worth $315 after tax? I’ll wear them 5 days a week.  Sam



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