Welcome to the first post in a new series I’m starting up. Smart or Dumb is a great game that I play with my best friend. We invented it in college and have been using it to make some very important decisions ever since. It goes a little something like this: You ask your best friend/life partner/nearest person “Smart or Dumb?” and follow it with the question you’re struggling with. Classic examples include- Smart or dumb…paying two months of rent at once? (Smart!) Smart or dumb….having one more shot even though it’s 1am? (Usually dumb, occasionally brilliant!) Smart or dumb…making out with that guy over there? (Usually smart, occasionally really dumb!)
It’s a wonderful game and the way I have made a shocking number of decisions. See, your friend has to justify why they think you’re being smart or dumb, so it’s a great way to get a different perspective on things. And there is no middle man- your friend has to pick either smart or dumb. Forcing them to make a call on your problem makes it much easier for you to make a decision yourself.
So now that I am a super mature, real world adult who is making serious headway on paying off her loans, beginning to save for retirement and generally being a financial wizard, I am applying this game to my finances. And you, dear readers, are going to have to help me make the call.
One of my very good friends got engaged last November. It’s very exciting and something she is thrilled about. She wants a group of about 10 of our friends to spend a long weekend this May in San Diego to celebrate each other and her upcoming nuptials. It’s sort of a pre-bachelorette party. (She’s having a traditional bachelorette sometime in 2016, the year she’s getting married.) We would rent a house, cook meals at home, have one fancy dinner out, go surfing, paddle boarding, hiking and do lots of drinking.
Now. Here is the first ever Smart or Dumb: Financial Decisions.
Smart or Dumb…should I go to San Diego this May?
Why it may be smart:
-I was planning on opening up a credit card this year, in order to take advantage of travel reward offers. I’m torn between the Barclaycard Arrival World MasterCard or the Capital One VentureOne Card. Both have good enough rewards offers that I think I can pay for most, if not all, of my ticket to San Diego with points. That’s one major expense at least brought down a few notches.
-My friends are planning on renting through Air BnB, to save some money and have a house we can cook food at. I would definitely keep my eyes on rentals that cost a reasonable amount of money, and the cost would be split between at least six people.
-For the past three months, I have been saving all my $1 bills and all my change. It accumulates slowly, as I tend not to spend cash, but it’s about $75 right now. I was planning on cashing that coin jar in around June anyway, and treating myself to something. By May, I could easily have $150 in there, just waiting to be spent on this trip.
-I only get to see many of these people once a year, and they are my nearest and dearest. I consider them all my sisters. We’ve been friends for over 10 years and I would love to celebrate a milestone like our first engagement with them.
Why it may be dumb:
-I am still $12,000 in debt! How can I do any traveling of this magnitude? Any and all extra money not already allocated specifically to fun (like the coin jar) should definitely be put towards my loans. Even spending $200, which is a conservative guess, on this trip out of pocket would be a major sacrifice to my loans.
-I’ve already been to San Diego.
Am I willing to postpone my debt payoff plan by around a month to make this trip? Am I willing to postpone saving for retirement to make this trip? Is this a smart of dumb decision? Help me blog readers! You’re my only hope!

Kara Perez is the original founder of From Frugal To Free. She is a money expert, speaker and founder of Bravely Go, a feminist financial education company. Her work has been featured on NPR, Business Insider, Forbes, and Elite Daily.
I am an optimist and will say Smart. Here is my reasoning:
This is an opportunity for you to prove to yourself that you can still reach your goals and enjoy your life at the same time. This is not an extravagant expense and your plan for paying for the cost of the trip is already coming together. Challenge yourself to find ways to pay for it without slowing down your debt repayment plan. You have a little over 4 months to raise $200. I think you can do that.
I’ve basically already talked myself into it! I have been very clear with my friends about my financial limits though, and won’t go over them. Thanks for the optimism!
Smart or dumb may not serve you as well here. Financially it my not be a “smart” move due the reasons you’ve listed, but we aren’t just considering the financial aspects here. What price can be put on friendship and the memories created with time well spent?
I’m a big fan of cutting spending that brings little value to our lives, but spending unapologetically on things that are of genuine value. As Tim mentioned above, you can easily make up for the expense by making adjustments elsewhere.
Enjoy the trip. 🙂
It’s hard for me because I have been so deliberately avoiding any extra costs for months now, that an expense like this seems wrong. I think you’re right- I need to spend a little on genuine value!
I’m super frugal, and I say go! Ten of your best friends who you rarely see all together for a whole weekend? Absolutely.
However, will you also have to travel & buy dresses/gifts for the second bachelorette party, a shower, and the wedding? That’s a ton – but maybe you can skip some of those expenses for the more meaningful weekend with all your friends? I’m sure the bride would understand, and love to have you for the special trip!
Thanks Lauren! I WILL have to travel for the wedding but I will skip the ‘real’ bachelorette party and the shower. I will probably get a smaller gift for her, as she is well aware of my dedication to getting out of debt. I’ve been discussing this with everyone I know and no one has said ‘don’t go.’ Guess that makes it smart!
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