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Checklist for a Holiday Season with No Money Stress

by Ashley Feinstein Gerstley, Contributing Writer

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The holidays are a wonderful time of year but can also be really stressful. One of the biggest culprits of that stress is money. Every year, without fail, we hear those around us (often ourselves), complaining and worrying about money. We either don’t have enough of it to do what we want or we spent too much of it and are now worrying about how to pay off our credit card bills. While there are financial surprises we can’t plan for, the holidays should not come as a surprise: They happen every single year. If you follow this checklist, you can minimize the stress you will experience during the holidays and eliminate money stress going forward.

Start with your vision.

If we don’t know where we want to go, any road will get us there. When you think of your ideal holiday season, what does it look like? Does it involve a couple of trips, gifts for certain people, decorations, parties and/or hosting dinners? Start with the big picture and work your way down to the details. If money were no object, what would your holidays look like?

Ask yourself why.

Then it’s important to understand why we want what we want. What do you enjoy about giving gifts? Why do you want to take a vacation? Why did you choose that specific destination? Get really clear on what you expect to get out of your holiday plan and why it’s important to you. What value is each of these items or experiences honoring? Is it important because you value your family, giving, friends, faith, laughter, joy, etc.? I’ll explain more on why this step is important later.

Give it a price.

One of the missing pieces to a lot of our goals and dreams is knowing how much they will cost. Some of the things we want may be right within reach but we wouldn’t know if we didn’t price it out. This might take some research. Do a little searching around. What can you reasonably expect to pay for something? For example, you might figure out how much your holiday travel getaway would cost or put together an estimate of the gifts you’d like to buy for your family. This doesn’t have to be perfect. You can always adjust as you have more information.

Make it fabulously frugal.

Fabulously frugal means that you increase the fabulousness of something while decreasing the cost. How we can do this most effectively is by making sure to maximize and spend money on the things that are most important to us while letting go of the rest. By letting go of the things that don’t matter and focusing on those that do, we’ll be spending a lot less while living better and more meaningfully.

Here’s an example: You are excited to host a holiday party this year but have estimated that the cost would be prohibitive. What’s most important to you about the holiday party? You decide it’s the quality time spent with friends and family and the holiday-themed food and cocktails. To make your holiday party fabulously frugal, you would want to honor the time spent with loved ones as well as the holiday-themed treats. Maybe you decide to have everyone bring their favorite seasonal dish or host a cocktail party rather than a full dinner. When we are clear on what’s most important, we can create win-win creative solutions!

Revisit the price.

Now that your holiday season is going to be fabulously frugal, you’ll want to revisit the price. Make it a game. How little can you spend while still having and experiencing everything that’s most important to you? Always build in a bit of a buffer in case your plans or prices change.

Decide on a timeline.

When would you need to have the money available in order to execute your vision? For example, you might plan to take a trip in December. When would you need to have the money available in order to pay for the flights? You might plan to buy plane tickets many weeks in advance. Create a timeline that includes when you will want to pay for each part of your holiday vision.

Break it down by week or paycheck.

How many weeks or paychecks do you have remaining, according to your timeline? Let’ say your holiday party will cost $300 and you have two paychecks left until you will need to have access to the money to prepare. You’d decide to put aside $150 per paycheck for the next two paychecks so that you have $300 for the party by the time you need it. Voila!

Separate and automate.

After the careful planning, it’s time to separate and automate. Where will you keep your holiday savings? Set up that per paycheck amount to transfer automatically to your holiday savings fund. This way you can rest assured that it’s going to be there when you need it and it will make your life easy because you don’t have to remember to do it!

Plan for next year.

While the holidays are quickly approaching and you might not have enough time to prepare this year, plan in advance for next year. If you start setting aside money in January, you will have to put aside much less per paycheck to reach your goal than if you start a couple of months in advance. The earlier you start, the less you’ll feel the impact in each of our paychecks. For example, if you plan to spend $1,000 per year during the holidays and you only have two paychecks to save up, you will want to put aside $500 per paycheck. If you start in January and have 22 paychecks until you start spending on the holidays, you’ll only have to put aside $45 per paycheck to reach your $1,000 goal. Why not make it easier on yourself?

The holidays can be an expensive and stressful time of year when it comes to our wallets. Create and execute a plan so that you can spend this special time and your energy on what’s most important!

Ashley Feinstein Gerstley is a money coach demystifying the world of money and personal finance. Get her exclusive how-to guide “30 Days to Financial Bliss” (, free for Military Transition News readers.


Return to November/December 2016 Issue