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5 Things to Do Now for a Happier Holiday

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Today I am happy to welcome back my friend Cherie Lowe from the Queen of Free, who has graciously joined us here at LWSL as a regular monthly contributor. Cherie is the author of the amazing book, Slaying the Debt Dragonwhich she wrote after paying off more than $127,000 in debt! I am so excited to have her bringing her wealth of knowledge & experience on this subject to LWSL–please join me in making her feel right at home!

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Happier Holiday | Holiday Planning | Stress Free Holiday | Tips For Happier Holidays

This is a Guest Post from Cherie at Queen of Free

Look. I can’t see through the other side of the screen but I know some of you are glaring at me right now. I can even hear what you’re saying (even if it’s just in your head).
Quit talking about Christmas.

We haven’t even had Halloween yet.

It’s not even October.

Everyone just wants to skip right over Thanksgiving.

I mean, can’t you even be grateful before you start talking about gifts?!

I get it. And a part of me completely agrees with you. It seems like the decorations and the store displays creep out earlier and earlier each year. Before you know it, the aisles of your super-center will be bedecked with green and red in the middle of August.

However, as a family who has tackled and then paid off quite a bit of debt ($127,482.30 to be exact), I know what can happen if you don’t prepare for the holiday season. In January, you’ll hate yourself for overspending and maybe even borrowing to celebrate Christmas. You’ll wish you could travel back in time and make better decisions. You’ll long for a way to undo the financial damage you’ve done and you may never even recover from a lack of planning.

So while I’m not rushing the season, I’m basically future you, here to remind you that each year December 25th pops up on the calendar and to celebrate well, you need a blueprint to keep the happy in your holidays.

Happier Holiday | Holiday Planning | Stress Free Holiday | Tips For Happier Holidays

Have Difficult Conversations (Now)

Let’s be legit. Some of you purchase gifts for too many people. Passing presents around in a circle has gotten wildly out of control. You’re buying for your cousin’s aunt’s neighbor’s nephew. You drop $50 on the checkout clerk at the grocery store.

Don’t misunderstand me. It’s OK to be generous. It’s a wonderful thing to bless your friends and family with gifts at Christmas. However, it’s not OK to have zero boundaries.

But you can’t wait until December 24th or even 1st to have difficult conversations about gift giving. For some families it may even be too late in October if there are shoppers who begin their process midyear.

Time is on your side the earlier you begin to wade into the waters of who you are and aren’t purchasing gifts for this year. Looking for some strategies to open up the discussion? Check out this post on Uncomfortable Christmas Gift Giving Conversations.


Start Saving Money (Now)

I’ll be honest, I’d prefer you begin the process of building a holiday fund on December 26th. However, there’s still plenty of time to begin socking back cash so that you don’t have to spend money you don’t have this Christmas. You can choose to set aside a percentage of your regular paycheck.

Have unexpected funds come your way? Don’t blow through them. Bank them and keep your seasons merry and bright.

Make Extra Money (Now)

Again, time is on your side to help you make extra money to fill in the gaps you need to keep your budget balanced this year. Even if you can’t pick up a second job or seasonal employment, there are plenty of ways to rake in the dough.

Begin by sorting through your jewelry box to find any broken or unwanted gold pieces. I’m not talking about your great grandmother wedding ring. But you might be surprised at how much that necklace you never wear (or can’t wear because it snapped in two) is worth.

You can also sell other items in your home. From the treadmill piled high with laundry to the collection of baskets you have amassed to the décor items from three years ago, one person’s trash is truly another’s treasure. You could choose to have a garage sale during the pleasant fall weather. Or you could simply post pictures of items to Facebook, seeing if anyone is interested.

Books, clothes, kids’ toys – your inventory is much larger than you realize. For even more ideas, check out 5 Ways to Make Christmas Cash.

Happier Holiday | Holiday Planning | Stress Free Holiday | Tips For Happier Holidays

Begin Budgeting (Now)

A handful of years ago, I would have groaned and made ugly faces at you if you told me I needed to budget for Christmas. Budgets and I did not get along. In fact, I saw budgets as killjoys and ugly ogres.

After six years of faithfully forecasting our finances, budgeting is now my best friend. By the way, I found that merely changing my lens on the process and referring it to as forecasting instead of using the “b” word gave me a better attitude. Instead of focusing on what a budget limits me to do, I recognize that a budget actually allows me to accomplish so much more.

Think through all of the areas of spending possible. Believe it or not, this might be easier now than when the holiday approaches. From food to photos or even fashion (you might need a new ugly Christmas sweater after all), holiday spending reaches far beyond gift giving. A little distance will allow you to drill down each category and target an amount you’d like to stick to this year. Don’t know where to begin? Check out these free printable Christmas budget forms.

Pledge to Remain Debt Free (Now)

In the fall, everyone’s an idealist. We won’t overspend this year. We won’t borrow money to celebrate a holiday. We won’t over eat or over do it or over commit.

Somewhere mid December, all of our “won’t”s turn into “Why not?”s and then in January we’re left with only the “Why did I?”s. This is precisely why you should take a pledge to remain Debt Free this Christmas season now.

Long before you purchase your holiday ham or turkey, in a time before Black Friday ads and irresistible deals, make yourself a promise to refrain from using plastic to make your purchases. I love this free printable because I can put it on my refrigerator and in my planner for a visual reminder of my goal. It anchors my soul and keeps me focused.

Pen your own promise or borrow mine, but dedicate yourself to the pursuit of remaining debt free this year.

You don’t have to rush through the days that lead up to Christmas. However, you do need to use the time you have to ensure this holiday season is truly happy. Solomon – the wisest man to ever live – once said “Careful planning puts you ahead in the long run; hurry and scurry puts you further behind.” Proverbs 21:5 The Message

There’s no need to hurry and scurry. Plan your holiday spending to safeguard your bank account and your soul.

Happier Holiday | Holiday Planning | Stress Free Holiday | Tips For Happier HolidaysCherie Lowe is an author, speaker and hope bringer. Her book Slaying the Debt Dragon details her family’s quest to eliminate over $127K in debt in just under four years. As her alter ego the Queen of Free, Cherie provides offbeat money saving tips and debt slaying inspiration on a daily basis.



Happier Holiday | Holiday Planning | Stress Free Holiday | Tips For Happier Holidays


  1. September 25 at 11:22AM

    Another thing you can do is come up with some alternative means to get what you want. For instance, this year I learned that you can get BRAND NEW Christmas cards at the thrift store for DIRT CHEAP. I got 100 for under $3! 🙂

  2. September 25 at 01:46PM

    Making extra money now can make the holidays so much easier and less stressful. This way you have more money for the things you may want to buy, and it may help lower some of the money stress you may have later. Great post!

  3. September 25 at 09:57PM

    I try to complete my Christmas shopping throughout the year, sometimes even starting the day after Christmas. It’s my goal to be done by December 1 so that I can enjoy the holiday season. I stockpile presents throughout the year as I find great deals or clearance items that I wouldn’t be able to find at the last minute. The trick is to use a gift tracker, like you suggested! Santa’s forgotten a present, so I now use my checklist to make sure that everything is wrapped and ready, too!

  4. September 26 at 11:38PM

    We have 3 little kids and more toys then they could ever need. We started asking family to give them experiences and activities. They’ve given them tickets to the zoo, and personal lessons on how to sew or bake. I love this change because not only do we not accumulate more toys, they make memories and become closer to those that love them.

    • Liz
      September 29 at 04:46PM

      I love your idea about giving kids experiences and activities as gifts instead of toys! i´ve been trying to come up with the perfect gift for my 3 lovely nephews but as they get older their presents become more and more expensive, i will definitely make them some coupons to spend time with (movies, the zoo, going to the park and so on…) i might even do that for grown ups as well! 😀

      • Missy
        November 6 at 09:21PM

        There is a place called Skyline here in Orlando. It is a trampoline place that you purchase time on in half hour increments. We started with a half hour and added another 30 mins after seeing how engaged they were. The whole hour for 2 kids was about $55.00. So if you average $20 per nephew you have already saved $5. We started doping the experience instead of toy thing with our grandchildren and it totally works! I bought marshmallow guns and lots of marshmallows for our annual Dec 24th bonfire. This year I think we will do bubbles!

  5. September 28 at 09:00AM

    Love the honesty in this post! It was so good for me to read now.

  6. October 22 at 10:57AM

    This is a great post that explains a lot of people’s money spending issues at Christmas time.
    I come from a large family and we started doing a grab for only our kids every year. The adults bring the food to the get together and the kids each get a gift. This avoids over spending for everyone and limits the amount of gifts we have to buy for one another.

    Thank you again for this post!

  7. Missy
    November 5 at 07:51PM

    As my kids have gotten older I have tried to make their “Santa” present something we do together. Concert tickets for my daughterI didn’t realize they didn’t have seats at a Black Veil Brides concert lol. I think she enjoyed the crowd more than me but it was great memories) Tickets for Lego Fest for my 8 year old. They whole family loved that one. And they didn’t get “stuff” they didn’t need plus we had a great time

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