The Mommy Guide to Managing the Holidays Like a Boss! For less Stress, More Organization, and Less Holiday Debt!

Hey Boss Mom! Here is your guide to Managing the holidays like a boss! I will show you the way to less stress, more organization, less chaos and less holiday debt! Follow my tips and your Holidays will be smooth, simple and stress-free!

Let’s get you organized and jolly for the upcoming holidays! Make your list and check it twice, and grab your bonus daily planner guide & FREEBIE printables too! All from Little Hat Family. Now let’s get to the good stuff!


You can also check out my helpful holiday blog post:

15 Unique Gifts for Christmas, $20 Gift Ideas!!!

 Pin and Save for Later!The Mommy Guide to Managing the Holidays like a Boss

Organized Holiday Tip #1: Use your Planner!

Utilizing a planner will change your whole day for the better. You will be able to stay on track for the day and for each week. When I stay focused and inspired, I am even be able to keep in mind the larger picture goals for the months, seasons and years!

It’s easy to get caught up in the excitement, pressure and the stress of the holidays. I try and keep in mind small goals I want to achieve each day, and remember I am doing my best! After all, this holiday season will come and go, but life keeps moving! What are your larger goals? What project are you trying to jump into? How can you tangibly work towards them? Most importantly, what goal will you wish you started working on- in a year from now?

To keep on track, in my own planner: I mark any important meetings, outings, play groups, appointments, doctor visits, bills, paychecks, Yoga class, family events, rehearsals, time with friends, dinner plans, babysitter schedule and anything else important to our week! This is what works for me, and keeps our house organized! Find a system you like, and make sure it’s all in there! Keep communication open and adjust as you go.

Utilizing a planner is a wonderful way to stay on track with: your holiday schedule, family visits, work events, travel, gifts, holiday finances and regular bills! My tip is to stay consistent and make note of everything. I feel in control when I have my week laid out clearly. In the words of Leslie Knope, I love to be: “Jammin’ on my Planner“. (Parks and Rec.)


simple budget

Tip #2: Set your Holiday Budget!

Talk with your partner (and possibly even include your kids as well, if they are age appropriate) about your financial limits and goals this holiday season. My suggestion is to maintain a strict amount for your TOTAL holiday budget. It should be realistic, attainable, and hopefully not breaking the bank. This is the time to be honest with yourself. You don’t want to be regretting your holiday overspending once the January bills come in! What can you really afford? What is your cap?

To help calculate your holiday spending, you should first know what your regular monthly budget looks like. It is extremely important to track your budget and bills now. You should know what is coming in, what is going out, and the exact dates of all of your bills. Are you already stressed out? Don’t worry, you are here to get help now! Great job! And I am here to keep it simple and to help empower you, boss mom! I’ve got you covered. I’ve got your quick and easy budget guide. This will change your game completely! Take control of your bills and your debt. I can hep you with one click!

Tip #3: Shop at the thrift store for party goods, gifts, housewares, decorations and clothes!

Tip #4: Christmas shop early and spread it out!

I usually start my holiday shopping in October. Generally, my plan is to buy 1 or 2 individual gifts per week until mid December.

Tip #5: Have items delivered online!

early and spread it out!

Tip #6: Use coupons! And sales!

Shop sales and coupons for departments stores, restaurants, online shopping, big chains, and even local businesses!

Tip #7: Suggest a Grab bag or Secret Santa gift setup in your family.

This will save you from having to buy for everyone. Maybe you can just get a great gift for one person, or a small grab bag amount of people.

Tip #8: Spread out your fun events for the family

This will ensure a less stressful holiday packed into just a few crazy days. Spread it all out throughout weeks. Maybe 1 fun activity or outing per day! I know with my baby, one outing per day is all he can handle.

Tip #9: Schedule your outings and events when kids and babies are the happiest during the day

Tip #10: Prepare for travel

don’t fight it. it’s going to happen. Flying, driving, waddling with a penguin… you will more than likely be traveling for family events this season.

Tip #11: Get Your Holiday Cards out early!

I even make my own, to save a lot of money. I use a general photo app to make my own photo collage. Then I can even add a seasonal greeting and a few snowflake graphics, with our family pictures. From there you can load it into Walgreens and print this as a 4×6 or 5×7 photo. This trick will actually cost you pennies on the dollar versus buying a stack of personalized photo cards from any of the printing services.

Tip #12: Get your Holiday outfit from the thrift store or a discount store like Marshall’s.


Tip #13: For immediate family: I usually stick to one purchased gift, and one home made gift.

Limiting gifts is not only cost efficient on your budget, but I always feel more appreciative of one great gift versus getting a bunch of little ones I don’t care about.

Tip #14: ‘Need, Read, Play and Stay’:

I like this rhyme for reminding myself that we practice minimalism. I like to focus on something that he may need (like a new car seat, or larger pajamas), a gift for him to read, a new educational toy, and “Stay” refers to an outing. We can go to the children’s museum, the aquarium, or even a stay in an indoor water park! For my family and children, I plan to implement this rule for gifts now and in the future.

Tip #15: Make the food you Make Best (Whatever it is)

For the Holiday parties and events, make your best dish, whatever it may be! If it is a delicious dessert, make that! If it is homemade bread or muffins you can bake those! It may even be a casserole, a yummy cheesy side dish, delicious deviled eggs, famous cookies or even a dip! (I’m hungry… hahaha). Maybe you have a traditional dish you like to cook in your house. Whatever you love to make: everyone will enjoy that! It’ll show a loving, personal touch to your holiday parties! Home made items always beat out anything store bought!

Still, I won’t judge if you throw some Oreo cookies on a platter… I’m not even mad! 😉


Tip #16: Pot Luck Holiday Dinner:

Assign sides or desserts, or any part of the meal to your extended family. Have everyone chip in and help (with the work and the cost)!

Tip #17: Take pictures and videos during the holiday season!

This is my absolute priority! I’ve got to get those pics! (at Harry’s birthday part I didn’t even eat dinner I was so focused on pictures. hahaha. Oh well. I got great, wonderful pics as least!)

Last year for Christmas, I took a picture of Harry every single day for the holiday season. (Starting on December 1st). I called is “25 Days of Christmas” and posted a photo to Facebook every day. He was only 2 months old, so we were all able to see him change over those weeks! It was so fun setting up all of the little pictures, and thinking of cute poses! He was a good sport… he was a newborn, he didn’t have a choice. hahaha.  😉 My whole family really got into it! Here are some pics from last year, and I plan to do this again this holiday! It truly lets me savor the moments we had, all year long!


LAST Tip #18: Write your baby a Special Christmas Letter!

Here is another wonderful way to give your child a truly unique gift for Christmas: Write him a keepsake letter he can have forever! This is especially wonderful for family members across the world, as well as your elderly relatives. This could be a gift he could treasure for years to come!

I have made it simple to write your own letter to your baby: Grab my Guide! This Letter would make a unique and wonderful gift for your baby, to treasure for years to come!

Write a letter to your baby


There you have it! 18 awesome tips to have a more relaxed, organized and stress-free Holiday season.

Enjoy with your loved ones! Savor the miracles you are grateful for in your life. Tell your babies you love them! The season will come and go, but the memories and love should last forever.

What traditions do you share with your family and children? I would love to hear from you. Comment below!


Since you love Organization… let’s take it one step further! Dominate your finances this year! Enroll in the FREE, super easy, email course for basic budgeting, bills and guide to handling your debt and finances! Join the Boss-Mom revolution with actionable steps you can implement today! My free Printables and step-by-step guidance will give you the confidence to organize your bills once and for all, so you can get back to those precious kiddos! Enroll Here:



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Hi, I am Kelly! Creator and administrator of Little Hat Family, I absolutely adore my squishy, smiley, 10-month old son, Harrison (Harry), and my kind and cooperative husband Stefan. Our little millennial, hipster family lives in Chicago and yes, we do love hats!
As a professional nanny for 11 years in Chicago, and now a new mommy myself, I have picked up so much useful, modern, mommy advice and life hacks! I would love to pay it forward to my fellow mommy tribe!
I also love creating thrifty projects, organization, an organic lifestyle, dancing, blogging, cooking and spending time with our large families!
I absorb every drop of Mama advice I can get; and I’ve created some Modern Motherly advice along the way! We Modern Mommies have to stick together! Subscribe to my blog today, and let’s connect our Modern, Family Tribes! ~Kelly


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