Holiday Happiness: How to Plan Ahead and Find Joy Without the Stress EP#117

Episode Summary:

The holidays are just around the corner—are you ready? Whether you’re the type to have your Christmas shopping done in September or you prefer to wing it, this episode is for you! Today, we’re diving into how planning ahead can transform your holiday season from chaotic to calm. With practical tips and personal stories, you’ll learn how to set boundaries, create new traditions, and design a holiday season that brings more joy and less stress.

Inspired by Brené Brown’s approach to family vacations and my own happiness journey, I’ll show you how asking the right questions—of yourself and others—can lead to more meaningful holidays. This episode will help you reflect on last year, prioritize what matters, and prepare for the holiday season with intention and balance. Let’s make this year’s holiday season your best one yet!

In This Episode, You’ll Learn:

• How planning ahead can help you avoid holiday overwhelm
• The importance of self-awareness in creating a holiday that works for you
• Why asking your loved ones what they really want can lead to less stress and more joy
• How to set healthy boundaries before the holidays start, so you can enjoy the season on your terms
• Simple, actionable steps to reflect on last year’s holiday and plan for a better one this year

Resources Mentioned:

• My recent conversation with Diane Sorensen on setting healthy boundaries: EP#117
• The Brené Brown book I referenced about family Venn diagrams: The Gifts of Imperfection

Quotes from the Episode:

• “Planning is bringing the future into the present so that you can do something about it now.” — Alan Lakein
• “What if this year, you’re the one brave enough to try something different? You might just find more joy and peace in a simpler, more meaningful holiday.” - Bona Normandeau

Join the Conversation:

I’d love to hear how you’re planning for the holidays this year! Share your thoughts with me on social media or in the comments below. What traditions are you keeping, and what new things are you trying?

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Transcript

Are you the type of person who starts shopping for Christmas gifts in September, or do you find yourself winging it, hoping this year goes smoother than the last? Whether you’re a meticulous planner or more of a last-minute adventurer, one thing is for sure—the holidays are coming, and they can either fill you with excitement or overwhelm.

In this episode, we’ll explore how taking a bit of time to plan ahead can transform your holiday season. Whether it’s navigating family gatherings, creating new traditions, or setting healthy boundaries, there’s a way to make this year’s holidays the best yet. Drawing inspiration from a powerful story by Brené Brown, we’ll dive into how asking the right questions—of yourself and those around you—can bring clarity and joy to even the busiest season.

From identifying what truly matters to avoiding the stress of unrealistic expectations, we’ll uncover practical tips to help you enjoy more of the good stuff, and less of the overwhelm. Because when you plan ahead, you’re not just organizing your calendar—you’re setting the stage for a holiday that leaves you feeling happy, rested, and ready for the year ahead.

Well, I do not have my presents done by September, far from it, but I have evolved from the fly by the seat of my pants and now I am much closer to the planner side of things.  I have found planning and reflection and review a big part of my happiness and the holidays is no exception!

Today I want to talk about the holidays…because they are coming…even if you are a head in the sand person, you cannot miss the Christmas displays that have started popping up everywhere!  In this episode, I’m going to share the planning tools and insights that have helped me create holidays that actually bring joy instead of stress. By the end, you’ll have a clear plan to make this year’s holiday season better than ever."

I remember a few years ago I was reading a Brene Brown book, and she talked about creating a Venn diagram for their family holidays.  She interviewed her husband and each of her kids and asked what they wanted to get out of their summer vacation.  When she looked for the overlap, she was shocked to see that a simple get away to a local lake with swimming and hanging out as a family would bring the most joy to all of them.  

Before doing this activity, she talked about spending hours trying to create the perfect holiday for everyone.  Dealing with the crowds and cost of Disney and of course the travel to get there can’t be discounted.  When she realized that her family would be the happiest to rent a cottage at a lake close to home she wished she’d done this exercise sooner!

That story really struck me.  I mean, being a reformed people pleaser, holidays can be super stressful because you are taking everyone’s needs into account.  But rarely did I ask what my family wanted.  I just assumed they wanted the same as last year, or something worthy of bragging about when you came back after Christmas/spring break or summer holidays.

How many of us get caught up in

1.       What has always been done

2.       What we think our family wants

3.       Doing something over the top so we have great stories to tell

When really, if we spent a few minutes asking ourselves what we really need this Christmas, we might find we would make completely different decisions.

By planning ahead we can do our best to set up a holiday season that doesn’t leave us feeling awful.  We have time to set up events with people that matter to us.  When we leave things to the last minute, coordinating can be harder and we might just hit the holidays and sleep for two week.  AND if that is what you want, great…but knowing that is what you want and deciding to make it happen ensures that you don’t come out of the holidays feeling guilty because you “think” you should have done more, or something different.  If you take some time now to decide what you want your holidays to be, then you have time to set your plan in action, anticipate how awesome your holidays will be AND you also have time to prepare yourself if you are going to have some events that are part of the holidays but are maybe not your ideal situation.  

What do I mean? 

Well, as part of my happiness journey I realized that despite loving people and being very social…I’m actually more of an introvert that an extrovert and I love people, but I also NEED quiet time without too many people to recharge.  After years and years of constantly being surrounded by people the majority of the time, I finally realized that I show up as my best self when I’ve had plenty of quiet time, alone or just with my husband and son.  Crowds are stressful.  Noise is stressful.  Groups with multiple energies is overwhelming.  

• So when I think about being around people, I have to prepare so that I show up as my best self…not the cranky overwhelmed version of myself.  : 
• "What about you? Do you thrive in social settings, or do you need space to breathe? This is key to planning a holiday where you don’t end up feeling drained."

One of my favourite happiness tools is self-awareness.  So many of us get so caught up in the busyness of life that we rarely slow down and ask ourselves if we are doing what we really want to do.  And are  we focusing on what really matters to us.  Those realizations don’t usually just happen…you need to carve out time for them.  And by time, I don’t mean hours, I mean you can make a big difference to your holidays with just a few minutes of reflection and planning.

Here are my tips on making this year’s holiday the best you can make it:

1. Tip 1: Reflect on Last Year – "Spend 5 minutes thinking about what you loved and what didn’t go so well last holiday season. This gives you a blueprint for what to prioritize and avoid this year."

·         Of the things you loved…ask yourself how you can create more of that this year.

·          

1. Tip 2: Ask for Input – Get your family or friends involved by asking them what made last year memorable or challenging. Be open to the idea that simpler might be better.

·         If you live with other people, as them to do this activity too.  You might be shocked as to their answers.  I know when we did this exercise with our son last year my husband was surprised with one of his answers.  The cool thing about knowing about what is important to everyone, it is easier to make a plan that is a win for everyone.  And if you can’t get a full win for everyone, maybe you can get a comfortable compromise.  Don’t assume you know what everyone wants.  Taking time to ask helps others feel valued and is also a great skill to learn…don’t expect everything to work out, take some time to analyze what you loved about last year and what you want to go better and then plan to make this happen.

1. Tip 3: Set Boundaries Early – Refer to your conversation with Diane Sorensen on boundaries and why setting them before the holiday craziness hits can make a world of difference.

§  Of the things that didn’t go well…ask yourself how you can better navigate that situation.  Do you need to change expectations of yourself, of your family of your work as to what you are willing to do and not do this year?  I am going to refer you back to a great conversation I had with Diane Sorensen a few weeks ago about boundaries.  Her definition of boundaries is what are you willing to do or not do?  If you plan ahead, you will have a better chance of setting healthy boundaries.  They are easier to implement if you have thought about them and you have your list of why you are making certain decisions.

·          

1. Tip 4: Prepare for Less-than-Ideal Situations – Not every gathering or event will be perfect. Plan how to manage these moments with grace, whether it’s shortening a visit or shifting your mindset to accept things as they are.

One of the biggest things I hear form people is when they struggle with what they perceive as being expected of them.  They don’t come out of the holidays satisfied, rested or anywhere near close to happy because they keep doing the same thing, they think is expected of them every year.  

What if this year, you are the person who is brave enough to shake things up and try something different?  You might just find more joy and peace in a simpler, more meaningful holiday."

Disclaimer, there are people around you who have never done this and don’t like change.  You will have to ask yourself if you are going to let their opinions and crankiness affect you.  If you are going to accept that, then just go into this holiday season already knowing you are choosing to give in and make the best of it.  Maybe this year, your boundary is that you spend one less day with that person, or you spend less time stressing about it because you know its coming…and you’ve decided that it is what it is and for this year, you are going to go into it with a positive attitude.

I promise that even if you only spend 5 minute son this self-awareness activity, you will notice something different in your holiday.  This year it might just be awareness…but it also might be an amazing discovery of a new tradition for you!

Remember, time spent on planning in never wasted.  And I would just like to add to that, that time spent on learning from your experiences is never wasted.  EVER.  What can you do this year to make your holidays even better?  What do you want from this year’s holiday?  Rest?  Relaxation?  Family time?  Adventure?  Renovations and projects?  Studying?  Quiet time?

Whatever it is, take some time and look for your best scenario and then figure out how to incorporate more good into your holidays and plan for the tough stuff so you can help yourself through the struggles.  Even small steps in planning and awareness can shift the holiday experience from chaotic to enjoyable.  

I love this quote by - Alan Lakein

"Planning is bringing the future into the present so that you can do something about it now."