In this episode of Holiday Headstart, we dive into how understanding yourself through Gretchen Rubin’s Four Tendencies framework can completely change the way you plan for Christmas—and reduce your stress while you're at it. We break down each of the four tendencies—Upholder, Questioner, Obliger, and Rebel—and explore how your response to expectations shapes your ability to plan, prep, and actually enjoy the holidays. Whether you love a checklist or resist all structure, this episode will help you create a holiday planning system that works with your natural tendencies, not against them.

We’ll share personalized tips for each tendency, including how to build in flexibility, avoid analysis paralysis, use accountability to your advantage, or embrace your inner maverick. If you’ve ever felt like your holiday prep always falls short or leaves you burnt out, this episode might just be the mindset shift you need. Plus, check the show notes for a link to Gretchen Rubin’s quick Four Tendencies quiz so you can discover your own type and start planning smarter today!

Episode Highlights:

[00:01:03] - Tradition Spotlight on a Today’s Your Special Day plate

[00:02:51] - Introduction to the 4 Tendencies

[00:08:26] - Using your tendency to thrive

[00:10:16] - Tips for Upholders

[00:12:38] - Tips for Questioners

[00:15:49] - Tips for Obligers

[00:19:07] - Tips for Rebels

[00:21:37] - This week’s Get A Headstart Tip for getting holiday tasks done in advance

[00:24:37] - What’s on our to-do lists this week

[00:27:47] - Our Nice Lists

Resources Mentioned:

• Gretchen Rubin’s 4 Tendencies Quiz
• Kitchen Shears
• You Are Special Today plate
• Grab The Holiday Headstart Playbook
• Take the Holiday Profile quiz
• Follow on Instagram @theholidayheadstart 
• Leave us a review on Apple Podcasts! 

If you enjoyed this episode, you'll love this too:

• Episode 25 - Why You Should Write Yourself a Permission Slip for the Upcoming Holidays

And we are here to help you do the same. Join us each week as we share how with a little planning and a little prep, you can ensure that the days that make life special don't become the days that make you stressed. You can check out the show notes@theholidayheadstart.com. Ready to get a headstart on your holidays.

Let's go.

Heidi: But first, we have a tradition Spotlight Traditions are an important tool in building a healthy, happy, connected life.

This week we have a tradition from Emily about a special day plate.

Tell us more about this, Emily.

Emily: Well, the special day plate is a tradition that I have carried over from our mom. We had a cute version that I think probably came from Current magazine, don't you think, Heidi?

Heidi: Oh yeah. Wow. That's a throwback.

I bet some of you had it too.

I actually think maybe one of the aunt sent it to her for.

Her birthday. Oh, kind of

rings a bell.

Emily: That's a good gift. Hey guys, this idea I'm gonna share would be a good gift for your sister if she's got kids. Okay, so the one that I have now is a little nicer and a little cuter and definitely more expensive. I'll link to it in the show notes if they still make it.

I actually think those moments would probably be more meaningful if I would remember to pull it out then. So I'm glad that I'm thinking about this out loud right now. Or you could just

Heidi: do it 'cause it's a random Thursday. Obviously if you have children, you're gonna have to have a system to do this fairly.

Yes. Because you know, they will keep track of, wait, he just got up just because I and I haven't, you know? Yes. So if you're gonna do it for one, make sure you commit to do it for all. But it would just be lovely to be surprised at dinner or breakfast and just like, oh, it's a special day 'cause it's a Thursday and I'm in it.

Emily: Yeah, absolutely. I love that.

Heidi: We would love to hear more about your favorite traditions. So come join us on Instagram at the holiday head Start.

we love the Enneagram and we are both ones, which I think would surprise no one. And we definitely feel like we've learned a lot about ourselves from the Myers-Briggs type indicator. And we are both IN fjs if you know that one. But there is one framework that we feel has helped us know ourselves and others better than any other, and that is Gretchen Rubin's four Tendencies framework.

Heidi: We are longtime fans of Gretchen Rubin. You might know her from her decade long podcast. Happier.

Emily: Which she hosts with her sister.

Heidi: We love a sister podcast or from her books like The Happiness Project or Better Than Before.

She also has a book called The Four Tendencies, where she lays out how our responses to expectations impacts our lives in major ways.

It's a game changer for understanding why some planning methods stick while others fail miserably. So can you break down the four tendencies for us, Heidi?

Heidi: Oh, I would love to, I could talk about this all day. So the Four Tendencies is a framework that looks at just two things. Unlike, you know, the Enneagram that y'all have, all the nine different things.

We're just looking at two things, how you respond to inner expectations and how you respond to outer expectations. Inner expectations are things that you expect of yourself, like your personal resolutions and goals. Outer expectations are expectations that are placed on you by other people, like deadlines and assignments.

Emily: If you wanna know what tendency you are, definitely keep listening because you may recognize yourself in the descriptions we're about to share. But if you want to know for sure, check the show notes for a link to Gretchen Rubin's. Really quick, four tendency quiz.

Why don't you kick us off by telling us about Upholders, Emily

Emily: Upholders respond easily to outer and inner expectations. I'm guessing we have a lot of upholder listeners because we're the sort of personality who thrives with the checklist. And you know, we love a checklist around here. Upholders are usually good at following guidelines and schedules, but might find it challenging to be flexible when things don't go according to plan.

Heidi: And you know, spoiler alert, we are both upholders. Yes. I probably pretty obvious.

Emily: Yeah. Don't think that's gonna be a shock to anyone.

Heidi: We are great with a plan, but not so much with a pivot. Flexibility is definitely not a trait that I think anyone would ascribe to me. I'll let Emily speak for herself on that.

But, a challenge for me as an upholder is that I often feel compelled to follow arbitrary rules, even when I know it would make sense not to,

Heidi: And that brings us to our second tendency, questioners.

Emily: Yeah. Questioners, as their name suggests question all expectations. They can meet the inner expectations they place on themselves, but when it comes to someone else's expectations for them, they need a logical reason for why that expectation matters, and they really dislike arbitrary rules.

Heidi: But if they can see the value in an expectation, then they can accept it. One of questioner strengths is they do well analyzing information and making decisions.

Emily: And that brings us to the third tendency, obligers. I'm pretty sure I've heard that this one is the most common tendency.

So can you tell us about Obligers Heidi?

Heidi: Yes. Obligers are people who can easily meet outer expectations, but they struggle to meet their inner expectations. They may have a hard time saying no to requests from others, which can lead to burnout and exhaustion.

Heidi: One of the biggest strengths of Obligers is that they are reliable.

If they say they will do something, they are very likely to do it. Obligers are often easy to work with and they are great to have on your team.

Emily: But the downside is that they struggle to meet their inner expectations or their personal goals without some kind of external accountability.

The good news about that though, is there are lots of ways to add in that accountability to help obligers with their inner expectations.

Heidi: And that brings us to our last tendency. The rebels. Rebels, resist all expectations, inner and outer alike. If you are a rebel, you might value your independence and creativity, but find it hard to follow strict guidelines or routines.

Emily: It can be difficult for rebels to work with others. They can feel a lot of joy in disregarding rules. And rebels like to prove people wrong.

Emily: If you are a rebel or know a rebel, one thing to be aware of is that the advice that works for other tendencies doesn't work for rebels, but they can often meet expectations by thinking of their core identity and how meeting an expectation will help them live as their authentic self.

Heidi: Alright. What does all this talk about tendencies and expectations have to do with holidays?

Well, a lot really, for starters, knowing yourself better just helps you thrive more as a human being. And we all know that taking care of yourself benefits you in every aspect of life.

Emily: But what's fascinating is how these tendencies affect something as emotionally loaded as holiday planning.

Understanding your tendency is about giving yourself the tools you need to plan in a way that works with your natural inclinations, not against them.

Emily: I know, and I don't even know if it's possible to change your tendency.

It probably isn't.

Heidi: Yeah. It seems to be pretty hardwired into our systems. So instead of trying to force ourselves to fit what we see as a more appealing mindset, our goal is to know ourselves better so that we can set ourselves up to thrive just as we are.

Emily: Exactly. Instead of feeling bad about not being a naturally organized upholder with a color coded spreadsheet, which I'm an upholder and I'm not naturally organized or color coded all the time, either you can create a system that plays to your strengths regardless of your tendency.

Heidi: Our goal at the holiday headstart is to intentionally plan a little and prep a little so that the days that make life special don't become the days that make us stress. But the key to making that happen is the hard part. It's actually making it happen. And if you don't know what circumstances will allow you to thrive, you're going to end up with good intentions that just

Emily: So let's look at each tendency and talk about how they can approach holiday planning throughout the year, because we all know waiting until December is a recipe for stress. Oh, and burnout. And credit card debt. Yeah. All the things we're trying to avoid. So let's get started.

Heidi: Well, let's circle all the way back to Upholders.

They're good at planning ahead and sticking to schedules. They respond well to both inner and outer expectations, which makes year-round Christmas prep a perfect fit for an upholder,

Emily: because upholders can get lost in the details. The key is creating a structured system that breaks Christmas down into smaller, manageable tasks, which makes sense since you're listening to a podcast from a couple of upholders who try to do just that.

Emily: Yeah. In this quest for optimization, we can burn out trying to meet all the expectations.

Even the ones no one actually asked us to meet.

Heidi: Oh, I have been there. Oh. So our tip for holders is to create structure. Yes. But remember that spontaneity and joy are important parts of the season Two. The point of structure isn't to get everything done perfectly. The point of structure is to give joy space to come to the surface.

Emily: If you're an upholder, give yourself permission to deviate from the plan. Sometimes give yourself permission to let some things go, maybe even scheduling some unstructured Christmas joy time. I know that sounds counterintuitive, scheduling spontaneity, but for upholders, it can be really effective.

Heidi: Flex time in your holiday to-do list.

Emily: That way Christmas doesn't take over your entire year, but you still get the benefits of advanced planning.

If you want some guidance with that project, look back at our podcast episodes from this year where we're giving you five small holiday related tasks that you can do each month.

Heidi: Okay, next up are questioners. The but why are we spending $25 on a secret Santa for someone we barely know Kind of people.

Emily: Yeah. These are our deep thinkers who want to know why they're doing something before they commit. They meet inner expectations, but resist outer ones unless they make sense

Heidi: for our questioner listeners. Emily, how can they approach year round Christmas planning? For questioners, everything starts with why?

Emily: Why spread Christmas prep throughout the year? Well, because research shows it reduces financial stress, allows for more thoughtful gift selection and prevents last minute panic.

Emily: Yes, and for our questioners, maybe the quintile system would help you keep on track. Use January and February for reflection. Analyze what creates the most meaningful holiday experience. Use the post holiday journal pages in the holiday headstart playbook to track which gifts were actually being used months later. And note which traditions generated the most positive feedback.

Heidi: Questioners, do love data-driven approaches as you move into the next quintile, March, April, and may figure out what you want from your holidays, June, July, and August are the perfect months to get your planning underway, and that leaves September and October for putting all of those plans into action.

And then you're gonna be in great shape for celebrating come November and December.

Emily: The questioners listening just said to themselves that this is an arbitrary system and you are right questioners. It is arbitrary. Split up the calendar and task, however makes the best sense for you.

Our system logically progresses from abstract reflection to concrete tasks as the holidays draw closer through the year. So use it as a jumping off point for tailoring your own even better, more efficient system.

Emily: Yes, questioners excel at optimization, but it's not all data and optimization. What pitfalls could questioners watch out for?

Well, the biggest danger for questioners is definitely analysis paralysis. , they can get so locked into researching the perfect approach that they never actually implement anything.

If you're a questioner, who knows that trap? Try setting research deadlines and embrace the concept of good enough.

Give yourself permission to make decisions without perfect information.

Instead of the alternative, which is spending weeks hunting for the absolute best option.

Emily: Also, give yourself a deadline. Decide I'll research gift ideas for two days, then make the best choice and move on. Done is better than perfect. No hairdryer is so fabulous that it's worth stewing over for three months.

Heidi: Oh, absolutely not. And remember that not everything about Christmas needs to be logical or efficient. Sometimes traditions have emotional values that just can't be quantified.

Emily: That's a hard but important lesson for questioners. One more tip. Channel your research skills into finding unique deals throughout the year.

You'll satisfy your need for efficiency while getting holiday prep done.

Emily: Right.

Our darling Obligers are the people staying up all night making handcrafted gifts for everyone else but who forget to enjoy the season themselves.

Heidi: Because Obligers are so focused on others, planning in advance for the holidays can be a real struggle. If this is where you land, please know that you are not doing anything wrong.

You just need a different set of tools to make

Emily: planning work for you. The number one tool that Obligers need is external accountability.

Heidi: Yes, our obligers excel at meeting others' expectations, but they struggle with keeping promises to themselves. That's why all of those promises, like I'll start shopping early this year, rarely work. You need outside structure.

Emily: This may sound tricky, but Obligers are very clever at coming up with external accountability if they put their minds to it.

One suggestion might be to adopt the holiday planning buddy system.

Emily: The key to following through is making sure that your friend is counting on you to show up for her. She needs you to follow through so you can help her follow through.

Heidi: I love that. Another strategy for Obligers is remembering that others are counting on them.

Obligers have a gift of rising to the occasion, so they can often do things for others that they can't do for themselves. If you can consider your holiday preparation as benefiting others instead of yourself, it might be the motivation that you need to get started early.

Emily: If Obligers can tie their personal commitments to their commitments to others, it can be the push they need.

If you finish your Christmas shopping in November, you have more energy in December. If you have more energy in December, you're able to make the holiday special for your loved ones instead of drowning in stress and expenses.

The busy, tired, overworked person that you'll be in December deserves a break. Think how grateful she'll be to you, if you can help her out by taking care of some of her tasks Now.

Emily: Another tip for obligers is to learn to say, no. We know it's not natural and it doesn't feel good, but setting boundaries is such a gift to yourself and others.

Heidi: Yeah, not every event or expectation needs to be met.

This is especially true when it comes to the holidays, when it is physically impossible to do it all. One way to make this more manageable is to try reframing it. If you say yes to something you don't really want to agree to, by default you're saying no to something that would be more beneficial to you. Saying no to going to your coworker's ugly sweater party means you can say yes to a cozy family movie night.

Emily: If it feels like you're letting someone down, remind yourself that you're freeing yourself up to lift someone else up.

Meeting Christmas expectations does not need to be a full-time job.

Emily: Okay, let's look at our Free Spirit Rebels who want to do Christmas on their own terms. They resist being told what to do even by themselves.

Heidi: Honestly, we probably don't even have too many rebel listeners here, partly because Rebels make up the smallest tendency group, but also because our detailed planning system is likely to feel too confiding for them.

Emily: But if you do happen to be a rebel or have to plan the holidays with one, which is much more likely, you're going to need to lean into creativity. Many tools and tips that work for other tendencies likely will not work for rebels. They want to do what they want to do in their own way, in their own time, and if you ask or tell them to do something, they're very likely to resist.

Emily: Another strategy that might be useful for rebels is to consider the freedom that comes from having holiday tasks out of the way early.

Heidi: Yeah, rebels love, choice, and freedom. If you are a rebel, maybe consider that prepping now means freedom later. How much more enjoyable could the holidays be if you are free from a list of tasks and expectations?

Emily: I'm not even a rebel, and that's motivating to me. Rebels have a great strength of being able to do whatever they put their minds to. They just have to do it in a different way than most other people do.

Heidi: Now, by this point in the episode, chances are good that you know what tendency you are, but if you are not sure or you want more information, make sure to check out the link in the show notes to Gretchen Rubin's free quiz.

It's super quick and crazy helpful.

Heidi: Just remember that whether you're an upholder, questioner, obliger, or rebel, there's no wrong way to prepare for Christmas.

The key is knowing your tendency and using it to your advantage.

Emily: Let's make this the year you prepare for the holidays in a way that actually feels good, not just obligatory, and maybe you'll even enjoy the process. Imagine that.

Heidi: We would love to hear about your tendency and how you use it to work smarter, not harder. Connect with us on Instagram at the holiday head start.

Emily: Now it's time for a get a Head Start tip. Each week we leave you with a small actionable tip to help you get started on your holiday planning. This week's get a ahead start. Tip is schedule your Holly Day. Tell us more about it, Heidi.

Heidi: Well, we have definitely talked about this before, but I wanted to revisit the topic of Holly Days through the lens of the four tendencies.

Emily: And they don't just have to be Christmas tasks. Holly Days are a great time to figure out upcoming birthdays, family trips, other holidays, or any other event on the horizon that needs some planning.

Heidi: The hope is that instead of needing last minute panic to get things done by purposely setting aside planning time, we can actually enjoy these big events instead of drowning in stress and exhaustion. But the key to doing a Holly Day day is that you have to actually do a Holly day. This is where knowing your tendency can be so valuable.

Emily: So for our upholders, this technique is probably right up your alley. Maybe you can set aside a certain day each month for your holidays, depending on the family schedule. I use the third or fourth Sunday of the month for an hour or two of holiday planning.

Heidi: As a fellow upholder, one thing that I have found helpful is to have a list of tasks that I do each Holly Day.

Emily: If you're a questioner, the idea of a Holly Day might resonate with you or you might feel some resistance toward it.

If you need some help deciding whether or not scheduling a Holly Day is worth your time, try making a list of pros and cons. Seeing, what you stand to gain by doing it or by skipping it can help you optimize your system.

Heidi: For our obligers, you need outside accountability. Try teaming up with that buddy that we mentioned who also wants to get some planning done.

Maybe you could make it a regular thing where you bring your laptops to a favorite coffee shop for a couple of hours, one weekend a month.

Emily: I love this because not only are you making progress on important goals, but you pair that with spending some time with a friend or two.

The key is to make sure you actually use that time to work and not just catch up.

Ugh, being the boss of ourselves sometimes is the hardest part of getting things done

Emily: and for our rebels. Do what works for you if a regular Holly Day vibes with your personal identity as someone who is prepared or as someone who takes charge of deadlines so that the deadlines don't control you, this might work for you, but if not, you'll figure out something else.

Rebels are wonderfully inventive.

Heidi: Remember, it's not about forcing yourself to follow someone else's system. It's about finding a system that works for you. We're all about working smarter, not harder.

Emily: Now it's time to share what we're working on this week as a way to keep ourselves accountable and give you some ideas of what you can do in advance for your own celebrations. We're sharing what's on our to-do lists. Heidi, what's on your to-do list this week?

I could have used one yesterday after Easter, to be honest of you.

That was a lot to have to put together. And it was beautiful. Everyone you should be sad that you didn't get to see Emily's beautiful table. It was lovely. She did a great job. But it is a lot of work. So I don't have too much on my list yet. I'm just trying to think of like. Coming in the door on Christmas night, collapsing on the couch.

I always watch the holiday, , what do I want in that moment? And so, so far I only, I bought some fuzzy slipper socks, so that when I stand up and wanna, you know, wanna get a drink from the kitchen or something, I don't have to like put my slippers on. They're already on my feet. And then weirdly, I bought a pill case.

But, but now they're in a cute pill case, so I've got my special holiday, evening Aleve all set aside. But yeah, I gotta come up with a few more ideas.

Emily: Yeah. But it'll be so much easier. Just grab your little self-care kit and know that whatever you need is in there. Yes. Just plop it right next to me on the couch.

Heidi: Watched Jude lot. Fall in love, it'll be great.

Emily: Yeah.

Heidi: Sign me up. Okay.

Emily: Emily, what is on your to-do list? I am just bouncing back from Easter this week, so still have a, a few more serving dishes that didn't make it through the first round of dishwasher. Oh yeah. So gotta do another round today and just, you know, picking up the detritus from Easter baskets and, and such.

So that's, that's what I'm doing this week.

Emily: Yeah.

Heidi: We'll think of something

Emily: I suffer. It's really hard to come up with something that will like overcome the immense tiredness I think.

I think that something would be hiring a team. Yes. I think when you go, if you're the type of person that goes hard on a holiday. I think a lot of us crash hard after the holiday. Maybe you're one of those magical people that can go hard and keep going hard, but a lot of us, I think, go hard and crash hard.

So I think just knowing that is reality is probably key.

Heidi: Yeah, that's true. Just accepting that it is what it is and we'll crawl our way out of this hole too.

Emily: Yep.

Heidi: All right, to wrap up the show, we're sharing our nice list. Emily, what made it on your nice list this week?

Emily: I'm putting kitchen shears on my nice list, partially because my children stole them and were using them as regular scissors.

Kitchen shears are always handy, but especially for salads. They

Heidi: were made for salads. Oh. Or cutting up meat that is also, yes. So much easier than using a knife. Yeah.

Emily: Yes. What's on your nice list this week, Heidi?

Heidi: Well, mine is also kitchen related. I'm putting heavy duty foil on my nice list.

Now, you don't think it would be that important, but it really is so much nicer to use. A few years ago, I think someone online, I don't even remember where I got the suggestion to do this, but someone recommended using heavy duty foil instead of regular foil. So I just, decided to give it a shot.

Oh, always. Yeah. Nope. Don't have that problem. It is wonderful. Oh, I had no idea. Guess I gotta get

Emily: some foil.

Heidi: Well write it down because today is the day your life changed. Mark it in the diary. Yeah. That is it for today's episode. Take Gretchen Rubin's quiz to identify your tendency and then use the strengths of your tendency to make a get ahead for Christmas plan that works for you.