Podcast EP41: Your Easiest Holiday Season Ever (as an Entrepreneur)

Oct 23, 2023

Welcome to Podcast Episode 41: Your Easiest Holiday Season Ever (as an Entrepreneur) 

Want to know how to keep your own peace this holiday season, rather than worrying about how to keep all of the plates spinning?

In this episode of the 3-Day Workweeks for Millennial Entrepreneurs Podcast, I give you all of my practical tips on how to make sure you can actually enjoy this holiday season, instead of being stressed out and overwhelmed.


[02:52] Adding important dates and reminders to your calendar
[03:53] Blocking off events and traveling in your calendar as well
[05:01] Communicating with friends and family members so they know your plans
[07:58] Making gift-giving really intentional
[15:13] How to prioritize making memories
[17:14] Only visiting family if you really want to – you’re allowed to do your own thing


  1. Calendar
    • block off family time & downtime
    • include travel days because nothing gets done on those days
    • plan ahead with your partner and family
    • communicate with everyone involved EARLY
  2. Gifts
    • make a locked note on your phone
    • write down & link gifts throughout the year as you think of them or get inspired
    • buy early but not too early…unless you have tons of extra space and/or a good hiding spot, you don’t want all the gifts cluttering up your house
    • go for experiences over stuff – but make them cute & invest in cute wrapping
    • wrap early
  3. Make Memories
    • think about small things that make the holidays special – baking cookies, drinking hot chocolate & driving around to see Christmas lights, looking at old Christmas cards, etc.
    • you don’t have to do big grandiose things
    • when you have time, gather those things so you have them available when you feel like doing them → then it’s not a rush
    • do something charitable
  4. Family is Optional
    • controversial but if family doesn’t light you up, you don’t have to spend all (if any) time with them
    • your peace is the most important thing
    • skipping Christmas is okay (you can see family before or after the actual holiday)
    • this removes so much stress & lets you enjoy the actual holiday

Related Links:


Connect with Kate Waldo here:

Kate Waldo + Co Programs:

Happy Holidays! 



Owner + Founder, Kate Waldo + Co. 

Creator of the Smarter Not Harder: 3-Day Workweeks for Millennial Entrepreneurs©  Program

P.S. Curious how you can grow your 6-figure business while slashing your workweek in half? Click here to learn about the Smarter Not Harder© program!


β€ŠHey, and welcome back to another episode of the three-day workweeks podcast. I'm your host, Kate Waldo Jones. And if you've listened to any of the previous episodes, you might know that I had a second podcast called the simplified Lux life. And we have an episode that is called your easiest holiday season ever. I want to just share it with you here because it definitely applies to everyone, but especially as a business owner, we can make your holidays a lot easier and more enjoyable. All the things that you really hoped you would get the value out of being an entrepreneur. When it comes to special times in the year, it doesn't have to just be the traditional November, December holiday season. It can apply to any time a year. But I hope you enjoy the episode. And if you hear me say things about simplified Luxe life podcast, that's where it came from. So make sure you check out the show notes and enjoy the episode.

Today we're gonna be talking about how to make the holiday season the easiest you have ever had, and this can definitely apply to summer, or, I don't know, spring break, back to school, whatever you want it to apply to. I have found throughout the years that this is the easiest way to make the holidays go a lot more smoothly, be a lot less stressful, and really have the time and head space to enjoy the season instead of feeling super stressed, spread thin.

Going all over the place and just not actually enjoying it, like the whole point of the holidays. So if y'all don't already know me, my name is Kate and I am the creator behind the Simplified Lux Life blog and podcast where we talk about how to have luxurious things in your life, but way simplified.

Cutting out all the clutter, all the excess, and being more of an essentialist, not a minimalist, but an essentialist where it's things that we have really curated. We're curating our lives to be easier and more enjoyable so that we spend our time in a way that we are actually feeling good about what we're.

So let's get into the holiday season now. I just to give you a little bit of background, I grew up around. 12. My parents divorced. They moved to different cities, so we were always switching back and forth between holidays and parents. And then when you start dating and you get into serious relationships and you have their parents and their parents might be divorced, and there's different holidays that people celebrate and different things are different.

Traditions are important to each of you, each family member, all these. , it can get really stressful and it can. Really overwhelming, not to mention if you have children, adding all that into the mix, and so I've found that these are some things that make the entire holiday season a lot easier. As I mentioned earlier in the podcast, you can apply this to any time of your year.

If you don't know this about me too, I have a business called Kate Waldo and Co, where I am an efficiency expert and systems expert. So I apply those things to all aspects of my life. And this is on a more personal note, how I handle the holiday season in a way that just makes it all go so much smoother.

So first thing is, as soon as you can. As early in the year as you know that you have things happening during the holiday season, go ahead and put it on your calendar. I live by my Google calendar and my boyfriend and I, we will send each other calendar invites for things that the other person needs to know is happening or that we are both a part of.

Sometimes if he sends me things so that I know he's doing. X, Y, Z, or he's gonna be tied up for a period of time. I leave those invites on my calendar. I don't accept or decline them, but it'll just sit there. So it won't block up my time, but I see it on my calendar and know that he's busy. So we'll go through, I mean we, this year we were really on top of it and we went through in August our holiday calendar, and we had already talked to family about what we were planning to do, but we went ahead and blocked the times that we were going to be outta town when we were going to be traveling.

So not only block the holidays themselves and what you're going to be doing when, but also make sure to. Block off the travel time so that you give yourself that travel day. I don't know about you, but nothing really gets done. , nothing work wise or. Anything that's not related to getting ready to go out of town ends up happening on a travel day.

So I like to block that and have very low expectations that anything else gets done, especially if you're an entrepreneur or you have kids, , you just know there's a lot gonna be going on. So blocking off those travel days gives you those bookends to your trip so that you have plenty of prep time to get on the road or.

on your flight, and then when you come back, you also have some reset time to unpack, get the house clean. Get everything put away, get back on your schedule. That makes a really big difference. And then communicating with your family members and friends that you are going to that you're gonna be seeing during the holidays or not seeing during the holidays.

We'll get to this in a second about how I handle the holidays now. I've really changed it up, but getting those things on the calendar ahead of time as early as you can helps you fill in everything around that. And we've found too that for John and I, it helps us to plan our schedules and trips.

Around the holiday season knowing okay, in November we're going to be traveling a good bet in October. We've got a lot of family coming to visit us, so we probably don't want to over commit to going to events or going outta town for any kind of trips that we know might be really exhausting if we stack all those things together.

and it helps with all of our parents that we communicate what we're doing early on so that they have expectations set. For, Are they going to see us on Thanksgiving? Are they gonna see us on Christmas? Are they gonna see us around that time? For some people have to take work off. Should they plan to take work off?

Are they are the dogs coming? Are they not? If you have kids, are the kids coming who's taking care of them? All of those things. It makes a really huge difference to get those things handled early on. And then We're going outta town these dates, we can't bring the dogs, so we need to book a dog walker planning that stuff well in advance.

I know that our dog walkers, they're already booked up for overnights like months in, in early October. They booked up for all of the holidays through the Christmas season. So planning ahead makes everything go a lot easier, and then you can be so much more present and. Enjoy the holidays more so the first things, first calendar, everything makes it easier.

Once you have that. It's handled and you can always add to it. But getting those big chunks especially if you're a business owner, go ahead and mark yourself out of office for the time that you're going to take off. You absolutely should take time off. You need to for your sanity. Make sure that your team, your employees, know when they're taking time off, what your expectations are of them.

I'm gonna do an episode on that over on the Three Day Workweeks podcast, which is for Kate Waldo and Co to get a little more in the weeds. How running your business during the holiday season, but handle that calendar as early as you can. Update it as you go share with anyone who is involved in the process.

The second thing is gifts. At Simplified Luck life, I am not a big fan of access, of giving people tons and tons of stuff. Even my loved ones like. I just don't buy a lot of excess. I like to give really intentional gifts. So what I do is I have a locked note on my phone that it has, you have to have a password to get into it, and I will write down each person that I plan to buy gifts for during the holiday season and throughout the year.

I, I have the memory of a goldfish. It can go in one year and out the other. If I don't write it down or it's not on my calendar, it basically doesn't. So it helps me a lot to write down throughout the year, gift ideas on a note, and then I can come back to that when it's time to start buying things. And I'm not just following whatever random Instagram ad that I'm like, All right, I guess that'll work

So things are a lot more intentional and. They are well, more well thought through. I like to give gifts that are really intentional and also I find that gifts that are something great rules with them. A gift that is something that you would want to receive is typically a good gift to give a gift that someone can actually use, consume.

In a short period of time, all I always find those to be really great gifts like food jellys jams, checks mix. Pai, those kind of things make really great gifts and they're, great to have on hand so that you, if there's somebody that you forgot on your list or there's somebody that gives you a gift and you want to return the favor, you have something on hand.

That's something that you can start thinking on early, and then as you go, when you have free time, you can start collecting those items. so that you are prepared and you're not scrambling last minute. Because we all know that the holidays sneak up fast and then so much is happening and we don't want it to be stressful.

You don't have to be Martha Stewart, but if those are things that you care about doing, you can plan ahead for it and make it a lot easier on yourself so that you're not trying to do everything at once and it's not a scramble. The next thing I would suggest is buy your gifts early, but not too early.

Because unless you have a ton of extra space or a really good hiding spot, you don't want all those gifts cluttering up your house you probably will end up over buying because you don't even know what you have. Personally, I like to, I don't set up terribly early for the holidays. I'll probably put my tree out like mid-November.

Sometimes I'll wait until after Thanksgiving, but I find that if I buy too many gifts too early on, then put them away. I'll forget what I bought and I'll end up just impulse buying other things. And then I end up giving people like junk and, or not junk, but just too much that doesn't even, it's just not even necessary.

And so I would recommend once you are able to, Get the gifts and plan ahead. But if you can do it in a way where you can wrap them and have them ready to go out under the tree, so they're decorative, that is really nice. I also buy in bulk, similar wrapping paper so that it is very cohesive and I actually like looking at the gifts when they're out there.

If you buy a gift from any type of local place, which always recommends shopping local. , I ask them to gift wrap it for you, to save you the time. Even if it's five bucks, it's worth it and you don't have to spend the time doing it because that can take. A lot of time. And as far as gifts go, I always recommend experiences over stuff.

If you can give someone experience where you can make a memory together, that's so special. Those are the gifts that I always loved. And still love, but you can make 'em cute and you can invest in cute wrapping, make it a thing, print off some stuff. You can go cheesy with it to make it look like more.

It is if it's just a gift card to go on some cool excursion, wrap it up, put some cellophane, like print out some like cute little clues or something like that to make it even more fun. And then it doesn't feel like, Oh, here's a card in an envelope, and it just, you get that experience of unwrapping something, which is.

and as I mentioned, wrap the gifts. When you start buying, go ahead and once you get at least three or four gifts, start wrapping them, Get your wrapping stuff together, and then that way you don't have to hide them as much. I It depends if your kids are really sneaky. , you know what you have to do, to keep those from them.

But but if they're not too bad, then you can wrap. Go ahead and wrap and as soon as you can put 'em out, put them out under the tree. So they're nice decorations. And as far as your own stuff, I know this is a little bit taboo, but I find that I love gifts that I ask for that are things. For the most part, I buy whatever I need, but there are things that fall into the category of Oh, I would like to have that, but I don't necessarily want to go outta my way to buy it for myself.

Those often make really great gifts, and with my family we have an understanding that we just tell each other what we want and that prevents a lot of like extra pajamas and dish towels, , those kind of things. It's not like just, huh, you end up with crap or things that you don't want, or somebody tries to be really thoughtful, but had you told them that you really wanted a Kindle for Christmas, that they would've loved to get that thing for you instead of buying you like three random things that they saw when they were on a trip.

Use that at your own discretion. Communicate so that people don't think you're saying, Buy me this gift. It obviously works better with people who are the most close to you. I do think that we should have like friend registries you can do that on Amazon. You can make a list. I think if you like, had that with your friends where you could say Here's my registry.

If you ever wanna buy me a gift, you can. Which I don't know, that's a little whatever, but I always like to get people. They want. So that's where that rule of thumb of buy people things, if you're gonna buy a thing, that you want, or an experience that you want for yourself that either you've loved or you've wanted to have.

And then most of all, like. The holidays should be about making memories. It's not about the stuff, so think about the small things that make the holiday special to you. Talk with your loved ones about what are some traditions that they really liked or that they always wish that they had done, and start to put those in place.

Whether that's baking cookies or drinking hot chocolate and driving around to see the Christmas lights, looking at all the old Christmas cards. Those kind of things have an idea. You can have a list if you're, like me, have make lists, like that's how I operate . So it helps me a lot to have those things to refer back to.

Otherwise I just get stuck in routine and don't end up doing anything special. Go the opposite end of the spectrum and feel like I need to do some big grandiose thing, get tickets to the Nutcracker and have a fancy dinner out and all those things. Nothing wrong with that if that's something that you want to do, that you plan to do.

But it's great if you can plan ahead so that you don't feel obligated to do something big and over the top just to make the season memor. when you're out at the grocery store go and pick up the ingredients for baking cookies so that you have it on hand or for making some homemade chocolate, or later when you go and watch the lights so that it can be something that's impulsive, but you already have a lot of the pieces, so it doesn't have to be too much of a big deal to make it happen.

And yeah, just. , think about what makes a holiday season special to you. If there are new traditions that you wanna start, like doing some kind of charitable act of some kind, whether that's volunteering somewhere, or making Christmas cards, or Hanukkah cards or whatever, holiday cards, and you wanna start those new with your family, do that feel like you can and create those new memory.

And then this one is probably the most controversial, but I have found that family being optional for the holidays has made it so much less stressful starting during Covid. It was just too stressful to try and travel my family lives. In Georgia, and it's either five hours, five to six hours away or almost eight hours away to see my family.

And I just decided to skip Christmas. And I know that it's really controversial. The first time I did it all my friends were like, Are you sure? Are you okay? Do you wanna come to Christmas with us? Just so kind so, kind. But I found. It was so nice to skip Christmas because I could just do what I wanted to do on that day, and I've kept that tradition going and it makes it so much less stressful.

There's something about family and the actual day of the holiday. I don't know about you guys, but it just makes it so stressful to try and plan to see all the family in one day and do all the things, get all the traditions in one day. When you spread it out, it makes it feel like the season is lasting long, like the good parts of the holiday season are lasting longer.

And ultimately your piece is what is the most important. So if you need to, if your family doesn't light you up, you don't have to spend all, if any of your time during the holidays with them. I'm giving you a permission slip that you don't need from me , but if you needed to hear it, this is your. Your permission slip to skip the holidays if you want.

If it doesn't light you up, go do the things that you want to do. Make new memories, have different traditions that you want to do now you, you get to decide because your piece is the most important, and it just removes a lot of stress during the holiday season that isn't necessary. I would love to hear if you guys tag me on Instagram at Kate Waldo and Co.

Tag me and let me know what you're doing to make your holiday season easier. I want to hear your life hacks for this because. Always learning and refining these things. But I hope this was helpful for you. I hope you enjoy it.

πŸ“ I hope you guys enjoyed this episode thank you for tuning in make sure to check out the show notes for anything that we talked about and a link to the full blog on this episode we will see you again next time on the three-day work weeks for millennial entrepreneurs podcast.




50% Complete

Two Step

Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua.