8 Simple Strategies For A Stress Free Holiday

Smooth sailing for your season with these simple tactics. 

1. Plan your finish line celebration
2. Set an intention
3. Formalize a goal
4. Use the past as your planner 
5. Spill the beans
6. Write a permission slip
7. Create a place for "not now" ideas + observations
8. Set an end of day ritual

Get our low-key holiday planner
Join our Holiday Planning Power Hour on October 16th

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Transcript

[0:04] Welcome to Retail for the Rest of Us, a podcast for indie retailers, makers, and shop owners who want to do business differently.
I'm your host, Janine Malone, retail expert, small business cheerleader, and the founder of Feel Good Retail.
On this show, you'll hear insights, strategies, and ideas on how to sustain and scale your shop without sacrificing your sanity.
Each week you'll hear from me and the occasional guest expert in what I hope feels more like voice note from your retail BFF than a business podcast. Additional goodies and support can be, found in our show notes and at feelgoodretail.com. Now, let's get into the show.

[0:40] Music.

[0:48] Hey, everyone. Welcome back to Retail for the Rest of Us. I'm your host, Janine Mulone. And today we are diving fully into the holidays. But don't panic.
We're not going to go stress. We're not even going to really talk about like sales strategy.
The goal today is to get you set up for a stress-free season. And if you're like, girl, yeah, right. I have compiled all of my favorite tips and tricks and things that I find myself repeating over and over and over again, every Q4 of every year to help indie retailers feel like they're grounded in the season and not get to December 26th and feel like they've been hit by a bus. And let's be real. Some of that is just the pace of the season. It's a time of year that you're doing the most sales most likely. You know, that's why Black Friday is called Black Friday. It's the day where a lot of retailers find themselves in the black for the sales season.
For the year and.

[1:57] So, I think built into that is, of course, plenty of work. You're making product, you're stocking shelves, you're going to the post office.
It can be kind of a taxing and grueling physical season.
So what I want to do is help you take away as much stress as you can and help you feel better set up to handle the stress that, you know, maybe just comes with the territory.

[2:23] But before we get into the meat of this episode, I wanted to let you know about two ways in addition to this podcast that I am here to support you during the most wonderful time of the year.

[2:34] The first is totally free. It's our 2023 Holiday Planner, and I've kind of been thinking about this as like a low-key planner for your craziest, busiest, potentially most stressful time of year.
Inside you'll find gentle reminders, divinely timed to-dos, and a little bit of inspiration week by week, month by month, through October, November, and December. It is really visual, it's a nice just kind of place to ground yourself. You could print it out and have it at your workspace, you could have it set as the background on your computer, you could just reference it as you're planning your weeks, but just kind of getting a sense of important dates, reminders, what's going on cosmically, what's going on with the moon, and some suggestions that I have about little tasks that you can accomplish one a week and make significant progress in, again, not only having a super successful season, but having as stress-free a season as possible. So you can check that out at feelgoodretail.com holiday. Download that completely free. With that, you'll also start getting our newsletter if you're not on that list already. And every week between now and Black Friday, I am going to be diving even further into tips and tricks for that week's particular task. So if you are needing additional support, that's where you can grab that.

[4:04] The second thing I wanted to let you know about is I will be teaching slash hosting what I'm calling a holiday planning power hour on Monday, October 16. That is right around six weeks before Black Friday, Cyber Monday when things really kick into high gear.

[4:21] And I wanted to hold a space for us all to gather together and kind of co work. I will be doing some light teaching and giving you instruction on what tasks and how to handle them. But we are going to get an entire plan for your holiday season done within one hour. And we're going to do it together. So if you have any questions or hang ups, or you're feeling like this is the planning and the strategy that gets shoved to the bottom of your list because you're too stressed out when you think about sitting down to do it, let's sit down and do it together. I haven't hosted a live event, I don't think at all this year. So I'm super, super excited to see all of you and get that time together to really put our strategy in place. And you can get more information about that at feelgoodretail.com slash holiday as well. It's kind of our little holiday hub. Tickets to that are going to be $44. Very, very accessible. I wanted this to be something that just felt, really approachable and exciting and a nice way to connect in community and solidarity before the season starts. So, again, freebie 2023 holiday planner and tickets to our holiday planning power hour both exist on feelgoodretail.com slash holiday. Head over there, sign up. I literally I really can't wait to hear from you.

[5:46] So a stress-free holiday. Is it possible? My hot take is of course, yes. Certainly, I can't take away every stress. However, I think that there are some things that we can be doing as small business owners to prepare for busy times. And we started talking a bit about that last week as I was kind of waxing poetic on different systems and structures to help us plan for sustainable growth in our businesses.

[6:20] And today I really want to get into some brass tacks tips. I want you to be able to walk away from this episode and be like, check, check, check.
I've got all that set up. I know I'm in a place that feels as grounded as possible, going into a time that doesn't feel very grounded.
And so what I came up with was eight rules for a stress-free holiday season.
And I really think that these things are, they're not only really effective, but they're holistic.
They have to do with the operations of your business, your sanity as a business owner, the strategy for communicating with your customers in a way that feels really like sensitive to their needs in a stressful time of year for them as well.
And I feel really proud of this list, actually. feels kind of like a manifesto for a feel-good holiday season. I guess that could have been in its other name, but.

[7:20] I think putting an exclamation point and an underline and an italic on stress-free is pretty important this time of year. So let's get into them. I'm going to give you all of our eight rules and a little bit more context and color around them.
And if you have any questions or comments or things to add to your own feel-good list, I would love to hear from you at feelgoodretail on Instagram. You can always slide into those DMs.
I'm not an active poster these days, but I do creep around our DMs pretty regularly.

[7:51] So the first thing, the first rule, the first person we are going to take care of is you.
Okay? Before you do anything, before you set a goal, before you set a strategy, before you plan an Instagram post or an email, I want you to plan your finish line celebration.
Whatever that means for you, I want you to pick a date on the calendar, mark off some time, and decide now how you are going to celebrate completing another holiday season, and really another year in business.
That could be booking yourself a massage, making a dinner reservation, buying a bottle of champagne now and putting it in the fridge with a little note on it that says, do not open until December 26th.
I want you to think now while you have the bandwidth and you have the capacity to create that time for yourself. And I don't want it to be something that you decide in.

[8:56] Alignment with how well the season went. Maybe you hit your goal, maybe you didn't, maybe you had the best year ever, maybe it was really, really trying. I don't really care how the next few months go when it comes to this rule, I want you to just have a light at the end of the tunnel that you know you've created that space for yourself. So again, whatever that means for you, that is rule number one, that is step number one, that is you'll find it in the planner, just what I want you to do at the beginning of the quarter, which at the time this episode airs was just yesterday. So that's your homework for the week. Set your finish line celebration, get it on the calendar, get it booked. You'll thank me later. And you'll thank yourself later. Rule number two.

[9:55] I really like to set an intention for the season and make myself some kind of reminder. I mean, I love branding. I brand everything, even in my personal life.
But I find it really helpful in times where I know my decision making brain is going to be a little bit tired to have like a word or a phrase or an intention that I can come back to to sort of guide those decisions. And I think in business, sometimes when we think about decision making, we're always trying to like focus on increasing sales or the bottom line or.

[10:39] Growth in some way. And sure, that's great. And I think that naturally, as a business owner, you are likely taking those things into consideration. But what we don't weigh is how something is going to feel. And so I'll give you an example of setting an intention and using it as a reminder. This year has been a little bit challenging, personally, nothing crazy, nothing dramatic. It's just been a time where I have had to have a lot of focus in my personal life. And for the beginning half of this year, my husband, Dean, and I were looking to buy a house.
Spoiler alert, we are still renting. But that was an intense, stressful, strenuous, overwhelming process to go through.
And when we decided we were just going to resign our lease and stay put, I decided that the summer was going to be the summer of sweetness because I just needed to feel really joyous and connected, to my husband and connected to our dog and connected to our house. And I really wanted to enjoy the summer because it had felt like I hadn't had a single day to myself the entire year.

[12:02] And just by saying the summer of sweetness, it was so helpful for me when I was thinking about what I wanted to get done on the weekends to be able to say, okay, yeah, sure, I need to go grocery shopping, and I need to vacuum, and I need to do all the things. But how could I make that sweeter?
Is there a playlist I could have? Is there a little treat I could get myself? Is there something that Dean and I can do together and kind of add on to our errands? And also, when it came to making decisions about how we wanted to spend our time, sweetness was at the core. So that's what I want you to do for the holidays. If you want to think about how you want to feel, how you want to make your customers feel, how you think of the holidays, what's a word that comes to mind that you want to like just imbue the whole experience with, I want you to come up with that and kind of set a reminder for yourself. I like to make little graphics as my phone background. Sometimes I change my passwords to special words, just to kind of keep it top of mind. I often have post-it reminders all over my desk. So that's gonna help you in those moments where you're like, I don't know, should we run a promotion or should we add an extra day of being open?

[13:29] And I think by going to like, I wanna feel really joyful, which of those is gonna make me feel more joyful. Sometimes in a state of burnout or a state of exhaustion, it's easier for us to imagine things emotionally than it is to imagine them rationally. And I found that that's just a really handy tool. So I would highly recommend setting your intention, picking a word, like I said, a phrase, a vibe, and allowing that to be one of your guiding lights throughout the the season.

[14:07] Number three, formalize a goal. If you don't want it to be financial, that's totally fine.
Make it something else. But you have to have a definition of success in order to know whether or not you achieved it. And I don't say that because I want you to look at something and.

[14:29] Think of it as a failure if you don't hit the exact mark that you were hoping for.
But I find that small business owners and entrepreneurs so rarely feel confident in.

[14:42] Their success or in their progress. And oftentimes, it's because there isn't really something tactical that you can look at and either say yes or no. And listen, I'm not about a binary. I'm not about black or white thinking. I don't say this to put you in a box. But I think that by creating something really firm, like a true measuring stick, you're able to really analyze and reflect on how the strategies that you utilized took effect towards your goal. And so again, I think that financial goals are really important inside of businesses, not to make you feel bad, but to actually make you feel really good and make you a better business operator.
But if that is feeling like too much pressure, you can set all kinds of goals. How many of certain bestsellers did you move? How many customers did you help? How many reviews did you get? How many gifts did you sell? There can be something that's a little bit more, slightly more emotional. I won't say a lot more, but I think it's really important to have some kind of formalized goal that you can really work towards and reflect on at the end of the season.

[16:10] Number four, use the past as a planner. I cannot tell you how many times I have talked to small business owners, to indie retailers, or have done this myself, frankly, where I start to work on something that I've kind of done before and I just start from square one. I don't go back and look at at what I've done successfully in the past.
I don't reread old emails.
I don't look at old outlines or projects.
And I just decide to build from the ground up yet again.
We're not gonna do that. Odds are you have a holiday season in your back pocket or at least have another season in your business that felt pretty successful.
And you can use things that have worked well and just rinse and repeat them.

[17:06] Odds are, with everything you've learned since the last time you did those things, you're gonna be able to make them markedly better.
And really, this isn't the season to be doing like crazy innovation, because again, think about your customers.
They're in a place of just like, they're busy, they have work, they have holiday plans, they have gift buying, they have their corporate holiday party, they have family obligations, like this is the time to keep it simple for them.
So keep it simple for yourself as well. Look back at the promotions you did last year, the emails you ran, what was going on in your social media, what kind of products you were bringing in, and let that be part of, if not 75% of the work.

[17:57] That you're doing this year.
Just make things a little bit better by looking at what you've done in the past and repeating.

[18:06] Number five, spill the beans. This is my like tried and true.
I think that you just need to tell your community what to expect.
What products are you gonna have?
Do you have gift recommendations? What days are you running sales?
What are those sales? When is your shipping cut off?
The sooner that you can get that information out there and the more often that you can get that information out there, the more your customers and your community prepared to support you. I personally find it extremely stressful in the holiday season when I know I want to buy something and maybe I'll wait until Black Friday or maybe I just found out about it and I don't want to buy it yet because what if it goes on sale or what if they're doing free shipping next week and then I just forget. And I don't love that about myself, but I think to give people the expectation that like, hey, we want to make the season as easy for you as possible.

[19:05] Here are the things we're doing. We really hope to see you. They will also get excited.
They'll start building their wishlist. They'll start building their gift list.
And then the second that discount code goes live, there they are ready to fill their carts and checkout and support your small business.
Love this rule. I will die on this hill. I've had so many of you in years past reach out to me and tell me that you did this and it worked really successfully. I just I want to revolutionize the holiday season where none of us are guessing anymore about when the sales are gonna be.
Because they're gonna happen, you know? And if they're not, let people know. Let people know that they shouldn't wait, right? Maybe there's some language or some storytelling you can do around that. But I think making customers guess just doesn't feel great to me and leaves them in the dark and leaves you in a place of having to do a lot more legwork once that promotion goes live.

[20:11] Number six, write yourself a permission slip. Try to make a list of the priorities that are.

[20:19] Kind of non-negotiable no matter the time of year, right? Maybe you need to restock at the end of the night. You want to post, let's say, three things on Instagram. This should be extremely bare bones, the list that I'm talking about. And then I want you to write yourself a permission slip, not to do anything else when the season gets busy. And I mean, really commit to keeping that priority list and knowing that things are going to keep running, they're going to keep going smoothly as long as those are the only things you're handling. Because once you're already exhausted, that is not the time to be trying to decide to do less. Because you've ever noticed when you're burnt out, your brain almost goes the opposite direction. Instead of getting a trigger or a warning that like, okay, I really need to slow down. Actually, our brains go into like hyper drive. And we're like, what if I actually did so much more? Would that be helpful? I don't know about the science of this, but I do know it from experience. And it's almost like when I think I need to do more is actually the time I need to do far less. And And so I think, again, before the season really kicks into gear, if you're able to be realistic about like, okay, what is non-negotiable to make sure this business runs, make that list.

[21:48] And everything else, give yourself permission come the first week in December to just push, to the side.

[21:57] Push it all to the side, give yourself that permission, and really focus on non-negotiables.
Because the beauty of this time of year, despite its kind of insanity, is the fact that we often have the ability to do that. Whether we take advantage or not is sort of up to us, but the customers are there as long as there's product in the store and we're excited to talk to them and share with them and have an offering that we know our community is really going to love, then the rest can kind of go on the back burner for a moment. So I would keep some minimal marketing tasks, keep the tasks that are going to keep your shelves stocked and your products made.

[22:44] And that's pretty much it, frankly. There's a lot that we're able to press pause on, and don't worry, that work will be right there, right where you left it, come January.
And aligned with that, our number seven idea is to create a place for your not-now ideas.
I like to call this a parking lot. I think it's really important for clearing space in our brains and not putting pressure on ourselves to remember everything that we notice or think of over the the next 12 weeks. And what a parking lot can do in the holidays is just be a place for all of the ideas that you have for new products, new merchandising, events, content.

[23:30] All sorts of ideas, as well as any observations that you want to address in the new year.
Obviously, if there's something that's really pressing and won't take you a significant amount of time, like let's say one of your employees is giving incorrect information to customers and you notice it, that's something you want to handle in the moment. But anything that's kind of observations in terms of how you want your POS station set up or how you want to package things or functions on the website, things like that. As long as they're literally working in that.

[24:05] Customers can check out, I would say most projects can go into that parking lot. And then when you do your 2024 planning, you already have this treasure trove of ideas that will kick the year off in a really energetic and momentous way, as opposed to doing what I sometimes do. And I know you probably do too, which is just like, oh, I'll remember that, and either definitely not remembering that, or my brain likes to remind me of it every three days. And then by the time it reminds me for two weeks, I think that thing's an emergency, and then I'm panicking because it feels like all I'm doing is thinking about that thing, when really all I wanted to do was get a different chair for my desk. And that is not an emergency at all. But that's the power of writing things down instead of using your sweet, precious, creative, visionary, intuitive brain to try to remember things is that there's not a lot of nuance there. So create that safe space that is going to help you with step number six with writing that permission slip with saying that you will defer certain tasks until the season is over. And lastly is number eight. This is a really important and quick one and something that I find.

[25:29] Really powerful is to set an end-of-the-day ritual. And this can be five minutes. In fact, I wouldn't make it any more than ten. But I want you to reflect on what went well that day. Maybe, just like take note whether you're keeping a to-do list or you have some kind of task management software. Take a look at everything you got accomplished. Make a priority list for tomorrow, like three things that have to get done. I would not make it more than three of your next working day. And I would just take like three breaths or maybe you ceremonially like blow out the shop candle and like say goodnight to your space and close your computer and tidy up your workspace, tidy up your POS, like write a note to the people who are working in the morning just of encouragement, something that kind of closes out the day and allows you to step away from the business and be a person, just a regular human being who's going home for dinner and won't have to necessarily bring all of that stress and all of that kind of like wound up energy to your home or outside of the business. And again.

[26:46] This isn't a perfect science. It doesn't mean you'll never have to answer an email when you go home or that you won't kind of have those moments of like, crap, I forgot to do that or like I'm really stressed about this thing. But I do find that kind of ritualizing the end of our day and helping us transition from being a business owner to like going home and being a person, can feel really critical in the holiday season where then you're waking up the next day and doing it all over again, it's nice to know that you took care of your future self. You have your list of priorities. You wake up in the morning confident about what you have to get done that day, and to me, that just feels like the greatest gift. So set that end of day ritual, like I said.

[27:34] Five, ten minutes max, and try to stick to it throughout the entire season. It's really gonna help. So that's it. Eight rules for a stress-free season. I think if you can implement as many of those as possible, you're going to seriously notice the difference. And remember, it's never too late to go back to these rules and start implementing them in the middle of the season.
None of these are necessarily time-sensitive. So if you're feeling like you need a little bit of a break, I hope this is something that you can come back to and find a little solace.
If you find yourself getting a little bit stressed out, which, again, is natural.
If you want more support, you can go to feelgoodretail.com slash holiday and grab our 2023 holiday planner.

[28:23] You can also sign up for our holiday planning power hour on October 16th.
I am so excited for this, so I really hope to see you there.
Both of those, again, feelgoodretail.com slash holiday.
Until next time, thank you for being here. Thank you for being in business. Cheers to feeling good.
Thanks for listening to Retail for the Rest of Us. Find additional information and resources related to this episode in the show notes or on our website feelgoodretail.com. This, show was lovingly produced and edited by Softer Sounds, a feminist podcast studio.
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Thank you for being here. Thank you for being in business and cheers to feeling good.

[29:17] Music.