Episode 661
Bill argues that the holiday season exposes how well your business and relationships actually function under pressure. When deadlines collide with shorter days and family expectations, the stress reveals whether you've built systems that work or just habits that keep you busy. He breaks Thanksgiving into two practices: appreciation for what people bring and acceptance of what you cannot control. This framework applies equally to family gatherings and team dynamics.
The exercise starts with identifying who will gather, what traditions exist, and what typically goes wrong. Bill asks leaders to plan for friction points, then shift to gratitude and generosity. Where could you appreciate someone you find difficult? What accommodation could you make that costs you comfort but creates ease for them? He suggests extending this reflection to your team by asking what support they need rather than assuming autopilot works.
Bill shares his own process of thinking through which family members will travel, which dishes create tension, and where he tends to dominate instead of include. He encourages leaders to use the same intentionality with their organizations. The goal is not perfection but presence, building a holiday season and a business year that runs on generosity rather than control.
Key takeaways
- Ask each team member if they have special requests or needs heading into the holidays instead of running on autopilot.
- Identify what typically goes wrong during this season with family or work, then plan specific acts of generosity or accommodation to address it.
- Practice acceptance by setting aside one opinion or preference that creates friction and replacing it with appreciation for what that person brings.
- Use the holidays as a diagnostic tool to see where stress reveals gaps in your systems, leadership, or capacity.
- Extend gratitude to people you find difficult by naming one thing you appreciate about them or one act you could do to make their experience easier.
In this episode
- 00:00Holidays reveal stress alongside joy
- 02:21Breaking Thanksgiving into thanks and giving
- 03:44Who will gather and what could go wrong
- 06:16Where could you bring appreciation and acceptance
- 08:12Generosity means accommodating what you dislike
- 11:20Setting up the best year by being intentional
Read the full transcript
Holidays reveal stress alongside joy
00:00Bill Gallagher: Have you ever had a week when you're completely slammed, but somehow nothing actually moved? Is this one of those weeks? That's not really a time problem. It's a busyness habit problem. My new book, Busy Is Broken: Do Less, Scale More, is all about growing by doing less, not more. Read or listen to a sample chapter over at busyisbroken.com. That's busyisbroken.com. It's also on Amazon and other booksellers.
00:27Bill Gallagher: Hey there. Holidays are fast approaching. As I record this right now, the holidays are nearly upon us in the United States. It starts with Thanksgiving, really. Depending on your culture, where you are, there's often a time of holidays and that kind of thing, and it's supposed to be happy and joyful. It also brings stress. This time of year, the fall holidays, there's also less time. The days get shorter. The expectations, we race towards the end of the calendar year or the end of the quarter, whatever that means for you and your business and your company. In the United States, we start with Thanksgiving. It's an awesome day in many ways. Families gather. We have a good meal. It's fall season. There are symbols and things like that, traditions. All of us have it a little bit differently.
01:12Bill Gallagher: There's a spirit of something that I think is useful. First of all, I think it's useful to know that at this time that's supposed to be joyful, there is also stress. There is also pressure. And we're all supposed to put a smile on it and plaster over stuff even if we're feeling angry or irritated or frustrated. And the mix of the business and personal life, it's not all separated, right? It isn't one way when we go home and one way when we go to work and then we leave them behind. We carry things back and forth between all of that. And if it's true for you in any degree, it's also true for your people to varying degrees. So you as a leader want to be mindful of everything that's going on in the world that would have an impact on you and your business.
01:58Bill Gallagher: Makes a difference. It'll make a difference always to lead by example, to lead from the front, to set the example, to go through your process, to be accepting of people, that kind of thing. I have a practice for you and an exercise to lead you through right now that you might find really helpful. I know it's helped me many times since my coach first introduced me to it many, many years ago.
Breaking Thanksgiving into thanks and giving
02:21Bill Gallagher: So, Thanksgiving, right? Thanksgiving. There's two words there, and I think they're really helpful. First of all, there's thanks. What are we thankful for? What do you appreciate? So we can start with being thankful for the people on your team, the people in your life. What is it about each of them that you could be thankful for?
02:43Bill Gallagher: There's another aspect to being thankful that can make a difference, and that is kind of acceptance. So accepting people for the way they are then bridges into the giving part of things, generosity. So when I am accepting of you, myself, a situation, whatever, I'm giving. I'm giving something up. I'm being generous in a way. I'm setting aside my opinion, my reservations, my whatever. So I give thanks, and then I'm thankful, and then I'm giving. That's Thanksgiving.
03:24Bill Gallagher: So be thankful, then start to bring generosity, acceptance. And what is it that people need and want from you? So the thing to do with this is to dig into it, to use it a little bit. And we want to think about who, what, and when. Like, how do your holidays go? They'll be different for everybody on your team. They'll all have different family backgrounds, traditions, situations, and things like that.
Who will gather and what could go wrong
03:51Bill Gallagher: But if you start to do this and then share what you notice and open it up for you with your team, allow them to do it, invite them to participate in any way, it could make a real difference for the way your business, the lives of the people professionally and otherwise, like integrating, come together. So who, when, and what? Will your family gather? What are the practices? What does it typically look like? It's useful to stop and think about, okay, well, my family comes together like this or like that or doesn't come together or, some come together, but others don't. As I think about my family, I know some people will come to my house and others won't for any variety of reasons. Some can't. Travel is beyond my mother at this point. And my wife's mother, very difficult for them to travel, so they probably won't join us unless we go to them before or after. In this case, I'm visiting my mother before the holiday, and I'll express something. But some of us may go to her and so on. So some will travel, some won't.
05:00Bill Gallagher: There'll be a timing. People will stay in different homes and go around and, there are all those kinds of things. So I like to think about what will happen, how will it go down. What are the specific events? Like, is there a meal? Are there rituals? Are there traditions? That kind of thing. And we're not just talking about Thanksgiving. That's where it begins here. But then I'm thinking into the major other religious and other kinds of holidays that you might celebrate depending on your culture, your country, wherever you are. So I think about how that would go. I'm starting with Thanksgiving, but this extends to all the other holidays all the way up through the New Year celebration in this case. So I think about that. And then I ask myself, what could go wrong?
05:47Bill Gallagher: What has gone wrong in the past? What's likely to go wrong? Well, what could go wrong, maybe even likely to go wrong this time? I think about the family members who won't join, the family members who want a different thing, a different practice with any of the holidays. I think about friends. I think about people on my team. How is it likely to go that's not good, or could it go that's not good? I want to think about that.
Where could you bring appreciation and acceptance
06:16Bill Gallagher: And then I want to ask myself, where could I bring appreciation? Where could I be thankful? Where would that make a difference for me to be thankful with the people on my team, the people in my life, my friends, my family members, my extended family members? What could I say about them? Whether they're with me or not, where could I bring appreciation for them? Where could I bring acceptance for them? Hey, I appreciate this about you. I like this about you. I love that dish you make. I love how you put yourself out for something. So I start to bring appreciation to all of who they are as a human being and what they bring to the holiday and the season.
06:58Bill Gallagher: And then I want to bring some acceptance as well, and that's where we start to move into the giving. So first part of acceptance is more me with them. The second part is a little more active. So first part, what is it that I could grant acceptance to, someone or something that I don't particularly like? I don't like the way they do that. I don't like what they do or what they say or that kind of thing. Where could I just be graceful and generous in that? That's the giving part, right? Give of myself. Set aside my thoughts and opinions about them, the situation, and accept them. So then go back to appreciating something about them.
07:45Bill Gallagher: So that is the first part of acceptance. Then the next part is the generosity. Like, what specific acts? Is there something that I could do that would make it easier for them? Cook food a little bit differently, right? There was a time in the recent past where members of my family had different dietary preferences, and I didn't particularly like to cook those things, that kind of thing. But I did.
Generosity means accommodating what you dislike
08:12Bill Gallagher: And could I do it with love in a way that's like, okay, I don't like to do this, but I love to do something that takes care of you in some way, even if I don't like this food, this particular dish, or this style of eating, or this accommodation. Right? Where could I be generous? Where could I do something for the others that would make a real difference? Do something for them, include them, their preferences in some way, and not just run my own show.
08:41Bill Gallagher: I think it's particularly useful for people like me, and I suspect some of you are like me, who are used to being in charge. We create companies. We lead departments. We do things like that. And there's a tendency of us to be bossy and dominant and that kind of thing. Where could we set that aside and be a little more generous in this season?
09:08Bill Gallagher: So if you stop and you think about each member and all the people that are important to you and what there is to appreciate about them and what there is to accept, to let go, set aside of your things. And what is it that they need that they would really appreciate? Like an act you could do, a thing that you could, an accommodation, an effort, a gesture that you could provide to them to make it? And then you could extend out to the people on your team the same thing, and you could share with people what you see about the particular challenges or joys or that kind of thing.
09:45Bill Gallagher: As I start to gather with my family, I'm thinking about, so we'll host some of the holiday gatherings at our house for our family, but not all family members will join. So I'm thinking about that. And I'm thinking about the practices, the foods, the traditions, how I'm going to accommodate something a little bit more this year. I'm thinking about the people and the actions of my family that'll make me more uncomfortable and the ones that'll be really easy to be with. We've all got that, right? And I think then, what's it like for them? What's it like for them? I'm not even sure. Some of the things and the people, I know that if it's uncomfortable for me in some way, it's maybe also uncomfortable for them. So I could even ask them, hey, do you have any special requests this year? I know that we're on autopilot. We've been doing this for a couple of years. Is there anything that you'd love to have or you want to emphasize or want to make sure I protect or that kind of thing? Is there any special request? Right? This is all in the world of giving. This is the generosity piece of it. Right? Listening for and creating openings for people to be exactly as they are and have the best experience is a way to bring us all together. Let us and our families have a happier time. Let our people, people on our teams, part of our organizations also have the best and all that. Anyway, I found this reflection creation, like, being intentional about the holidays, planning it out at the beginning, imagining whatever they are.
Setting up the best year by being intentional
11:20Bill Gallagher: Starts with Thanksgiving, Christmas, Hanukkah, Festivus, Kwanzaa. I don't even know what they all are. New Year's, et cetera. Like, what does it look like this time of year for you? What do you want to think about all the way through? Create what is a new chapter or a new way that you could have this be the best year ever? Start with your family in your home, take it to all the people on your teams, and set yourself up for the best New Year soon to come. Hope that's been helpful. We'll talk to you again soon. Until then, have a happy holidays.
11:56Bill Gallagher: Thanks for listening today. One last thing. If anything in this episode hit home, my book digs into it further. Busy Is Broken: Do Less, Scale More. It's all about how to stop drowning in work and build a business and a team that scales without you. Available right now with content samples at busyisbroken.com. Go grab it. Be less busy.
Bill Gallagher coaches CEOs and leadership teams on the Scaling Up framework. If something in this episode landed close to home, the free 20-question diagnostic is a good place to start.
