Episode 262 // Taking Time Off as a Business Owner with Dana Kaye

July 6, 2021

While boss life allows the benefits of personal freedom, deciding when and how to take a vacation from your business can be challenging. In this episode, Dana Kaye of Kaye Publicity, Inc. shares how she learned to balance responsibility and freedom, what she does to set up her team for success, and why vacations are essential if you want your personal and business life to thrive. Dana and Emily talk about the ways they’ve learned to overcome stress when it comes to stepping away from work and how they find empowerment from taking the space that’s required to recharge.

Learn More about the Topics Discussed in this Episode
This Episode Brought to You By:
"Vacations and taking time off are necessary both for your physical and mental as well as the health of your business."
- Dana Kaye

Discussed in this Episode

  • Why business owners should take time off
  • How Dana set up the systems necessary to take time off of her publicity business
  • Planning and delegating work projects to teams with trust and ease
  • Managing the mindset of guilt that can come up when taking time off from your business
  • Why communication and clear expectations are crucial for success and fulfillment
  • Different types of time off and how to take vacation as a small business owner or solopreneur
  • Balancing work, parenting, and time
  • Remembering your core values and incorporating them throughout the steps to take time off as an entrepreneur



More from Dana Kaye

More from Emily

Almanac Supply Co.


Emily Thompson: [00:00:00] Almost every boss I know chooses the path of business ownership and entrepreneurship because they want more freedom, more agency and control over their time to live and work however they please. We want flexibility in the ability to travel, to take time off, to spend with our families and to make money while doing it all.

[00:00:32] But you have to get there. And the road to that freedom is often wrought with fear and guilt and insecurity, which usually looks nothing like a freedom and agency and control over your own time. Welcome to Being Boss, a podcast for creatives, business owners and entrepreneurs who want to take control of their work and live life on their own terms.

[00:00:52] I'm your host, Emily Thompson. And though a lot of what I just said, maybe sounds familiar. Know that it is totally possible for you to make it through that phase of entrepreneurship, the phase where you feel like you can't leave your business baby behind and move into the next phase. The one where you're able to travel to take time off and unplug from your inbox, your clients, and even your team to both take the time to live the life you want to live and take the time to recharge your batteries

[00:01:21] to be the best boss you can be. To help me dive into this topic of taking time off, I invited my friend and fellow boss, Dana Kay, who you first heard from an episode number 250, to join me in a conversation about the journey, to feeling at peace with taking off as much time as you need from your business to do what you need to do from vacations and retreats to taking the time to take care of the responsibilities of your life.

[00:01:48] Dana Kaye is a lifelong entrepreneur who believes in the power of storytelling and authentic personal branding. In 2009, she founded Kaye Publicity, Inc, a boutique PR company specializing in publishing and entertainment. Known for her innovative ideas and knowledge of current trends that she coaches her clients on how to identify and establish their unique personal brands.

[00:02:10] She is also the author of two books. Your book, your brand, the step-by-step guide to launching your book and boosting your sales and the personal brand workbook and serves on the advisory board of propel PR.

[00:02:26] As the podcast industry rapidly grows your looking to really lock in on the best podcast for you. Value packed shows and episodes that fill your brain with the must know tips and tactics for growing your business. Along with a big dose of motivation. If that's the case, check out the HubSpot Podcast Network, the audio destination for business professionals, seeking the best education and inspiration on how to grow a business with a wide array of industry experts that act as on-demand mentors to entrepreneurs, startups, and scale-ups through practical tips and inspirational stories.

[00:03:05] Listen, learn, and grow with the HubSpot podcast network at hubspot.com/podcastnetwork.

[00:03:17] Dana, welcome back to Being Boss. I'm so glad you're here. 

Dana Kaye: [00:03:20] Thank you for having me. It's great to be back. 

Emily Thompson: [00:03:22] Of course, well, we are recording at the beginning. Oh, this is technically the very end of spring, almost summer,  vacation season. Hopefully remember when we used to have vacation seasons, but I feel like it's still a thing.

[00:03:40] I came back from vacation a couple of weeks ago. I know you have been taking some, some trips, some safe trips over the past couple of months and having this conversation about what it looks like to take time off. I knew that you were the person I wanted to chat about with this chat about with, for this, you know what I mean?

Dana Kaye: [00:04:01] I do. 

Emily Thompson: [00:04:04] Perfect. Okay. So let's just dive right into it.  Let's talk about, I want to take a moment and just sort of think back at the early days cause you and I have both been in this over a decade, right? Yeah.  

Dana Kaye: [00:04:20] It'll be 12 years, 12 years, 13 in February. It's a long time. 

Emily Thompson: [00:04:27] Congrats.  Let's try to think back 10 years ago, right?

[00:04:33] A decade ago to those first couple of years of trying to take time off being on vacation. Do you remember what that was like? 

Dana Kaye: [00:04:42] I do.  I'll go back even further. And I think you probably understand this from your days with the tanning salon, like way back when, where I used to work at various jobs and always my ability to earn money was tied to whether or not I showed up.

[00:05:02] Yeah. And so I had this mindset of that. If I was taking time away, then I wouldn't be earning money. And that was a big mindset shift to overcome because everything I did was just tied to my time. And so before, when I would take days off, I would be hustling to pick up extra shifts the week before, or trying to save up money or cut expenses.

[00:05:27] It was this constant juggle. It was less about the time and more about the money. And then when I launched my business, I, I kind of, it went really quickly. I grew really fast. And so for the first couple of years, I did not feel like I could take time away. And when I did, it was a lot of stress. I actually went back to one of my emails to, I send out to all the clients saying that I was going to be out of the country and not accessible.

[00:05:55] And the subject line was refill your Xanax. Dana is not going to be available. And that mentality, I mean, everyone had a good laugh. It was, I mean, it was cheeky and fun, but the reality was is that so much of so many of my clients felt that they needed me to be accessible at all times. And so it took many years to start putting systems into place and to start training my clients to understand that just because I was not accessible for a day a week or multiple weeks, that didn't mean that their stuff wasn't getting done, that they weren't supported, that they weren't, that their work was on pause.

[00:06:39] And it takes a lot of when you have a mindset, when you have this kind of scarcity, rigid mindset about time and money that gets passed on to your clients and for other bosses, potentially your customers. And so you have to have that mindset first that I'm doing the work. I can take time away, but it comes after the client mindset will come after you have to demonstrate it first.

Emily Thompson: [00:07:08] Yes to all of this. I also love that you were totally projecting with that Xanax subject line because you really needed to refill your Xanax.

[00:07:19] But like, I also,  I totally resonate with all of that. I remember those first couple of years and feeling the exact same way. And you sort of even shared like a little like mindset journey, right. At the very, the very beginning you can't, it's hard for you to even fathom taking time off because time is money.

[00:07:39] Right. And if you're not there, you're not making money. And if you're not making money, then like you're not being a business owner or entrepreneur, or you can't pay your mortgage, like all the things. Right. And then it sort of turns into, you can do it like you work through the mindset of, I can take time off.

[00:07:57] Like I build a business that can either, you know, run without me being there. Or I can take a week off for my clients and nothing will fall apart, whatever. But then the struggle is the stress of it. Right. And I remember, I definitely remember that first phase, but for me, what stands out the most from my early years is that piece of stress around taking time off.

[00:08:19] And I remember saying, you know, multiple times, like it's not even worth it to take vacation because of how stressful it is to take a vacation, right. To take time off. Like I'm not going to enjoy my week off because the week before and the week after we're going to be held in order to even make it happen 

Dana Kaye: [00:08:36] Well and I think if you think about it in the context of most of our, so if you were, when you were doing Indie Shopography and you had websites to build, you had your list of websites that need to get built this month. So if you were taking a week off, that means four weeks worth of work had to be jammed into three.

[00:08:52] And if you make X amount of candles or do X amount of markets in any given month, then, and you're going to take time off, then either that needs to be delegated, which means less money, or it means that you have to do double the work and all of that puts so much stress. So that by the time you do take a vacation, like you extra, extra needed.

[00:09:14] And so what I've attempted to do, none of us are completely successful at this. But what I've attempted to do is look at our vacation times and look at are the tons that we're going to take time off for the whole year and really plan my projects around it. So for example, you know, the summer in public, I work in publishing.

[00:09:37] Publishing slows down in the summer. Right? Like it just slows down. So there are less clients. And so that's the time where I'm like, okay, I know those clients are going to be here. There's going to be less stuff coming in, less urgency. This is the time I'm going to allocate that between Christmas and new year's also publishing slows down.

[00:09:58] So I can plan for vacation for that. Now that's an ideal world, right? Like, so, you know, I remember Emily when you were doing Indie Shopography and Being Boss that you and Kathleen were taking December off, and now you're a maker business. I would think that Amber might be a difficult time to take time off. 

Emily Thompson: [00:10:21] The worst. The worst.

Dana Kaye: [00:10:24] And so I feel like by leaning into the seasonality of your current business and knowing your current flow, it makes it so much easier on your side. That being said, there's certain things that happen. Like for example, September and October is probably are our busiest months, but I'm also Jewish and the Jewish holidays always pop up around that exact same time for me, that's a non-negotiable I can't, I don't work on those days.

[00:10:53] And so, and my son doesn't have school on those days. And so it can't really work if even if I wanted to. And so I think that if you can lay the groundwork for taking your vacations and taking time off at times that you are slower, it'll be less stress, less stressful, and it will also be easier to take that time away if need be.

[00:11:14] Even when those, your general workflow is a little bit busier. 

Emily Thompson: [00:11:18] Absolutely. Okay. I wasn't planning on this, but I feel like we are almost creating a journey of like how you make making time or make taking time off happen, like over the years of being a business owner. Right. Because you're right. The, you minimize the stress of taking time off by planning it at good times.

[00:11:43] Right? Because whenever you are just sort of pop and I also love spontaneous travel. So know that a lot of this totally goes against my own natural urges and how it is that I like to travel. There is this plan that goes into place at the beginning of the year where I do the exact same thing, where I look at my year and I know from experience from doing it at least a couple of years, like where the ebbs and flows of business are, and every business has ebbs and flows.

[00:12:08] If you're just getting started, you may not know exactly when and where they are, but you can probably eyeball them, right? Like if you are, if you're a product business, the holidays are crazy, right? You, you know, that that November, December timeframe is going to be when you are going to be at your busiest.

[00:12:25] If you are, you know, a wedding planner, those wedding seasons are going to be your busy seasons and, and anything in between will be a little slower. So you can minimize the stress of taking off by planning your vacations during those windows, when business is going to be slow as much as humanly possible.

[00:12:45] And so, yeah, I've definitely like worked into a flow over the years of like summer, for me, same usually pretty slow in terms of business. I can take lots of vacation dining during the summer.  But you're right that I can't take my December's off anymore. Instead I take off January as much as possible.

[00:13:05] Other than sort of the big picture planning that I do. And I do have to make a CEO day kit plug here because they feel like this is just right for it to right. But as we both use CEO data, And really sitting down at the beginning of the year and looking at that entire plan for the year, part of that plan is not just business, but it's life.

[00:13:24] Right? So it's thinking, okay, I'm going to have this marketing push. I have these projects, I'm having these events, whatever. Okay. There are some holes. Here's where I'm going to put my, put my vacations or vice versa. Let's say you're taking a, you know, big European vacation. That's on my to-do list for ASAP.

[00:13:41] I'm going to plan my business around these big life events that you have. So using something like CEO Day Kit, or really just making a year plan really helps deal with the, with the stress of traveling during some of your busiest times, because that is [00:14:00] not fun.  Any other sort of fears or hesitations or mindset, things that you had to deal with in the early years?

Dana Kaye: [00:14:11] I think the biggest one was the guilt that goes both ways. Yeah. So I'll re iterate. I'll embellish that a little bit as many entrepreneurs, we love our work. Like I think you had talked about Emily one time that, you know, we'll just like curl up on the couch and play with the spreadsheet. I love testing new software or do any of those things.

[00:14:40] And we feel so guilty. Like, oh, this is my downtime. I'm not supposed to be working. And so I think there's a lot of guilt around first taking time away from your business, right? There's this guilt of, oh my gosh, I'm taking time off and letting my clients down. My team members have to do extra work for me.

[00:14:55] And there's a guilt around that. Then there's this other guilt of I'm on vacation. And I kind of want to take this call or I kind of want to tinker around with this platform or whatever. And so there's this guilt that goes both ways. So I think the biggest thing for me is not only letting go of the guilt for myself, but also communicating my, what would make me feel best to my family members.

[00:15:26] And so if I'm going on a vacation, it may make me feel best to spend an hour in the morning, going through my inbox and looking through. And that is the way that I am able to be fully present the rest of the day. It may mean that at night, when we come back from our touring or our hiking or whatever that might be, that I kind of want to get on the couch and like play with the spreadsheet that I haven't been able to do because everyone's bothering me, but now I'm on vacations and no one can bother me and I may want to do that.

[00:16:02] And so I think it's, or communicating on the flip side to your team members, I'm trying to prepare for vacation please don't, I have this conversation today. In fact, I had marked off, I am taking tomorrow and Friday off and I told my team members that, and yet in my Asana today, some things popped up from, for me do Friday, me communicating to my team members that I'm not going to be in the office.

[00:16:31] So please don't assign me tasks or do things that need my review during my vacation, or just before my vacation. I'm communicating that I want everything done this week so that I can review it before I leave that sort of thing. I think communication will help assuage some of the guilt cause a lot of the guilt comes when we're not communicating our needs. 

Emily Thompson: [00:16:54] And like unapologetically communicating.

[00:16:58] And I think this is both for team and also for clients. So like both sides of like being very communicative, probably more than once. Almost definitely more than once that you are going to be out. So the expectations are set so that people know they can like adjust their plans. They can either there'll be aware they're prepared all of these things so that you can do it.

[00:17:20] And I think, I think you're right there, there can be a whole lot of guilt that comes up both around dealing with the other people who need to deal with you being out, but also that allowing yourself to work or not work. And that's something, that's something that I continue to continue to work on. Um, but I do want to like, almost back up a set a step and talk about how to get used to taking time off.

[00:17:45] And the topic for this in particular came from a conversation that I had with a boss friend of mine recently. And she's just, I don't know, maybe three years in. So like still very new, fast growing company. Has it recently hired a couple of team members, so has really set herself up so that she can start taking time off, but is legitimately struggling with actually doing it.

[00:18:08] And so we were having a drink and she, I, it was actually just before I went on my vacation that I did a couple of weeks ago. It was like, I was actually having a drink with her was like the beginning of my vacation. Right. So it was like Thursday evening. I was taking off Friday. We were leaving on Saturdays and we were having a drink on Thursday evening.

[00:18:27] And she was like, how do you do it? Like, how do you take a vacation? I looked at her and I was like, you just put up your auto responder and you go, it's kind of as simple as that, but there is a lot of things that go into it. I think you have to build yourself up to being able to take off a week or two or four weeks even.

[00:18:50] Right. And so my tip for anyone who like can't even fathom taking any time off is start with a long weekend, right. Start with taking a Friday off and then take like a Thursday, Friday off and then work your way up to a week. And then two weeks and three weeks, a couple of really amazing things happen whenever you start doing this for yourself.

[00:19:14] And it's not just that you have brain space that you've given yourself a vacation that you can arrest and relax and rejuvenate and recharge recharge and yeah. Of those rewords. But you also, you start seeing holes in your systems. You start seeing aware communication could be better. You start seeing how you can make things more efficient and effective.

[00:19:37] You start seeing how you can, you know, fix your schedule up so that you can work smarter, not harder or batch things or all of these things. Whenever you start changing your routines and how it is that you do things to make room for that first long weekend or that first week off, it just sort of start snowballing into it becomes easier and easier for you to delegate or for you to take more time off.

[00:20:02] But you just have to do it first. You just have to get started.  So anyone who is struggling, anyone who is in that place where you're like, but how do you even do it? One, it literally, it just put your autoresponder up and walk away. Unless you were,  you know, saving lives, literally it's fine in most cases.

[00:20:21] But by just doing a long weekend to get started, you start seeing the things that you can put in place to allow yourself more and more time off. 

Dana Kaye: [00:20:31] And you'd be surprised that no one cares. 

Emily Thompson: [00:20:35] Yeah, no one does. 

Dana Kaye: [00:20:37] I love, I, someone told me that this recently, because as you know, I've been toying with my contribution to various social media platforms and kind of wanting to walk away from it all.

[00:20:48] And I was like, I kind of just want to do this in front of me. I was like, no one cares. Like, just walk away who cares? No one will even notice. Like, it's this idea of people putting up there I'm going on a sabbatical from social media or whatever. Like no one cares, just do it. Just don't even say anything, just do it.

[00:21:06] And it's the same with the auto responder thing. It's you can there's even days where you don't have to put it on, but even just doing it because you need to get some work done and just saying, I'm not answering email today. That's actually a really good tip that I use for people who have challenges walking away from their job or walking away and taking time off is like, just put up your auto responder for one day and you'll realize that one, no one cares.

[00:21:31] And if you have team members sometimes magical things happen, like your client contacts, another team member, and they do it for you while you're gone. And that's just like one less thing you had to do. And so I think that if you're really nervous put up your autoresponder, even though you're working, just don't answer email.

Emily Thompson: [00:21:50] Yeah. And like that, like is a mindset shift, right? Of like you've disconnected yourself from your email. And literally that is sometimes the biggest thing is my email. Like what happens when I'm not looking at my email every day?  One of the really awful things that's happened for me and by awful. I mean, I love it is that I don't give a shit about my email anymore.

[00:22:08] I mean, I do, and I'm looking at it and I'm responding to like the important things, all of those things. But like sometimes I can literally go three days without even like really glancing at it. Like you can begin, you begin detaching yourself from these things because one no one cares, two like, as long as you have ways of communicating the most important things, and like, I do keep an eye on it.

[00:22:28] The important things that are happening in real time, like are getting done, but you can operate your business without being tied to your inbox. 24 7 basically is what I'm saying. So, yes to all of that.  So long weekends is a good way to get started. I do want to hit on this communication piece because that really is key because we are talking about putting up your auto responder.

[00:22:51] We're not talking about walking away for a week and not telling it like don't ghost don't ghost, your team members. Don't ghost  your clients, don't ghost your  customers like communicate that you will be gone and you're right. Magical things will just happen without you even being there.

[00:23:11] You'll see the power of what you've built when you step away to look at it 

Dana Kaye: [00:23:18] Yeah. And it, and that communication piece is really important because you want to give your team members or your clients, if you're a solo preneur that giving your clients the tools. So a great example is we have. And I'll, and also for context, we do publicity.

[00:23:36] So like we do have urgent things come into our inbox, right. We have, you know, the Today Show calls that needs to get dealt with immediately. And so I don't want people to think like, oh, she doesn't have to check her email. It's not my business. I, we have urgent, timely things that need to get done and in my business, but the communication piece is what keeps the systems going.

[00:23:57] So we had one publicist recently go on maternity leave, and that's a, that's a big time away. And she had so many interviews, so many things that were happening while she was gone. And what she did was for every single interview, she put an Asana task for me to reconfirm the interview and gave me the name of the client.

[00:24:23] The time, like all the details were in Asana along the way.  We have a Google calendar of where our clients are in the world at any given time. But the most important is it wasn't just the interview. It was the, the topics, the talking points gave me all the information I needed. So while she was gone, I must've dealt with 10 to 15 interviews, reconfirming sending press kits, sending whatever, but she made it so easy for me that it was just getting done.

[00:24:55] And when she came back, she had told me she was gonna come back quietly and not tell anyone and just go in her inbox. And just quietly come back. She came back to the Monday meeting and said, I'm back, fully, everything got done. There was nothing really for me to deal with. And that's really what you want.

[00:25:11] You want other people helping you. If you're a solo preneur, give your clients the power to fix things. And this is where the practice comes in. So like Emily you've mentioned that, we have this idea of, okay, we'll do a long weekend. We'll do a week and you start to see where the breakdowns in your systems come and use those as learning opportunities to say, okay, I told my clients how to fix their Instagram page or how to fix their Twitter or how to delete a tweet or whatever it is.

[00:25:46] I made them a Loom video. I taught them how to do that, but what I didn't tell them to do is what happens if they get emailed by this type of person, how to respond. So next time, I'm going to include that in my documentation. So the more you can communicate to your clients and give them the tools to take care of it for themselves, while you're gone, you don't necessarily need a team member to watch out for yourself.

[00:26:10] They can handle it themselves. For a week for maybe even two weeks and it's fine, but if you don't communicate that to them, they won't have the tools and then they will feel neglected or abandoned or any of those things. 

Emily Thompson: [00:26:25] Yes, yes to all of that. So it sounds like the core of being able to take good time off is to communicate like a boss and teach your team to do so, too.

Dana Kaye: [00:26:37] Yes, absolutely. Cause I think she, I felt very empowered. I, I was empowered to do these things for her while she was gone and it wasn't a headache. And now what's great about this is we have another publicist going on maternity leave and I said, please meet with Sammy and do whatever she did because it was so smooth and it was so great.

[00:26:59] And she had peace of mind.  And it gave me pleasure. I think the other piece is I sometimes feel guilty about leaning on my team too heavily, like, oh, I chose to. Go camping this week. And so now my team members have to do double, but if I make it really straightforward and really simple for them, it's not that they actually don't mind.

[00:27:17] It's actually fairly easy that you have to communicate exactly what to do.

Emily Thompson: [00:27:25] Okay boss, trust me. When I say I know the struggle of growing your business and expanding your network and trying to remember everyone's name, email address connections, and what it is you talked about with them last, if only there was a tool to let you keep track of all of that. Oh, wait. There is meet HubSpot, a CRM platform that helps you keep track of the people who are a part of how you do business from vendors and contacts to clients and customers.

[00:27:54] What is CRM? It stands for customer relationship management, and it helps you stay connected to your people. And in HubSpot they're the best at what they do with special features like a contact at timeline, which gives you the historical context. You mean to get work done and connect appropriately with customers.

[00:28:14] It puts all your customer data in one. So it's easy to make a call, put a contact into a sequence or schedule a meeting. And if you're on the go, you can do all of this from the HubSpot mobile app. So you can manage your customer experience, grow your network, and collaborate with your team from anywhere.

[00:28:33] Learn more about how you can scale your company without scaling complexity at hubspot.com. I get it. You want to take time off? And so does your team. Offering benefits like time off or vacation or sick days should be part of the benefits that you offer? The employees that enable you to build, grow and run your creative businesses empire.

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[00:29:35] Yes. Okay. I actually want to touch on this one because this is something I kind of struggle with. Sometimes I am have been actively working on this for a long time. Lots of practice, lots of practice, but one of the layers of guilt that I get is literally weaving and my team's still working. Okay. How do you deal with that?

[00:29:54] Walk me through, you can coach me on this Dana. 

Dana Kaye: [00:29:59] Our roles in our companies are different than our employees. And so what our employees don't see is the time we do spend tinkering at night instead of, you know, reading or watching Netflix were like playing with spreadsheets and apps and things. For me, we, we represent author.

[00:30:22] So I read a lot and all of my reading is done at night. It's just one of those things where they, so for me to say, I'm taking a day off. They don't seem before, you know, two to three hours, I spend each night reading manuscripts. They also don't see the time that I need to create these new ideas like this.

[00:30:40] You know, Emily, your role at Being Boss and at Almanac is very like the visionary role, right? So you are looking at business strategies, big picture things. And in order for you to do your job, 

[00:30:53] you need to take that time off and get that. I forgot what the word, what part of the brain it is, [00:31:00] but whatever part of the brain cannot is like thinking you need to like, let that part of the brain that marinate and that muscle kind of do its thing in a way that it can't do when you are answering email or on client meetings.

[00:31:12] Like right now, you and me are talking, this is all you're thinking about. And so it's hard to have ideas for the business when you're actively doing something else, our team members, while they have ideas, that's not their primary role. Their primary role is to help you deliver the products or services that you are creating.

[00:31:35] And so they are entitled to their vacations too, but we may take them either more frequently or more, less, or, or less formally than our team members do, because they don't see that. I also think one of the things that comes about that our team members don't see is that they, most of our [00:32:00] team members have salaries, right?

[00:32:01] Like they're getting paid. I have more control over my salary or my profit margin or whatever that might be. And if I'm thinking about the most important thing, so for a great example was in March 2020, I no longer had childcare and not only did I not have child care, I was also a homeschooling parent.

[00:32:26] All of a sudden, I had not created that life for myself. You do it so beautifully Emily, but so I, all of a sudden said, okay, time is way more important than money. And so I did take home less that year,  not that year, but for a good chunk of time, because it was more important. I only have the capability to work 15 hours a week.

[00:32:51] Again, I didn't necessarily communicate that to my team members didn't feel that was important. I did communicate however that I was only available for 15 hours. These are meetings that I would not be taking. I would coach them on how to take these meetings and kind of figure that stuff out. So I think that the guilt is kind of a swayed by understanding.

[00:33:14] This is understanding this piece is that there's are our roles and our compensation are very different. And therefore our time off should also feel a little bit different. 

Emily Thompson: [00:33:24] Amen. Amen. To all of that. And I will say too, I, I thank you for sharing that with me, but also this is for you guys, like I've also definitely worked myself through this and I will say one of the, one of the moments and is editing this, I'm going to say, hi, Corey.

[00:33:40] I will never forget a couple of years ago, Corey actually told me to take time off. Right? We were, we were due, I can't remember exactly what was happening in the business.  But I knew I needed to do some ideating. I knew I needed to figure something out and I was having a hard time. And there was some, I was having a hard time doing my brain work and Corey in a meeting goes, and we need to take a vacation.

[00:34:03] Like you need to go like have your brain space so that you can figure this thing out. And in, I remember in that moment thinking. The communication right. Has happened where the roles are clear and it's my job to solve this problem in order for me to solve this problem, I need the brain space. And Corey has seen over the years that whenever I leave, I come back with the next thing almost every time, or at least with like some rejuvenated energy to attack all of the things.

[00:34:35] And so I just, I want, I want to share that so that anyone, if anyone here is feeling that guilt, like it is really important and your team will see that too. And if they don't see it yet communicate that need and necessity. Cause all of the things that you said also are completely. Right.  So I want to talk about like what it looks like.

[00:34:56] What it looks like these days. So we're both a decade plus into business ownership. We have both crafted these business that allows us to have some ownership over all of our time, more or less. How much time are you taking off?  Like in the course of a year, how many weeks do you think you take off? 

Dana Kaye: [00:35:17] So this is a really good question.

[00:35:18] Cause I knew you're gonna ask me, look through my Google calendar and see much. So I also think it's really important that people understand that what one person's needs are, is very different than another. So like for example, I am not the two week vacation person. I don't like that much extended time off.

[00:35:38] I would much rather have four day weeks for a month. Yes. That's just my preference. Yeah. So I think that when I was looking through, I probably in total. In terms of full days, not working probably anywhere from three to four weeks a year [00:36:00] and some of it. So this is the other piece that I think is funny.

[00:36:05] So in my early days of business, probably the first trying to do math in my head for six or seven years of business, it was just me. I could work as much as I want.  And then we had a kiddo and all of a sudden that time is constrained, right? Like the nanny would be done at a certain point. I would have to come relieve her. School ends, camp ends. Like there's these times, these, all these constraints around time, I can no longer just like work until the late night until I finished the project. I was like, whatever got done and got done. And so that those sorts of constraints also really help when it comes to taking time off.

[00:36:44] So for example, this week, There's no camp and no school. And so what are we doing? Well, I have the choice of saying I could, you know, plop the kiddo in front of the TV and hope for the best, for a full week. That didn't make me feel really good. [00:37:00] And so instead I said, I'm going to take three days off. I took off Monday, we went to six flags, great America. 

Emily Thompson: [00:37:07] Nice.

Dana Kaye: [00:37:09] And then tomorrow and Friday we're going camping. And these two days I got the help of my in-laws and they took them him for these full two days. And I'm like hustling and grinding these these two days to get, to make it all do. And so I think that when you have these constraints, like spring breaks, winter breaks, school breaks, camp reduced schedule, whatever you're kind of forced to take the time off.

[00:37:35] So I could just total up the days off of school. And I'll just say that that's probably my time off. And so you have to just make a dis I think I have to make a decision. You know, you could do the thing where you try to work and try to parent and try to do it all, which I find way more stressful. Or you can just say, you know what F it takes a day off.

[00:37:58] And just know that you have to shift shift a lot of things around. So like this month, because of again, camp schedules and whatnot, I'm taking three days off this week. He has a, he has a one-week camp next week. And then the week after my wife is off work. So we are taking a full week. That full week is going to be a little bit worky for me.

[00:38:18] I think I'm going to do the morning check-ins and then maybe the evening stuff, just because it will make me feel better, but that time is blocked off no meetings during the day. So I think it really just is knowing yourself. She likes my wife likes taking full, extended weeks off, like full to decompress.

[00:38:38] I would rather have kind of a couple of days here. What about you? 

Emily Thompson: [00:38:44] So for me, I just went through and just did a quick tally up on my calendar.  I think it's more like anywhere from six to 10 given, given the year. And I will say, you're right, you have to know your needs. For me, I discovered a couple of years ago and it was very much so accentuated for me on my last week off that I do need large chunks of time off.

[00:39:05] So I will occasionally pepper in, especially if I have a long period of time where I don't have any time off, I will pepper in some like Fridays off or Thursday, Fridays off, give myself some long weekends as much as possible. I also like to work in some flexibility so that I can just like take a spontaneous morning off occasionally too.

[00:39:24] Like that for me, we're a reasonably in one of our, and one of our calls talking about like, what makes, what makes you feel most boss?  Or like what makes you feel like you are succeeding in this moment? And I remember mine was, um, mine was when I can just take it. A spontaneous morning off to do what I want.

[00:39:41] Let's say I wake up and the weather's beautiful. I just want to take a hike, right? It wasn't on my schedule, but like, I'm going to take the first two or three hours of my morning to do something like that. Or, you know, take my kid to the park or whatever it may be. So that for me, building in that flexibility is really important to me.

[00:39:57] Whenever I don't have, vacations, like a good chunk of vacation time coming up doing a long weekend often is important. But when it comes to vacation time, legit taking time off, I need two weeks.  A couple of weeks ago, whenever I took a vacation, it was the first just family non-work vacation that I have done in far too long, like two years-ish.

[00:40:22] I didn't feel like I was actually on vacation until about four days in. I need a lot of time for my brain to like settle down, to get into vacation mode. And I know a large part of that is I'm running two companies. Like there is a lot going on in my head at any given moment. And there's always like this detox period, maybe that has to happen where I need to detox for my business to like settle in my heart rate needs to like chill out.

[00:40:53] Like do I don't know what's going on with me in my body. Um, but apparently some things where I need, I need time to chill. And for me that one week wasn't enough. I felt four days. I finally settled in two days later, we laughed and I was like, okay guys, I got like two days vacation. We could do this again.

[00:41:10] Like I need to do it again. So I need two weeks of vacation time to really have a vacation. I do love around the holidays taking three to four weeks and it used to be December now. It's  but after Christmas I will take the first couple of weeks off with some CEO days there in the middle to get everything planned out at the beginning of the year, but still just sort of settle.

[00:41:36] So for me, it's six to 10 weeks as much time as I can. If I were to calculate up all of those, like, lingering Fridays that I decide not to work or, or it could be even more than that. But for me, time off is a very important part of my process. And it's one of those things I discovered a couple of years ago, I realized that all of my like best ideas, like the ideas that did something, the idea of starting this podcast, the idea of starting Almanac, the idea of buying Kathleen out and taking this thing,  further came from space.

[00:42:12] I didn't come from me sitting down for a planning session and I'm just going, I'm going to like come up with my great idea today. Right? My different Almanac came on a vacation, that I was having with my family in New York city.  Whenever I had my idea to buy out Kathleen, it came from,  it came from having taken a large chunk of my summer off to sort of settle in and heal from burnout and give myself space.

[00:42:40] At that point, I knew I needed space to have my next idea. So I prioritize it for me. This is a long way of saying six to 10 weeks.

Dana Kaye: [00:42:48] But I think that's very common because if you think about, we talk about habits, a lot habits and routines and taking a vacation is breaking your habit and your routine. [00:43:00] And it doesn't happen for most people instantly.

[00:43:02] It takes a few days to get out of the habit of waking up and looking at your phone. Or popping open the laptop right after breakfast like that, those are habits that we have to undo. And so it makes sense that for many, they won't be in full vacation mode until they won't be in full vacation mode for a few, at least a few days and therefore need that extended amount of time.

[00:43:28] But it's about not having guilt around that. Indeed. Again, everyone's different. 

Emily Thompson: [00:43:33] Indeed. And for me to get over that, I had to see the value. Right. I had to understand that there was legit value in me creating this space for myself. And for me building my businesses in a way that I could take that space for myself, the effort to create a business that allows me that is worth it because it allows me to continue building the business.

[00:43:56] Right. 

Dana Kaye: [00:43:57] Yes. And there's also just value in taking care of yourself. Yes. A lot of it, people to think like, okay, I'm on the beach. Now let all my ideas come. Right. 

Emily Thompson: [00:44:09] It doesn't work like that guys. 

Dana Kaye: [00:44:11] Need to make it worth it. I was, I'd had such an unproductive vacation. Yeah. Because this is where I just know that this is where bosses minds go.

[00:44:21] Where's your you. And simply saying, I need to sleep. I need to rest. I need to not look at a screen. There's value in that because the more rested and rejuvenated you are, the better you're going to serve your clients and customers and burnout is as you know, Emily, you've experienced it in many other bosses have experienced it.

[00:44:44] You don't want to get to that point. And once you get to that point, it takes so much more. There's a saying, there's a phrase. The body keeps the score and the body always wins. Am I right? Yeah. Right. Yeah. And so your body will know your body will tell you, oh, you want to keep working or let me just handle that for you and give you a migraine or shingles or whatever, crazy things that pop up.

[00:45:15] And so I think that vacations and taking time off are necessary both for your physical and mental health, as well as the health of your business. 

Emily Thompson: [00:45:25] A hundred percent. Absolutely. So I am wondering, I want to go back to this, like working vacation and then like legit all the way vacation, because. I hadn't really, I mean, I guess I do think about it in those terms, but I hadn't really thought about it in that way, because I do have vacations.

[00:45:45] And I'm wondering if you do this, I do have vacations where I will not allow myself to check my email. Right. I will. Or like, I will not, I won't take my laptop. It's like those vacations, like I will turn off my phone when I leave and not turn it back on until I get back. Like I will occasionally, and I don't do those very often, but I will occasionally have a complete unplug vacation.

[00:46:07] And those for me are the most rejuvenating, but I also usually deal with this. Like, there is also this. This denying of the need or desire that happens usually in the middle of those, of like, I want to go play with that spreadsheet. Right. Like, you know what I really love do right now build a database.

[00:46:29] That's what I'd really. But I can't because I'm unplugging and I feel like that's like an interesting thing to juggle, but then there's also legit just work vacation. So retreats or conferences or,  staycations where your purpose is to set up this new tool. I don't think that literally is a vacation, but it is like taking time off from the day to day to do something out of the ordinary.

[00:46:55] Do you think about them in those terms? Do you just, like, what does that look like for you? 

Dana Kaye: [00:47:01] Yeah, so I, when I think of vacation, like I, I have a, my, again, it's a mindset. There's the vacations where it's mandated meeting. The kiddo has spring vacation, and therefore I will have to be off, but there is there's those, there's a little bit of a difference with like I'm intentionally taking a vacation and I am unplugging cause I, I don't, I can task agency task, switch mindset shift fairly quickly between work Dana and life vacation Dana.

[00:47:33] But what I notice is that the vacations where I completely unplug, they don't need to be as long. I get rejuvenated a lot quicker. I, if we want to think about charging your phone, if you turn your phone off and charge it, it'll be charged real quick. If you're charging your phone and also watching Netflix while checking your email and have a podcast going.

[00:47:54] It's going to take a little longer to reach full charge. So those are the differences to me. So if I'm taking a longer vacation, I feel okay about maybe doing a little work in the morning or doing, or taking a call in the evening or whatever that might be. I don't, I'm not upset about that. But for example, when we were going to go camping for just one night, two days, one night, but there's no self service, we don't have power.

[00:48:19] There's nothing that we can do. And so I'm confident that I'll be pretty recharged even after that short time, because there is no social media. There is no internet. There is nothing that I can do other than look at trees and listen to birds and do all those things. But I do think I, I make, so when you think about the six to 10 weeks, when I, when I counted those three weeks, I'm only counting solid vacations.

[00:48:47] I'm not counting. Working the virtual retreats that we've been doing. I haven't been counting, you know, I, in the summer I try to do my CEO day by the pool when possible, because it feels like a little [00:49:00] vacation.  And so, or if I'm doing a big project and I want some alone time, you know, doing it, I haven't done this, but I've been thinking about is getting a hotel room and doing something, but, and just really like unplugging in that way.

[00:49:16] It's like unplugging from your world in which you currently live, even though you're plugged into your laptop, phone, wherever. So I think that there's this, I don't like, I don't consider these days vacations. I consider these a necessary part of my business. And so me doing a CEO day, four times a year, me doing a virtual retreat four times a year, well now three.

[00:49:37] And hopefully in person, I think that those are all really important aspects of our business. So I actually, I don't even count those as vacations. I count that as my job . 

Emily Thompson: [00:49:47] Same, same, same. I will say one of the things that I do is I do sort of differentiate when it comes to like official time off, like all the way time off.

[00:49:58] I do create these events where there's like zero, like total unplugs. And then like, I can't, if I want to. Right. Of like, or like, I'm just going to take this meeting one day because part of the dream is being able to work remotely. Right. And if you're always completely unplugged every time you're remote, like if your dream is taking meetings by the pool, but you never take meetings by the pool or at the beach or wherever.

[00:50:26] So there, I do differentiate between those two in terms of like legit vacation time. Like there are vacations where I will completely unplug. And even if I want to, I'm not picking up a business book. Right. Like I'm unplugging.  And then there's the vacations or staycations because I do love a good staycation.

[00:50:45] I will say, like blocking off all of work,  or not doing any work for a week, not going anywhere, but just like putting around the house and doing some yard work and like just living my life at my house and in my city.  [00:51:00] But let's say I do get the desire to build that database. Like, it's fine. I can do that because I want to, I legitimately I don't need to, no, one's expecting, I don't have to talk to anyone while I'm doing it, but I can do a little bit of research or sort of light building or tinkering or whatever it may be.

[00:51:17] I do think it is important to have both of those, like just sort of free time to work on the things you want to and live the dream life of taking meetings by the pool, if you so desire, but then also having those completely plugged, you know, really allowing yourself to completely recharge. Time off as well.

[00:51:38] Both of those are important. 

Dana Kaye: [00:51:39] Yeah. And I think it's funny because knowing, like what makes you feel most jazzed? Like knowing what that, what you feel, what makes you feel most boss? It might be different. I remember this past summer. So the summer of 2020, where we were all still, you know, sheltering and distancing and all these things.

[00:51:58] I laugh because in some ways I was living the boss stream because every Monday I took my every Monday morning, I took all my calls at the beach and every Wednesday did all my work at the pool, but that was the only reason was because again, my kiddo needed to be occupied. So he gave him a beach full of sand.

[00:52:19] I interrupted time on my calls. Give him a pool. I could do work. Just watching him over the screen of the laptop. Like he, he was fine. And so it's, what's interesting to me is that once he went to camp, I stopped doing that. And in my head, I'm like, why don't I go take some calls at the beach? Why don't I just sit up at our pool and not our pool, but the pool and do some, you know, and I think that it goes back to this idea about like boundaries and constraints.

[00:52:51] And so putting it on your calendar. So I started putting those pool days on my calendar. So meetings don't get booked and that I can just work. Saying, okay. I have three calls in a row. None of them have to be on video. I can just go to the beach and sit or the park and sit outside and take those calls.

[00:53:10] And so I think it's also having that mindset shift about what really lights you up and removing any obstacles from that, because we can all find reasons why we just have to sit in front of our cameras. Right? We all have reason. We can always think of a reason why we can't leave the house, or we have to take this call on video, or we have to do this.

[00:53:30] But I think that it's important that we really ask ourselves and put things into place. The other thing that we've been thinking about, we were going to do it this summer, but you know, travel is complicated at the moment.  My family lives in Israel. It's been like a long-term plan to spend August in Israel.

[00:53:51] And that is not a, I mean, it's a vacation in the that. For the first half of every day, everyone we know is sleeping. So we have nothing to do in the morning, so we can go be, you know, vacation, do our thing and then begin our Workday at noon there. It's a seven hour time difference. And so, but again, it goes back to the communication and putting things in place to make that happen.

[00:54:16] August is a slow time for both of us. We can condense meetings to happen. Know we could do some of our work in the morning, condensed meetings only to the afternoon. And then, you know, again, you can any dream that you have, you can probably make it work. You just have to plan and communicate. 

Emily Thompson: [00:54:34] For sure. Oh, and I feel like you too, just,  sort of summed it up.

[00:54:39] I was thinking like, here's like keys, I think, to being able to take time off. Right? Put it in your calendar. Cause similar, I have my, my working pool days on the calendar too. Right. Like I blocked them out. Like I do any other meeting, same thing with my vacations. They go on my calendar. I'm busy for days, nothing can be booked.

[00:54:57] The team can see it, all of these things. And I show up for those things, like I do any meeting, right? Any meeting or like task or whatever, everything that's on there is equally as important. And so I show up for those things. So if you are looking to take some time off, open up your calendar, put it in there, prepare for it, show up for it.

[00:55:20] Just like you would anything else. And then two was really about communication. Yeah. Making sure your clients and customers know, make sure your team knows and make sure everyone, like you can prepare everything so that they can continue doing things while you're gone, if that needs to happen. Or like, it can just pause for a couple of days for a week or two weeks.

[00:55:41] But there is some preparation and some just showing up for yourself that has to happen. So you get what it is that you need to get. Anything else you want to add about taking time off any good nuggets or things you need to share? 

Dana Kaye: [00:55:55] Just do it. I don't know, like you just have to do it. I also think that to remember that, you know, we're only on this earth for a short period of time, and I think that it's really important for us to

[00:56:12] understand that, you know, when we look back on our lives, we're not going to necessarily remember fondly, all the amazing Zoom meetings we had or all the amazing time we spent in Gmail. We're not going to remember those things. Um, we're gonna remember our kiddos. We're gonna remember our parents. We're gonna remember the travels.

[00:56:31] We took the adventures we had. And so incorporating that into more regularly, there used to be this idea that you work really hard. You retire at 60 and then, then you can live your life later. But so much time has passed. You missed so much. So how can we incorporate more of those things into our daily lives?

[00:56:54] And if you sprinkle it in, it'll feel less urgent, you'll feel better. You'll feel more fulfilled. You'll feel more well well-rounded. There's no reason to put things off. 

Emily Thompson: [00:57:07] Yeah, amen to that. I do want to point out things that sort of come up for me as we've talked about, this is, you know, over the years we have developed this in a way that taking time off is simply how we do things, right?

[00:57:21] It's, it's so much a part of how we plan our year of how we show up of how we integrate our work with our life of how we, you know, make our business work for our families. Like all of these things that it's a non-issue to take time off. It simply is a part of how we show up and do this work. And I think that's an answer really.

[00:57:40] A really important mindset shift. And I will say too, that over the past year, as we have been quarantined and not going anywhere, getting in my little photo, highlights on my phone and it's showing me how much fun I have had over the past, you know, five, six years, however much, however many years of photos are in my phone right now.

[00:58:03] Right? Like I've traveled so much, I've done so many things that it has really the past year has really allowed me to shine a light on how much building this work has afforded in my life. Right. And like, how fun I am. I go cool places. And like, I've so many vacations and short trips with friends and those sorts of things have popped up, but like, it has been nice to see that I have accomplished the life that I've wanted to, by not only showing up for the work, but incorporating that time off into the businesses that I've built.

[00:58:44] So that for me is like my summation of it is like, just make it a part of what it is that you do, of how it is that you operate. 

Dana Kaye: [00:58:53] It's one of your values. 

Emily Thompson: [00:58:55] It is freedom. Legitimately is guys freedom and adventure are two of my core values.  And it's, it's amazing to see that I'm showing up and living them.

[00:59:05] Now, can we please. Travel again, as much as possible. 

Dana Kaye: [00:59:09] I have a trip on the calendar. I'm very excited. I never been more excited to book a flight, so excited to venture, to . And, and this goes back to, to like the work, the work trips versus the personal trips. I have a speaking gig that was bombed that is now rescheduled.

[00:59:34] And, you know, I am much more likely to say yes to speaking gigs that are in cool places than ones that aren't. So I'm excited to be in Nashville this September. Like, that'll be a fun one. And so if you can incorporate. The work and the travel at the same time, like you went on a book tour, you went to lots of fun places.

[00:59:54] So that's another, another way to kind of do it both, but I'm very excited to next. I did get on a plane, I guess I'm excited to be dropped down somewhere other than the city in which I live. 

Emily Thompson: [01:00:04] Right. Exactly. So just C-suite is having a retreat in New Orleans in October guys. We're both going to be there.

[01:00:11] And like, I think we're just going to like mosh pit, like hold each other, like all of was just going to be group hug and then cocktails and in group hugs. And then I'll jump in the pool and then I'll jump in the pool. It's gonna be great. It's gonna be real great. Perfect. Dana, this has been such a pleasure to have this chat with you.

[01:00:33] I'm so glad that I'm so glad that to share this conversation with someone who has prioritized travel and time off and vacations and building a business that supports it as much as I do. 

Dana Kaye: [01:00:45] Thanks. Thanks. This has been a really fun conversation and I hope it inspires whoever is listening to put some more things on their calendar.

Emily Thompson: [01:00:53] Yeah, just do it. Do it. Perfect. Dana, where can people find out more about you? 

Dana Kaye: [01:00:58] Of course. So I service authors and publishers at kayepublicity.com. That's K-A-Y-E. And if you want more nuggets about my life taking time off work-life balance, you can send my newsletter@danakaye.com, D-A-N-A-K-A-Y-E. 

Emily Thompson: [01:01:18] Perfect. And we'll include links to all of those in the show notes.

[01:01:21] And my final question for you, Dana, what these days is making you feel most boss? 

Dana Kaye: [01:01:27] I felt really boss yesterday or see, we didn't get our, our days mixed up. I felt really boss on Monday, we have our bi-annual. Or bi-annual conference, the, your breakout book conference on July 24th. And I felt really boss that I was at great America with my son.

[01:01:54] And when I got to the car and finally checked my phone, that an email had gone out, announcing the conference and we had a bunch of signups all of this happening without me. And I think that's in keeping with taking time off, but I see my business doing well and thriving without me physically present.

[01:02:15] If that makes me feel pretty boss. 

Emily Thompson: [01:02:17] Love that. Agreed. Agreed. Perfect. Thank you, Dana. I'll see you later.

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[01:03:11] Go to freshbooks.com/beingboss and enter Being Boss in the how did you hear about us section. Now until next time, do the work, be boss .