Ep. #49 – Tips for planning a solo work retreat/offsite

March 22, 2022

Subscribe to the show on: Apple, Google, Spotify


Hello, and welcome to today’s episode. This is a really fun one for me because we’re going to talk about work retreats and work off sites and what those look like, how I take them in my business, what they do for my business and why they’re so important to me, and why I think that you should take one. Whether you’re in the early stages of your business, whether you’ve been in business for a long time, I truly think that these offsites and retreats are ways that we get clarity in our business, but also just reinvigorate it. When we feel like things have been going at the same pace, or we need just a little bit of extra oomph in everything, these retreats are the best way of doing that. So I’m really excited to dive into that today. 

Why You Need to Have a Solo Work Retreat Off Site

What I want to start with is why I think this is so important. I’ve had lots of conversations with women business owners who want to go on these work retreats. They want to take off sites, they want to spend the money to invest in themselves and their business, but they feel a lot of guilt around it. And I want to talk through that because I think that the reason why we feel guilty spending this money is because in our head, we think that we’re just spending money on nothing. We’re just treating ourselves, it’s this extra expense and this money that we’re spending, and we’re not going to gain anything from it. But I think it’s so important to realize that the whole purpose around these work retreats and off sites, and this can be different depending on what the outcome is that you want to achieve. But the ones I’m going to talk about today are very intentional in that we’re going in them with the clear reasoning and intention of getting work done. Going out on a sprint and doing projects that we’ve been putting off doing, things that we know that we’ve been wanting to do that are going to make an impact. And because of that, we have to be able to flip that script in our head that says this is just an added expense, this is something that’s nice to have, and really understand this is a crucial part of our business if we want to continue growing and reaching that next level. So what I want to talk about today is to just dive into that a little bit more and talk about how I structure my work retreats, what they look like for me, and why they matter. 

How to Find a Place to Stay

So first things first, depending on my intention of the work retreat, I have two different ways that I’ve structured them in the past. So for example, I think it was either last year or the year before, I can’t remember but I took a trip down to Venice Beach near L.A. I’m pretty sure I was gone for three days. I drove down because part of me also really enjoys that time in the car to be able to listen to audiobooks, and mentally prepare myself for the retreat. So I like going to places that I can drive to, just because I feel like it heightens the experience and helps me because it’s that alone time. I think that’s one of the reasons why I love these work retreats is because it’s time for me to just be by myself. And so when I can drive places by myself, it just gives me more time to be able to consume the things I want to consume and mentally prepare myself for the weekend ahead. Whereas I feel like you could do the same thing if you’re flying somewhere but there’s just a lot more things you have to think about, you’re on a plane with a bunch of people, you’re trying to get connections. There’s just like a lot to plan, and for me the energy and the space that that takes up is just not really worth it to me. So I just like to be able to choose places that I can drive to because it’s easier. It’s stress free and just adds to the whole experience. So I drove down to Venice Beach and I booked a little house. One of the things that’s always a top priority for me whenever I’m booking an AirBnB or somewhere that I can stay, I want to make sure that it’s easily accessible for me to be able to work outside in a private, enclosed area. So this is why I choose Airbnbs over hotels. Hotels are absolutely an option if you prefer staying in hotels, if Airbnbs feel a little bit, hit or miss, if you’re not really sure, you can definitely stay at a hotel. But for me, hotel rooms don’t really bring the same vibe. Because I don’t really want to spend all day in my hotel room, whereas I’m totally comfortable spending all day at an Airbnb. 

But if you find a hotel that has great outdoor working space, and an outdoor patio space, where you can see yourself working all day, they’ve got a charger, they’ve got a place where you can go while being shaded under the sun, so that way you can actually like work on your computer. These are all the things that I’m looking for when I’m planning the location of where I’m going to be. So I chose a place that had a little private outdoor patio and an outdoor furniture set. I could sit at the table, I could work. It had shade, all of that. So that was really nice to me because that weekend especially felt like it was a mix of a little vacation. But it was also very intentional. And we’ll go into that in a minute of how I planned for it and the agenda that I created. Because yes, I created an agenda because that’s how I am. And again, I like to be very intentional going into these retreats. But as far as location, those are the things that I really look for. Is there going to be a space that’s very easily accessible, where I can work, no matter what time of day it is, comfortably, easily, and not have to worry about finding a charger or moving around or finding privacy or any of that. So for me, number one, when I’m looking at spaces, that’s the first thing that I look for. 

Create an Agenda 

The second thing that I do to plan is creating this agenda. So for that retreat specifically, that was when I was going to be launching the coaching side of my business. So I already had my podcast, I was really specifically going to start launching the one-on-one side. I already had my membership. So I created this retreat because I wanted to structure the one-on-one side of my coaching business. So I’m actually going to pull up the agenda that I created for that. And it was three days. And when I say that I’m a little bit extra when it comes to this kind of stuff. I went into Canva and I found a super cute Genda template. And I created my Thursday schedule, Friday schedule and Saturday schedule. And this was important to me because when you think about going on a retreat or a conference or spending money to go somewhere, you always get an agenda. Someone hands you something of this is what you need to be available for, this is what’s happening. So I treat these work retreats the same. Even if it’s just me, even if there’s no one else there, I think so much of the time with running our business, we have to think of our business as a running, functioning business. Because when we start to have this mindset of Oh, it’s just me, it doesn’t matter. I’ll just jot some things down on a piece of paper. Our brain doesn’t look at this like it’s a serious thing. So I go into this as if this were a big thing. This is an agenda and this is what I’m gonna do, this what I’m gonna accomplish. So even on Thursday, not that I hesitate sharing this because I know some of you will probably be like krista, that’s so over the top. But the first thing on Thursday’s schedule was to check. Because when you go to a hotel, when you go to a conference, when you travel anywhere they give you the check in time. And it’s the same thing with Airbnb, I have to know when I’m getting there when I’m arriving, and then the next thing after that I put for 30 minutes, happy half hour with music. You’re probably thinking that’s so silly. But for me, I have that space to be able to unpack my things, put on some music, before I even got to the Airbnb, I stopped and got some of my favorite drinks so that I could have them that weekend. 

So I went and I was unpacking, I had my favorite drinks. I had some music going. I had my portable speaker that I had brought. That’s another reason why I love driving. I can bring some of these additional things that I love to have and not have to worry about packing them into a suitcase. So I had my portable speaker playing all my favorite music. And I was able to get settled into the space in something that felt fun and in a way that felt really fun and exciting and new. From there, the rest of my day started so I had about an hour and a half of work time where I designated what it was that I was going to be working on in that hour and a half of time and then I put time for dinner, dinner on the patio. And during dinner the first night when I’m at a new space, I always just prefer to order food because it’s easier. Usually check-ins are later in the day. So anytime I’m going somewhere, you already have lost a big chunk of the day. So I don’t like to spend that initial day going out to eat or going to get food, I’d rather just order in and make it easy on myself. So I had dinner on the patio outside, which was great. I had my favorite glass of wine, I had my music playing, it was a really great little space. And then after dinner, I let myself do a little day one recap of the work that I had done and a little bit of prep into what I’m going to be focusing on for day two. And then day two it’s the same thing. In the morning I have a space for breakfast. At this location, actually, I found a cute little spot, a brunch spot that was a walking distance from my Airbnb. So it was like a 15 minute walk. I went and had brunch in the morning, treated myself, had that time and then came back and had my afternoon session. I did all of the work that I wanted to do. 

Why You Need to Treat Offsites Like an Actual Retreat 

So my whole point in this is to treat this like an actual retreat. When you do that, it’s going to shift so many thoughts. Because sometimes I think we feel guilty about, you know, Oh, this feels like a luxury, I shouldn’t do this. But when you go into it with a detailed agenda of exactly what you’re going to be accomplishing, it truly is a work trip. And there’s no reason to feel guilty. Because sometimes we have to remove ourselves from our day to day workspace in order to really get things done. Especially if you have kids, if you have a family, if you have pets, if you live with other people, it’s so easy to get distracted. I have to pause, I have to make lunch for everybody, I have to go run errands, I have to bring someone to this thing. Those small distractions throughout the day really do add up to a lot of time. So when you can have a space and a few days to be able to, uninterrupted, get your work done. It really does make so much of a difference. So that’s the outline of how it’s structured. And of course, depending on what it is that you’re working on, what your agenda is, what it is that you want to accomplish. That’s going to define what your agenda looks like. So you do have to give yourself some thought around what is it that I want to walk away with? What do I want to accomplish? What are my goals for this? What do I easily think, on day one, what can I accomplish in an hour and a half? What would be something that I realistically could do? And then on day two, what could I realistically accomplish before lunch, and then what could I realistically accomplish after lunch and before dinner? Making sure that you’re not packing your schedule with way too much stuff. And if you’re worried about it, I mean, just go in with an agenda and know that there might be some things that don’t happen, or you might finish some things early, and that’s totally okay. But just having the intention of having the agenda in the first place is going to make it so much easier to plan. 

Plan Fun Meals For Yourself

And then a few tips that I have outside of the agenda and outside of the location and where you’re going to be. I already mentioned this, but plan fun meals for yourself. So whether that’s lunches or dinners or brunch, you can balance between going out to eat and maybe eating at your Airbnb or wherever it is that you’re staying. I’m not necessarily saying that this needs to be a weekend where you’re just throwing money at everything. Obviously, one of the first things that you want to do is to clarify what your budget is going to look like for this. Because it can be really easy to overspend on these things. For this retreat in LA for example, I think that I went out to brunch both days because I treated it as my breakfast and my lunch. So that’s technically two meals that I’m getting in one spot and then I could just have snacks for myself until dinnertime. And on my last night there, I went out to dinner. I took myself out to dinner and I actually ended up working through dinner, so it felt like a work meal, something I could actually write off. But I actually worked through dinner, not that I recommend that. But I took myself out to a nice dinner one of the nights and the other two nights, I either ordered in or just got something really quick and easy. 

It doesn’t have to be this big extravagant over the top thing but find out what’s comfortable for you and what you feel comfortable spending as far as food and all of that goes. But give yourself at least one or two meals where you can take yourself out to somewhere nice. Maybe you’re not comfortable eating by yourself, I don’t really feel that uncomfortable doing that. When I went out to dinner I brought my book and I brought some of my work notebooks and I was just able to review things and read my book and that’s fine for me. But maybe you’re not as comfortable going out for a nice dinner and maybe you get it to go and then you go eat, either in a nice outdoor spot at your Airbnb or a nice outdoor park or you find somewhere that you can be that maybe doesn’t feel like you’re just sitting by yourself in a restaurant. But if you’re like me, and you’re comfortable doing that, absolutely go for it because it was so enjoyable. And it was nice to take myself out for a nice little meal. 

Give Yourself Breaks

Another thing is to make sure when you’re planning your agenda that you give yourself some breaks throughout the day and some time to relax. So I gave myself a couple of stretch breaks. But more importantly, for example, I would have a morning session where I would get work done. And then during my lunchtime I purposely planned an hour to an hour and a half to just go get lunch or go get food or even if I had food at the Airbnb, I gave myself that hour to just go for a walk or get outside or do something relaxing, and give myself that space to be able to just have time away. Because it can be really easy to feel like we need to get everything done. I’m just going to sit all day and do nothing but work. But that’s not great for our creativity. And the whole purpose of this is to let yourself have this as a work off site and retreat. So don’t get too into the weeds of trying to just sit all day and knock everything out. Make sure you give yourself some fun breaks throughout the day when you can. 

Do Something That Leaves You Feeling Really Good 

Another thing that I recommend, I actually didn’t plan on doing this. But I had watched a movie that weekend during the retreat that I had heard about, someone had mentioned it to me. And I was like, Oh, interesting, I’m gonna watch it. And I don’t know if you’re familiar with it, it’s called The Secret. It’s almost like a manifesting movie. But it’s just a feel good movie, it makes you feel really good. So people had told me about it and told me I should watch it. And I watched it that weekend. And honestly, that might have been my favorite part of the entire retreat was watching something that was really inspirational and just made me feel so good. So now, that’s something that I incorporate into all of my retreats and all of my work off sites is planning time to be able to watch or consume or read, or maybe listen to an audio book, something that will just leave you feeling really good. It can be business based, it can be an inspirational book in general. But I would suggest reading something you’ve never read before, or something that you’ve been excited to read or watch that you just haven’t had time to. Because it really does elevate that experience so much more and it’s just so memorable. So I definitely recommend doing that too.

Get Yourself Branding Photos

If you want to make it even more fun, if you have a little bit of money to spend, and maybe you’ve been wanting to get professional photos done of yourself, use this weekend as a time to get branding headshots. Because that can be you know, maybe you give yourself a few hours off one afternoon, meet up with a photographer, obviously you have to plan and book that ahead of time, but meet up with a photographer and get some headshots done. You’re in a new space, chances are you’re booking wherever it is you’re staying, somewhere that you enjoy going, or somewhere that you’d like or somewhere that is relaxing or fun. Use that space and use that time to be able to update and get some new branding headshots for yourself, because that’s just going to elevate that experience so much more. And you’ll get photos in a place that is a little out of the ordinary. So those branding photos will set yourself apart on your social media, on your Instagram, because they’re in a new place that you don’t normally take pictures off. 

How to Use Offsite Retreats to Get Rid of Your Money Blocks 

The last tip that I have, if you’re if you’re hearing this, and you’re like, Krista that sounds great, but I still just feel like I can’t spend the money on it. This is a really great practice and a way to start practicing money abundance and getting rid of our money blocks. Because when we plan these retreats and off sites, they can bring up a lot of feelings like that. I feel guilty spending money, I feel like I don’t deserve spending this money. Dig into those feelings. Why is it that you feel guilty spending the money? Are there bigger, deeper money blocks that maybe you haven’t addressed yet in your business? Are you afraid of spending this money because you’re actually afraid that you may not make money in your business? Are you afraid that you don’t have what it takes to be successful? Dig into those feelings because these retreats can often bring up a lot of those blocks that we may not have even realized we had. So this can be a really great exercise for figuring out your money blocks and being able to move past them. And yeah, that’s really what I wanted to share today. And I truly do think that my work retreats have been so beneficial for me. I’m actually going on another one this week. I didn’t want to have to drive and take the time because this month has been a little crazy for me. But again, these are so important and I know how much they helped my business. So I actually found a really great shared workspace, local to where we live, that has a beautiful outdoor rooftop space. And they have work areas, private work areas that I’ll be going to during the day. And so I’m actually going to be staying local for that. But I just know that I accomplish so much more, and I’m so much more efficient when I can get out of the house and out of my normal workspace, and into someplace where I can really sit down and concentrate and get things done. So I hope that this was helpful. I hope that this inspires you to go on a work retreat. If you haven’t taken one on yourself. Or if you haven’t taken one for yourself, I highly recommend it. And as always, if you have any questions, always feel free to reach out to me. I’m happy to answer any questions about how I plan the retreats, or anything that I didn’t dive into today. But otherwise, thank you so much for listening in. And I will talk to you in the next episode. 

Leave a Reply

Your email address will not be published. Required fields are marked *

see PHOTOGRAPHY services

You deserve to feel (and look) confident & joyful in your photos. From wedding to personal branding sessions - I've got you covered!

Let's Work Together

I'm Krista! Wedding and Personal Brand Photographer & business coach based in Northern California. I’ve been photographing weddings & women business owners since 2010, and I fall more in love with my job everyday. 

Meet Krista


As your coach, I'm here to help you:
  • Overcome your limiting beliefs & embrace your fullest version of success
  • Eliminate the overwhelm & create actionable goals for your business
  • Create healthy habits & a mindset that is focused on growth
  • Find alignment and fulfilment along your business journey
  • Create more abundance and take inspired action towards your goals

I also help you implement tactical strategies like: creating an irresistible brand, marketing to and attracting your ideal clients, creating an incredible client experience, and pricing your unique services & offers.

Ready to uplevel your business?