← This Can't Be That Hard
This Can't Be That Hard
354 - The Importance of Organizing your Business with Ashley Pendergraft
00:29:08
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- [00:00]
A
Before we dive into today's interview with Ashley Rose of systems over stress, I just have to say I have been looking forward to this conversation for a long time, and it was everything that I hoped that it would be. Ashley is brilliant when it comes to making organization feel doable, not daunting. And I really think about her as kind of this guru in my own life who came exactly when I didn't know that I needed her and then really revolutionized the way that I run my business. And in this episode, she is sharing so many great gems about how systems can support, not stifle your creativity and how organization is really key to all of that. But before we dive in, I actually want to tell you about the conversation that Ashley and I had after I hit Stop on the record button, which tends to happen.
- [00:55]
B
Right.
- [00:55]
A
So we kept talking. I was waiting for things to upload, and I asked her, I was like, I meant to ask you, you know, if you had one tip for everybody to take action on this and do one thing that would help them become more organized, what would you recommend? And I loved her answer because it was so simple. And that is to just make a note in the next couple of days, couple of weeks, to really pay attention to those moments when something in your workflow feels unnecessarily hard or time consuming.
- [01:28]
B
Right?
- [01:29]
A
Right. Those things come up all the time in our businesses, but oftentimes we're just kind of like, plowing through them. And because they're taking extra time, the last thing that we want to do is, like, make a note of them. She's encouraging you to actually, like, pull out a notebook and just write it down every single time that something feels unnecessarily difficult. Right. That friction, no matter how small it may seem, is a clue. Those dumb little things that feel too small to even pay attention to, much less build a full system around, those things can add up. And when you take the time to actually think about them, identify them, and then clean them up in the end, those are the things that save you the most time and energy. So I want you to keep that in mind as you listen to today's episode and to the rest of the episodes in this organization theme, because our businesses are full of those moments. And this episode is full of light bulb moments. So let's get into it.
- [02:30]
C
Welcome to this Can't Be that Hard. My name is Anna Mi Tonkin, and I help photographers run profitable, sustainable businesses that they love. Each week on the podcast, I cover simple, actionable strategies and systems that photographers at every level of experience can use to earn more money in a more sustainable way. Running a photography business doesn't have to be that hard. You can do it, and I can show you how.
- [02:57]
A
Ashley Rose, welcome to this Can't Be that Hard. I am thrilled to have you here and honestly cannot believe that it has taken me this long to get you on the show. How are you today?
- [03:08]
B
I'm great. We're here. I'm so excited to talk about all the things. I love, the name of your podcast and your business because I think we're very. We're very aligned on that ethos.
- [03:17]
A
I know, I know. So, and we'll get into, obviously your whole story here just in a second. But, yeah, I always was like, when I first heard about you and your business, I was attracted primarily by the name, like, Systems Over Stress. It says what it means, means what it says, and. And you deliver on that promise, and I. I love it. So, yeah, just to give everybody a little background from my perspective, I was introduced to you, actually in person first by our mutual friend Coley James, who everybody listening to this podcast probably knows because she's been on the show plenty of times, who had been telling me about you and your business for a while, and she was like, you need to know, Ashley. Da, da da. And then we met at a conference. And then after meeting you and everything else, I was like, yeah, I'm gonna sign up for this woman's course primarily because even though I have always considered myself to be a bit of a systems nerd and everything else, you were clearly like you had taken that to the next level. And I was like, we're always. There's always somebody out there who knows more than us on something. And I could tell that that was you and systems. And so I almost had you come on the podcast for our first theme of the year, which was systems. But then it occurred to me that you were kind of the perfect person to bring in to bridge systems and organization, because that's really what a lot of your systems and the systems that you teach come down to, is organization. But before we get all the way into that, after my rambly preamble, why don't you say hi and introduce yourself and tell everybody a little bit about you and your backstory.
- [04:45]
B
Yes. So I'm again, so excited to be here. So my name is Ashley and I am an airtable and automation expert. My business is called Systems Over Stress, and I take that, like, very seriously in both my business and my personal life. I have ADHD and depression. Like, I am neurodivergent. I also got a divorce, like, two years ago. And so, like, I have a lot of, like, things going on in my life and my. And like, business felt hard. It felt hard when I started five years ago. Like, all those little things that people are like, oh, that just takes a couple minutes to open up a spreadsheet and do your money Monday. And like, all these, like, sending off a proposal after you have a sales call, like, those things felt incredibly hard for me. And I couldn't. I would wake up each day not knowing if I would have, like, the emotional capacity, the mental capacity, the energy to, like, get up and do business. And when I was diagnosed with ADHD in 2020, it gave me a lot of permission to be like, you're not broken. You're not. Like, you're not broken. The systems you have aren't built to support you.
- [05:46]
A
Right.
- [05:46]
B
And so when I looked at everything of, like, it's not a you problem, it's a systems problem, the shame went away and I was actually able to create, like, sustainable systems and organizational tools that really worked for me. Like, when I was younger, my mom had to make me checklists because she's like, there are 37 towels in your. Like, the towels are all gone. I went to your room. There are 37 towels in your room. And I was like, I don't know. And like, now you put a. You put a basket near the, like, near the shower and you drop it there. It's like those little micro things that you think, like, oh, I'm just a bad person. There's just a system missing for you. And systems and organization to me are very, like, synonymous and go in tandem. So that's what I do. I specifically, with that ADHD hyperfocus, I got really into a software called airtable. And because it is such a powerful piece of tech that really can handle and create systems and organization for anything in my business, so it really, like, can do so much. So that's why I got really niched into that, because any system I need to build airtable is like, the tool to deliver it. So that's what I teach. I teach airtable systems to entrepreneurs who are growing and scaling so they can automate the. The hard parts and actually focus on the things like get them results and make them more money.
- [06:58]
A
Yeah. And I have never been diagnosed with adhd, but I certainly think that even if that diagnosis is not appropriate for me, I, like so many other creatives and business owners, tend to have this, like, Constant bright shiny object syndrome. And I just think in our world right now, you know, you can blame it on social media or the way that the attention economy has gone and grown over the past decade. Also just the news right now, it's like everything is constantly vying for our attention and we are task switching all the time. And I really found that Airtable and today's conversation, for those of you listening, it's either going to be good news or bad news. It's not going to revolve all around airtable. We will get to that in a couple of months during, I think it's April when we're doing software and like we'll get into the tech piece of it. But airtable really was an amazing solution for me in the same way where it was like I had tried all kinds of different, you know, project management tools and even my CRO, which I love, wasn't doing everything I needed it to do. And airtable was the piece that like tied it all together. And I think a lot of my success with Airtable was the way that you taught that, which had this very organized, methodical, like a place for everything and everything in its place sort of ethos around the whole thing. So one of the things that I really, when I was thinking about this organization theme, one of the foundational principles that I wanted to introduce is the difference between fun organization, which is like I went to Staples and I bought all these, you know, different color pens or folders and like my desk looks really pretty and nice and everything. You know, that, that feels good. I love doing that just as much as the next person. But that can often fall into the category of like procrastina working where you're like, I feel like I got something accomplished today, but actually it didn't move the needle at all. So that's fun organization. Then there is what I really want to focus on, which is functional organization, which is putting systems and organization in place that help you get your work done faster, better, more efficiently, you know, show up better for your clientele. And I would love to hear a little bit back in the beginning when you were diagnosed with adhd, how this started to show up for you and some of the things that started to transform that really made you kind of lean into this as your focus.
- [09:31]
B
Yeah, I mean, the fun versus functional, to me, I totally relate to, oh, new planner. I'm going to, I'm going to be a new person if I buy this planner. Yep. Like all of my habits, all of the ways that I am, it's just, it's because I didn't have this $37 planner. But get that then like everything is good. And I think the more if that's something that is exciting to you and is sustainable to you and you notice that helps you. A lot of people love bullet journaling. That is overwhelming to me. I don't stick with it. And I just noticed over time the fun pretty stuff like wasn't actually moving me closer to getting things done. So it was just that awareness of like this dopamine hit of, of pretend of like getting organized. Actually there's not, there's not follow through for me. And what I want is the end goal. Like I just had to be really real. I do not buy especially dated planners anymore. I have a $4 like notebook with a spiral above the top. Because I'm left handed. I was like, that's a system that works for me and like that's all I do now. And I found the thing that works for me and instead of looking for the fun thing, I'm like, I found the functional system for me. This is handled. Let me move on to the next one. And so that's really where I think the fun versus functional, like when you're looking for fun and dopamine, especially in your systems, especially with organization, you're really stunting your growth because you're restarting all of the time. I do not look at not like free trials for software. I don't look at cr. I do sometimes like once a year just to be like what, what's everybody yapping about on threads? Like let me go check out Moxie. Is it really better than Airtable? I do it for like product like research. But so many times I see people on threads being like, I'm thinking of breaking up with this tool. It's like if we just stopped like seeking the fun new like new stuff in tools and tech and organization and just sat down and got our work done and let the tools function like be functional. Your business would grow so much more. And so that's like really where it started for me. And when I was like, oh, it's actually this is an ADHD dopamine hunting thing for me. It's why I don't really. Notion doesn't work for me because notion is a place where you can build pretty beautiful dashboards with your brand colors and all these things and at the end of the day the emails that you wanted to get out and the automations that you needed to send to the client still aren't Built it actually didn't move the needle, but I felt good doing it. But I don't want to feel. I mean, I want to feel good, but that's not my main goal. I want to, like, support my clients and make more money, and, like, I need to figure out the tools for that and the organizational system to do that and then keep it moving. So I think that's why I've been able to grow so much, and my clients are able to grow so much is that they're not reinventing the wheel every three months because they're bored or because, you know, of whatever reason, and they find a function. Their goal is functionality. They're like, I want this to work, and then we could build upon it versus having to, like, restart our foundation every few months.
- [12:20]
A
Yeah, amazing. So as someone who regularly coaches people specifically on this, you know, with this transformation in mind, going from, like, everything's in a thousand different places to everything's in one place, I know how to access it. It's all at my fingertips at all times. What do you see? And I know that you serve people in all different kinds of niches. This podcast mostly is photographers listening, but I want to be clear that you're not serving just photographers. So what are the. But what are the first systems that really create that kind of breakthrough for people that you see on a regular basis?
- [12:55]
B
Absolutely. It's having, like, a central source of truth for their leads and their clients. So what that means is if you're. If you are a photographer knowing, like, a list, and you know, some of the tech tools like Dubsado Honeymoon, they just, like, there's kind of a CRM, but it's not as robust or comprehensive as you, like, need it to be, necessarily. But having one central place where you can see. I have seven active clients. Here are their photo shoot dates I've sent. Like. Like, just having that place where you can see so many people don't have just visibility on that or their client notes. They default to opening up their notes app or opening up a draft in their Gmail or, like, writing something down, and they're. They're hunting and everything feels very scattered. It's scattered through that. And if they have onboarding forms, it's like in a silo in your Dubsado form, or it's in a Google form, and you're having to open that and reference. Okay, I know they sent me their, like, brand colors and. But what form did they send it in? Like, that is really eating up so much of your mental capacity. And bandwidth, but you don't know that there's another way basically. And so having a central place where you can open up a client profile and see, okay, here's Ashley's onboarding form and her photo shoot day and important milestones and all of those things in one spot. Even before you play with automations or do anything like that, having that one central spot where everything about the client lives totally changes your relationship with your business.
- [14:22]
C
Hang on guys, I have a quick message for you. If you've ever found yourself nodding along with an episode of this can't be.
- [14:28]
A
That hard thinking, ugh, I need to actually do something with this.
- [14:32]
C
Then you are going to want to.
- [14:34]
A
Join us inside the Darkroom.
- [14:36]
C
The Darkroom is a brand new online space that I created just for our podcast listeners. And it's specifically designed to help you take the ideas and inspiration that you're experiencing exposed to here on the podcast and develop those ideas into action and results. But it doesn't stop there. You also get access to bonus content, special discounts and giveaways. And you have the opportunity to shape our future episodes by sharing your feedback, your questions and your guest recommendations. Best of all, the Darkroom is totally.
- [15:06]
A
Free, so all you need to do.
- [15:07]
C
To sign up is go to thiscantbethard.com darkroom. I can't wait to see you there. Now back to the episode.
- [15:18]
A
Yeah, and I just want to emphasize like a good CRM for photographers is going to have most of the things in it that what you're talking about right now, where you can sort of track like this is when their session is going to be in. CRMs were really the first software tool that I came across many years ago now that I was like, oh my God, this is so much better than just trying to do what I was doing before that, which was like spreadsheets and notebooks and you know, everything in a million different places. However, no CRM does it all right? And you can, you can get really good. And the more you learn about the tools that you're using, the better you become at using them to their fullest potential. But you run into limitations with just about everything. And I feel like one of the things that I'm actually working on this month and going to be releasing here shortly is I ran a portrait membership in my photography business for a bunch of years where it was my members would come back year after year and they were paying me on a monthly basis and it was a great solution for I needed more stable income. And I knew that a Lot of my family photography clients wanted regular portrait sessions. So why not like make it so that they could just sort of sign up and make these monthly payments and come back year after year. That was all great. The hardest part about that was managing like none of my, my CRM was not set up for somebody who was coming back again and again because most portrait photographers don't do it that way. So anyway, because of the flexibility of air table and I know I said.
- [16:48]
B
I wasn't going to talk about it.
- [16:49]
A
The whole time, but that really, it was a solution that allowed me to then track all of the things that I needed to track. So I do think that what you're saying about kind of being able to customize that experience for your unique business, because every small business is slightly different in some way, shape or form, really makes it so that, because it's really easy to take a system and be like, okay, this is great, this is great and I'm using it to some degree, but because it doesn't fit everything, then I end up with, you know, the back of the envelope note taking in some way, shape or form in your business.
- [17:22]
B
That's what I see with specifically industry specific CRMs is that it's good for this one part of your business, let's say photography sessions. But if you want to create a course on photography, Dubsado cannot handle 47 people coming into a course, like a course model, like it's not built for that. And so that's why I specifically teach airtable because it can be your CRM for your one on one clients, for high ticket, for retainer, for masterminds, for group programs. Like whatever your offer type is, airtable is flexible enough to be the CRM to support that and organize that. And so that's where I think people get stuck when they're like, well, I've been using this one CRM but now I want to add a new offer suite. And it totally like, it's like square peg, round hole and it's, you're going to hit a ceiling with it. And so that's what I love about picking tools, especially when you're trying to be more organized. It's like, okay, what are all the different ways I want this to work and is it flexible enough or am I going to hit a ceiling?
- [18:18]
A
Right, right. This is somewhat off topic. It makes sense in my mind, this connection makes sense in my mind. But one of the things that when I'm talking to people about tools for organization CRMs, all these different things, a question that People come up against a lot is their desire balancing their desire or navigating the desire to just have one tool that they use for everything versus, you know, so kind of the all in1 tools versus the one off tools that are sort of specialized in certain things. Now I will jump in here and say I think, and I know you think Airtable is great for so, so, so many things. But like for instance, it's not gallery software that a photographer would use to share photos with a client. So outside of airtable, just in the world, do you have strong feelings about multiple specialized tools versus general tools or more kind of all in one tools?
- [19:10]
B
That's something I've been thinking about a lot because everybody is mad about honeybook and Dubsado raising prices. And that is like the conversation that's dominating the industry right now. It's like, I want to ditch Dubsado and I am always zoom. I have been desperately trying to figure out a free or cheaper alternative than Dubsado or honeybook for contracts and invoices because airtable can't do contracts and invoices. So I'm like, okay, Airtable can be everything else, but it can't do contracts or invoices. And when I zoom out and I think about what actually when people are having these issues with these specialized tools is that they're upset that they're paying so much for one feature that they're using. Yeah. And so I my thought process with like, let's just use Dubsado as an example. It's like what, 35, it's like 400, 500 a year, let's say. I like to look at it as hiring. And my friend Karanda says this too. Like hiring your software as a team member. $500 software. If you are bringing in $50,000 in revenue for your offers that sell like contracts and invoices, like, that is worth it to have a streamlined, automated, to have the best tool to easily send out contracts and invoices. So I make peace with my software costs because I'm like, like my revenue. Like I can't make this much money as easily if I didn't have this special tool. So that's one way to look at it. The other thing is that Airtable, when it becomes your source of truth in your hub, what we do is we say you open up the client profile on the sales call and you can say in airtable, create contract and proposal that will automatically create it over in Dubsado. And you can have the little note that says step two Go into Dubsado and customize the proposal if you want. And so it's, it's adding the gallery link, adding the Dubsado link, all the other things that are floating, floating around in your kind of client experience. You put it in airtable still. So it's still like the one place. Even if it's not the best thing for your gallery software or even if you're using ClickUp as a client portal for your clients. You put that link in your client, you're in your airtable place. So there's that one central place where everything lives. So I hope I kind of touched on a bunch of different things, but I hope that kind of answers it.
- [21:09]
A
Yeah, totally. My feeling on that question is just, you know, for the most part those all in one tools are. It's. I totally get that desire to just, just. Okay, I just want one thing. Whether it's because of cost or just the simplicity of having one place to log in or whatever. But yeah, nine times out of 10, when it comes to very specific things, you really do. You want to find the right tool and then just stick with it.
- [21:34]
B
If your business is incredibly basic and you have one thing and it's like you are the person that Kitchen or Moxie was thinking of when they built this thing. Maybe. But like so many of us, our businesses evolve and we want to add this one thing that like Kitchen didn't think about, Moxie didn't think about. And now it's not going to be the perfect. It's not all in one. So it's, it's figuring out like unless you're the cookie cutter thing that this all in one made for which none of us are right, it's gonna hit limitations.
- [21:59]
A
Yeah, totally. Yeah. And it, what you were saying too, reminded me of when I was going through your course. I remember one of the big aha moments for me that really ties into organization and helped me in my organization was there were two tools that used to drive me completely bananas that like I use all the time and didn't anticipate not using cause they were both free or I pay for the paid vers of Canva. But like Canva and Google Docs, I was like, why, why, why are these such a disaster? It's like I'd go into Canva and unless I was really disciplined about remembering every single time that I made that quickie graphic or whatever, to then rename it and name it in a way that I was going to like, remember how to search for it later, whatever, which I Didn't that I would just lose things and then I would end up either recreating them or spending, you know, 45 minutes scrolling through thousands and thousands of graphics trying to find this needle in a haystack. And you were talking about out one of those two. I don't remember which, but it applied in my brain to both. And you were like, they can be a mess. It doesn't need to be organized in there as long as you have an organization system in airtable. And I guess this, you know, you could also have this in a spreadsheet or something. But because of the extremely searchable nature of airtable, as long as you've got that somewhere that you can kind of make sense of, then that link lives there. As opposed to worrying about out how organized or disorganized Google Docs or Canva is, you just go find it in airtable, click the link, and there you are. And that was kind of a magical. Seems obvious but like really revolutionized some of the stupid time that I was wasting.
- [23:36]
B
We want to be good and we want, like, we want to be good, organized business owners because like, we feel like if we're, we feel like we're hiding our mess if like some, if like something is messy, right? And I had an OBM that was like, hey, Ashley, like, I organize all of your Google Drive folders. I was like, thank you so much much. Never do that again. Like, that is such a waste of time. And the reason was, was because we'd have to have a naming convention for Google Docs. And then Canva has its own kind of folder organization system and Loom has its own kind of folder setup system. And like, we'd have to like, again, my brain just can't comprehend doing that. And so I've trained like the system that works really well for me. And a lot of our clients is like, Airtable is our source of truth for everything. Our SOPs, our clients, our content. Like, because it's so robust and so it could totally be spreadsheet. But it's nice to have like anything we need that is, anything we need is an airtable. That's just like the rule of our business. And so to be able to have. We call it a quick links table where it's like, here's the seven Canva things that we reference all the time. Here's the seven Google Drive SOP folders. Here's, you know, whatever those look like, training the team to go to the quick links or Acuity links. That's a huge one for us. It's like, where's my 30 minute call scheduler? Where's the 60 minute one? One. Instead of having it be organized in acuity, just you have this one place where we can go to easily quickly reference things. That's a really easy thing for a lot of business owners to do and set up that again, it takes so much mental, like less capacity digging.
- [25:03]
A
Yeah.
- [25:03]
B
And I'm like, some people like show on Instagram, sometimes they're like watching Heated Rivalry and organizing their Google Drive file files. I'm like, why you could just watch Heated Rivalry and not do that.
- [25:14]
A
Yeah, funny. Yeah. And so I actually closed my photography business at the end of 2025, which was its own. Like here I was like, my business is really organized. I'm super organized. But I learned airtable from you two or three years ago and I was really using it more for my teaching business. I hadn't, you know, I had everything was taken care of for my Megapixie stuff, my photography stuff in Dubsado and sort of my old systems and I hadn't like, like changed those. So then when it came time to like get in touch with all my clients and be like, hey, just want to like, last chance to download files or purchase additional things, whatever. I had to do so much work at the end of last year to organize myself in order to be able to reach out to those people. So again, pretty organized business. But like finding which, you know, this client has, has seven different galleries that have, you know, that I've created for them over the past 15 years and now I need to go hunt those down and they might have different names and you know, they're different links and who's named as the primary client on this one. Anyway, I ended up building myself an airtable for that in order to then be able to communicate with those people. Because of course people were coming back to me and being like, oh, I think I have unused print credit. Da, da, da. And rather than having to go hunt those down in a one by one, I was like, I wish I had done this years ago.
- [26:40]
C
But.
- [26:41]
A
And I always use that like the best time to plant a tree is 20 years ago. The second best time is now. It made me feel even more strongly and again like without going too far down the brand specific route road yet, finding a system where you can truly like look me in the eye and say, if you ask me to find, you know, not only where these, where this person's gallery is, but where the files exist in my own computer or server system and all that sort of stuff, and you can do that within, you know, a couple of minutes. Then you could be. Be more organized. And I feel like it is some work to set it up and to do it, but it's so worth it. And that feeling of, like, organization and calm that comes with that, all the energy that gives your brain back to do the stuff it's supposed to do, has really been a magical transformation in my own business.
- [27:32]
B
So, yeah, and it's such a. It helps you be such a better service provider as well, because if you have somebody come into your inbox and say, hey, I need that gallery from two years ago that you did for me, you could just. You, or not even you, if you have a team member can go into that place and say, oh, here's the link. Here it is. No problem. Or if there's a customer service issue, like, they. You have this place where you can hunt things down and have, like, have all of that. Instead of spending 30 minutes going to hunt for that thing and feeling the anxiety of, like, yep, I knew I was a bad service provider. Cause I don't know where that. I don't know where that link is.
- [28:02]
A
Right.
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B
It takes you a minute to send that off and be like, cool, have a good day. And like, those little, like, client experiences better. Your peace of mind is better. You're able to delegate easier because it's all in one spot. Like, there's so many benefits and having that centralized source of truth, especially if you. I think a lot of service providers are like, oh, I only have two to three clients at a time.
- [28:21]
A
Right.
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B
But if you want. If you're in this business for the long haul, you want to, like, have that documented place so you can just keep. You can. You're gonna get more clients, it builds.
- [28:31]
A
And by the time that it gets going, then you're like, I wish I had already set this.
- [28:35]
B
I wish I had systems.
- [28:36]
A
Yeah, totally. Well, I am already looking forward to diving deeper into a little bit of the nuts and bolts of this. This. But I knew that you would be the perfect person to chat about the why behind organization and get everybody motivated. So thank you so much for coming on today, and I would love for you to let everybody know where they can find you.
- [28:57]
C
We'll put all this in the show.
- [28:58]
A
Notes and all that sort of good stuff. But yeah, let them let. Let everybody know where they can connect with you.
- [29:04]
B
Yeah. I am most active on Instagram and threads. I love a voice memo. So if you've made it this far into the episode Please shoot me a DM on Instagram and say that you you listened from there and that's the best place to figure out. I have have you know, I have airtable templates, DIY done for you. Completely done for you. Done with you. Group programs like there's so many ways that we can help you set up systems so you can learn more about that on on Instagram. I'm very prolific on email as well. So you'll be able to opt in to whatever opt in I have through Instagram and we can stay in touch there.
- [29:34]
A
Love it. Amazing. Ashley, thank you so much. I will talk to you soon. Have a great day.
- [29:38]
B
Awesome. Talk soon.
- [29:41]
C
That's it for this week's episode of this Can't Be that Hard. I'll be back same time, same place next week. If you like the show, be sure to check out thiscan'tbethard.com to explore all the resources we have for photographers. And of course, it would mean the world to me if you would leave a review of the show on itunes or Spotify. As always, thanks so much for joining me. I hope you have a fantastic week.