How I’m Prepping my Business for Vacation
S2 #474

How I’m Prepping my Business for Vacation

Welcome to the Streamlined Solopreneur. A show for busy solopreneurs to help you improve your systems and processes so you can build a business while spending your time the way you want.

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There are perhaps two stories that have really shaped my viewpoint on working in the 21st century. The first was the first vacation I took when I was working at the University of Scranton. I landed and the first app I impulsively check is my email, I think, because I have associated email with making money more than stress. And so I checked my email and I saw an email from my boss who was, then working at the University of Scranton as well. And she said in her email,

“Joe, if you have some downtime on your vacation, can you…?”

And I don't actually know what the rest of that email said because I deleted it. I, and she never brought it up. And, part of me felt like it was like a loyalty test, which I hated. She's not there anymore. But part of me was like, how can you have the audacity to email me on the first day of my paid vacation and ask me if I have downtime to do something?

Contrast that with the, one of the first few months I was working in my previous agency job, and I had tickets to see a comedian, and I had to forego those tickets for work.

But even worse than that was the next time when, Erin, my wife, who I was dating at the time, came to visit. She drove an hour and a half to visit me on an off night. And my boss told me that I had to work and I was, I was absolute. I don't curse on this show, but man, I was absolutely furious because how dare they take time away from me at the drop of a hat.

And so after that, I made a vow to put my foot down. And towards the end of my tenure there, I was told that I had to work a weekend if I wanted to get paid on time. And I said, I've got tickets to Hamilton. I'm celebrating my anniversary, and that's not the social contract that we have. You pay me every two weeks, and I work for you. Right? If I wanted to get paid based on client deadlines or when the client pays me, I would work for myself.

And I've carried that with me for a long time, but I haven't strictly stuck to it because as you know, if you are a solopreneur or a small business owner, and you can bring your computer with you, well, when I have some downtime, maybe I'll just do some work because now, the income, the paychecks rely on you.

And so I've done kind of a bad job at that for a really long time. I, you know, after my honeymoon, I didn't bring my laptop or an iPad on my honeymoon. I didn't even bring my primary phone. I had, like, a burner phone, like a travel phone.

And but, like, since then, I usually bring my laptop and I'll usually open it up. It may be in the morning, I'll write before the kids wake up or something like that, or I'll have some coffee or just, like, work. You know, when we're on our beach vacation, I'll work at the beach. I've recorded podcasts from the beach. I've written full scripts for courses, and I don't really like that. Now that my kids are getting older and they're more cognizant, I really want to be fully present on our vacations.

And so, we are taking the kids to Disney World as you hear this episode. In fact, as you hear this episode, we are in Disney World. And I don't have my laptop with me. I have my iPad with my keyboard for emergencies only, and I gotta tell you, there's not a lot of emergencies in my space. I'm not doing Fortune 100-level websites anymore. I'm not doing e-commerce websites anymore. And so most of the time, things can wait. So I am not working at all on this vacation. I'm gonna be fully present.

And so I thought it would be a good topic to talk about how I'm prepping my business for my vacation. Because as solopreneurs, something I talk about is putting the right systems and processes in place so that we can work less. But very few of us feel like we can fully step away from the business.

And a couple of weeks ago, you heard an episode with Maegan Megginson about how solopreneurs can take a sabbatical. And she said, start small. And I think starting a family vacation or any vacation without working for five days is a good way to start.

So today, I'm gonna tell you how I'm prepping my business, what I'm doing as far as communication goes, devices, how I'm gonna stay present. And, when I get back, I'll follow-up probably over at Joe's Audio Notes. So go to notes.casabona.org to get that podcast because that's like, my much more frequent kind of raw thoughts podcast, because I'm usually scheduled a month or so out for these. So, if you want the latest follow-up, you can go over there or join my newsletter over at casabona.org/join. You can do that too. But for now, let's actually dive into how I'm preparing my business for vacation. So like I said, I am not bringing my laptop.

Let's start here. Right? How am I shutting off while I'm there? Because everybody said, oh, well, yeah, I'm shutting off, but they're still checking email, and they're still doing this, and they're still responding to stuff and this and that.

So first, what hardware am I bringing, and how is that going to limit me? I'm not bringing my laptop. I am bringing, like I said, my iPad with keyboard for emergencies only. This will work well because it's the 11 inch iPad, and I hate working from it. I use my iPad to sketch and write notes and watch stuff and as a secondary screen and reading sometimes, I guess, though I've been reading on my Kindle primarily. I hate doing any kind of work from it. Sometimes I'll write. Writing is fine, but it's even not a full-size keyboard, so it's not my favorite thing to write on. So it really has to the pain of the emergency has to be greater than the pain of me working from the laptop or from the iPad.

I'm also bringing the brick. I've talked about the brick a lot, getbrick.app. Not a sponsor yet, but hopefully soon. So I will I'll bring this. I'll put it on the refrigerator in our hotel room, our resort room, whatever. And whenever we leave, I will scan it or I will brick it manually from the app.

So I won't even be able to check email in the parks. And I've thought this through because I'm going to Disney World.So everything's done through the app anyway. I'll have push notifications for that app on, but I won't be able to check my email, or at the very… actually, if I break my phone, I won't be able to check my email at all. Right? So the emergency has to be from somebody who has my phone number as well.

I'll also be using my vacation focus mode so only certain people can break through unless someone calls more than once. So again, if we're talking emergencies, there it is.

And that's really the… so I'm bringing my phone. Obviously, it's pictures. I might bring my DJI mic because inspiration could strike. And if I might record a quick audio note or two, I don't really count that as work. That's just like thinking out loud, and it's certainly not work for clients or anything. And so I might do that. Right. There might be a nice opportunity when we're at Disney Springs or something, to just capture some thoughts.

Okay. So that's really all I'm bringing. I'm not bringing a camera. I'm not bringing, like, my, The SwitchPod. Is that what it's called? Or, like, a tripod or anything like that. It's just gonna be me and the family, really enjoying our time at Disney World.

I don't have, I've already talked about how I don't have social media apps on my phone, but they would also be bricked. Again, like, I want to be fully present. My kids are old enough now and they're excited and they're actually saying things that they wanna do, and I wanna be there for it. So bringing the brick is really important to me.

And, like, so, you know, I could, like it would be a little risky to, like, brick my phone at the house and then leave because I may need to access email for reservations or so. I'm trying to put all of that in the notes app and make it offline accessible outside of email, but you never know. So, at the very least, I'll break my phone at the parks, and I don't foresee that being an issue, which kinda brings me to the next thing. Right? How am I managing this from an expectation standpoint?

So the first thing is I've already notified all of my major clients, that anybody that I'm actively doing work for, I should say, that I'll be out of the office for the duration of the vacation, and inaccessible. Right? I won't have Slack on. I don't have Slack on my phone. I don't have it on my iPad. So it's only on my, I only use Slack on my computers, so I won't be seeing Slack messages. I'll set myself away.

I communicate with some clients via Google Chat, and so something I will likely do is log out of those accounts, because that Google Chat doesn't have, like, the fine grain control that say messages has. It's it's an all or nothing thing. And I communicate with some friends in Google Chat and some work in Google Chat. And so I'll probably just end up logging out of those accounts.

But everyone has been notified that I will be out of office and inaccessible. I have said I'm not even ringing my laptop. So they'll know that they it'll be tough to get ahold of me. And the expectation is managed there.

I'm also going to set up an away message for my email. I didn't do this for a long time after I left my agency job. Cause I didn't think that it mattered that much and it does matter. Right? I think it's important for people to know if you're out of the office. It's just like a a common courtesy thing, but it also does manage those expectations.

And then the other thing I'll be doing is I'll be setting up a kind of forwarding address for my VA. My VA also doesn't really have immediate direct access to me, but she'll be keeping an eye on my inbox if there is this kind of emergency that I don't see, say, within 24 hours. Right? I'll say, like, if there's an emergency, please email, like, help it, whatever. Right? And that'll just forward to my VA. And then, you know, we'll, I'll probably set up, like, a separate way for her to get in touch with me.

But, you know, I think that's managing expectations. So I've already told the people, who need to know that I'll be away. And then, I'll have an away message up for my email. I'll set myself away in all of the Slack places, and my VA will know how to get in touch with me if there is really an emergency from somebody who is not, who who can't get in touch with me any other way.

So that's the communication side of things. I've also completely blocked off my calendar, so nobody can put meetings on my calendar. And that hasn't been, it hasn't been like that for a long time. This is, like, a mistake I used to make all the time is I would, like, set a trip, but something frustrating about most calendar apps is all day events still show as free. And so I made sure to set the vacation as busy immediately, so that people couldn't put meetings on my calendar.

And then, like, this week, I'd be looking at the following week going, oh, no. I'm an idiot. That's actually how I ended up recording. You know, I had a pretty big guest, and they booked time for when I was away at the beach. And I knew that the fact that they scheduled at all in this time frame was difficult. And so I didn't wanna reschedule on them. And so I did end up recording. But, yeah, all meetings were blocked.

And then finally, and this is the most important part. Right? This is where my systems and processes come into place. I have a list of all the things that I need to do before I leave. Because this is part of it. Right? Like, I have made an agreement with my clients, and I can't just say, well, I didn't get to it. See you in a week.

I need to make sure that I get the things done that need to get done. And so, yes. That does mean that I worked this Saturday, before I went away. Right? Or well, the Saturday before I went away was my daughter's communion. But, I did work, like, the Saturday before that. Right? I ended up working a night or a day I wouldn't normally work to get this stuff done, because I also know that when we get back, my daughter is not gonna be in daycare and summer craziness is happening soon. And I don't wanna come back to work I didn't get to as well as now less time to do the work I have to do. So it's gonna be a packed week, but it's gonna be a manageable week. We've known about this trip for a long time. And so I have been managing deadlines around that.

And so I'm really excited for this. I don't think a lot of business owners or working people in general take enough time downtime on their vacation. Right? When I tell people I'm not taking my laptop on vacation, I get, like, good for you. And, like that's not the reaction that I should get.

And I know they mean it nice. Like, wow, that's really great. Good for you. Like, you you shouldn't. Right? But, like, it should be incredulity that I would even say that. Like, that is such a norm. Right? They should really be like, of course, you're not. Why would you? Right? But everybody, a lot of people bring their work on vacation with them.

And so this is a trip that the last time we went to Disney, it didn't go the way I wanted it to. And I know my kids were still happy, but two of them were really little. And I'm lucky enough to get a second crack at it for a bunch of reasons. And I, and we love Disney. And so, like, we are gonna make the, make it a priority, but my daughter's been asking since we left to go back, and she's so excited.

And I think the worst thing that I could do is be distracted by work in the happiest place on Earth where my kids are gonna be so happy and I'm gonna be on my phone checking email, getting stressed by some like, by something that's probably not as stressful as it needs to be. I don't want that. And so I'm taking a lot of precautions.

So to recap, quick recap.

Not bringing my laptop, bringing the iPad with the keyboard. In case of an actual emergency. I'll be on my vacation focus mode most of the time. So the only message I will be seeing, the only notifications I'll really be seeing are from the Disney app, and the in the MLB. I'll still be keeping tabs on the Yankees and, my family, and the contacts whom I have told my phone, yes. Let these people get through to me. Right? I'll be, so that'll be the focus mode.

I'm bringing the brick so that I can brick my phone when I leave for when we leave for the parks so that I'm not, I won't even be able to check my email when I'm at the parks.

I'm communicating or I have communicated my out of office status to everybody I'm actively doing work for. I will be setting an away message in all of the communication channels where people will be expecting me to be.

I am letting my virtual assistant know so that she can keep tabs on things and will have like a super secret way to get a hold of me if necessary.

I am completing all of the tasks I need to complete before I go away.

I have blocked my calendar so that there are no meetings.

And the last thing and maybe the hardest thing for me, it's something I'll be practicing, up until when we leave, is, this willful forgetfulness. I think it's easy to get anxiety about when you start thinking about work. And because I'm doing these nine or so things, I'm also telling myself it's going to be fine. I am not the president of a huge corporation or a company or a country. I'm not even high level management.

And the work that I have chosen to do in this stage of my life is by design, not mission critical. And what I mean by that is that doesn't mean it's not important, but it means that I can disappear for a week and my clients will be fine. And we've prepped, and we've taken precautions in place.

And every time I've gone away on a vacation and I worried about emergencies, it's only ever happened once where my server, when I was a Web Developer, the server went down. And I couldn't do anything about that anyway.

So, yes. It would suck if my websites went down while I was away, but that's not going to be something I'm going to be able to handle anyway. That's going to be up to my hosting company to handle.

And so the best thing I'd be able to do is communicate with my clients, which is what my VA is there for. So, and I'm not hosting that many client websites right now anyway. So I have a couple. I cheated. I said I was getting rid of all of them, but I'm cheating a little bit.

So anyway, that's it for this episode.

What I would ask you, right at streamlinedfeedback.com, streamlined with a “d”. streamlinedfeedback.com. How much work do you do on vacations? Or if you don't do any work, how do you shut off? Right? I really wanna know because I think it's one of the hardest things that we could, that we can do.

And I am driven by family. I want my kids to have a great time, and I love Disney World, and I want us all to be fully present. So, how do you stay fully present on vacations, especially if you have your own business? Let me know. streamlinesfeedback.com.

Again, if you want to, you know, I get back the end of this week as you're hearing this. And so if you want to get my thoughts on how I think it went, subscribe to Joe's audio notes over at notes.casabona.org, or you can join my mailing list over at casabona.org/join. All of that will be in the show notes in the description for this episode.

Thanks so much for listening, and until next time. I hope you find some space in your week.

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