A Type-A Business Owner’s Guide to Taking a Break (Or Trying To!)

Have you ever felt the weight of your business responsibilities holding you back from truly enjoying life? In this episode of Pickled Perspective, we dive into the struggle of delegation and taking a break as a small business owner. Join our host, a self-proclaimed Type A personality, as she shares her journey of preparing for a long-overdue vacation—a surprise cruise to Bermuda! Discover relatable stories about her past trips, from the chilly North Sea to the bustling streets of Barcelona, and how those experiences shape her approach to relaxation.

This episode is packed with invaluable insights on how to step away from work without guilt. Learn how to effectively use tools like Trello for project management, automate processes, and set up a foolproof out-of-office message that liberates you from the constant pull of work. With tips that can transform your vacation from a working trip to an actual getaway, you’ll be ready to recharge your batteries and come back stronger. So why wait? Tune in now and unlock the secrets to balancing business and life!

Host: Welcome to another episode of, oh, that's always fun to get a repeat of the intro music. Welcome to another episode of the Pickled Perspective. Today, as promised, we are not going to just talk about pot up. So the goal of this podcast, like I said, is not just to be a business podcast. So I wanted to actually talk about taking a break from business. So I, well, I'm a self-proclaimed A type personality, which means it is very hard to step away from work or let go and you kind of think you have to do everything yourself. So delegation can be really, really difficult. About a month ago, Brian, my husband, he surprised me, well, semi surprised me with a vacation that was part of a birthday present. So we're going to be going on a cruise to Bermuda, which is really exciting. He couldn't be completely spontaneous and had to tell me at least a month, five weeks in advance so that I could try to plan for that and make sure that things were in order because it's been well over a year since we took any trip. And the last trip we went on, I worked pretty much the whole time. I will bring a laptop with me. I will have my backpack the whole time. I always want to make sure I'm available for support or the development team if there's a question, if anything comes up, if there's an escalated user issue. So there's always a feeling of I need to be connected for the team because as a small business, I feel there's like a guilt that exists there. So it's really difficult to let go. And I think a lot of small business owners can relate to that. On one hand, you need some time to decompress, but you also feel like you're not allowed to, especially if the company is still growing and you're still building it. That's a real, real struggle. So I'm trying to determine the best way to do that.

Host: What's funny is since we're going on a cruise to Bermuda, which is exciting, we've been on cruises before, we're going on the MSC line, which I don't think they're as popular here in the United States as they are in other places. We've been on them twice before in years past out of, where did we start before? We started out of Southampton in the UK once, and that was a great cruise, except we went in November. And so, and that was a great cruise, except we went in November. And so, and if you know anything about the UK or the North Sea, it's a pretty chilly time of year. So every city we stopped at, though beautiful and a lot of history, very, very chilly. And then we did another one several years ago where we did the Mediterranean Sea about that same time of year, which was perfect because it was warm and beautiful and went to like, I think we started in Rome, went to Sicily, which I was very excited to go to Sicily because, not to make myself gayer than I already am, but I was like, oh, you'll get that Golden Globes moment where you'll get to go picture it, Sicily, you know, whatever year it was. We stopped in the capital and it was kind of grobes, there was human feces all over the place. So Sicily was not what I expected, but Rome, beautiful. Where else did we stop at that one? We went to Barcelona. I love everywhere in Madrid. I'm desperate to move to Madrid one day, or Spain, I should say. And then we hit France, another place in Northern Italy, anyways, not the point.

Host: With going to Bermuda, what's interesting, so I know the Gulf and Florida, they're getting hit by Helene, that hurricane in a day or so. And there is another tropical depression, which I know most people in the US don't watch the NOAA.gov website. That is a website I am constantly keeping my eye on. I used to live in Puerto Rico from 2015 to 2020, and I lived there during 2017 when Irma and Maria, the two hurricanes that were Cat 4, Cat 5, hit back to back and just devastated the island. So there's a, currently it's a tropical depression that's forming in the Atlantic with, it's still a rough trajectory, but it has the path to hit Bermuda and it could potentially be there while we're there. And so in my head, I'm like, oh my God, I'm like a hurricane magnet. I have complete PTSD from those two hurricanes, which is why after COVID, I never moved back to Puerto Rico since I ended up here in Baltimore, 22 days on that island without power or running water, taking baths in the ocean, which at the time seemed like a really good idea because you're so hot and sweaty and sticky and disgusting, but then you get out and you're salty and crunchy and it's actually worse. So it's a catch 22. Yeah, I'm just kind of picturing like, oh God, what if like the ship got to the island and then we got stuck there and now we're there living on a boat that could be 10 times worse because at least I, even though I had a house without power, I had a place to live sort of. Yeah. So those are the crazy thoughts going through my brain at the moment.

Host: But today I was also trying to prep for, okay, how do I do my podcast episodes next week as we're on the go? Already running into trouble with that, trying to run it on the iPad, Google Chrome, which if you want to stream through YouTube because we have a scheduled live cast for the announcement on the 30th, I have to do the episodes directly through YouTube. I can't stream them through studio because YouTube will block the stream. So I need to use Chrome, which is interesting. So on the iPad, it says the browser's out of dates, checked it, updated it, all that good stuff. You're trying to get your tech engine in check. Doesn't work. So had to default back to my normal setup and setting. Things are already off to a rocky start. I was going to try using the phone this morning, but I will never show you all a picture of my desk. Maybe someday. But it is covered in technology and garbage. So I have my Rode is here. So I've got that. Here's my mic. There's phones, headphones, keyboards, piles and piles of Post-it, aside from the most important thing, the coffee that's to the right. There is no space for the phone to be set up in its tripod to make it work last minute. So that got thrown out the window. So we had to quickly pivot back, which is why also the lighting is much darker today, even though I have my partial lighting on. For those who are watching the video version, it is incredibly dark here right now, as we're not only moving later into the year, we're getting kind of those pre effects of the storm that's in the southern part of the country. And so it is just downpouring. It's very dark outside. So I'm not well lit. I do have my pickle behind me. So at least there's a little green light. So kind of gives you that ominous feeling, very Halloween, which I'm excited for. I love Halloween.

Host: So getting back on topic there, I definitely segue, how do you let go and try to just delegate and take a break? Because everybody does deserve a little bit of a break now and then. So automation is the biggest thing. One thing that we've been shifting is our support and help. We've had a chatbot for a really long time within pod ops. We've recently shifted to a new platform called the intercom. We're still configuring some things, but that also allows the chatbot pie to connect to a live agent. So that's one way that the team can be more connected, which then takes me a level out. So it ensures there's some human interaction and tickets can be routed more efficiently in case there's an issue. The development team, I don't really worry about the development team. They know what they're doing. It's mostly I just like to meddle and be a part of what's being developed so that I know what's going on. It's always exciting to test and break and make sure things are working. So I just like to not be a hold up in that process. So me being out does hold it up because I'm kind of that final step of approval. But planning and communicating, so letting the team know what you need done. So especially if you are a small business and you might be a team of two or three, or maybe if you're lucky enough to be five, 10 or 15, which I think then starts to verge you on medium, but we'll still call you small. It's having some sort of tool, whether it's Asana or Trello, or even just a Google Sheet, something you can all look at where all of your tasks are managed, everything can be put in, they can be checked off, and it's centralized and make sure everybody's using the same tool. I was just talking to a client about this yesterday and they were kind of walking through how they manage things and that was the one thing I pointed out for them that a lot of their systems, it's not that they have bad processes, it's that for their four different teams, they each manage everything in a different system with slightly different processes. So that's why it's so difficult for them to align on projects and do things together. And it would be so much easier to get their systems in sync or their processes in sync, I should say, if they use one system. So for us, we use Trello boards, you know, because we do so much more development and marketing items, it's really easy to have boards that say, these are the tasks, this is the stage of the task, here's the person working on it, these are the dates. It also has those really handy Gantt charts so that you can see timelines, anybody can hop in and out of there, and then if you are like me and you're obsessive, you can easily get to a browser, assuming you have internet connection with a ship, this is where things get really sticky, those days at sea, even though ships tell you they've got an internet connection, hmm, that's a little sticky. I definitely do not recommend paying for their upgraded internet, I have never felt like on a ship it was truly upgraded, it seems like it's just as bad as the internet they include for you, that's personal opinion. And if you're close enough to land, depending on what kind of cruise you go on, sometimes it's better to just hotspot on your phone. So take that with a grain of salt. And then out of office message, it's truly the most important thing you can do for yourself to give yourself a break. I've made that mistake where I go on a vacation, and I don't set that out of office. And then people really do expect a response from you, and you have to respond. So if you put that expectation out there, when somebody gets it, they are much more respectful of, oh, great, you're out of the office, I'm not going to hear back from you until X date, or whenever you put in there, or at least they know there's a delay. That way you also avoid somebody getting upset because they didn't hear from you. Or if you have somebody who can be your backup, they know to go to them if there's a critical issue, which I do, if you have somebody you can put as that second in command, I definitely recommend having a backup that gives you another layer of comfort so you can take some time off, take a break, recharge your batteries, come back as your best self. I'm really bad at kind of doing those self mental health checks or whatever you want to call them. But it does help you avoid burnout and ensure that you're a better team member, better for your customers, and just all around ready to come back and go full force. Especially if you're like us, if you are building something or you're in software, it's really helpful with getting those creative juices flowing. So those are just some tips I would put out there. If anybody has been to Bermuda during this time of year, I would love to know your thoughts on what we should be doing. We've never been there, so very excited to go. We did get snorkel masks because not paying for the excursions, they are way too expensive both through the ship and on the island. Yeah, I'm cheap. Let's just be honest. Again, small business owner, we are trying to save money left, right, and center. And then if you have your own tips, like what would you suggest? How do you unplug when you need some downtime, when you need to recharge? Definitely interested to hear from you. Share those in the comments, not only for myself, but other listeners. I'm sure they would benefit from it. If you are in the South, going to get hit by this hurricane, please stay safe. Definitely take any of the warnings from your local officials seriously. Hurricanes are a big deal. I know in Florida, they do wine parties. But when we're getting over those category one and two, it is serious. So take those warnings seriously. You'll be glad you did. I know that I regretted some of my choices when we had those four and fives hit us. So again, thanks for tuning in. Let me know your thoughts in the comments and happy creating.