MBA884 The Working While Traveling Experiment P5: My Working While Traveling Challenges
2 Feb 2026 · 17 min
Omar Zenhom runs two businesses with 23 people across time zones while traveling through 15 Italian cities in eight weeks. He hits the real problems: team decisions pile up at 3 a.m., he can't stop working, and moving every few days kills momentum. His fixes include appointing managers to handle day-to-day calls, blocking work time around his team's schedule, and planning one goal per session instead of trying to do everything.
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Hey O.
Welcome to the $100 MBA show, the business podcast that gives you practical business lessons for the real world. I'm your host, your coach, your teacher Omar Zenholm. I'm also the co founder of the Hundred Dollar MBA and webinar Ninja and it's part five of our Working While Traveling experiment and I'm in iconic Venice. The city of Venice is everything you would imagine it to be and more. It's really incredible. More about Venice in a bit. If you're just joining us on this eight part series, Nicole and I are embarking on an eight week trip, an eight week experiment to see if you can really travel the world while running and growing a business. Previously on our last episode in Part four we were in Sicily and and I shared with you what you can learn from businesses abroad. How you can take away some really great business practices and apply it to your own business when you travel. You should take full advantage of it. Yeah, it's a ton of fun but the experiences you have along the way can really impact your business. So if you haven't listened to Par four, make sure you listen to that. Now go back and download it and listen to it. We're on itunes, we're on Stitcher, we're on Overcast, we're on Google Play or You can check us out on our website over@100mba.net in today's episode, we're back in the north of Italy in Venice, the city that made lemonade with lemons. With their low tide, they built a city of waterway canals that weave through, like concrete streets In a major city, there's nothing like it. And you know you're somewhere special the moment you arrive. And as enjoyable and magical as Venice is, it's beautiful, it's charming, it's enjoyable. Not all travel is sunshine and rainbows, especially when you're trying to travel while you're working. And I've had my challenges in this experiment, trying to travel while running a business. In today's episode, I'm going to get real and share with you the challenges I've been having and how I'm taking on these challenges. Now, I have to be honest, working while traveling for an extended period of time is not easy. It's really tough. Don't get me wrong. Knowing what I know now, I would definitely do this again. But when you're working while traveling, things happen that really test you and had me question how to approach this experiment, how to approach this experience of working while traveling for this long eight weeks. It also made me think about all these people that run their businesses abroad full time, these digital nomads, these location independent entrepreneurs. And from the surface or from the Facebook feed, it looks all beautiful and gray and poolside, you know, laptop sessions. But I'm learning in reality and a different story. But that's natural. Anything worth something is challenging, but the key is to adapt and to address the challenge so it doesn't ruin your experience. And let me tell you, I had some doozies up to this point in this trip and I'll share them with you. These challenges that I've had, I want you to avoid these issues. I want you to learn from my experience on how I took them on so you can preempt and you can make sure that you don't face these challenges. So I got a lot to share with you, the reality of the challenges I face while working, while traveling. We got a lot to cover, so let's get into it. Let's get down to business. Nicole and I run two businesses with a team of 23 now, just made a couple hires recently, and we love to travel. We've traveled up to three weeks before at a time. But in this experiment, we're going all in. Eight weeks of travel, 15 cities. We've been to Milan, Florence, Rome, two different cities in Sicily. Sardinia and now Venice. And like I mentioned, Venice is gorgeous, but boy is it pricey. So I know that going in Venice is not cheap, but it's a beautiful attraction. You can get a water view at anywhere you eat, you know, because there's canals everywhere, there's gorgeous art and architecture, and everything is walkable. So you really get to enjoy the atmosphere. Now, like I mentioned, I really have been enjoying this trip, this whole travel experience, but I'd be lying to you if I told you this was like some sort of really relaxing vacation. It hasn't been. It actually has been pretty challenging. Maintaining your business working while you're traveling is no easy feat. Anybody who tells you otherwise might have a different situation. I can say they're lying. They might have a different situation. They might have a small business where it only requires them to work. Maybe they're a solopreneur, like a blogger, or they do coaching calls once a week or whatever it is. If they're not managing a large team, then this might be a lot easier. And I want to say that business model, being a solopreneur or running a very small team, one, two, three people, maybe there's nothing wrong with that. That fits your lifestyle. If that fits your goals, if that fits what you want out of your business and your life, then please do. That will make you happy. But if your business is growing, if your business is a little larger, if you have, you know, more than a handful of people working on your team, things get a little bit more complicated. If you have hard deadlines, if you have to answer to more than just yourself, whether it's a large group of customers, whether it's other business partners, whether. Whether other people on your team are accountable to each other. Like, for example, with us with our software business webinar Ninja, a lot of our teammates are dependent on each other. So our developer really can't develop unless they get the designs first from the designer. And those designs have to be implemented by a front end developer. And then once the front end developer is done with it, the back end developer's got to work on it. And when it's all put together, you know, there's got to be some sort of server administrator that's going to put this up on some sort of server infrastructure to make sure that it's stable. You get the point. Everybody relies on each other and they're waiting on each other. So there's communication, there's dependencies, and there's you who is responsible for managing this whole thing. So I want to Share with you some of the challenges I've had working while traveling. These are not easy to share, but, you know, in order for everybody to learn, I'm going to have to. I also want to share with you how I decided to take on this challenge, how to adapt and make sure it doesn't ruin my whole travel experience.
So.
So the first challenge. I'm gonna call this challenge urgent issues with horrible timing. Now, earlier in part two of this experiment, I talked about making time for work and play and designating a certain time of work, time that aligned with your team. Meaning that if your team has some questions for you or you need to approve things or you need to make some decisions, you need to make some time that aligns with their time. I'm talking about time zones here, you know, so if you are traveling abroad and everybody who works with you works on your time zone back at home, then you need to account for that. Now, for us at Webinar Ninja and the 100 MBA, we have a very global team. We have teammates all across Europe, in Russia, in the US In Asia, in Australia. So pretty much there's somebody on our team working at all hours of the day. That means if somebody on the team has an urgent issue, they need something to be solved, they need help. They need a decision to be made. They're gonna be up when you're not up. They're going to be working while you're trying to enjoy your travels or enjoy a dinner with friends or enjoy a dinner with a loved one. This happened to me. We were in Florence, and we just wrapped up eating dinner, and we were supposed to, you know, go out for some ice cream later on. And then I got a little message on my phone on Slack saying there's a serious issue that I need to, you know, attend to. Now, serious is relative, but the point is, this person needed my help, needed a decision to be made so they can continue working. There's a roadblock now. As amazing as smartphones are, I couldn't manage everything on my phone. Like, while I was walking in the streets of Florence, as we were walking to get some ice cream, there were certain things I needed to go on a computer for. It's just faster for me to go through emails or to go through some certain applications or to test some things out that need to be tested. The bottom line is, is that I needed to get to my computer. I just couldn't solve this problem or make a decision on. On my phone. And in just five minutes, I realized really quickly, wow, okay, this Is something I need to really do something about. And at that point, I had to make a choice between work, my business, and travel. That experience of travel and trust me, gelato in Italy is an experience. So within a few minutes, I realized I need to go back to our place, to our accommodations in Florence, fire up my computer and do some work. I needed to solve this problem. I need to make some decisions. I knew that it's not gonna be, you know, five minutes. It was gonna be maybe an hour or two now. The first feeling I had in my gut was, man, I really didn't expect this to happen, and I don't wanna disappoint those around me. I was with Nicole, my wife, as well as a couple of friends of ours who met us up in Italy. Jason Zook and Caroline Winegar, fellow entrepreneurs. Both were on the show before. We're enjoying ourselves as friends on this trip or in this part of the trip. And I really felt like, wow, if I leave, I'm gonna let them down. I wanna enjoy with them, and at the same time, I don't wanna leave them. So really, I felt like I don't want to disappoint others. But I gave one look to Nicole, and Nicole kind of got it. She knows me very well. If I ever have to choose between my own entertainment or pleasure in our business or our work or what we're building, I'm always going to choose our work and our business, because that's what really drives me in my life. She looked at me and told me, omar, Florence will always be here. Go and take care of business. Go take care of what you got to do. And that was great, because it made me feel like, okay, she's cool with it. Everything's gonna be okay. I gotta go and solve this problem. And allowed me to focus on that problem. So I headed back, I fired up my computer, I worked with my team. We solved the problem. Everything was okay. We made a decision. Everything was all right. But that was kind of the first major challenge where I was like, man, you know, this is hard because, you know, when you're building a business and you have people that depend on your decisions, sometimes you kind of have to be on call, and it's gonna be a little bit inconvenient. As much as I planned and made, you know, a certain time for me to work every day and balance, you know, work life and travel life, this still happened. Now, I know it's an exception, but it's still something you have to learn from how to handle it. So I realized in order to handle this problem or this conflict or not feel bad about this whole situation, I needed to make sure that I set up expectations properly prior to this happening. You know, before a problem happens, it's good to set up expectations with the people around you. So with Nicole as well as in this portion of the trip, you know, we met up with some friends in Italy, Jason and Caroline. So I really should have sat down and spoke to them beforehand before that night when we started traveling together and say, hey, guys, this is what's going on. I got a lot going on in my business. We're growing, we're expanding. There's certain positions that haven't been filled yet. So I'm really working on managing that. Also, I might be interrupted at some time and I want to let you know, guys, and set that up so you know that, hey, if I have to leave a dinner or ice cream trip or a trip to a museum or whatever it is, please, you know, forgive me in advance. You know, don't take advance. And of course, everybody would be cool about that. And in fact, they were cool when I kind of said that afterwards and said, hey, I'm really sorry about that. You know, I wanted to set them up for the rest of the trip. But just as important, you need to set that up within yourself. You need to set those expectations so you understand that, hey, this might happen, I might be pulled away, so I have to take care of something that is urgent so you're not disappointed. So you know that, hey, this is just gonna happen. And that's just part of it. And that's part of working while traveling. And the timing is never gonna be perfect, you know. You know, these issues are not gonna come up when you're working on your laptop all the time that assign time. Just know that the timing might be horrible and that's okay. Now what it also did, it also highlighted some areas where we need to hire for some manager positions that need to be filled. And I jotted those down immediately and realized, okay, we need these position filled as soon as possible. Because in this area business, we have somebody who's in place to take care of some decisions, but in some other areas, I'm the one who's always making the decisions. Nothing wrong with that. And you know, it's good to have big picture decisions, but day to day decisions, we really need to make a hire for those decisions. So that was challenge number one. Urgent issues with horrible timing. It's gonna happen when you travel, it's gonna happen when you're working while traveling, Just expect it and understand how to deal with it. Communicate to everybody around you that this might happen and this is what you'll have to do if it does happen. All right, challenge number two. If you're going to decide to work while traveling, understand you can't really shut off mentally. This is not a vacation, it's not a holiday, it's an experience. Especially this type of traveling where you're seeing cultures, you're learning about different things, you're going to restaurants and museums and historical sites. These are learning opportunities and again, experiences. This is not a beach holiday where you zone out. Don't get me wrong, I firmly believe in beach holidays. I think they have their place and they need to be done. I personally love those kind of vacations because I like to shut off and not think about anything other than, you know, whatever comes to my mind, you know. But you can't shut off if you're constantly getting re tapped into your business. When you're working while traveling, you're working, right? You have a certain amount of time every day where you're working. And then even when you're on your off time, you're thinking about work, right? If you're an entrepreneur through and through, you know exactly what I'm talking about. Constantly thinking about how to improve your business, what you could do, the challenges you're having. So it's kind of hard to switch off completely. So don't expect to and just be okay with that. Be okay with the fact that you're not going to be completely shut off, especially if you're traveling for extended amount of time. And I knew that coming in. This is not a quote unquote holiday. This is not R and R. Now, having said that, Nicole and I do schedule once a year some R and R time, a complete shut off period, a week of just no work. And that's where we plan for the next year. And it's big thinking. It's aspirations, it's goals. It's not day to day work. Problems, challenges, issues. It gives us a time to really just think about what we really want and what we want to do and how we want to move forward. And it allows us to relax and recharge. But going into this, you have to know this is not that you're not going to relax. You're going to be working every day a little bit. So your mind is going to be thinking about business all the time. Now, of course, there are going to be periods of time where you're just consumed by the experience you're having. You know, when we went to see the David in Florence, I was just in that moment, I couldn't think about anything else other than, you know, Michelangelo and his work. By getting to the gallery and leaving the gallery and between meals, I can't help it, I'll be thinking about work. Why? Because it's all about intentions. When I went into this trip, I knew that I'll be working. So I'm not on the off mode. You know, I didn't switch my brain to off when I go on these R and R trips. Yes, I know. Intentionally I need to shut off so I can recharge. So that's challenge number two and the way to kind of just go in and be prepared for it. Understand this is not R and R and it's okay if you don't mentally shut off. This trip has been incredibly stimulating mentally for me. I mean, you could tell by all the things I'm taking away and sharing with you in this eight part series of working while traveling. When it's all gonna be over, I'm gonna need a little bit of a break, maybe a day or two. But the point is, is that, you know, this is a little bit strenuous. It's a little bit of work and traveling is exhausting in a lot of ways. So understand that this is an experience and not R and R. Does it.
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All right, I'm revealing all all the challenges I've had up to this point on this trip. Working while traveling. Let me share with you challenge number three. When you travel, your consistency goes down the drain. You have like, no consistency because you're going from city to city, you're unpacking, you're packing, you're going from one accommodation to the next. You're hopping on planes and trains, you're spending time getting there. In some cases, you're changing time zones. And really the travel itinerary takes precedent. Now, when you compare that to your normal work schedule, when you're back at home or in your office, things are pretty consistent. I mean, I look at my own schedule. I get up pretty much the same time every day, have breakfast, I know exactly what I'm gonna do for the day. I have my plan, I get to work, I have my certain time for lunch at exact same time around, I know exactly what time I'm going to have lunch, how long I'm going to spend at lunch. I get back to work at the same time, I know when I'm going to go to the gym. The point is, is that it's consistent, it's predictable, and I know how much I can get done every single day. I can plan accordingly. But with travel, you have to be really flexible because there is no consistency. And if we're going to be honest, consistency is the key to productivity. It's hard to be productive or consistently productive when you don't have any consistency in your schedule, when you don't know for sure how much time you're going to spend on something every single day. So predicting your own deadlines, like how long it will take you to write a blog post for this week, or how long it's going to take for you to script or record a podcast episode, these things are a little bit loosey goosey. You know exactly how long that takes when you're in your controlled environment, but when you're traveling, you really don't. Even if you dedicate the time and you say, hey, I'm going to be writing my blog post from this time to this time in my hotel room. You might be planning to work today and tomorrow go and see a museum, but then you realize ho tomorrow the museums are closed, we got to go today because we're leaving the day after tomorrow. So then you got to switch your schedule so you're a little bit off. Or another thing is that you're sitting down to get work done. You're trying to work, you're getting through your blog post and you're just getting tired because you haven't eaten. Why? Because you don't have a kitchen, you don't really, you can't just go and grab something to eat from the fridge and not that simple. You have to go out to eat. When you travel a lot, even if you're used to going out to eat, when you're back at home in your office, you have your go to place, you know exactly where you're going to go, you know exactly what you're going to order and it's really quick and efficient. But when you're traveling, and especially when you're traveling abroad in different countries, you don't know where to go. And therefore your meal times are a little bit messed up. You get hungry at weird times, things take longer because there's a language gap. You know, you're learning how to get to somewhere for the first time. You don't know how long it takes to be served, all that kind of stuff. So you get the point. It's hard to be consistent when you're traveling because there's so many variables that change. There's so many variables that you can't predict even when you try to plan, even when you make time to work and to travel. So what's the solution? My solution is to have one goal for each work session. So if I'm sitting down to work today, I need to just have one goal because I don't know for sure how long it's going to take given all the variables that are, you know, against me. So as long as I finish that goal, I'm good to go. So if I need to write a blog post, I just gotta finish that blog post, forget about everybody else. If I need to write a blog post, I just need to finish that blog post. I need to sit down and make sure it gets done. This ensures I don't put too much on my plate and be over ambitious with my goals. Even if I say, hey, I have three hours, I usually get these things done, all these things done within three hours. Back home. You're not back home. It's a different environment. You have a different circumstances. So you need to make sure that you don't put that much on your plate. Understand you're not going to get as much done when you travel as when you're at home. Number two, use a checklist. Make sure that you have a checklist for all the things you need to do for that week. This will help you stay on task and navigate between the inconsistencies. So you may have a lot of time right now, but you might get some time later on when you're on a train or on A plane. Open up that checklist and go back to the checklist so you don't have to rethink. What do I have to do now? You got to let the inconsistency work for you. So you might be wasting some time, you know, on a train trip, a couple hour train trip between Milan and Florence, but you can get some stuff done then. These are gaps of time that you're not accounting for. You can work. You can actually get things done. Some of us think that, no, I can only work during that assigned time where I'm working at a desk in a room with my laptop. No, you can work virtually anywhere. Make sure you make use of that time that in between time when you're traveling number three, you might get a little bit of anxiety when there's a lot of inconsistency and you're not getting as much done as you're used to, tell yourself, hey, this is temporary. This is not how my life is going to be. This is just for this trip. Another tip that I took on is I had so much on my plate. I overestimated what I got done. I realized I still have a whole bunch of stuff I need to get done that hasn't got done. I'm behind schedule. I outsourced it. I hired somebody to do some of the stuff I needed to get done. Some admin work, some editing, some proofreading, some research I needed to get done, outsource it. And you can take some things off your plate. You might think to yourself, well, sometimes when I give it to somebody else, I delegate. It's more work than actually doing it. No, it's never more work than actually doing it. It's always gonna be less work. Just explain what needs to be done. Give it to them. Let them have autonomy. Let them surprise you. It's better to pay a little bit more than you want to to get the job done properly. So outsourcing, you know, that is something that is really viable that you can think about if things are getting too piled up on your plate. Lastly, when things are inconsistent and, you know, plans change and you have to work in different places, different, you know, areas, whether it's at the airport, whether it's in a public cafe, whether it's somewhere else. Use earphones. Earphones allow you to block out any noise and allows you to zone in on your work. Headphones really allow you to zone in and allow other people to know that, hey, you don't want to be disturbed. It also allows you to not be distracted by other conversations. You hear now, if you're in a foreign country and you don't speak the language, you have an advantage. You're not distracted because you don't really understand what's going on. But this technique really helps you be flexible and be able to work anywhere when things are inconsistent. Guys, that wraps up today's lesson. Thank you so much for joining me on this eight week experiment. Working while traveling. We have so much more in store in our next stop. We are in Naples. Naples is a beautiful hustle and bustle city and we're going to be focusing on what makes a great global business. If you have an online business or an online presence for your business, you need to listen up to this episode because your marketplace is the world and you need to make sure you understand your audience and that you cater your business to the world. Some of us, sometimes you just really narrow into our own local area or our own country and don't realize that we have customers that can really benefit from what we have to offer around the world. But let's make sure that we can actually communicate with them and resonate with them. Now, I'm not talking about within their language. You can have it in English thanks to Google Translate and the automatic translation feature that Google has on websites and on the Chrome browser. I'm talking about culturally, we get into all that in the next episode. So make sure you hit subscribe so you can get that automatically. If you love our show, show us some love with an itunes rating and review. We love to hear from you. Let us know what you think of the show, what your favorite episode is, what your favorite takeaway is. We'd love to hear it. All right, that's it for me today, guys. But before I go, I want to leave you with this. Even though working while traveling has its challenges, has its ups and downs, there hasn't been a better time to work while traveling with technology and a global economy. It's definitely doable with the right planning, with the right preparation, with the right mindset, with all the advice that we're sharing on this journey. So even though I shared my challenges with you today, I don't want to discourage you. This is definitely worth the experience and you'll see exactly what I mean with all our upcoming episodes in this series. Thank you so much for listening. I'll check you in the next episode. Take care.
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