Mollie Conway 00:57
So my Nomadtopia is essentially half of the year mostly at our home base here in Nashville. We’re currently kind of in that six-month span, I am traveling a bit back and forth from my company’s headquarters, which is in Florida. So this is kind of our offseason of me traveling, which is nice. But then the other six months of the year, I’m traveling a bit around the US, depending on where my husband is playing baseball. So he’s a professional baseball player, and it’s quite an unpredictable life. So working remotely and kind of being a nomad allows me to kind of go along for the ride with him, but also keep some stability and also keep a home base here in Nashville. So yeah, that’s kind of the long and short of it. I’ve been doing this for about a year, a little over a year, kind of semi nomading, since the beginning of 2014. And just given my husband’s situation I have always kind of felt like a nomad. When we were engaged, we were long distance as well. So there’s a lot of traveling and not feeling really settled in one spot. So I think I’ve kind of always been a nomad, but it’s been about a year since I’ve been kind of officially in this scenario.

Amy Scott 02:35
Excellent. So yeah, I was telling you before we started that I think this is a really great example of how, even if one person in a relationship is not technically location independent, or has, you know, various specific locations he needs to be in, that the other person being location independent can really open up the possibilities in terms of being able to travel together and be together, move to another country together, whatever it might be for somebody, and yet still be able to continue doing the same work and all of that stuff, which I think is really cool. And you’re definitely the first baseball player’s wife that I’ve talked to. So that’s a cool example to be able to bring to listeners. I’d love to hear a bit more about the backstory in terms of what your life and his life was like at the time you met and how it transitioned to where it is now.

Mollie Conway 03:39
Sure. So, you know, I think most people in my situation, usually have to end up kind of choosing. It’s either, you kind of drop everything and travel with your spouse, or you make the tough decision of being basically long distance for six months out of the year, while you kind of keep things running back at home, which is a different difficult decision. I think a lot of people have misconceptions about professional sports, and specifically baseball, there’s a lot of kind of paying dues, and once a player gets drafted, they really have to kind of work their way up the system, which means playing in little towns in the middle of nowhere. I’m sure most people have seen minor league baseball stadiums if they’ve traveled anywhere in the US. It’s a very unpredictable life. So like I said, when we were engaged, Josh was based primarily in Arizona, and I was working for my current company in Florida, and I have family down there and was living with family, so even then I really felt like a nomad. I didn’t have most of the typical belongings people have, you know, mostly just clothes, clothes and a suitcase. And during that time, it was really challenging. I was trying to progress my career, but also was living away from Josh, which made things really difficult. So just kind of naturally, almost naturally, I was just trying to work out in my mind a way that it could all work, as we were preparing to get married, you know, what would the ideal situation look like for both of us. And so without really doing any research on being a digital nomad or anything like that, I kind of just naturally came to the conclusion. And it wasn’t till after I kind of decided in my mind that this is what I wanted to do that I realized there were all of these resources for people who maybe weren’t in my exact situation, but are certainly taking advantage of all of the opportunities that working remotely brings. So I just remember when once I kind of made that discovery after the fact, it was like, a weight off, lifted off my shoulders, not feeling like I was the only one kind of struggling to come to terms with some type of lifestyle choice.

Amy Scott 06:28
Right, right. So you came to the idea to work remotely on your own, and then discovered that it was kind of a thing.

Mollie Conway 06:37
Right, and there’s all these people kind of making it work. And my travel is very much limited to the US, but you hear that people are making it work abroad and in all of these, you know, sometimes remote places. I think that just kind of gave me the extra push I needed. It was definitely very encouraging.

Amy Scott 06:58
Yeah, absolutely. And so it sounds like because you were wanting to progress in your career, that this seemed like a better option than like quitting your job to do something else that would be more flexible.

Mollie Conway 07:14
Right. Yeah.

Amy Scott 07:16
So tell me what kind of work are you doing?

Mollie Conway 07:18
I’m in corporate communications.

Amy Scott 07:20
Okay. And what does that mean exactly?

Mollie Conway 07:23
So it’s kind of everything from employee communications—I work for a large corporation, so several thousand employees—so there’s a lot of employee-driven communications and also externally, so media press outreach, things of that nature.

Amy Scott 07:45
Okay, got it. And so, once you decided that this seemed like a good way to go, did you know at that point where you guys were going to be living once you got married? How did you sort out that part first? Or I don’t know which happened first, you tell me.

Mollie Conway 08:07
Yeah. So I guess we were kind of just talking about, you know, we needed to find some way to live in the same city. But so Nashville was kind of the first stepping stone, there’s some reasons for Josh wanting to be here, for offseason training it seems like a great place to move, you know, there’s a lot of growth in the city. So we kind of agreed upon Nashville being, you know, at least to start, that would be our home base. And, if I could somehow work out a remote working situation, and be doing that from Nashville, that would be ideal. And then from there, the season is always kind of up in the air. And, you know, there’s very little planning we can do for that. So Nashville was kind of the first stepping stone.

Amy Scott 09:07
Got it. Okay, so then what happened next, in terms of pitching this idea to your boss. How did you prepare for that? And how did it go?

Mollie Conway 09:17
Yeah, so there were months where I was kind of dreading it a little bit. One part of just being in professional sports in general is you kind of shy away from making decisions in advance because things can always change. So, I think a lot of people kind of put off big life decisions, whether it’s, you know, moving somewhere or whatever it might be, they kind of put those off just because there’s always these kind of variables. So I think it was about like a month or a month and a half before we were looking to move that I plan to pitch it to my boss, and at that point, my boss had been flexible with kind of like a semi-remote situation. So I had been working remotely one week every month before that, to accommodate traveling to be with my husband, so I knew I had kind of proven that I was able to stay on top of things, and I never kind of let anything slide, and I knew I had kind of like built up my rapport with him as far as that goes. So, I felt like he’d be understanding and supportive as far as that went and really, for me, it was just kind of thinking about how I could position it as a benefit to the team.
It’s not really an environment where a lot of people are working remotely, so I was really kind of breaking the mold as far as that goes, and I really just tried to think of how I could position it as a benefit. The company I work for has a large-scale field organization, so most of the employees are decentralized from the corporate headquarters. And there’s actually a small office here in Nashville. So I positioned it as I would be able to kind of understand the day-to-day of a field employee by spending time in that field office here in Nashville, which as a communicator, and one that communicates to employees, you know, it can really help kind of educate our strategies and all of that. So that was my main kind of benefit that I presented to them. And I think, also just them understanding that my husband and I had been long distance for so long and making it work that way. So there was also just aside from the business component, I think, the team was really supportive, just because they knew we had been apart from each other for so long. So they were supportive and understanding that we wanted to make a change.

Amy Scott 12:14
Right, absolutely. So then, obviously, you got a positive reaction, did that happen right away? Or did it take some time for them to warm up to the idea?

Mollie Conway 12:27
It happened pretty much right away. My boss, he’s a great boss. I was upfront with him that if this wasn’t gonna work out, I’d have to leave; it wasn’t like if it didn’t work out I was gonna keep my job. We were at that point where it was like we need to make it happen, and whatever we have to do to make that happen we would do. So he was supportive from the beginning. I think he took more of the brunt presenting it to his boss. So I wasn’t there for that conversation. But he let me know that everyone was supportive. So, you know, it was much less painful than I anticipated. I thought there would be a little bit more kind of steps in the process I had to take, but it was pretty painless.

Amy Scott 13:25
Good. That’s great. And yeah, I feel like the more stories, if people are thinking about doing something similar, and they hear stories about it going smoothly, it gives them some hope. So that’s good.

Mollie Conway 13:40
And I kind of anticipated, I had like a Plan B, so if he wasn’t receptive to it, or someone else wasn’t, you know, I was ready to propose that I could work remotely till you find my replacement or something, that was kind of going to be my concession. But thankfully, I didn’t have to come to that point.

Amy Scott 14:06
Yeah. So that’s good. Did you propose to them what it would look like in terms of your availability and your schedule, and all those kinds of things? Or did they tell you what that needed to look like?

Mollie Conway 14:29
So it was a little bit of both. I think since I was semi remote, you know, doing that one week a month schedule, I’d kind of set a precedent, we together kind of set a precedent for what was expected of me. Like I said, not many people have a similar situation as me so I really kept myself to a high standard as far as trying to stay as consistent with the team hours and schedules as I possibly could. So I think it was kind of expected that I would do the same. I’m just an hour behind the corporate office, which, you know, is hardly anything. But when I was traveling on the West Coast and stuff like that, I was actually keeping East Coast time and like, really just trying to keep it as normal as possible. I don’t think everyone needs to do that. I think it was more just a way for me to kind of feel more comfortable. Like I said, it’s kind of breaking the mold, in a sense. So I think that was my way of trying to stay as much within the mold as possible. So I think that was just the assumed expectation when I wanted to transition to being full-time remote that I would keep kind of that same schedule.

Amy Scott 15:54
Got it. Yeah. Okay, so I’m curious about how that all plays out. So when you’re in Nashville, do you spend quite a bit of time in that field office?

Mollie Conway 16:06
Uh, yeah, I actually was kind of surprised. I thought I would just, you know, as a nomad who kind of likes that flexibility, I thought I would just prefer to work from home, and then every now and then go into the office. But it’s really been a great experience, and just such a change of pace from the corporate office that I was used to, that I’ve really just enjoyed going in there. So I definitely, when I’m here, I’d say 90% of the time I’m at that office. And being in such like an unpredictable situation in general, having that stability is kind of nice, you know, I have a desk there, and those type of like, mental cues are really helpful, especially if I come back from being on the road or something. It’s really kind of nice to just have a week or so to get back into a quote, unquote, normal environment.

Amy Scott 17:07
Mm hmm. Yeah, it sounds like it’s kind of the best of both worlds. It’s almost like a coworking space for you, but happens to be related to the company you work for. That’s nice. So you talked about how there’s lots of variables and unpredictability and stuff. Tell us a little bit more about how this pro baseball scene factors in in terms of not being able to make decisions far ahead, and all that kind of stuff. So you said he’s still playing minor league, which is kind of the paying the dues you were talking about to work your way up to a major league team?

Mollie Conway 17:56
Yeah.

Amy Scott 17:57
So where’s his team based? Are they in Nashville?

Mollie Conway 17:59
No. So it’s, I have to describe this like, you know, several times a day, usually, because it’s such a confusing thing. But basically what happens is, so a player gets drafted by a major league team. So Josh was drafted by the Chicago Cubs; he’s in their system. So once you’re drafted, they assign you to one of their minor league teams. So each major league team has probably like four or five different teams, and they kind of ladder up.

Amy Scott 18:38
And they’re all over the country, like not related to Chicago?

Mollie Conway 18:41
Correct. So and those teams can change, you know, different minor league teams will change affiliation in the offseason. So that’s kind of how the minor league system works and you kind of work your way up the ladder until it kind of feeds into the major league team. So this past season, Josh was playing for the Cubs Minor League affiliate in Myrtle Beach, South Carolina. So he actually was there the entire season. But what often happens in the minor leagues is you’ll make moves both up and down several times throughout the season. So for example, the team below Myrtle Beach is in South Bend, Indiana, so a player could be in South Bend one day, the next week they’ll be in Myrtle Beach kind of giving him a promotion to the level up, but maybe that player doesn’t perform well and they’ll move him back down to South Bend. So as a spouse and for the player there are a lot of variables, and you never really know what the next day holds. So the season before Josh was in Boise, Idaho, so I spent time there. There’s just, you really never know and like I said the minor league teams will change affiliation, meaning the South Carolina team in Myrtle Beach, the year before they were I think a Rangers affiliate.

Amy Scott 20:11
So he never would’ve played there.

Mollie Conway 20:13
Yeah, right, exactly. So once they changed to a Cubs affiliate, that’s why Josh was there. So that’s kind of the unpredictable-ness. In addition to, you know, at any time a player can be traded to another team, the Cubs could trade him to the Blue Jays or something like that. And that would put him into a whole different system of minor league teams. So that just adds to the level of not really knowing what the next day holds some seasons. Like I said, this past season we were kind of ready for it to be very unstable, and it ended up being very status quo, which was, which was nice for me, but you kind of just have to be ready for anything.

Amy Scott 21:01
Right, yeah, it sounds like it. And so even when he was based in Myrtle Beach for the whole season, was there still like traveling to away games and that kind of thing?

Mollie Conway 21:11
Yeah. So, you know, each team is kind of within its own league. The league that they played in, the Myrtle Beach team played in, they were traveling to Virginia, Maryland, North Carolina, and it’s all by bus, which is just an added bonus for them I’m sure. So yeah, it’s just like I said, it truly is paying your dues for sure. And you know, very different from the perception I think most people have of what that life is like.

Amy Scott 21:43
Yeah, exactly. So okay, and this is fascinating to me, so I’m thinking, not only am I learning a lot about the baseball scene, situation, but also you know, thinking about how this is for you, and other spouses. So when he’s in Myrtle Beach, for example, how much were you there? Where do you stay, you know, all that kind of stuff? Did you travel to games, etc.?

Mollie Conway 22:11
Yeah. So it differs, each team kind of has its own setup. He was able to, and it’s, as I’m describing this, I’m realizing like, Josh should really be on this because he’s like, the super nomad, but he actually knew someone who lived full time in Myrtle Beach, so he was staying with them, which made things really nice, I was able to just stay there while I was in Myrtle. I was also traveling, I was spending time in Maryland when he was playing there. We’re both from Maryland originally so that was really nice. But a lot of the players were, you know, living three guys to an apartment sleeping on air mattresses, kind of with the expectation that things can change, and you can move around a lot, people are hesitant to really have anything super long term in nature. So this past season, I was spending, I’d say, probably like two weeks with him, either in Myrtle or at another, mostly Maryland, just the way the season turned out. And then I also have to have time to travel back to Florida where my company’s headquarters is, and there’s some travel with that as well. And then I would come back to home base in Nashville, and like wash my clothes and decompress a little bit, and then pick up and start the whole cycle again.

Amy Scott 23:48
Wow, that’s amazing. And so how do you handle trying to keep some kind of regular hours for work in the middle of all of that? It seems like it must be hard to make the two work together.

Mollie Conway 24:04
Yeah, it is. And I think there’s definitely people who wouldn’t be able to make it work. I think it’s definitely a mindset. I think I’m well suited, just in terms of I’m able to kind of set mental boundaries for myself, I’m not someone that necessarily needs boundaries set for me. But, oddly enough, I think keeping that strict schedule with my team, while it was definitely inconvenient sometimes, it meant waking up at 5am when I was in Boise or whatever it was, that really helped just keep things clear for me, I guess. Like for example, my computer, my work computer, I’ve never changed it from East Coast time. It’s always set to East Coast time and hasn’t ever been changed and that just helps me kind of stay oriented, oriented around what my team is doing, and kind of what it would be like if I was in an office, even if I’m working from like a host family’s kitchen counter, in what would be an uncomfortable situation, keeping that I think like mental boundary helps. And, you know, just working, trying my hardest to keep things as normal as possible from a work perspective, taking a conference call from a closet so that it’s quiet. And I don’t have to be the person with the dog barking in the background, just little things like that. I definitely have put the bulk of the responsibility on myself, but I think for some reason or other it helps keep me kind of grounded and feeling like, even if the situation around me is very odd and unpredictable, and most people can’t relate, feeling just very normal.

Amy Scott 26:04
Yeah, actually, that’s come up in other conversations I’ve had for the podcast. I think this is true, whether you work for yourself or you work for somebody else, whatever the situation is, if you’re moving around a lot, I think there’s really some value in making your lifestyle and your location as irrelevant as possible. And that really sounds like what you’re describing, you know, to be able to show up for work in the same way no matter where you are, and no matter what the situation is, to the extent humanly possible. You don’t want to drive yourself crazy either trying to fit it all in. But the other thing, too, I was just thinking is that, I wonder if there’s some difference there, either in mindset for you, or for the people around you. Because you still have a regular job, versus working for yourself. I think some of us who work for ourselves, people around us are like, Oh, you don’t have to work today or your schedule’s really flexible or there’s not necessarily that respect for like, No, I gotta sit down and work all day today, believe it or not. Whereas if you’ve got a boss who is expecting that of you, it kind of shifts the dynamic there.

Mollie Conway 27:32
Yeah, and there’s definitely been times, whether it’s like Wi-Fi cutting out, or sometimes just even my cell reception, going in and out while I’m on with my boss, times where you’re like, the pressure is on and I’m feeling really frazzled, because it’s kind of like I’m trying to, like you said, I’m still working for a traditional kind of company, and in a traditional type of role, so there’s a lot of pressure at the same time to kind of maintain that. And being one of the only people in a company that does this, even more so I always like I really want to be at the top of my game. It always annoys me, people in my company might kind of like abuse the whole work from home, quote, unquote, work from home situation. And it’s like, they’re working from home. But yeah, all your email responses are coming from your cell phone, it’s like, are you really working from home? Sometimes that’s frustrating, because I’m over here, kind of like busting my ass up at 5am on the West Coast, and really trying everything I can to accommodate my coworkers. And then some people kind of abuse that flexibility.

Amy Scott 28:56
Yeah, totally. I know. And that is tricky, because that’s the kind of stuff that gives working at home a bad reputation, right? People are like, well, I don’t know, if you’re out of our sight, how do we know you’re actually getting anything done? But then at the same time, I know there are studies that have shown that for some people, not having those distractions and being on your own actually makes you much more productive.

Mollie Conway 29:22
Oh, absolutely. I’m the biggest believer in that. I was just in Florida, four days at my company’s headquarters, and every time I go there, it’s like I’m just so looking forward to coming back and being remote again because I can actually get work done. And for better or worse, I think working remotely and as a nomad, you get used to being autonomous and being able to really, you know, work in peace in that way, so I think I’m now more susceptible to distraction in the office, just because I’m not used to being surrounded by people who, you know, want to talk about whatever it is, or go down and get lunch together, go get a coffee together, whatever, all those kinds of workplace distractions that you really don’t even notice when you’re used to working in an office, but all of a sudden, when you’re used to just being you and your laptop and your cell phone, it can be really distracting. So I am totally much more productive working remotely, even if it’s on the couch of someone that I just met, I’m way more protective than when I’m in the office and kind of in the open work environment with, you know, all these cubicles and all of that. So, yeah.

Amy Scott 30:51
And because you’re on your own, I’m curious, I’m thinking about people I know who have like distributed teams and whatever. And there’s all these fancy services and software and stuff you can use these days for internal chat and things like that. And so I’m curious, because you’re one of the few who’s doing this, or maybe the only one, did you have to set up any other kinds of systems to stay in touch with people in the office? Or how do you make that stuff work?

Mollie Conway 31:28
Yeah, so I mean, we definitely don’t, I think, have all of the resources we could. Like you said, being one of the only people doing this, the company definitely isn’t investing in any large-scale implementation of a software or anything like that, so I’ve kind of adapted to the tools that we have. So we have, you know, internal chat through Microsoft Lync, which is really kind of like my lifeblood to the team, just being able to instant message with them for like, quick one-off requests and things like that. And they’ve kind of learned what it looks like, as well. So they know that if I’m pinging them or emailing them, they need to pay attention because that’s my main way of communicating with them. Obviously I call people if I need to, but that IM feature definitely helps me stay in touch. We also have a platform, enterprise social network chapter, which is a Salesforce platform, which also kind of helps me stay connected to what’s happening around the company. So that that’s been nice. But yeah, there’s tons of really awesome software now that just through my research I found, but I’ve just kind of had to make do with what’s available. I FaceTime with them during meetings and stuff like that, so, you know, sometimes it’s not the best way, but just doing what I can to use what’s available.

Amy Scott 33:18
Yeah, that makes sense. I wanted to also just hear a little bit more about the logistics of traveling around like this. And, you know, how do you plan to the extent that you can, you know, like accommodations and flights and who pays for all of that. And especially when that stuff is short notice, it can be pricey, right?

Mollie Conway 33:59
Yeah, yeah, it’s, I mean, I try to plan in advance as best I can, but there’s always kind of that looming threat. I’ve definitely heard stories of like a family will book a flight to come visit their son who’s playing and then like the day before they get sent to a different, you know, get moved up a level or something like that, and the whole family has to cancel their entire trip. You kind of just have to be prepared that that could happen and deal with it if it does, but I’ve never had that situation, thankfully. As you’re talking about when you think about booking a trip and flight considerations and hotel considerations, I also have to factor in a baseball schedule. So what might be a great span of time for me to go visit Josh, he might be playing at like three different teams, and there’s like a bus ride involved or whatever there is. So I also kind of have to always keep in mind, okay, well, what’s Josh’s team going to be doing? Are they going to be home, you know, in a homestand, at this point, are they going to be away on an away game, you know, one week traveling to different teams. So that adds so much complexity as well. And there’s no science to it at all, it’s just crossing your fingers and hoping you can find the perfect intersection of, you know, good priced, well priced flight with the team being home for an extended period of time, with also whatever work considerations need to go into it as well. So it’s definitely frustrating, but I try to just plan in advance as best I can.

Amy Scott 36:03
And so you mentioned a little bit about how it sounds like your work does provide a sense of stability in that way. And I’m curious, you know, what else? Well, one, do you feel like you need to have more of a sense of stability? And if so, how do you get that?

Mollie Conway 36:21
Yeah, I think, you know, even just for both of us as a couple, my work is a sense of stability, just in the sense that for me, Josh’s career doesn’t provide that, and even for him, you know, he’s the one sleeping on a bus floor driving in the middle of the night to a different team. So there’s a lot of lack of stability just in his own world as well. So having a full-time permanent job with a brick-and-mortar company, I think just that mental stability is helpful for both of us. And keeping home base has been huge. So when I was living in Florida, like I said, I was living with family. So even that I was kind of nomadic to an extent. And he was primarily in Arizona. So during that time, just the fact that we didn’t really have a home base, I was bouncing back and forth, taking vacation days, or taking that week remote, I was doing that for about a year and a half, and it was just very mentally and emotionally draining not having that home base. So, for us, actually having an apartment in Nashville where we have things and a couch and just very basic things has just been huge for us even though he isn’t here six months out of the year, but I think even for him to know that it’s here is reassuring. Yeah. It’s kind of interesting how that works. But that’s been a big force in just helping us feel a little more grounded, even if things are very up in the air.

Amy Scott 38:17
Yeah, that makes sense. So then, for you during the season, how much time do you spend in Nashville versus elsewhere?

Mollie Conway 38:25
Um, it kind of depends, and it’s very fluid. But I would say probably about two weeks, not straight, but total, probably two, two and a half weeks. It just kind of depended this season on the schedule and all of that. But yeah, I would say that’s kind of the average, usually, like at least one week would be with Josh, about one week would be back in Florida with my company. But, yeah, it just kind of depends.

Amy Scott 39:12
Sure, that makes sense.

Mollie Conway 39:14
And there’ll be a whole different story this season. It’s kind of like each season has its own story in and of itself. So we’ll just have to see what cards are dealt to us this coming season and adjust from there.

Amy Scott 39:28
Right and so how far in advance? I mean, it sounds like it’s changing all the time. How far in advance will he know at least where he’s starting? For now?

Mollie Conway 39:36
Um, yeah, so that happens in spring training. So he’ll leave for spring training, the Cubs have that in Arizona. So he’ll leave at the end, last year he left at the end of February. So assuming that’s the same this year, but it could change. So he’ll have his assignment I believe it’s usually at the end of April.

Amy Scott 40:00
Got it.

Mollie Conway 40:01
So they train basically March and April, in spring training, and then they’ll give him his assignment.

Amy Scott 40:11
Got it. I forgot about the fact that this is only half the year. So that sounds like a good thing. This isn’t like all year, year in year out. That sounds like it’d be really intense. So then what is the transition like? So you’ve kind of just been through this, right, of like the season ending, coming back to Nashville, and getting a little bit more rooted? And what was that transition like? Especially because Nashville is still kind of new, I guess, right?

Mollie Conway 40:46
Yeah. Yeah. Everyone kind of expects, like, when Josh comes home, like, Oh, what are your big plans, and because we’re so transient throughout the year, in the offseason, it’s just so nice to be like, totally homebodies. I think we’re like, to some people, we’re still not at all homebodies. But for us like to just have some regularity. You know, it’s like I work from Monday through Friday. And we have the weekends to enjoy off. And just all of that normal life stuff is so nice for us. And like you said, Nashville is still new. So there’s a lot of exploring as far as that goes. And of course, I’m still traveling about every month or month and a half back to Florida. So there is still a little bit of travel for me, but not nearly as much. So it doesn’t take long, I think, to try and get back into the swing of things. It’s definitely kind of like the exhale of the year when the season is over. It’s like, okay, regroup, establish some sense of normalcy. And of course, once that is really set in stone that’s about the time that he’s leaving again, but I think, again, it’s just like this idea of having a home base is such a great thing for us.

Amy Scott 42:17
Yeah, yeah, absolutely. And then will you go to Arizona during part of that time he’s in spring training?

Mollie Conway 42:24
Yeah, I usually am there for spring training, just kind of depending on how things look, but I’ll definitely be out there for some part of that. I think some players end up making, wherever their spring training is, they kind of end up making that a home base. But, yes, I’ll be out there at some point.

Amy Scott 42:53
Yeah, got it. So what would you say is the best thing about having your new lifestyle in terms of working remotely, and all of that.

Mollie Conway 43:10
I think there’s a part of it, and I’m sure other nomads would agree, there’s part of it that is just so empowering. Sometimes I kind of sit back and I’m like, wow, I’m making this work, you know? While it’s normal for me, I sometimes reflect and realize that not everyone could continue to succeed in this type of situation. And, I’ve continued to be successful at work and everything as far as that goes. So I think just the sense of empowerment that I get, it’s very liberating, it kind of just makes you feel like you can make anything work, which just personally has given me a lot of confidence. And, of course, the ability for me to continue to pursue my career while also participating in this crazy once-in-a-lifetime chance that Josh is getting. As important as things like paying the bills and all of that is, I still want to be able to participate in and experience what he’s going through, because not many people do. So working remotely allows me to have kind of both. There’s definitely times where, you know, they’re not perfectly in balance, and I’m not always 100% succeeding in both aspects, of course, but just the option to not have to choose, I think is huge.

Amy Scott 44:52
Yeah, totally. And I imagine also, it’s satisfying to feel like you have control over some aspects of your life, when it sounds like there’s a lot you don’t have control over.

Mollie Conway 45:03
Right, exactly, yeah. And that’s kind of just one less worry. Like, there’s always considerations for work when traveling, it’s not like I can just pick up and go and everything’s fine. But it’s definitely something I don’t really need to stress over when the situation itself might be stressful.

Amy Scott 45:26
Yeah, absolutely. That’s awesome. And we’ve talked a little bit about some of the challenges already, but what else would you say is the challenge of the lifestyle for you?

Mollie Conway 45:38
Um, one realization that I had, and I think it was an aspect of continuing a job I had in person, is that networking doesn’t come as easy working remotely. I think people are very aware of that when they’re kind of starting out new in a city or working consulting jobs or trying to freelance and it’s very much about building a network. But for me, I didn’t really have to do that initially because I was keeping my same job. And there’s this field office, and as far as networking goes there wasn’t much that was really critical to me being successful. But realizing that I have to work harder to do that than someone, you know, in a typical working situation does.

Amy Scott 46:36
Do you mean more professionally or socially?

Mollie Conway 46:39
Um both, I’m speaking more on the professional side, though, just building your network and making those professional connections is so important to lots of things. And I think that’s the biggest challenge, especially when, in the season, I’m not in Nashville much, so it’s hard to really build those connections. So I think just working harder at that, and realizing that it’s not a given that you’re going to make, you know, professional connections when you’re in a remote situation. So that was definitely a learning for me. And, like I said, I think that’s a little more apparent and obvious to someone who’s trying to build a network of freelancing clients. But for me, it wasn’t critical to my job, so definitely something I kind of learned along the way.

Amy Scott 47:34
Yeah, that’s interesting. I’m curious about some of the logistics in terms of how you have set up like renting an apartment and bills and cell phone and all that stuff. Do you pretty much handle all of that the way you would if you were there 100% of the time?

Mollie Conway 47:59
Yeah. That’s definitely a judgment call you have to make. We did renew the lease kind of on a yearly basis, we chose to do that, but initially we did a short-term lease just to make sure it was what we wanted to do. But we feel as confident as we can that we’ll maintain a home base here for the foreseeable future, so at least like through next season, into the offseason, so that’s helped a bit. If things keep kind of progressing with Josh’s career, we’re probably not going to do that. You just kind of have to see, but yeah, as far as bills and everything goes, because I’m coming back here frequently, I’m able to maintain all that, which is nice.

Amy Scott 49:00
Yeah. And it sounds like it’s way too unpredictable for you to be like renting out your place while you’re gone or anything like that.

Mollie Conway 49:09
Yeah. And that’s something that’s on the table for future seasons, but just a little bit too much up in the air. We’ll see.

Amy Scott 49:24
Yeah, so what’s, what’s kind of the next step? And if things go well for him, what would kind of the next phase of this look like?

Mollie Conway 49:36
So we’re hoping he continues to progress up the ladder, so to speak, you know, next season and the season after that. I think as he would get closer to like that big league level we might kind of reevaluate things, again, like I said, this is such a once-in-a-lifetime opportunity that I can see there coming a time where maybe I want to transition into like freelancing full time as opposed to being tied down to traditional work, or as much of a traditional work situation as it can be. I can kind of see it progressing that way, if I just kind of want more flexibility to really experience this whole thing with him a bit more as he’s getting, you know, hopefully to that big league level. We just kind of wait and see, and cross our fingers and all of that, and just hope that the season goes well, and he stays healthy and all of that fun stuff. The team above, the level up from Myrtle Beach is in Knoxville actually. So that would be very conducive to having a home base in Nashville. But like I said, it can kind of always change.

Amy Scott 51:11
Right, that might not be the case by next year.

Mollie Conway 51:14
Exactly.

Amy Scott 51:14
Geez that’s crazy.

Mollie Conway 51:16
Yeah, yeah, it really forces you to live in the moment, which, as we all know, is a great thing. So sometimes I wish I could be a little bit living in the future. But we definitely don’t take anything for granted. Which is a good mindset to have in general.

Amy Scott 51:36
Yeah, that’s good. And so what tips would you have for somebody who was thinking about working remotely, or who is doing it, or about to start doing it?

Mollie Conway 51:51
If they’re in a position where they’re pitching it to a traditional employer, not really thinking about going out on their own, just trying to find some benefit to the business or to your team. I think I was kind of lucky in the sense that I was moving to a place where there’s a field office, which made it a bit more simple for me to kind of show that benefit for them. But trying to find any benefit you can, whether it’s having someone in a different time zone, or having intel on a key market, or just something that can show that, aside from the benefit it’ll have for you personally, there’s also some type of benefit to the team. Having something to set boundaries for yourself, whatever it is. For me, it’s keeping East Coast hours, no matter where I am in the country. Like I said, I wouldn’t really recommend that. It works for me. But finding something that gives you a sense of boundaries and stability is key in the way that you work. And just pushing yourself to build your network as much as you can, both personally and professionally.

Amy Scott 53:43
I wanted to ask a little bit more about what you’re saying about boundaries. I guess there’s a couple different aspects of that, right. It sounds like there’s kind of boundaries for yourself personally, and then related to work. And then also related to, in your situation, like the people around you.

Mollie Conway 54:08
Right. Yeah, I think there’s a lot of ways you can set those boundaries for yourself. And like you said, it can be kind of for the people around you. Personally, I think one key thing is, when you’re working remotely, there’s a lot of ability to mix personal and professional, like for me when I was traveling to Maryland, like I said, we’re both from there. And so we have family there, which was great because I could spend time with my family while I was working. But you really, that’s a really slippery slope. Just I find that mentally it can be a struggle when you’re trying to kind of combine both a bit too much. I find that for me personally I kind of have to draw a line where, okay, you know, I can have lunch with a friend or family, or maybe, you know, go do something over my lunch hour that isn’t work related. But I really need to set a clear kind of timeframe for myself when I need to shift back into work mode. Because I find just mentally, when I’m kind of going back and forth too much, it’s just stressful. You wouldn’t think that it would be, but always trying to shift gears can get a bit exhausting. So that’s a learning I’ve definitely had is just setting boundaries for how much I’m willing to make a trip both personal and professional or work and play. If you don’t have that kind of mental ability to draw those lines for yourself, it can kind of get out of control in a way.

Amy Scott 56:03
Mm hmm. Right. And also, when people around you think that you’re on vacation, right, to set some expectations with them as well, yeah.

Mollie Conway 56:11
Yep, definitely. Communicating those boundaries to the people around you is also important to get using that slippery slope term again, if you don’t upfront make it clear to family or friends, or your spouse, what is and isn’t possible for you in a remote situation, I think it can get really stretched. There’s definitely days like if I’m working before a holiday I’ll communicate, like, for example, I’m working, you know, the day before US Thanksgiving this year, and I’ll communicate that I need to just kind of be around, I’m not necessarily putting in hard hours, I’m just kind of on call if someone needs me. I’ll communicate that to my family so they understand kind of where I’m at. Sometimes that isn’t fun, but just explaining what your schedule looks like ahead of time: I’m on a conference call these hours, I’m meeting with my boss at this time, just being upfront with those around you to kind of educate them that being accountable for your work responsibilities is still important, even if you’re not, in a suit in an office.

Amy Scott 57:37
Yeah, exactly. The other thing that came to mind while you were talking about this is vacation. I assume because it’s a regular job that there’s some vacation time tied into that. And so, given your situation, I’m curious how you decide when you’re actually not working, and you’re going to take vacation time.

Mollie Conway 57:57
Right. And that’s something that was also a surprising struggle for me. I found myself feeling really reluctant to take time off, almost, I can’t necessarily put words to it, but just feeling like, well, they let me work remotely, so I’ll kind of be the sacrificial lamb that works the day after Thanksgiving or whatever it is. I found just kind of naturally I was taking that position. And I’ve had to remind myself not to do that so much, and even though I can have freedom to travel, and I’m not tied to an office like my coworkers, taking that R&R time is just as important. So I tend to just kind of take days here and there as opposed to long trips, because like I said, Josh and I tend not to really travel as extensively in the offseason, because we’re traveling so much during the season. But, you know, if I can kind of include a family visit in a trip to see Josh play or something like that, then I’ll definitely try and take days then. Yeah, it gets kind of tricky. And that’s not something I anticipated. Having to kind of push myself to take more time off. But I think it’s very common for people who work remotely, that kind of goes hand in hand with that thing of not having normal working hours. So you end up just working all of the time. You know, you hear that reflection a lot from people who work from home, even if it’s not in a nomad situation, but finding yourself working at 9 pm just because you never left the office so to speak. I think it’s kind of the same principle, so that’s something I definitely want to do a better job of because you can have just as much burnout I think from working remotely as you can in an office.

Amy Scott 1:00:07
Yeah, absolutely. I definitely can speak to that one, the kind of never leaving the office, so to speak, that’s definitely a challenge whether you work for yourself or you work for someone else. And also, the vacation thing is surprisingly difficult. I think, especially when you’re traveling, it feels like, oh, well, I’m traveling all the time, and maybe I’m not working the same hours, or I’m not working a full workday or whatever. So I don’t need any time off, or I really like my work or whatever it is. But even if all of those things are true, it still feels really different when you actually make the decision and make a commitment, like, I’m not logging on today, or I’m not available, or I’m not in the office, whatever that means. Yeah.

Mollie Conway 1:00:59
Yeah. And I’m lucky, my team is really supportive as far as that goes, you know, like people taking vacation and truly taking vacation, not answering emails and all that. Our team definitely encourages that. It’s hard just for me personally feeling like, like you said, when you’re traveling all the time and working, you don’t have as much of a sense of like, oh, I need to travel to, you know, have a break from work or something like that. You’re kind of like, well, anywhere I travel, I can work. So yeah, you kind of have to look at that through a different lens. Yeah. Shifting into that type of lifestyle for sure.

Amy Scott 1:01:42
Yeah. And it can be as much needing to take a break from traveling as from work. Right. Sounds like you get the opportunity to do some of that in the offseason, which is good. Well, thank you so much for joining me, this has been fascinating to talk about, you know, a whole, it’s kind of a window into a different way to live the lifestyle. And I’m really glad to have you join me today. So thank you.

Mollie Conway 1:02:09
Of course, thank you so much. Nomadtopia was one of the first resources I really utilized when making the transition. So it’s great to be a part of it.

Amy Scott 1:02:19
Awesome. That’s great to hear. And so before we wrap up, why don’t you go ahead and tell everyone where they can find you online?

Mollie Conway 1:02:27
Sure. So you can find me on Medium. It’s molliecon, @molliecon on Medium, I have a couple posts up there. And I’m looking to build that out a bit more as I kind of tell my story. And you can also find me on Twitter, @mollie_con.

Amy Scott 1:02:44
Excellent. All right. Well, thanks again for joining me, Mollie. And thanks, everybody for listening, and we’ll see you on the road.