Ep 05: Solo Work Trips: Confidence, Connection & Advocating for Yourself, with Jenn

Jenn (00:00)
Don’t stay in your hotel room the whole rest of the time. Like force yourself to go to the hotel lobby or to a coffee shop that’s nearby, have lunch outside somewhere.

Just being around other people, you’re never gonna meet someone new or have a new experience if you’re not pushing yourself to do it.

Kelli Wall (00:18)
Welcome to Solo Travel Unpacked, where we explore the world one solo travel story at a time.

I’m your host Kelli and I believe that solo travel.

is a journey of self-discovery, empowerment, and connection.

Each episode, we’ll meet a different solo traveler and hear their insights, experiences, and lessons learned.

also take a look at a key solo travel topic

to give you the tools and inspiration for your own adventure.

It’s time to hear from today’s guest and unpack another solo travel story.

Kelli Wall (00:47)
Solo travel isn’t just about adventure. It can also be a powerful tool for building confidence and making meaningful connections.

My guest today, Jenn, knows this firsthand.

For more than 15 years, she’s traveled solo for work.

attending conferences and high-level meetings with C-suite executives and financial services.

Business travel is a major part of professional life. In the United States, more than 1.3 million people travel for business each day.

as the Director of Strategic Partnerships at a fintech company.

She’s mastered the art of networking and making an impact.

Beyond Business, Jenn solo travels for work, have also taught her how to advocate for herself.

whether managing type 1 diabetes on the road or striking up conversations with strangers.

In this episode, she shares insights on turning any solo trip.

into an opportunity for connection, growth, and confidence.

Now let’s dive in.

Kelli Wall (01:41)
Jenn, I’m so excited to have you on the podcast. You’ve been traveling solo for work for more than 15 years, navigating everything from conferences to high-stake meetings with execs. But beyond the professional side, solo travel for work has also shaped your confidence in unexpected ways.

Before we dive into today’s topic on networking and making connections, let’s start with a quick intro. So, hey Jenn, do you mind telling us a little bit about yourself outside of work?

Jenn (02:07)
Yeah, absolutely. And thank you, Kelli, so much for having me. I love the whole concept of this podcast. think that reaching people who are traveling solo, whether it’s for work or personal life, is something that if you’re not already doing it, I hope that you are reaching a whole new audience and inspiring people to do the same, because I know how much you love it. I know how much I love it. So it really is a cool experience.

But a little bit about myself aside from my work life where I love to travel and meet new people. I would say the things

I’m most passionate about are obviously spending lots of fun times with my friends like yourself and my family. I have a mild obsession with everything cat related.

Kelli Wall (02:49)
same.

Jenn (02:50)
So anytime I can, whether it’s cuddling up on the couch with my cat or meeting new kitties out in the world, that’s something that I really enjoy doing.

am really involved with Breakthrough T1D, which is a nonprofit for type 1 diabetes, as you had mentioned in my intro. It’s something that I’ve been living with for most of my life, over 40 years now. So anytime I can be a resource for newly diagnosed people or just help with fundraising efforts so that type 1 diabetes is no longer a thing or at least…

more easily managed. That’s something that I’m obviously have a pretty close tie to. So I want to help, help with those efforts. but I like to active. love to play sports and, keep with a workout routine. We can talk a little bit more about that and in the podcast too, and how you keep up with that when you’re on the road and maybe not in the studio that you’re used to going to and so on and so forth, but staying active and, and keeping up with,

Kelli Wall (03:28)
amazing.

Jenn (03:46)
My exercise routine is something that’s important to me too.

Kelli Wall (03:49)
And you just got married recently, right?

Jenn (03:52)
I did. Yes. November, early November in Key Largo was an incredibly ridiculously fun time.

Kelli Wall (04:01)
amazing. Well, congratulations and and thank you certainly for all the work you’re doing for type 1 diabetes That’s that’s really special to put that effort back into the community. So that’s that’s amazing. You do that. Yeah, awesome Yeah, that’s all right, that’s all right. I love it. Well, thank you so much Jenn So we will just jump right in here and as you mentioned in your intro You’ve been traveling for work for more than 15 years. So if we can just rewind and look back a little bit

Jenn (04:11)
Thanks. A little saltive cause, but…

Kelli Wall (04:27)
Do you remember that first solo work trip? Maybe what you were feeling and what that was like?

Jenn (04:32)
I don’t know if I remember the first one. I think I can remember just generally speaking. started, well, right out of

and through college, I was working for my family’s insurance agency. So I didn’t do a lot of travel with that job specifically. There were a couple classes I attended, but I was either with my family members who worked at the agency or somebody else.

When I started in financial services, I was a project manager and we would travel for that here and there. So yeah, was, I think for me, and specifically with that role, you’re the project manager, right? So the buck stops with you. having the, from everything from your physical appearance to just having, you know.

Kelli Wall (05:07)
Mm-hmm.

Jenn (05:14)
your shit together, knowing what needs to happen and when and

responsible. it’s a lot on top of then, you know, making sure you pack all the right things. just, the simple things that you need when you travel, right? Do you, what hotel are you staying at? How are you getting from the airport to the hotel? What time do need to be? How far away is that to the credit union you’re visiting or whatever it is. just, you know, a lot of logistics that we’re involved with it.

And those were wild times too. mean, wasn’t that, it doesn’t seem like that long ago, even though it kind of was. But back in those days, like we had to wear like business formal. So we were dressing in skirt suits and which is crazy because we were literally out at ATM terminals, like with technicians, know, like beep boop boop like programming machines. But yeah, so it was just an interesting time. then.

Kelli Wall (05:57)
Yeah.

Jenn (06:02)
At the end of the day when the work was done, would go explore, you know, whatever new city we were in and find restaurants and bars and cut loose a little bit. And so it was a lot of fun.

Kelli Wall (06:15)
Yeah. And shout out to all the project managers out there. Like Jenn, I am one as well. So I know we both know the work and effort that it takes that you guys put in to pull those together. So thank you. So Jenn, I know you personally outside of this. So I know your ability to connect with people is top tier. So how has your solo travel through work, whether for business or any personal trips that you’ve taken, really shaped your ability to network and connect with people?

Jenn (06:18)
No.

Mm-hmm.

Yeah, I think whether it’s business or personal travel, my motivation always remains the same, which is I just want to learn about this person. It’s not, I want to get this deal done or I want

try and get something free from the service. It’s just…

Hey, tell me about yourself. Like, what are you about? And, and especially in a business setting, if it’s something like a dinner or some kind of like forced interaction, my mindset going into that is always like, I, if I have to be here, by God, I’m going to find something interesting about this person sitting across the table for me. And we are going to enjoy our time together. And it’s never ceases to amaze me. Some of the like just fascinating things I’ve learned about people and the deeply personal stories that they

Kelli Wall (07:02)
Mm-hmm.

Yeah, yeah.

Jenn (07:28)
share that

out of that. And it’s all from that same just mindset of like, we’re going to find something interesting. Like, let’s do this. That person knows it or not, or how completely opposite they may be for me like on paper. It’s

Kelli Wall (07:35)
Yeah. Yeah.

Jenn (07:42)
that that’s how I approach it every time.

Kelli Wall (07:45)
Yeah,

absolutely. And you make such a good point is understanding kind of what makes people tick. And you don’t know that, right? You have to ask and dive deeper and really truly want to get to know them. So I think that’s something special that can’t be taught. And it looks like clearly you’ve mastered that. you talk about the different type of people that you meet with. And in your intro, we spoke about how you meet with C-suite execs. so for those of you that might not be in the business world, those are our chief operating officer, our chief marketing.

office or anything with a C in front of their name is referred to C-suite execs. So when you’re in front of these different crowds of these execs, how do you present yourself as self-sufficient and impactful in those settings in front of that crowd?

Jenn (08:26)
Yeah, so first and foremost, doing

research. this is the first time you’re sitting down with this person or somebody from…

you know, that company, whether it’s a prospect or somebody that you’re currently doing business with, just knowing who you’re talking to, knowing some of the things that I like to say, like within their worry circle, right? So read up on, on their, if it’s a public company, read up on their quarterly earnings reports, just do, do your due diligence. ⁓ but then again, aside from that, from a personal level, like who is this person? Like we’re all traveling, we’re away from our families that people have things they are passionate about outside

Kelli Wall (08:53)
Mm-hmm.

Jenn (09:04)
of just what they do at a company. So I will know in the back of my mind what I need to know from a professional perspective.

Or I will have questions that I want to find the answers to throughout that conversation. I’m not necessarily starting there jumping right into that. It’s a fluid dialogue. like, let’s start with something. Sports is usually a great place to start. I love sports. So let’s talk about it. you know, sometimes you find yourself in very interesting conversations just from that. Then that can ultimately lead to if from a business perspective, there are certain objectives you want to

Kelli Wall (09:32)
Yeah.

Jenn (09:37)
get accomplished, like getting those accomplished throughout the conversation, but it feels more natural that way versus, you know, this forced, all right, now tell me, our revenue goals are.

Kelli Wall (09:45)
Right, Yeah, absolutely. Yeah, do your homework.

Come in with your research. Yeah, that helps so much, right? Because as you said, you can cater the conversation to the person. So that’s super you’ve touched on this a little bit. So some people that might be listening in haven’t traveled solo yet for work, or maybe they’re a little bit new to it. So curious, how do you make that strong first impression? know, whether in a professional setting, when you’re at a meeting, or maybe you’re meeting up at the airport.

How do you really kind of dial that in and leave them with a good positive,

Jenn (10:16)
Yeah, I mean, it can be intimidating, Like I go, I attend a lot of conferences,

events where there are hundreds, sometimes thousands of people, and you’re in a room with, you know, for me, it’s a lot of bankers, it’s financial services, right? So I’m in a room with people who run financial institutions across the country or software companies that cater to financial institutions.

For me, it sounds kind of like a no-brainer, but just approaching a group of people, whether it’s like a cocktail hour or a dinner event, and literally asking them like, hey, do you mind if I crash your table here? If you’re just rolling solo, chances are they are too, and they’re just looking for other people to talk to. And nobody wants to go to these things and stand in the corner by themselves, but it can be awkward to approach a completely random group of strangers. But I’ve never had somebody saying,

Kelli Wall (10:53)
Mm-hmm.

Jenn (11:05)
know when I start that way, right? So, and it kind of gives them, I feel like the, you’re telling them like, I’m confident enough to come up to you. And it just breaks the ice and allows you to be able to talk to each other, you know, pretty easily from there.

Kelli Wall (11:06)
Yeah, yeah.

and it sounds like based on what we chatted about today that there might not be an instance you can reference here, but if you ever had a moment where maybe you’re just not having the best day, maybe you’re just not feeling your most comfortable self, where you’ve had to be fake some confidence, and if you did, how did that turn out?

Jenn (11:38)
So I like to describe myself as like an extroverted introvert, or maybe I’d reverse those. Either way, the point is I’m naturally an introvert, but I can turn it on if I need to, but it exhausts me, right? So if there’s a point, usually later in the, like if it’s a three or four day event, by day three, like I am just tired, I’m over it, but my work isn’t necessarily done, right? So I think that,

Again, getting to that main objective of like, just want to learn something new about this person or make a new contact. that can help, but then also making sure to set time for myself too. whether that’s hitting the gym, the fitness center at the hotel or, carving out time to go to the coffee shop and just work through my inbox that way. A lot of people will, you know, sit in the general conference hall and work on their email there, but that’s the

Kelli Wall (12:16)
Mm-hmm.

Jenn (12:32)
you’re lending yourself to more easily have interruptions and conversations that may just then, you know, add on to your exhaustion. So making sure you’re balancing what your needs are, whether that’s FaceTiming with a loved one at some point, getting that reset that you may need. For me, that’s really important and helps prevent some of that burnout.

Kelli Wall (12:54)
Yeah. And Jenn, you bring up such a great point that again, if maybe somebody hasn’t traveled solo for work before, or if they have It’s all day, right? Like you wake up, you go to the airport and if you’re meeting coworkers there, it’s starting there to all day at whatever conference meetings you might have, maybe having time to pop back up to change in your room and then right back out to dinner. So it really never stops. So that is such an amazing point that you bring up of finding that balance, you know, to take time for yourself.

to really kind of step back and reset, take a breather, have that moment. And I know in the beginning you talked about fitness and how important that was to you and whether you have a certain place that you go back home, but can you talk a little bit about how you incorporate that into your travel to make sure, one, you’re not just staying healthy for your physical self, but again, for your mental and emotional wellbeing.

Jenn (13:39)
Yeah, actually that’s one of

favorite things about traveling solo. If I have the time built into my whatever it is that I’m doing in that particular location, I love to go, so I love to do yoga for example. I will, and bar is another, love.

to do bar three. So I will ahead of time research yoga studios if there are bar three studios in the location. So it’s something familiar yet in a new setting and I will make time to go to those places, take those classes. One of my favorite things and it’s one of the best ways that I’ve also met people that in the cities I’m traveling to that is completely separate from work. It has nothing to do with that but it’s still just a really cool new experience even though there’s something a little familiar about it

Kelli Wall (14:25)
Yeah,

absolutely. That’s really thoughtful way of doing it versus people just thinking, I don’t want to go to the fitness center in the hotel and then I might see my boss. So look at those other places that you might be able to check out pending what city you’re in.

Jenn (14:37)
Yeah, and to add to, think.

The opposite is also true. So we talked about balancing the socialization with your own time too. But if you are a person who naturally seeks, you are more comfortable in an isolated environment. If you’re not there, you’re traveling for just one meeting,

Kelli Wall (14:48)
Yeah.

Jenn (14:57)
for example, Don’t stay in your hotel room the whole rest of the time. Like force yourself to go to the hotel lobby or to a coffee shop that’s nearby, have lunch outside somewhere.

Just being around other people, you’re never gonna meet someone new or have a new experience if you’re not pushing yourself to do it.

Kelli Wall (15:16)
Yeah.

Jenn (15:17)
the opposite can also be true.

Kelli Wall (15:20)
Absolutely. And again, meaningful connections, right? Like these are the opportunities when other people are around to really go up and introduce yourself to them. And I know you spoke about maybe if there’s other people around, you’re comfortable going up to the table, but can you play a little bit on that? all right, so you’ve gone down to the hotel lobby, you’ve gone on a walk, you see somebody else for the conference where it’s more just one-on-one. How would you maybe going up to that person and striking up a conversation?

Jenn (15:45)
the same way. mean, if it’s somebody that I

I would, you know, maybe have like a planted question or something like, hey, do you know what time the general session starts or something like that. Just have to having to do or hey, did you, this is what I’ll do a lot of times because I work.

Kelli Wall (15:54)
Yeah.

Jenn (16:00)
A lot of my conferences, I’m actually manning an exhibit booth. So I’m constantly in one-on-one conversations with either people I know or have seen before or completely new people too. So yeah, just asking them about, hey, did you happen to see the keynote speaker? What did you think? What were some of your takeaways from it? Or it could be as simple as I really love your shoes. Yeah. Yeah, but then, and then going from there.

Kelli Wall (16:14)
Mm-hmm.

Yeah, make it easy, make it easy. Yeah, I love that.

Yeah,

super helpful. And like you said, it doesn’t have to be over thought, right? It can just be a compliment on their outfit or maybe something that we’re all aware of to your point of a keynote speaker or something that if they’re at the conference, they’re going to be aware of as well. So you’ve had a lot of solo trips for work for the last 15 years. has there been one unexpected or memorable connection that you’ve made while traveling solo for work?

Jenn (16:50)
There have been a lot. mean, there are so… I’m very fortunate. Financial services is a huge industry, but it’s a lot of the same people. I like to say it’s…

It’s always the same names, but the only thing that changes is the company they work for pretty much. Having been in it for 20 years at this point, I’ve seen a lot of the same names and faces and I have like a really great network of people and contacts that I know in this industry. And a lot of them have become very close friends of mine. So it’s, it’s kind of cool when, you know, I’ve been to Hawaii, for example, for probably 10

Kelli Wall (17:04)
Yeah. Yeah.

Jenn (17:25)
10

or 12 different times and with a lot of the same people. So it’s like you’re almost like you’re vacationing with a group of friends, which can make it a really memorable But then conversely, like there’s there are the times when, know, like I met.

was one of the owners of the Cincinnati Reds in the Sky Club one trip and I had a connection for Diamond Seats for Reds games. Like you just you never really know you’re going to meet or who you’re going to see again. it’s a fun experience when you get to make a connection like

Kelli Wall (17:43)
Yeah.

Yeah.

Absolutely. And shout out to the Cincinnati Reds and Bengals. Jenn and I are both big fans. And actually, you made a good point talking about conferences in Hawaii. I don’t get to go to any cool places like that. But when you go to some of these conferences, have you ever extended the work trip to stay extra for some personal days? I’m hoping you say yes in Hawaii.

Jenn (18:14)
Yeah, yeah, I think every single time I’ve been to Hawaii, I’ve stayed at least a couple extra days, if not And there have been a few times too where that’s been, I’ve extended it and done more.

like work there outside So I know you’re in Hawaii, of course you’re going to be going to the beach and things too. But I did, there was one particular trip where I stayed there for about two weeks and five or so days of that were me making appointments around all the different islands. And then there were a few days where I was there for a conference too. So it was mainly for work. Although it was awesome because my day was around 3 PM their time because they’re time difference and the way that that works.

Kelli Wall (18:47)
Yeah.

Jenn (18:52)
out but I will I love to boondoggle a personal trip on the heels or before a work trip. My sister for a really long time lived in California, she lived in the Bay Area and she lived in Texas for a little bit too. So anytime I had a work trip remotely in that area I would go see her and my nieces before after that my brother-in-law.

yeah that anytime I can sneak in a visit with somebody or just you know I don’t have to be visiting someone it’s just I really want to go see this new city that I haven’t explored yet like tack on a couple days to do that.

Kelli Wall (19:18)
Yeah.

I love that.

And by the way, I’m to start trying to use the word boondoggle in any conversation that I have. I love it. So I don’t know if Hawaii is the peak or not, but are there any destinations or any dream conferences local here in the US or international that you have on your radar that you would love to go to?

Jenn (19:27)
Thank

So I am, yeah, like I’m very fortunate.

been to Hawaii several times. This is not a solo trip, but I do have a conference to Banff later this year, which I’m super excited about. So yeah, my husband and I will be making a trip out of that one for sure. Jackson Hole is another one that I’m really excited about.

Kelli Wall (19:52)
Amazing.

Jenn (20:01)
I have had a work trip. I don’t do a lot in Europe. That’s something that I, if I could change, I mean, just based on where I am in financial services, a lot of it is US based. But hoping to eventually get to do more and more international travel as part of it. I have been to Portugal for a work trip. So that was super cool. That was actually, I think, the first time I was ever in Europe.

Kelli Wall (20:11)
Mm-hmm.

Jenn (20:24)
for a work trip to Portugal. very, very cool experience. As you can imagine, a lot of personal exploration mixed in with work-related meetings and things that were going on there.

Kelli Wall (20:34)
well, I’ll cross my fingers for you. It sounds like you’ve got some amazing places coming up, maybe some more Europe trips in the future. Before we wrap, I always love hearing a favorite solo story from my guests. Since you’ve traveled so much for work, is there a trip that stands out? Maybe one that challenged you, surprised you, gave you an unforgettable experience, anything you want to share?

Jenn (20:40)
You

So I have a

probably. One of my favorite things to do, especially when I travel, is karaoke. So there’s a place called Wang Chung’s in Honolulu that’s probably my favorite karaoke bar ever. Amazing. Highly recommend if you find yourself in Honolulu, hit up Wang Chung’s.

Also, we talked a little bit about the diabetes. so that was a way for me to gain confidence with just managing my health by traveling on my own. mean, as a diabetic, there are some scary moments when your blood sugar can drop and you’re left to your own devices or asking complete strangers for help, which I’ve had to do before. And I think the first time, probably the scariest incident I ever had with that was at a yoga studio in San Diego.

Kelli Wall (21:22)
Mm-hmm.

Jenn (21:42)
I took orange juice with me, like I’m always prepared, but what I had brought wasn’t necessarily covering it and bringing me out of it. Thankfully, some super, super nice stranger at the yoga studio, he like abandoned the class, because he saw that I was having some issues and walked me to like a juice place that was down the street and helped, know.

like essentially helped me recover from it and make sure that I was okay to get myself back to my hotel and everything. So you just, you you put yourself out there, you see what good is out there in the world and how people are willing to help and, and, you know, make a new connection to. So it’s pretty, pretty cool.

Kelli Wall (22:13)
Mm-hmm.

Yeah,

yeah, thankful for him and to your point, there are some wonderful, kind people out there. So if you can be one of them, be one of them, please. Well, Jenn, thank you so much for coming on today’s episode.

Jenn (22:27)
Yeah.

Kelli Wall (22:31)
The last thing we’re going to do here is each episode of Solo Travel Unpacked will end with me asking the guest three open-ended questions. So here we go. The advice I’d give to someone considering solo work travel is…

Jenn (22:47)
The advice I would give to someone considering solo work travel is to do it. Whatever you’re afraid of, whatever’s holding you back, the worst possible outcome is that you leave with exactly as many new contacts and friends that you came with. The best outcome…

on the other hand, would be that you met somebody new or that you made a new contact or you progressed a deal, whatever your role is, the reason for your travel. So yeah, just push your boundaries and do it. I know for some roles like engineering, for example, that can be a really isolating type of a role where you are on a computer and don’t really get exposure to other teams or meeting new people.

A lot of those types of roles, I think fortunately, have remote work programs. So take advantage of those. Just put yourself out there and do it.

Kelli Wall (23:35)
My favorite part about solo work travel is…

Jenn (23:39)
My favorite part about solo work travel is probably the meditation, I would say, that I get out of by myself, but also sticking to my routine, if that makes sense. The mental clarity that I gain from sitting on a plane by myself and listening to a playlist that I’ve created.

Kelli Wall (23:53)
Mm-hmm.

Jenn (23:59)
Going through, know, whatever it is mentally that I’m needing to process, having the time where there’s literally nothing else that I need to be doing at that moment besides sitting on a plane, going to where I’m going. So that’s huge for me. And then once I get to where I’m going, keeping with the routine and the things that are important to me, but then also splicing in new experiences and people and places.

Kelli Wall (24:21)
Awesome. our last question. Something I learned about myself through solo work travel is…

Jenn (24:27)
Something I learned about myself through solo work travel is that I have a much easier time meeting new people than I ever expected or thought that I would. As I described myself as more of an introverted person, but I actually really enjoy meeting new people. So that’s something that I would not have

Kelli Wall (24:45)
Well, Jenn, thank you so, much for coming on Solo Travel Unpacked and talking to the audience about your experience with work travel. It was so insightful so helpful. So really appreciate you sharing your experience with us. Awesome, thank you.

Jenn (24:58)
Okay. Thank you.

Kelli Wall (25:01)
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