Helen Simkins created an ad campaign for Fidelity Insurance which grossed over 46 billion dollars in revenue (yes with a "B"). Learn how she did it while traveling the world as a nomad.

How much can change in a year… Helen went through an abrupt personal and professional breakup which proved to be a blessing in disguise and became the springboard for her nomadic transition. In this episode she shares the secrets of how she AirBnb’d her place in Boston out and secured twelve listings on the first night. Helen shares tips for growing your Instagram following and does a walkthrough of the design philosophy behind the campaign she did for Fidelity that grossed $46BN. Check it out.

Show Notes

Time   Topic
0:02:14   Welcome and context
0:03:12   What was your last year like?
0:05:46   How did you become an Instagram micro-influencer?
0:11:40   Are looks or beautiful images important for becoming an Instagram micro-influencer?
0:16:32   Did you had your Instagram following while you were living through your rough patch?
0:19:27   Sounds like you are really going for the core values of authenticity and being real
0:20:30   How did AirBnb allow you to become a digital nomad?
0:23:56   Was the AirBnb income at the beginning enough to sustain you on your travels?
0:26:32   Do you own that place or you are on the lease with it?
0:29:38   Do you have the desire to build an AirBnb empire like David Vu’s?
0:35:25   How did you get 12 AirBnb reservations overnight, on your first day?
0:39:42   Who’s your AirBnb Training for?
0:43:50   Will this training be published under Hostess Helen?
0:44:34   Can you show us some of what you’ve done for Fidelity Insurance?
0:48:59   What aspects of this campaign were you responsible for?
0:51:28   What was your process for winnowing the content down?
0:59:04   Do you know how big the retirement industry is?
1:03:59   What is the book that has profoundly affected you in someway?
1:04:39   What is your favorite tool that saves you time, money or headaches?
1:07:29   One piece of music or artist that is speaking to you lately
1:08:29   If you could go back in time, what would you tell your 20 year old self?
1:10:17   How can people get in touch with you?


Helen’s AirBnb listing in Boston
Fidelity Investments
Helen’s Fidelity campaign
Helen’s friend/photographer Crista
Furnished Finder
Martha’s Vineyard
Homeaway Vacation Rentals
Ellie Goulding, Diplo, Swae Lee – Close To Me
Selena Gomez – Back to You
Helen’s Instagram
Helen’s Website
August Smart Locks
Nomad Cruise



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Sean Tierney: 00:02:14 Okay. Hey everybody, welcome to the nomad podcast. I’m sitting here with Helen Simkins. Helen is a micro influencer on Instagram with over 15,000 followers. She has a degree in graphic design and a background professionally in UX UI, formerly with fidelity and responsible for producing a campaign that grossed 46 billion. And that’s B like as in billion in revenue, uh, now works as freelance UX and does it all living nomadically around the world. Welcome Helen. Cool. So we, uh, just some quick context here for the people listening. So we met on the nomad cruise, which, uh, ended a week ago here in Lisbon. And what I think is interesting and what I hope to get into with you, this conversation is how you build this lifestyle. You have a pretty impressive track record with the professional stuff at Fidelity, but also you kind of have done it on your own terms. And we were just talking a second ago about like how much can change in a year. Can you tell us what has your last year looked like?

Helen Simkins: 00:03:15 Yeah. So my last year completely flipped me around and basically put me on my ass to so to speak. So a year ago, literally I was living with my boyfriend at the time. Um, we had gone on vacation in New Zealand for two weeks and just as I left my Airbnb, I got a call from HR and saying that I was laid off. We come home and me and my boyfriend basically decide that we hate each other at this point ‘cos we’ve been traveling too much together and spending too much time that we ended up breaking up. And since I was living with him and I’m an airbnb super host, my place was fully booked until the end of the year. So all of a sudden in one month’s time I lost my job, lost my boyfriend, and had no place to sleep. So from where I was thinking, you know, I’m at a company and I’m going to move up in that company, you know, go from creative director to, you know, maybe you potentially owning something my own business.

Helen Simkins: 00:04:11 Um, as well as being with a guy and being like, okay, we’re talking about marriage and babies and where’s the wedding gonna be? We’re looking at real estate. That completely changed. And then, yeah, I also had no place to live. I mean, of course I was crashing on my friend’s couch. I also of course have my parents that I could stay with, but it basically overnight turned me into a digital nomad. It turned me into a freelance and entrepreneur and it turned me back into, you know, a, the single person. I’m still single right now who I am, but in made me put myself first again, which is so important and something that really gets lost in a lot of relationships. So what was a super devastating time for me turned into one of like the best things that could have happened to me because now a year later, I have an absolutely wonderful life.

Helen Simkins: 00:04:59 I travel all over the world wherever I want to basically. And I am now, have my own business like I actually wanted to before it made me be the true entrepreneur that I’ve always been. Um, it really made me reflect and see how much I really learned creatively in the past 10 years working and that I can do this on my own. And also you don’t just have to be with a guy and you’re perfectly fine on your own. And when things aren’t meant to be, they’re not meant to be. And obviously it wasn’t so, and here I am now,

Sean Tierney: 00:05:33 so we’re gonna, we’re gonna get into how you’re able to do this lifestyle and travel and live this way. Uh, but I think let’s start with the micro influencer thing. So yeah. How did you get this following 15,000 people following you? That’s quite a few people. It’s not like Gary Vaynerchuk, but it’s like, that’s a lot of people. How did you build that following?

Helen Simkins: 00:05:51 Yeah, so, okay, everybody loves, let’s say travel photos. And because I am a designer, I’ve always naturally, when I go anywhere, take photographs, and I’ve always tried to kind of put that out on the grand, but I never really realized all of the things that really takes with being on Instagram. And let me tell you, it is a lot of hard work. So before you’re going to just quit your job and be an Instagram person, don’t do that. So let’s see. This happened a year ago and I was still traveling just mostly around New England. I’m from Boston, so you know, being on my friend’s couch, I was able to capture photographs in, in Tucket, in Boston and Martha’s vineyard. I went down in Chicago. I’m taking beautiful photographs, editing them on light room. That just comes from my background naturally. Um, but then once I started really traveling, my first big nomadic trip was to Jordan.

Helen Simkins: 00:06:48 Um, that was in September. I had 2000 followers. So just over the course of a couple months, I really grew. But what really takes it really takes is a lot of preparation basically. So with every photograph that you take, you want to be constantly thinking like, what is it about this photo that would make someone read it? You know, like it, it’s really about the storytelling and what is your story. It’s also about having your feet aesthetically pleasing on the forefront. So when someone reaches your page, you really have a person’s like 15 to 30 seconds looking at your feed to say, I’m going to either follow you or not. So that’s something I also learned, like you know, if you have a beautiful photo with a camel, don’t just post it three times in a row because a, that’s boring. It doesn’t look so good. And you really have to concentrate on the aesthetic of your feed, which is basically, it’s like a landing page, but it’s your Instagram page.

Helen Simkins: 00:07:43 Now another thing is you really want to be engaging with others. So my niche target following is a lot of people who are just like me. There are girls in their thirties or in that age box per se. They either want to be traveling, they’re already traveling, they want to be a digital nomad. They can’t sit in their corporate job, anything like that. So what I love most about Instagram is I feel that I’m kind of a role model for these people. You know, I look at my niece who grows up with, you know, Miley Cyrus being on the Disney channel. And then being this pop star that kind of goes a little haywire and I couldn’t stand that. I couldn’t stand them. Also looking at Kylie Jenner and all of these other people, I’m like, none of these girls have any role models and no one that’s really transparent about the way they are living their life and how they’re doing it.

Helen Simkins: 00:08:29 And that’s kind of who I want to be for these people. So when it comes to engagement and people are liking your photos or commenting on them, you want to message them back and DM them back. You want to show them that you’re not this kind of celebrity who has a super luxurious lifestyle. You’re a real person. You stay at a hostel. You know, like we went to Jordan and it was an insane trip. We just went into a hustle, said how can we go to Jordan in four days? And she told us or we woke up and we had a hell of a day on a bus and but we captured that cause that’s a, that’s a story to tell. So you don’t want to just be the person that’s staying at a beautiful hotel in Paris or you have this insane photo with a Chanel dress in front of the Taj Mahal because that’s not real, that’s not realistic.

Helen Simkins: 00:09:13 And I want to be really honing in on the fact that this lifestyle is realistic. So in doing that, me and my friend Krista, who also is doing this as well on Instagram, we are kind of really lucky to have each other because we both like taking pictures. We both love, you know, traveling together and we both also have this nomadic lifestyle where we’re working remotely. So together we could really take pictures of each other and we could um, keep each other honest and make sure like, hey, did you make a story today? Like make sure you get that up or what’s your post going to be about? Or We’d read it back to each other and it’s taking that time to whoever is following you to go back onto their page. And like some of their pictures comment on some of their photos. If someone DMZ or asked you where you stayed at a specific location or I’ve had girls say, Hey, I’m going to this specific location, I’m going to be there solo.

Helen Simkins: 00:10:07 Like what do you recommend? You know, answer them back. Be that person for them. And I never really realized like how much it is to be like a mentor and a role model until it was actually the job that I got laid off from because my boss had said to me, he’s like, you have no idea how much these girls look up to you. Because I went from being kind of small potatoes at one company where everyone was older than I was and I was a huge sponge learning from them to a different company where I was the older peer and I had a junior team that I was kind of showing them all of like my creative expertise. But it was really having that sense of mentorship and being a role model of that translates now into Instagram, especially kind of being completely flipped on my ass in just a year and show them how you can do this.

Helen Simkins: 00:10:50 You know? I don’t recommend just quitting your job. Don’t do that. But there are a lot of steps that you can take to see if you want to have this lifestyle. If you want to have a career change, if you want to just even try it out. That’s was my thing. I’m like I’m going to just go off for a month and a half and see how much I like doing this. And at the end of that month and a half, you need to see are you dying to get back home or could you have stayed out longer? And the answer was I could have stayed out longer. So I did have to go back cause I think I probably had a wedding engagement or something like that. Um, but my next move was I packed up my entire apartment and I put all my stuff in storage and then I rented it out for, uh, six months sublet, so I could just go back and travel again.

Sean Tierney: 00:11:32 Cool. Well let’s definitely talk about the airbnb stuff, but just to kind of put a bow on the micro influencer stuff. So it sounds like there’s a couple of components here. There’s obviously capturing great photos, which you do. Um, how much, like if you don’t mind me asking like, do you think, how much does your looks play in like, cause you’re beautiful, but like beyond that, I think you’ve managed to leverage your expertise really well to, you know, build upon that to draw in. Right?

Helen Simkins: 00:11:58 Yeah. I think it’s more of the confidence honestly. And one something I love doing too is when I’m with a couple of friends or anyone who, you know, they know me, they know me from like childhood. I mean I was the girl who when I was 12 years old would take my little pink cannon camera and set up a self timer and take pictures of my back to school clothes. So that’s kind of just who I’ve always been. I should have actually made the app Instagram, but I didn’t really think about that. It’s, but it’s more like being, feeling confident and I think anyone can pull off a good photo as long as they feel that way. So, even just the other day, we went out with a couple girls and yes, we did have a couple bottles of wine to kind of make everyone feel more relaxed.

Helen Simkins: 00:12:40 But there is a beautiful sunset here in Lisbon and um, you know, we put on Beyonce, I was like, listen, when you’re taking pictures, just PR in our channel. Like anyone you want to be like, you want to be Katie Perry in her, you know, music video where she looks like Jane and she’s like super powerful. Do you want to be Beyonce? Do you want to be this person and just take a bunch of photos. Like we’re all girls, we’re all super comfortable. And that’s one of the things too is you know, the collaborating now and not being competitive against each other. So it doesn’t really matter. And that’s for men too. I’ve done this with guys as well and it’s like as soon as you actually capture a really great photo of someone and they see it, they’re like, oh my God, wow. Like I can actually do this.

Helen Simkins: 00:13:21 You know, there’s a lot of things that go into that. Like you don’t want to take photos in broad daylight because you’re going to have shadows all over your faces phase and no matter what it’s gonna look like shit, I’m sorry. It just, well, so we do, we wake up at sunrise and we shoot. You should basically always do because there’ll be no tourists. If you’re in a touristy area, you’ll see a beautiful sunrise and you’ll get a great start to your day as well. And if you go out and shoot for two hours and literally pack six opens, which we do, you basically have a month and a half worth of content and then you don’t also feel stressed out about putting them on the ground. You know you can take time and you can edit them and you can figure out what your, that it is going to look like and then you can go back and look at those photos and really or reflect that time.

Helen Simkins: 00:14:07 You can look up, I have a photo in front of Petra and I looked up, okay, what can I actually say about this place? There is other opportunities where you can write about solo travel or traveling in the low season or what it’s like to be a digital nomad working in someplace like Jordan. So that’s something there. What else? And then also the other great time of day is of course of course golden hour, which is just, you know, a couple of hours before the sunsets. But once you start getting into it, and I think a really big component is taking the pictures yourself of someone else, you start to see the creativity and the beauty of another person and you’re like, wow, this is amazing. I totally understand it. And then when you get in front of the camera, you start to own it a little bit more because you’ve now seen what can get captured.

Helen Simkins: 00:14:57 Of course being a good looking person will help you out, but you don’t have to be that. And I think it’s really just about owning it cause you know, we know plenty of celebrities that are overweight or they’re not the most aesthetically pleasing person to look at, but maybe they’re hysterical and they own that part of that. So that’s also going into picking your brand and what are your brand pillars you kind of always want to stick to for things that you talk about and making sure you do that. So for me, my brand pillars are definitely travel. I talk about, you know, the places that I’m going to and I kind of try to pick places that aren’t super cliche. So for instance, I went to Bosnia, which I highly recommend going to and that’s a beautiful country and it’s great cause you can talk about the beauty of that country, the culture of it, the people you’re meeting and all of the storytelling you can do within that.

Helen Simkins: 00:15:45 Then there’s the other brand pillar I have, which is being a digital nomad. So we call them literally digital nomad pics and we just have our laptop and we just pull them over and we’re like, this is a beautiful place. And it kind of shows the fact that I am traveling and you can talk about, you know, what time zone that you prefer to work on. Um, what projects you’re actually working on. Now you can talk about the struggles of being a digital nomad because sometimes you’re in a time zone. If you have to stick to one for instance, I usually try to stick to east coast time because that’s where a lot of my clients are and I like to be available online when they’re available if they need me. But if I was in Asia I would have to work until two in the morning and that sucks. So definitely make sure you’re also vulnerable and telling them the truth about your lifestyle.

Sean Tierney: 00:16:29 Did you have your account at that point where you had kind of the rough patch where you guys broke up and you lost your job and all that? Where were you? Did you have a falling at that point and were you being authentic with everyone and like revealing that or

Helen Simkins: 00:16:40 no, I wasn’t. I had a following of probably 1300 people. Maybe I did have nice pictures, but I had no idea how to really capture a photo. Let’s say like for instance more my photos were more like me and my girlfriends are all from my friend’s birthday and here we are at a bar and you’re probably just writing something like celebrating so and so’s birthday or we’re having a Sunday funday and here’s a beautiful photo of like the waffles we’re having or something like that. It wasn’t actually until I was in New Zealand and I got a nice, well I actually already had had the camera, but I was like, okay, you’re going to New Zealand. Don’t mess this up, and I actually started taking some courses. I took a photography course in school, but so much has changed since then though. It’s like taking your photos in raw and not jpeg.

Helen Simkins: 00:17:28 It’s editing them in late room after is where things really start to transform and really doing the storytelling. You can’t just throw up a quote, it just doesn’t work. Sometimes I will throw up a quote, don’t get me wrong, but it’s mostly because I’m really tired and lazy or Ellie is in at the beginning or of my, or the end of my caption. Just kind of the pull the reader in or to expand on what that quote really means to me and how I captured it in this photo. It wasn’t until later that it was like you need to just be who you are and just keep pushing that on every level. So besides the traveling and then digital nomad thing, I always try to be motivational and aspirational for mostly women to be honest because I think they have a really hard time. There’s so much competition out there and Instagram also doesn’t help that cause they’re constantly seeing these beautiful women in there at the capitol.

Helen Simkins: 00:18:23 Gay Balloons, which I’ve also been to. So I can’t say that that’s not a super cliche place to go. But I had also dreamt about being there for a year is to go see these beautiful hot air balloons. And I actually wrote about that. I wrote about the law of attraction because you can really have anything you want if you put your heart into it and dream that. So that’s another pillar that I use is you don’t have to just stick to society and do what you society thinks that you should be doing. So having a white picket fence, marrying the guy that you met in college, even though it might not be the right thing, sticking with your corporate job because you get a really good paycheck or really good bonus or a 401k match because if that’s not making you happy then just get rid of it. So I tried to be motivational with that as well.

Sean Tierney: 00:19:09 Well that’s a great message though. Like I feel like we are surrounded by such amount of impossibly beautiful unattainable lifestyle and that if that becomes the aspiration for everyone, it’s just this perpetually falling short of that type of scenario. And so what I like is that it sounds like you really are at the core of it, trying to have that authenticity and be real and you don’t, it doesn’t have to be perfect. Like just go take an amazing photo. Like, go put on Beyonce, go put on some sweatpants and like if that’s what your thing is like just be yourself in a so that’s good. That’s awesome.

Helen Simkins: 00:19:44 Yeah. You can take a beautiful photo at the Hammock at your hostel. I don’t know why so many people have a thing about hostels but they’re amazing. I feel like they had such a bad rap but I prefer to stay in Airbnb as in hostels all the time over a hotel. Cause I want to actually live in that place. You know, as nomads we want to feel home. The first rule of thumb I have is as soon as you get there, unpack all your stuff because this is home and get comfortable. And a lot of the time I won’t take pictures until maybe the very end of that trip cause I just want to actually live normally and just actually go into a coffee shop and work and yeah, try to keep myself sane sometimes because Instagram is definitely hard work for sure. Yeah,

Sean Tierney: 00:20:23 I can attest to that. If you don’t unpack right when you get there, then usually you’re living out of a suitcase and a week later you’re still living out of a suitcase. Yeah. Okay. Well let’s talk about the airbnb stuff. Cause that sounds like that’s what has allowed you to have this lifestyle. So can you just kind of explain what happened there with your place? So

Helen Simkins: 00:20:41 basically five years ago, I live in a really good area. I’m in Boston, but also in Fenway,

Helen Simkins: 00:20:48 which is right next to Fenway park. Like I can literally hear the screaming from the crowds of the Games. So I definitely have an upper hand on that. But I just wasn’t making enough money. I was living beyond my means, so I either could have cut back, but I was also living by myself, so I’m not cutting any of my cable bills or rent with anyone. It was all up to me and my friend actually started airbnb being his place and I was like, oh, that’s such a good idea. I had kind of always imagined this being a bed and breakfast just because it is so local to this stadium. And I kind of started over obsessing about what my place looked like. I know I had different colors of blue spot splattered on the hallway cause I wasn’t decided on the color yet. And he was like, stop obsessing, just take all of your crap that’s on your bed and throw it to the hallway and then take a picture of your bedroom and then take all the crap from the hallways, throw it back into your bedroom and take a picture of the hallway.

Helen Simkins: 00:21:41 And I was like, all right fine. He’s like, they just needed someplace to live. So that’s exactly what I did. And then I wrote like a little description about the area and the place and I put that up at 10 30 at night. I remember sitting in bed doing it and then I woke up the next morning and I had 12 reservations. So I was like, holy fucking shit. This is real. This just happened. And so I went to Home Depot and I got a lock from my closet door. I went to my neighbor and was like, do you have any extra sheets and towels? Cause I literally have a reservation coming in tomorrow and I just made it happen. And so once that money started coming in, I would do anything not to stay at my place. I was crashing on my friends couches. Thank you guys.

Helen Simkins: 00:22:19 Still it’s been five years and I kind of still do that sometimes. And I mean I always had the travel bug in me. You know, I talked about being in New Zealand and I would be at a job who would allow me to have 27 vacation days and I would maximize that to the fullest that I could and put them, you know, over vacations and sorry, holidays. So for instance, one time I went to eastern Europe and that was a 60 and day trip. I got two paychecks while I was there and I also made 3,500 from airbnb alone. So once that starts to happen, you’re kind of like, well I’m never going to live here again. Like, you know, I understand some people are like, how would you ever let strangers live in your place? Aren’t you afraid they’re going to steal things? And I always tell them, okay, I completely understand where you’re coming from, but no one is going to physically take the TV off my wall and walk out of it with people saying hotel rooms.

Helen Simkins: 00:23:11 I don’t think they understand how many bodies have actually been on that bed. So if you’re someone who’s worried about people saying in your own Airbnb, just kind of flip the script on that. But also with Airbnb, I’ve kind of mastered it in a way to where, you know, always buy all white sheets, white towels, white do vase, you know, send that out, bleach it. It’s the easiest thing you can do. There’s lots of hacks. Like for instance, I have a wine rack in my bathroom where all the towels go cause I’m in a studio apartment. But that’s really been a main factor of how I was able to afford this lifestyle in the beginning, especially when I first got laid off and I obviously had no means of income that season alone from May to September, I made 25 grand.

Sean Tierney: 00:23:56 And did that, was that enough to sustain you on your travels or you also had an income coming in from your job as well? At that point

Helen Simkins: 00:24:02 I actually had income from unemployment specifically just because I had gotten laid off. But yeah, it was super sustainable. I mean it really depends on where you’re traveling. So if I can rent my place out for two 25 at night and I can go to Bosnia and save at a hostel for $12 a night, it’s just like a no brainer. So it’s really picking places. I mean for me also like Boston’s definitely an expensive city. I can’t say it’s as expensive as New York or Paris or la. Um, so anywhere I go I feel like I’m making money because it’s just so much cheaper to live there. Everything is cheaper like across the board that it just makes so much sense. But also like the people, I’ve made so many friends through the people who have stayed at my place and they’re like, if you’re ever in Rome, come here.

Helen Simkins: 00:24:49 Um, an engagement has happened in my place. There is a very cute couple. It was their dream to go to every single stadium in America and they’re retired and they saved Fenway park for the last one and they were so grateful to have the place, which is amazing. And it just kind of makes you keep doing it. And it also kind of takes any barrier of being scared of WHO’s going to be in your place. They always ask me if you ever had a bad experience, and I can tell you honestly, I have never had a bad experience. I can say one time these people rearrange my furniture and I walked into my apartment and I literally dropped myself and it was like, oh my God, like this isn’t even my house. But to that end, I actually ended up keeping it the way they moved it.

Helen Simkins: 00:25:30 So it actually made more sense just because I did it over in 24 hours, I hadn’t really thought about, hey, maybe you should move the table into the center so more people can sit there and not against the wall where your computer was because it’s not a desk anymore. So a little things like that. But it’s been a great experience right now. I’m technically not air being being it and I’m using furnish finder just because it’s way more sustainable for my lifestyle. So for instance, you can sublet it for three to six months or even longer. And because I’m in Boston, I have a ton of hospitals nearby. So I have a travel nurse in there from December 15th to June 15th which is perfect and amazing. And I have one person in there, they pay a higher rent because it’s furnished. And I don’t even have to worry about anything happening with um, people being in and out. Cause that’s something you do have to not worry about, but be conscious of, you need to have somebody doing your switchovers for you if you’re traveling as much as I am.

Sean Tierney: 00:26:29 Can, can we, I mean are you willing to talk numbers in terms of Oh yeah. So do you own this place or do you, do you, are you on a lease, like a yearly lease with it?

Helen Simkins: 00:26:37 So technically my parents own it. Okay. So basically I own it. I pay my parent’s $12 in rent. And in furnish finder I put it up for 1900 and then with Airbnb I minimum rented for one 85 and I can get up to two 25 so airbnb has something called smart pricing and they can kind of, they’ve a really great algorithm where they see who is looking to stay where and for how many nights and how many people that they have and then they know how many listings are available for them. So in that it makes way more sense to have a studio than a one bedroom because no matter what, you’re only going to get two people in that place and a one bedroom is going to cost you way more in a mortgage or rent or anything like that than a studio one.

Helen Simkins: 00:27:24 I do know people that have just have leased a place and our air being being, and there’s, you know, every country in every city is different. I know people who work something out with their landlord. And so if they get a small [inaudible] they’re totally okay cause a lot of landlords, they just want to kiss their property goodbye. They don’t want to deal with it. Um, it just depends. You can also just go completely under the radar and not tell them and be perfectly fine. I’ve stayed at an Airbnb in New York and I know they’re having a lot of problems with the laws there. And what’s so funny is they put the listing under an address that was just right down the street. And so when you book it they tell you, okay the address is actually here. Then they put the, what is it, a lockbox on someone else’s different railing next door. And they were like, okay grab the key, here’s the code but take the lockbox with you. So it was basically like a leave no trace kind of situation.

Sean Tierney: 00:28:17 Speakeasy.

Helen Simkins: 00:28:18 Yeah, it is easy Airbnb, but there are definitely ways to get around, you know, the kind of was, and I’m definitely a high risk kind of person and at the end of the day, whatever they could find you is never going to be the amount that you can be making. So to me it’s worth the risk. It’s almost like investing, you know, you never know what’s going to happen in the market and you never know what’s going to happen with these short term rentals. Just throw it up there and just do it. You know, if you only get a couple of reservations out of it, you still get enough money to fund your next travel. I guarantee. So, yeah.

Sean Tierney: 00:28:50 Yeah. The personal story that, what this reminds me of, uh, I did a road trip in San Francisco and I obviously had a car up there so I had to pay for parking, but I figured out somewhere along the line that the frequency with which I was getting tickets, it made more sense to just never pay for parking and take a ticket every three days. And it worked out to my advantage. So I think it sounds like the exact same thing here. It’s like, even with the risk of,

Helen Simkins: 00:29:13 they actually did that in Fenway too, because usually if you park it’s residential, but if you park, you get a $40 ticket and it costs $40 to park for the game,

Sean Tierney: 00:29:22 you might as well take the chance and you don’t have to pay any for it,

Helen Simkins: 00:29:24 which obviously living there was a, you know, a little annoying. But, um, they actually did figure that out when they started charging $100 for it. But even still, it’s the convenience of having your car right there. Yeah. Don’t worry about it. So, yeah. Yeah.

Sean Tierney: 00:29:36 Cool. So you have one of these, and we were talking beforehand, like David WVU has this massive of bees. Do you have a desire to like replicate this or are you happy with just the one to fund your travels? What’s your plan with it?

Helen Simkins: 00:29:47 So I’m happy with just the one. There was, um, a time that I was really looking for other places to buy to do this. But with that, the market is so insane. So, for instance, when I said my parents bought this at 82 it could now be sold for four 50 so if I were to go and buy property now, yeah, to crunch those numbers, you would have to be airbnb being it for you to make your mortgage. And it was almost just kind of like too much. I did go through it. I put in lots of offers and I was like, I just can’t anymore. The Universe is telling me that this is not the way to go. So I just have the one. But it’s been really successful. I mean, I can make three grand in two weeks at this point. So of course I’ve had this for five years.

Helen Simkins: 00:30:33 So I have, you know, a five star rating. I’m a super host. I have I think like 75 to 95 reviews. So it’s also doing those really nice little details that I’ve always done. For instance, when you walk into my place, I have a video that’s set up that you can get on the Ivan Apple TV. So, you know, as part of a digital nomad, that’s a really great way to go. It’s way less than cable. And of course you still want to be able to have youtube TV, Netflix, Amazon prime and all of those things. And so today I have it set up where I actually give them a virtual tour around the place. So it’s kind of like people love to have a self check in so it’s less pressure on the host and the guests of like, you know, flights get canceled if they’re taking a road trip and their traffic or they just don’t want to have that kind of pressure to meet someone with a key.

Helen Simkins: 00:31:22 So a self checking process is really important and then they can turn that on and they can have a virtual tour if they want. Or I give them really detailed instructions about everything they need to know about the space. Especially, you know, you kind of always want to think about you as a traveler going into an airbnb out of the country. So if you have people coming in from out of the country, you know they might not have service when they land. Give them everything upfront. I give them photos. I mean I give them photos of me putting the exact key into the door. You don’t want anyone to be confused. I have a key fob that opens the apartment door. Some people don’t have key fobs they have like what do you mean an electronic key? And I guess that that they’re going to have to buzz in every single time. So I learned that lesson and I took a photo of me holding up a key fob to the little electronic panel in the front door to be like,

Sean Tierney: 00:32:15 just remove all uncertain,

Helen Simkins: 00:32:16 just remove all uncertainty. Because I’ve also been in the situation where I’m going to talk top bunk in Jerusalem at four in the morning having to buzz people in. So if they can’t get in, you know it’s hard because you’re on a different time zone and I definitely have my neighbor and other people that can help me if a crisis did happen. But you want to make sure like it’s as flawless and seamless as possible. I also, if they’re staying for a longer time, I have a bottle of wine there for them. I also asked them, you know, if there’s a special occasion, can I get you anything that you might want? And I told you guys there as an engagement. So I guess he had actually been planning that and you know, I went down to the supermarket, I got some flowers and some stuff that they would, that he requested.

Helen Simkins: 00:33:01 He Venmo owed me that amount and it was great and that takes way less of off them. So now he doesn’t even have to worry about that. It’s all set up. I always have, I have an espresso machine with all the different kinds of coffee. I leave almond milk. I always put two bottles of water, two diet cokes, two water. Seltzer is I have oatmeal, I have pancake mix, I have everything you could need. So because for me it just makes that guest experience so much better to walk into a place and feel like home automatically. I used to live in basket on the bed with toiletries that they could miss just, I just did a big Costco order and I got like, what do they call it? The loof Lu files. Huh?

Sean Tierney: 00:33:41 Sponge. Yeah.

Helen Simkins: 00:33:43 That I have like a bunch of those like razorblades some snacks. I got a big instacart order of like Doritos and things like that. Cause the other thing is as a host being in Fenway park, if people go out and they get crazy drunk, I don’t want them to come home and let’s say throw up. So I got snacks. They’re waiting for you. I have a binder of a little writeup of every single neighborhood in the Boston area. I have a handwritten note about me and the space and things like, you know, laundry is downstairs. How do you use the, the tub? Like make sure you put both of them on because if not it’s gonna get really hot and you might burn yourself. Like little quirks like that. Cause it’s definitely a very old building. And then I also have them right, which is actually a super adorable, I have a bunch of blank pages and they say, you know, rank your top three experiences that you had in Boston for the next guest.

Helen Simkins: 00:34:31 And they actually really do this. And I love reading the notes because they’re actually things that I’ve never thought of doing because you know, I’ve lived there for so long, I’m not going to really think to do it that and having guidebooks maps the whole thing. So you just want to create the best experience that you can for those people. And a lot of them I’ve had great relationships with and they email me and they text message me like, Hey, is your spot available for next time? And I do have repeat customers, which is also great. But

Sean Tierney: 00:34:58 yeah, I think what it sounds like you’ve nailed is that establishing that rapport and trust and like people want to do business with people that they know, like, and trust, right? Yeah. And so the virtual walkthrough, what an amazing way to get off on the right foot and then follow it up with some of these gift baskets and things that you’ve done that just show you’ve, you know, taking them the extra special mile to, to help make their stay better. That’s awesome. Um, okay, let’s maybe transition from the airbnb stuff. Well actually one more question on the airbnb thing. So how did you get 14 reservations overnight that first day? Like what do you attribute that to?

Helen Simkins: 00:35:31 So there were 12 but I’m 12 I think that I priced too low, which, so I priced it at one 25 when I first did it and now it’s five years ago. So I guess it’s relative, but I think what it is is when you’re a person is vacationing, you’re looking up where you want to stay really far in advance. So for instance, I would get booked in June and July from people in February and then in June and July I would get booked for the fall because they’re really looking ahead of time. So when I posted it, it was a lot of people that are like, oh my God, I can’t believe there’s a spot available that I can stay at. And it was for a low price. And if you’re someone who’s just launching an Airbnb, you’re going to become on the top of their feet and their algorithm being with a big old new tag.

Helen Simkins: 00:36:21 I had read that, you know, if you’re someone who’s new and you don’t have any reviews, you should price yourself a little bit lower. And so I did that. I immediately changed to one 75 after I had that. Cause then I realized, oh my God, I could have gotten so much more money. But who would’ve ever thought that I would have 12 reservations overnight like that? Cause I definitely wouldn’t have ever. So I guess that kind of explains that, but it’s also, you know, taking good pictures. Like I have a studio, so it’s really kind of maximizing that space. It’s taking a chair in the corner of the room and getting on your tippy toes and taking a nice photo and then doing that in every single corner. I had pictures of, let’s see, the Nice Crystal Chandelier that I got at Ikea for 40 bucks in the bathroom.

Helen Simkins: 00:37:05 I had a picture of the coffee maker there. I had a picture of um, how close Fenway was in proximity. I also had a picture of flowers that were on the table. So it’s kind of making it already look like a very homey looking place. That’s I guess super cute and adorable because if you think about it, just like grocery shopping, when people are designing packaging for like ice cream container, is there anything like that? It’s the women who are shopping, so just like in vacations, it’s mostly the women who are looking for a place to stay. So if you think of an audience, like you’re kind of targeting them and you want your place to look put together and those cute little touches, you know the, the candles around the place, like the framed Boston map, how the decorative pillows are on the couch, the blankets, things like that.

Helen Simkins: 00:37:55 They’re like, oh, I like this one little picture that I just saw on home feed. It’s new. It’s for one 25. I’m going to book it before it’s gone and to that in their algorithm, because I was a new person. If people are all searching for the same thing and I’m up there, it’s just going to attract more people. So then just like any site, if you’re searching and Expedia or booking, it says like five other people are looking at this listing right now and kind of prompts them. Yeah, it prompts them to book really quickly. So I think that kind of happened. Um, if I could guess now looking back. Yeah. But yeah, it was definitely a crazy 24 hours or crazy 72 hours getting an all put together for then I had to, I just crossed in my neighbors the next night. I’m pretty sure it was like, all right, I’m going to go do this. Then a true myself to a bottle of line because I just made you know, one 25 tonight.

Sean Tierney: 00:38:45 Perfect. Well we’ll, we’ll link to the listing in the show notes so people can see the photos and get an idea of, of what was involved. And My mother, by the way, is the person that books eight months in advance. Like we are actually going to Martha’s Vineyard for their 50th anniversary and I think she just had that book now for at least seven or eight months. Totally. Yeah.

Helen Simkins: 00:39:03 Yeah. And I actually do that sometimes too, depending on what their cancellation policy is. Because for me, this isn’t, I guess an airbnb host hack from the inside is um, they don’t realize like for instance, if you’re searching for ski season two, that really far in advance because Airbnb won’t let the host change the pricing of that that far because obviously if you’re in Colorado, you can get way more money for your listing in the winter than in the summer. And if they were free cancellation, you should just book it and have it and you can always cancel if you want, but at least you have something in your back pocket. So I think people definitely do that as well.

Sean Tierney: 00:39:40 Let’s actually plug right now, this is a good segue. Uh, you’re going to be putting together an airbnb training package, right? For people who want to what, who is it for? First off.

Helen Simkins: 00:39:50 So it’s for people honestly that are like me or were me. It’s for someone who doesn’t want to feel like they need to stay home because they have a lease or that they have a mortgage and maybe they want to try out this whole digital nomad experience or they want to go, they want to feel like even if they just want to go on vacation, that it’s not going to take a huge dip in their bank account and they can go away for a week and put their place up for a week and let that pay for itself. It could be something as easy like, like that or it could be something more where you’re traveling full time like I am and you want to make sure while you’re traveling you’re not paying double rent. You know, I don’t want to pay for an airbnb in Croatia and also be paying for our rent or mortgage at home at the same time.

Helen Simkins: 00:40:35 So it’s more of like a one oh one almost like here’s how to get your airbnb listing up within 24 hours and how to really maximize it [inaudible] the airbnb algorithm and making as much as you can in a short time depending on, you know, taking really good photos, paying attention to all those details, like I said, and just kind of getting an up there and don’t be afraid like I was of having like this picture perfect magazine Worthy Le Listing, cause it doesn’t matter. People just really want a place to say and they want to feel like home and just, it’s going to be mostly about that. But as well as AIRBNB has changed a lot in five years. And so depending on your lifestyle, something like furnished finder or homeaway or VRVO could be better for you. So it’s really about how to maximize apartment hosting in a very easy way, a really systematic way.

Helen Simkins: 00:41:29 I’ve been doing, I’ve learned enough and had enough experiences that you don’t have to troubleshoot and go through everything I did. And you can do it really easily just by how he said doing that virtual walkthrough or a self checking process. There’s a whole bunch of ways to do that depending on if you have a front call system like I do or I, we talked about the person in New York. There is a couple apps that you can have that is mostly for airbnb where it’s just punching a code and it’s for that person specifically to walk in.

Sean Tierney: 00:42:00 Is that the August lock?

Helen Simkins: 00:42:02 I think they actually have a couple more of them, but yeah, that is a great one to have, especially if you’re in an area like where I am, where the doors are super old and sometimes the keys don’t always work perfectly. I actually had a key got frozen into a lock in Boston. I almost really had a panic attack but it was 12 degrees that day and after that we were like, okay, we’re not dealing with this. We’re going to put an August law because no one wants to get locked out of their house. When is this cold out? And it’s a super old key and the key is stuck in there. So yeah, it’s going to basically be for the person who is like me who either just wants to make some extra income because they’re not making enough at their job. Who wants to just go on vacation and make extra means. It could be someone who has a two bedroom and maybe it makes more sense instead of having a second roommate to airbnb that shared space. Or it could be someone who really wants to try the full time travel digital nomad adding and who doesn’t really want to have an entire empire of this and make this like their job and business, but just have a, I’m not a complete passive income because it has work, but something like that to fund your travels and not worry about it.

Sean Tierney: 00:43:12 Yeah. Well it sounds like just the option to travel, you can basically decide that, oh, you know what, I’m ready to hit the road and go three months somewhere and I know now I’m fully capable of doing that with this airbnb. Yeah.

Helen Simkins: 00:43:22 And it really doesn’t take long. I mean now we have Amazon prime. You can have everything delivered to you in a day. But yeah, that’s mostly what the course is going to be like. I’m really excited it and I hope you guys will tune into it because yeah, if you guys want to travel, that’s the first step and it will make your life so much easier. And then of course, if you ever want to return home, you can, you know, you don’t have to be completely nomadic and have always been living out of a suitcase. You can return home at any time.

Sean Tierney: 00:43:49 And where this is going to be a host is Helen or is this under [inaudible]?

Helen Simkins: 00:43:53 Not completely sure yet. Um, yeah, hoses. This Helen is a really cute name. Um, that we came up with. I might have my own Instagram handle for it depending cause at the same time I’m always travelling at Airbnb is and kind of reviewing them myself. It also may live on my website, Helen Simkins design slash maybe apartment hosting, airbnb. It’s all still in the works right now. But I’m sure one day I’ll figure out the right name to where this thing will go.

Sean Tierney: 00:44:22 We’ll, we’ll, we’ll send them to, uh, Helen Simpkins design. It sounds like that’s your main site and there’ll be some way to get there from there. Yeah, for sure. Cool. All right, well for this last, what I want to do, if you’re up for it, um, I want to swap around here and I want you to show some of what you’ve done at fidelity. Sure.

Helen Simkins: 00:44:40 All right. So,

Sean Tierney: 00:44:41 and actually let me start. So this is just the preface here for people listening. Uh, this is going to be a visual part of the episode. So if you’re listening to the audio only, uh, you’re gonna want to come to the website and check this part out because this isn’t gonna be very design centric and there’s really no way to convey this in audio. So you want to see the video that we have going here? Yeah.

Helen Simkins: 00:45:02 Cool. So, yeah, part of my past life was working at incorporate, but in corporate they do have advertising agencies. So whether you’re out of house or in house. I was in house at Fidelity. And what was great about that, I know people are like, oh my God, so boring. But as a designer to be working in something in finance it really shows how much you know your shit because you have to be super conceptual with it cause you don’t have a physical product that you can sell. So it was a great experience for me, especially with a company like this cause they have tons of money also that you can really show off your skills in all mediums. So for this specific campaign, which is one that they repeat every year is for retirement. So these are the people that are like in their forties to 50s trying to figure out where they want to retire.

Helen Simkins: 00:45:52 And the biggest research thing that we learned here is no one wants a cookie cutter plan. The single minded idea here was the only retirement that matters is mine. So you know, as the generation is moving on, like no one just wants to retire and Naples, Florida and be golfing or be in a rocking chair. And knitting and they just don’t want that persona or outlook. It’s almost like when grandma’s turned into grandma’s and they’re like, oh, I hate that name, it’s so old. It’s kind of like the same thing with retirement. They don’t want to be looked upon as like this old fogy that’s now just going to waste their life away, but you can do anything. And it’s almost kinda like taking the step into digital nomadism, if I can call it that, is maybe I want to open up a second business or start a business or take up a new hobby.

Helen Simkins: 00:46:38 So that was kind of like this. And so the campaign is called, every Sunday needs a plan because you’re dreaming up your someday and maybe you don’t know what that someday is. And so this is kind of where this came to play and me and our writer worked finding visuals in stock photography and coming up with all the different Sundaes that a person could dream up of and putting those together and kind of flipping the script, the headlines with the photography. So if I scroll down and just kind of like what I said, like plans matter for you and your family and your future. So you know, these people, they want to have a plan. They may not know what their plan is yet, but they want to be ready for when that happens. So it’s kind of having your own personal Sunday. So, um, for this I did all of print out

Helen Simkins: 00:47:30 of home and out of home is something where you see bill, it can be billboards, it can be these huge structures that you see. Train station, dominations there, an airport, it’s there. Just literally anything that’s quote out of home. So I’m a direct mail package and just digital communications in general, whether it’s rich media that you get an ad, you know, as you’re flipping through your nook or something like that. And video, this is the case study in it. And let me flip it back. This will give a good overview actually of what I just said. Isn’t one,

Helen Simkins: 00:48:07 okay.

Sean Tierney: 00:48:08 Negotiation of what retirement could be.

Sean Tierney: 00:48:11 In early 2015 we set out to inspire our audience to think about their own personal future. Our goal was to help them build their unique a plan, snap them out of the inertia of a date day. We took a highly contextualized approach speaking to people through their interests and through their own idea of the perfect Sunday TV, told rich stories about how a beautiful retirement is woven over time through it on my retirement and never got left behind. So today I am prepared for anything we may want tomorrow to need. We used the sweeping storyboard at Lex to draw travelers into a range of distinct, some days we captured genuinely human moments through a mix of video photography and cinema graph.

Sean Tierney: 00:48:58 Yes, sir. While this is happening is to build a sense of what aspects of this were you responsible for? Seemingly endless. The print collateral that we see in all these places. You’d bet that’s your portion of this on the gas bill boards outside Penn station. Yeah, that’s positive.

Helen Simkins: 00:49:13 Okay. So yeah. Um, so here is a digital out of home piece that I did. I would say mostly did everything, the sides, the TV. And when I say everything, we also still had a team of let’s say 12 that were writers and designers. So I was working with a writer and there was then there’d be other designers and writers constantly trying to come up with these someday plans. But when you’re an art director it’s coming up with that idea. So this is the idea of we’re taking something that somebody could type in because, because someday and you would fill in the blank. And so we kind of did that for them in cases and that’s where it would turn into a print ad and direct mail and you can see it here how it’s beginning to type in. But we also took that design and put it on print, which is kind of funny cause obviously or something digital that’s on print, but it Kinda just made sense in the space.

Helen Simkins: 00:50:11 I can actually show you some of that. So, for instance, here was a really nice full bleed that because someday I want to live in a different kind of suit. So we’re talking about that corporate nine to five suit or whatever suit that you have to wear to work. And we’re going to flip that and have a on and be snorkeling, you know? And then under that you see alert fidelity, meaning attachment, retirement plan, reminder today, save. So it’s showing that whole the planner, it’s almost like these airbnb people. It’s, it’s the for the person who is the planner and the research. That’s what we figured out. Who is our target. It’s the people who are planners and they’re planning for retirement, but it’s not every kind of person’s retirement. It’s only my retirement that I want to plan for. So if we scroll down a little bit more, here’s kind of some more examples though. For instance, in the bottom you see a map and it’s because someday I want to run out of pins. So this is where the writers and designers had to really put their heads together. And sometimes the writer would come up with a Sunday. Sometimes it was the designer coming up with the idea and they would find the image to go with it. But that was definitely a challenge. Working with all stock photography, you’re kind of just like, Oh that looks nice. That looks nice. Download, download while they’re coming up with millions of some days.

Sean Tierney: 00:51:28 And what was your process for winnowing that down to what we see here? The final stuff I would

Helen Simkins: 00:51:35 say. Okay, so you’re constantly kind of looking for aspirational photos. So I want a new view every time I walk out my door. I think this is a case where we found the photo first and it’s a beautiful glowing tent looking at the northern lights in Iceland. And then on the other side you see kind of like a grandfather with their kids surfing because you’re talking about, you know, retirement. And maybe I just want to do something as simple as hanging out with my grandkids and show them how to surf. And then at the top, sorry, this parallax is not allowing you to see everything, but you can kind of see like very aspirational. This guy is just looking out at a beautiful sunset. There’s these two people that are looking at sunrise, another two people that are just enjoying a campfire together. So it’s kind of just honestly capturing beautiful photos that you could find.

Helen Simkins: 00:52:24 I think I do have, yeah. Okay. So right. Every day will be a personal day. I want a new view. Every time I walk out my door I want to go where the wind takes me. This one was a great one because someday this will be the only hand held device on the end and it’s a passport. I’ll turn on my out of office for good. You know, some of them are more ambiguous where this headline could kind of go with anything. But this was obviously a great photo. And then we took the tiling on top and made a transparency. You could still see the beautiful image behind it. And this I’ll work my socks off and he’s a surfer with his, obviously doesn’t have socks on. This was one of my favorites. I want to catch up on everything I missed. So you know, it’s the grandfather and his grandson.

Helen Simkins: 00:53:10 And you see the catch up park. So it’s like they’re catching fish and he’s like, yeah, I want to catch up on everything I missed. Cause maybe I wasn’t around because I was working crazy, um, through the beginning of your childhood. So it was kind of showing you every of someday that you could possibly have. And then we had to turn that into out of home. So in each medium we wrote specifically for that. So one is I won’t mind sitting next to somebody cause you know when you get on the Tran, you know, maybe you want to find that little quarters seat that no one will be sitting next to you. Um, so we did this one and again, it’s the grandfather and his son, like looking out, I’ll follow a different set of tracks and it’s a set of elephants going through and Africa.

Helen Simkins: 00:53:55 I’ll enjoy the background noise and it’s a girl in a convertible going, you know, wherever she’s going. But it’s showing you that same aspirational message. And then because someday I’ll go beyond the last top and it’s to hiker is like at the end looking at this beautiful view. So they all made sense for the space of being an out of homes, whether it was, so we did a whole train station domination. Here’s more of them, just showing more in a carousel, always to can really be them. Same thing because someday I’ll always get the seat that I want. And then this was for a bus shelter and we kind of had to change them a little bit for the space. And this was a billboard. I also did a direct mail piece, which is kind of showing the same thing. So you get this in the mail and you can see that there’s little cutouts of kind of each of these different images.

Helen Simkins: 00:54:40 So it was kind of playing like a game and you’re like, I don’t know what this is about. Um, I see some really pretty images. Maybe you’re automatically putting your eye towards some of them because it’s kind of picking up your own someday and you open it and you say, everyone has a different version of retirement. Let’s talk about yours. You know, close your eyes and imagine being retired. Are you on the beach? Spending time with your grandkids, giving back to your community. That’s a someday you’re planning for and we want to help you make that happen.

Sean Tierney: 00:55:09 Cool. I think that’s good. I think we can. Yeah.

Helen Simkins: 00:55:12 So yeah, that was a very big campaign, um, that we all worked our butts off for. I’m pretty burned into a great one because we brought in over 40 billion in new assets and they kept running with that. But it was amazing to see something just from a sheet of paper on a creative brief that says a single minded idea is these people who are 42 to 45 who are the planners and planning for their retirement and are saying the only retirement that matters is mine. And coming up with an idea and just writer and designer putting their heads together and saying, okay, how do we make this come to life?

Sean Tierney: 00:55:51 Yeah. And what was, so the, the original input, you didn’t pick this up from scratch, I think you said you started, there was some previous work that was in progress.

Helen Simkins: 00:56:00 Any of these things, like obviously the first product is never the end. It would actually be really fun to dig up the originals. But at cad, I don’t even know if we were using the words because someday, but we kind of knew, we’re like, how can we emphasize that anyone could have anything that they want, but it’s not super particular that anyone could look at this ad and be like, oh, that’s so me. You know? So it had to be super ambiguous at the same time. So I didn’t technically start from the scratch on this one. I actually was working on a different campaign. Well it was in the same campaign. So when you’re working in advertising and you have a really big project like this, basically what happens is you go into one room and you all put your heads together and you kind of start teaming up with people.

Helen Simkins: 00:56:44 So as a designer I grabbed a copywriter and we’re like, okay, how could we make this come to life? And you, you know, you go on Pinterest and you’re looking through different magazines and books and you’re just kind of getting inspiration from places. So I was first working on a different angle or a different concept I should say from what I just showed you. And what was so great about this whole thing is we started out with 12 concepts and then we boil that down to six. We put those six concepts into focus groups and then we ended up with three. Then we took those three and we showed, you know, the VP of marketing and fidelity. And then we wound up with two and those two went into ab testing. And this is the one that we came up with, but the two was the other one that I was working on. So,

Sean Tierney: 00:57:31 so you had both, both, both horses in the race where you’re [inaudible]

Helen Simkins: 00:57:34 it was like Hashtag blessed I guess I was, it was kind of insane. Um, it was also of course a lot of work because I was working on both of them, but it was also amazing to work on the same project but in two different concepts. So the other one is actually very similar. It’s still that juxtaposition of images. I think it would be great for when our generation is starting to retire because I think it’s gonna make a little bit more sense than let’s say our parents getting the message. Because what I love to do is show you an ad that only has a logo on it and you just get it off the bat. And I think that’s one of the biggest challenges with any advertising and marketing. It’s like, you know, when you make a logo, you need them to understand what that icon does like in 30 seconds.

Helen Simkins: 00:58:20 So this other campaign was highly visual, highly visual, my baby, so to speak, because I loved it and works really hard on it. Lots of photo shopping was involved, but it was let’s retire the tip, let’s retire the typical retirement. So it’s kind of saying that same thing. It’s not saying because someday Yada Yada Yada. Every Sunday needs a plan. It’s saying let’s retire the typical retirement, which is still going back to that single minded idea of the only retirement that matters is mine. Because at the end of the day you need to make sure you can hang your design on the hook that says that idea.

Sean Tierney: 00:58:55 Do you have a feel for how big the industry is? Like how many, I know in retirement planning has to be a multi multibillion dollar industry, but how so 40 billion was your guys’s take. But how big is the industry itself? Do you have any feel for that?

Helen Simkins: 00:59:11 Gosh, I actually don’t. I mean we do have competitors, but it’s kind of like an anything. So there’s probably like their Schwab, there’s e tread there, you know, vanguard, but they all kind of focus on different things. And I say fidelity is definitely more known as like the grandfather’s company, but I think we’re more known for retirement. So that could have been a little bit easier. But in the industry alone, I’m not completely sure. I think it kind of really depends. Like the boomers are so many of them. Right. And it almost depends on like the generation itself. Yeah,

Sean Tierney: 00:59:44 it’s needless to say it’s a huge, massive industry and you guys probably scratch the surface, but with the 40 billion is no, no slouch. That’s a chunk of shame

Helen Simkins: 00:59:55 too. Like working in advertising myself and I said before like it’s great working for some place like fidelity who has the money, but it’s also really taking that risk because they allowed themselves to buy, like have immediate buy in times square to be like, we’re going to blow this huge digital platform here. We’re going to take the airport at lax and Chicago and other places and totally take over every single digital platform that they have. We’re going to go on every billboard, we’re going to be in every single magazine and we’re going to buy, have a huge media buy and really push this idea. And so I think that’s really important. And something I struggle with, um, later having other clients that I want to be like, look, this is a brilliant idea and you always want to be like a couple steps ahead of the game.

Helen Simkins: 01:00:44 You want to be thinking for the future and not right now. So it’s like, just take the risk. You know, what’s the worst thing that you can happen because even if you fail, you’re going to learn from that and you’ll, you’re going to succeed the next time. So that was something that was kind of amazing that they did allow us to really push this idea. And of course being in the company that they are, they definitely did their research ahead of time as to who that target was, as well as putting all these concepts into focus groups and into ab testing to make sure which costs money to make sure that whatever they do put the money in and blow out everywhere is going to be the one that won and all of these other scenarios. So, and it’s educating your clients with that too.

Helen Simkins: 01:01:25 You know, just don’t just throw something on a wall and see if it sticks. Like take the time, do your research. I think we probably put this whole thing together and like a month and a half. I would say we always get the brief late, but I remember the guy was like, it doesn’t matter when you guys get the brief, you know, you’re all going to wait till the last minute to do it anyways. And we’re just like, all right, fine. I guess that’s true. So we definitely had some late nights in the office, but in the end it was super rewarding because to see your own idea that came off from like a little sticky note and a wall to live beyond like this is, um, it was a really great feeling.

Sean Tierney: 01:02:01 Well, an proliferate it sounds like then tax and other portions of the business, it was getting pulled into that as well. Yeah, totally.

Helen Simkins: 01:02:07 After this campaign was so successful, they started bringing it into all the other business lines. So if you guys are still on my website right now, there’s one that talks about tax prep, but it says, you know, being, and it was a trifold, so it says like the 10 tax year end moves. And then if you open it, you see a beautiful photo of a father walking his daughter down the aisle. So it’s saying all the prep work will be worth it. And we’re kind of visually talking about the prep work of a wedding. And we’re all about the life stages here too. But we’re also talking about the tax year and being prepared for that. And then at the bottom of my page, I have a video that I did with, um, a writer where we had to talk about more of the workplace people, not the 401k guys, but the four o three B guys.

Helen Simkins: 01:02:52 So we have the teachers and the nurses and the firefighters and we talk about each, um, individual life stage of, you know, having a baby, getting married, taking care of your elder parents and everything like that. And it was all of the same idea that we had. I was turning a Sunday campaign to these people specifically, but we also knew we had to give more of an emotional pole to these guys and we had a smaller budget with this. So we only had, we storyboarded the whole thing. We wrote it out together and we just did all voiceovers. And that was really successful too. And it was, I love concept being in TV and video because a, it’s just so much fun, but it also challenge you to get across an idea across in a very short amount of time, visually. So.

Sean Tierney: 01:03:40 Right. And working within the constraints, it sounds like how’d you had more budget? Maybe you could have done actual footage, but yeah, no constraint to, okay, what can we do with just this and stills. Yeah. Which is another interesting parameter. Yeah. So how I think we’re going to wrap it up were just over the one hour mark. And so, um, I like to end with a set of three questions for every guest. Uh, what is one book that has profoundly affected you in some way? Actually

Helen Simkins: 01:04:07 one book I’m going to say is gone girl, which I’m sure people are like, what? Um, but that’s because this girl owns her shit in this story. She is so ahead of everything going on. And I always tell my friends like, listen, be five steps ahead of everybody else and that’s kind of who she is. And she’s also just like a super bad ass that’s not going to let anything stop her with the whole society picket fence, the guy, the husband, whatever. She’s like, fuck you guys. I’m doing what I want. And she’s super organized and has so meticulously planned. Just like in anything that we’ve kind of talked about in this hour. Like you have to be a step ahead. You have to plan it all out, right. And you have to be empowered and confident in what you’re doing. So she actually does a good job in that story doing that. If you’ve seen the movie, the book is way better, just like everything else. So go read the book. If you haven’t, I’m sure you have.

Sean Tierney: 01:05:05 I have not seen the movie nor read the book. So I would put it on the list. A what about, what is one travel hack or a tool that you use to save time, headaches, money, et cetera. So,

Helen Simkins: 01:05:18 um, one thing I do that people constantly laugh at me about is I bring my own pillow, which is like a silly feather pillow. But why I do that is because a, I’m someone who packs and only a carry on and backpack. And if you have extra crap with you, you can kind of throw it in your pillowcase and they’re not going to know. Like if you have extra skirts or you throw your headphones in there, your toothbrush in there, you’re Walden. And yet they’re you, you’re calm. You kind of look like you’re walking around in Halloween with a bag. But it’s okay. They’re not going to bother you cause it’s technically you don’t have a personal item, but you have a pillow. Um, but also when you’re traveling, you never know where you’re going to wind up. It could be a terrible bed, it could be in a hostel with a terrible pillow. And it really helps to have a sense of home with you wherever you go. And that’s always helpful to have. You know, sometimes traveling like this, it can be depressing if you’re traveling really, really quickly and you’re just not in the mood. So keeping a sense of home with you. I actually used to travel with a travel size candle, so if I needed to just kind of walk myself in doors, I could have some Zen and have a candle and I have like a piece of my bed with me and my eye mask.

Sean Tierney: 01:06:27 Cool. Yeah. Especially with the cruise, I felt like it was super overwhelming. Just the nomad cruise for the people listening. We were on this thing with 222 digital nomads for a week and it’s pretty, uh, just the energy. It’s amazing, but it’s also overwhelming. So

Helen Simkins: 01:06:43 yeah, sometimes you just need like some time to yourself and just go back and collect yourself and yeah, having a sense of home with you is really helpful as well as guaranteeing you a perfect night’s sleep, having your own pillow with you and traveling with it. Because, especially when you’re stuck on like some of these really long buses and everything else, you’re like, I got my pillow with me, I’m good no matter what.

Sean Tierney: 01:07:04 Yeah. Sleep is something that I’ve actually struggled with personally and a hack that I’ve found, I travel with lavender. It’s a little essential oil and you can like literally, yeah, I just put like a little bit of lavender on the pillow and it kind of, uh, it’s a cue. I think it’s like a mental cue for sleep and wherever you’re at it kind of lets you make that your bed for the night. Yeah.

Helen Simkins: 01:07:24 And when all else fails, Melatonin is your best friend.

Sean Tierney: 01:07:27 Indeed. Okay. One piece of music or musical artists that is speaking to you lately?

Helen Simkins: 01:07:34 Oh Wow. Um, lately I’ve had a la Golding’s track on repeat, which drug? I think it’s called close to me. So as a designer I’d, I listened to what I classify as tropical robot ferry. It’s not something that really exists in the world. But if you were to listen to any of my playlists, it has like a little bit of like slow trans, like almost like one republic in a way. Um, this song is called close to me with Ellie Golding in Dubbo. What else do I have on here? I was just listening to on the way here too.

Sean Tierney: 01:08:11 Cool. Well we’ll embed that in the show notes if people wanna check it out.

Helen Simkins: 01:08:14 And there’s another one called back to you. And what’s really funny because I would say it’s my theme song cause he just says I’m just traveling the world. I’m not sure when I’ll be back, but I’ll be back someday and I’m like, Oh my God, this speaks to me because that’s me.

Sean Tierney: 01:08:27 Nice. All right, last question here. Um, if you had a time machine to go back to your 20 year old self and give yourself one bit of advice, what would you say?

Helen Simkins: 01:08:37 Oh, 20. Um, don’t care what anyone thinks ever. I’m definitely someone who used to be insecure. I had kind of a rough middle school where I would be bullied. Like for instance, guys used to call me and ask me to the dance and then laugh and hang up. They would, I was too tall or I had really frizzy hair or had acne on my forehead or whatever else and it’s like, just don’t let any of that stuff ever bother you. And just the zero fucks role. Like I am definitely somebody who just does not give a shit. I don’t care what I, there’s plenty of, listen what I’m not instagraming and being like, I need to wear this like really pretty skirt in Morocco or whatever. I’m rolling around in my sweat pants with no makeup on and, and just don’t give a shit. That’s what I would say for sure in your 20s like don’t care what anyone thinks, own it, don’t let things bother you and also just listen to the universe.

Helen Simkins: 01:09:32 Everything happens for a reason and you may not know where the end of your path is, but just take the first step. I remember that was something set on the nomad cruise is like you don’t all know it was a quote from Martin Luther King is like you don’t know where the end of the staircase leaves, but just take the first step and you know, life is just going to work out. I know people say I have a jeweled life, but you just have to believe that everything is going to work out for you and to just follow that, like follow your heart and the clues that come into your life and the people you meet and are surrounded by.

Sean Tierney: 01:10:03 Cool. And that’s a good segue. A, the guest that’s going to be after you is a Marissa and talking about the clues and finding that out. So that’s nice. They’ll say, wait, Helen, thank you so much for being on the show. How do people, where do they find the airbnb course? Where do they find your personal Instagram? How do they get in touch with you?

Helen Simkins: 01:10:20 So my Instagram is my name, it’s just Helen Simkins and my website is helensimkinsdesign.com So right now I think that will be the easiest way. I know, I’m sure I’m going to be promoting like hell on Instagram, all the stuff with airbnb and everything that’s coming and yeah, it’s just my name. Super Simple, and I’m probably just going to keep it with design because that’s who I am. I’m a designer, even though I’ve all these other facets, that’s who I am by nature. So yeah.

Sean Tierney: 01:10:50 Perfect. All right. Thanks for being on the show. Best of luck. Thank you.

Contact Details

Helen Simkins
Personal Site
Current Company
The Nomad Influence
Current Title
Founder, Creative Director
United States of America
Countries Visited
  • Australia
  • Austria
  • Bosnia and Herzegovina
  • Brazil
  • Canada
  • Croatia
  • Czechia
  • Germany
  • Hungary
  • Israel
  • Italy
  • Jordan
  • Morocco
  • Netherlands
  • New Zealand
  • Portugal
  • Puerto Rico
  • Spain
  • Turkey
  • United States of America
Where in the world are you now?
Where were you living when you decided to start a nomadic life?
In which (if any) of these travel programs have you participated?
  • Nomad Cruise
What were the initial set of circumstances or motive(s) that led you to experiment with a nomadic life?
I’ve always wanted to be able to travel and work remotely but I wanted to ensure that I had the creative expertise so that I could do it successfully on my own. I was learning so much from my peers, creative directors, and co workers I knew it wouldn’t be smart to start living a nomad lifestyle until I felt confident that I had all the knowledge gained to do so. Once I began advising junior designers, and my role as a creative turned into more of a managerial one– I knew I was ready to dive into being my own boss and would be able to handle my own clients. Coincidentally enough, I ended up getting laid off at my ad agency, my airbnb was completely fully booked, and my boyfriend and I (who I was living with at the time) broke up. In one month my life got turned upside down and was basically forced into a nomadic lifestyle having no job or place to live. I had always been freelancing as a means for extra income, but then I had to turn it into high gear. Even still, I asked myself what did I REALLY want? Do I work at another ad agency? Do I go back to start ups? Do I freelance? The world was my oyster, I had just turned 30 and realized I had a lot of different opportunities and decisions to make. While freelancing, I took a temp job for 3 weeks to get some income in and realized– I absolutely cannot work in an office, for someone else, or between the hours of 9-5. Realizing that, I began to take the appropriate steps to working fully remote. As I’m writing this, now it’s time to quit freelancing and create a more expansive business using everything I know from my past work experience in different start ups and ad agencies for myself and grow independently where my true value lies. It’s amazing what just one year can do!
Was there something specifically you were looking to gain or escape from that you’re willing/able to share?
What was it and did that play out as you were hoping?
I was looking to gain freedom really. I couldn’t stand the politics in a 9-5 job. I couldn’t stand the gossip around the cubical, and I couldn’t stand being underpaid for the amount of work I was doing. As a creative, you can’t be expected to be creative all the time, and especially not for 8 hours a day in the specific 9-5 module. Traveling help fuels my creativity. It also gives me the freedom to do whatever I want on somedays, and on others work three 12 hour days. That’s the thing with creativity, you never know where your next idea is going to come from, when you’re going to feel inspired, and when you’re going to hit the ground running with your nose deep into your laptop for weeks. By having this flexibility, you not only have a work life balance, but a work life harmony. I’ve successfully been able to harmonize my work and life together. I am always living, and I am always working. But that’s the dream right? Absolutely loving what you do, figure out your purpose, help others with your insights and expertise, and be able to travel the world (if that’s what you choose to do) all simultaneously together.
What did you do for income/work while traveling?
For income I’m spread in a few areas. One, having an apartment to rent out is a big plus. Whether it’s through airbnb, or a longer term through furnished finder, rent in the states is always going to be more than it will be across the pond, so I am always making an income as long as I’m not living in Boston. I have a few businesses I’m in. One I’m in a co-op company that me and a few others created to really own the design and marketing space in the cannabis industry. We have a team made up of a Creative Director (me), a developer, CEO, project manager, and 2 in sales. If we need more hands we outsource it, and we are all fully remote. I also freelance for a couple companies, one is actually the old agency I worked for that laid me off. It’s quite poetic actually, and also shows the importance of never burning any bridges, if you’re a hard worker and get laid off, it’s most likely because they can’t afford you, but when business becomes strong again, you’ll be the first one they call for help. You already know the system, the clients, and the work, and I can do it all remotely. Now I can be paid a lot more for what my salary pay check was. Try making in 2 days what you did in a week because now you’re hourly versus salary. Then I also have a few of my own clients that just work with me independently. They’ve all found me through word of mouth (another reason why to never burn bridges and work as hard as you can) Whether they need branding, strategy, website, package design, app design, social media, UX/UI, email campaigns, rich media, billboards, tv spots, honestly anything, I’ve done it all before, and it’s really fun to help someone’s business from start to finish and watch their own dreams come true. So it’s a big of a juggling act, multiple clients, multiple timezones, multiple projects, but at the same time, it’s exactly how I was working in an office, time managing your own projects, you just have to make sure to give yourself deadlines and factor in travel days that end up taking a couple days out of you.
Did that situation change at all during the course of your travels?
Are you still doing the same work today as when you went nomadic?
Did you find it challenging to do your work from abroad?
What type of personal or business growth did you expect to experience and how did that turn out in actuality?
What I learned in my first year being nomadic is to travel slow, stay on top of your work, and build a 3 year business plan. When you first become a nomad you’re just so happy to be working remotely you being to book yourself way too many plane tickets, and shiny objects such as the beach, festivals, socializing with other nomads, and anything that can result in FOMO – say no to it. The way I travel now is I book work-cations. Your personal business, career, and growth are of the up most importance. Once you’ve mastered how to travel, that comes really easily, there is always going to a beach nearby, as well as events and anything else. You have to limit yourself and keep the eye on the prize, and that is– your career.
What was the highest high-point and lowest low-point of your travels?
The highest high-point was when I first set out on my journey and I booked myself a ticket home and said– Okay, you’re going to try this whole thing out, working remotely, I gave myself a month and a half, traveled to maybe 5 different countries, and said, if by the end you’re rushing to get home and this isn’t for you, you’ll have your answer, if by the end you could keep traveling, you’ll know if this nomadic lifestyle is for you. The answer? I came home, packed up the rest of my stuff into storage, rented my place for 6 months, and was out a month later. I’m someone who likes to test the waters before going all in, and before that first trip I was hoping that I would love it, and it turns out I did.

The lowest point would probably be traveling just too damn fast. There is no exact “low point” but if you travel too fast, you can’t honestly get any of your work done, feel rested, explore your new location, before you’re off to the next place. I used to plan my trips to a T, but I was also living the PTO, now I just book one ticket, and probably only a few weeks before hand, and go from there. You want to be able to go with the flow, your mood, your surroundings, and allow yourself to truly have the freedom you’ve always wanted. Don’t lock yourself in a corner by booking airfare and lodging too far in advance, it ends up just stressing you the F out. Some days, you’re going to want to just not leave the apartment for 3 days, other days you’re going to meet people and want to be able to go to the next country with them. You want to live just like you did at home and stick to having a routine. I don’t go anywhere for minimum 3 weeks, but lately I think I’m going to be changing that to a month and a half. I’d rather be situated somewhere, and take weekend getaways from there, if that makes sense.

Was there ever a point at which you gave serious consideration to quitting the nomadic journey?
What did you learn from your nomadic existence that was unintuitive or unexpected but obvious now in retrospect?
I think something that’s obvious is setting yourself up with a system you know that works. I have my packing down, my travel day down, the first thing I do when I arrive to a new place down. It’s all just something you gain through experience. I’ve sat down in my seat stuck inside with a window and realized I needed something in my backpack, which got stored a few rows back and the people next to me are asleep, and you’re like welp, better luck next time. Everyone has their musts for a flight, as well as packing, as well as settling into a new place. The first thing I do once I’ve gotten to my new home for the next however many long weeks, is unpack. No matter how tired you are, just force yourself to unpack, and make this place a home. Wander around and find wifi cafes, (I literally type into google maps, “wifi cafe” or just walk outside and look around for them, locate the outlets near the tables, talk to the waitstaff and ask if it would be ok to sit there for endless hours and work. Do it all BEFORE your workday. Locate the grocery store, pharmacy, public transportation, bikes and if they need an app set up (those can be a headache in themselves). By giving yourself the first day in a new place to set yourself up for the rest of your time there is going to be the best thing you can do for yourself. I guess that’s still the planner in me. I don’t leave the house without my AirPods, battery pack, and a light sweater, cause more times than not I’ll end up being out for 12+ hours, something that seems so obvious to me– yet I still come across so many nomads that don’t travel with a battery pack or AirPods? I don’t get it, what if you end up having a call while you’re out? What if you run out of phone battery or want to charge your camera or literally anything else with you… I’ve taken so many calls while physically commuting, I’ve walked across the street in the middle of New York with my laptop open typing notes with one hand while listening to the client, or sitting in a park in Paris– isn’t this the whole point of this life?! Working ANYWHERE?
Was it hard to re-integrate back into society after your travels?
What can you not “un-see” at this point?
How many different religions, cultures, and peoples that exist. People are so focused on what’s going on in their own country, city, town, or their personal lives. There is so much out there, so much to open your mind and heart to. Don’t judge a book by its cover, instead start a conversation, ask questions, and learn something new. When I was in Jordan I was so curious about the muslim religion and the life of a Beduin wife, as well as if their black dress from head to toe and if it makes them SO HOT while in the desert. So guess what, we asked, and we listened. They were SO hospitable, and we were able to go back and forth on both of our religions and customs, and come to find out, we’re a lot more alike than you think. I didn’t even realize we ALL believe in the first testament, so why are we all so “different” now? And why have there been so many wars focused on religion alone?
How and to what extent has your group kept in touch after the experience ended?
All the freaking time. Facebook groups, WhatsApp groups, instagram groups, meet ups, masterminds, weekly calls, WhatApp audios, smaller travel meet ups. I talk to my nomad friends probably more than anyone else in this world, more than my family, more than my friends from home, more than literally anyone. It doesn’t matter your location, their location, your time zone, or theirs. In a single day I talk to someone whose in California, Australia, Bali, Budapest, London, and Lisbon. They’re all moving around too, honestly– they’re a group of people that you’ll never be able to get rid of even if you tried LOL.
How do you think you’ve changed as a person from the experience?
I am SO much more relaxed. I find I can spin any situation into a positive one, whatever small stuff I probably used to sweat, so to speak, don’t even occur to me anymore. I’ve gotten into so many conversations with people and ask, why does this actually bother you? Why are you wasting your energy? Who cares? Take the word can’t out of your vocabulary. If the grass on the other-side looks greener, what can we do to make your grass shine just as bright? Just flow and enjoy your life!
What would you say to someone considering taking a leap like this?
First I would ask why? WHY do they want it, cause you have to really want it to make it a successful reality. It’s almost like learning a language. You have to REALLY want to learn that particular language, work hard at it, and stick with it. That language can potentially change their lives, it can change the location they live in, the people they meet, the job opportunities that come with it. Don’t just learn it to learn it, we always have a reason for all of our actions and a goal in mind. So what will that person GAIN from living this lifestyle? What are their goals? Is it just to be free? What does being “free” mean to you? What are some of your personality traits and habits that you’ll have to work on? What are some things you’ll need to be open and adapt to in this lifestyle? For instance, there won’t always be hot water in your shower. You will experience a terrible travel day, (but you’ll also experience some really good ones). You WILL have a conversation with someone and have to get by with hand gestures. You WILL get into a taxi and be put in a situation where they will try to take advantage of you. Understanding yourself is the best thing you can do for yourself in your life. For example, I’m pretty damn terrible at languages, and a sense of direction. My solution? Download duo lingo before hand, look up conversational words you’ll probably need to learn to get by, research how much english is spoken in that country. Download the offline google map ahead of time, “heart” or “star” your airbnb/lodging location as well as where the supermarket, wifi cafes, hospitals, etc are. On my first day I wander around and do just that, pin places I want to come back to– it then makes up for a great itinerary and travel blog later, you’ve got it all mapped down! Literally. Now you have back up for when you do get “lost” you never will be. You a. have the map downloaded that can also be used offline, b. have your lodging starred, and c. you have your battery pack with you too =)
How (if at all) has your idea of work changed from the experience?
Well I went from working for people, to working completely independently, but still for people, to wanting to be my own boss. I never wanted to run my own business and always wanted to work for a successful company and get paid well. And I did that, a few times actually. Once you gain a ton of experience, figure out how to do it successfully not only on your own, but anywhere on the planet, your mind just gets opened up to more and more opportunities. I never thought about what my 3-5-10 year business plan would be and what I really wanted to do until I was on the road, I don’t even know why. If you give yourself a goal like working remotely and you accomplish it, and a goal of making an income anywhere in the world and also accomplish that, you then ask yourself, well what’s next? NOW what do I want? The possibilities are literally endless, and it’s what makes our everyday life so damn exciting, we’re in a world where we can accomplish anything our heart desires, you just have to want it, and consistently work at it.
What’s your best travel hack?
Travel with the things that you know make you happy no matter how ridiculous it may seem. I travel with my pillow, not the airport kind that go around your neck, or those turtle pillows, my real pillow from my bedroom at home. People think I’m nuts, but guess who consistently gets the best nights sleep ever anywhere in the world? Any bed I sleep in, whether its in a bunk in a hostel, outside camping in Colorado, a 5 hour bus ride, or hotel resort, I have a little piece of home sweet home with me. I keep my eye mask inside the pillow case so they are always together, and when I’m flying, that pillow case becomes my sack for all my essentials, like my passport, AirPods, and anything else. The airport can’t bother you either, they can’t say, you can’t bring your pillow, that’s an extra item, or an extra carryon. I’ve literally stuffed skirts and a purse in there that didn’t fit in my backpack– so that’s my travel hack for sure.
Is there a piece of gear you could you not live without at this point?
Please provide a link to this product
I guess they’re AirPods HAHA https://www.apple.com/airpods/
Any particular routines or rituals that kept you fit/healthy/sane throughout the year?
Coffee in the morning, detox tea before bed. Making sure to step outside at least once a day, and honestly, I need yogurt and fruit in my life to stay healthy.
What resources (if any) did you use in preparing to go abroad?
None. Ok I used SkyScanner to book my plane ticket, and airbnb to keep the money rolling in while I was gone.
If you were to do it again, what would you go back and tell your former self to do differently in order to get more out of the experience?
Just enjoy the ride, we’re so used to booking our travels due to our former lives of only have x amount of days for vacation and trying to get the most of out it. But– we don’t have that to deal with a travel time crunch anymore, so just book your first ticket and your first lodging and go from there. You can always extend your lodging if you want to stay longer, or go backwards and minus some days to go somewhere else if you don’t like that particular place.

Just remember, it’s not a problem until it’s a problem, and when it is, you’ll figure it out, just like you always have in the course of your life. We’re natural problem solvers, and we also have a million resources in the palm of our hand, literally. So why stress? it’s not going to get you anywhere, it’s not good for your health, or wellbeing. We can’t predict the future, so why are you trying to?

Any ideas for a product or service to solve a pain point for nomadic travelers you believe should exist?


Sean is host of Nomad Podcast, author of the Nomad Prep eCourse to help others successfully transition to the nomadic lifestyle. Sean is also founder of Problemattic, a global movement to mobilize knowledge workers for good. Read more from Sean on his personal blog or his business blog.

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Nomad Podcast is a series of conversations with nomads, founders and domain experts to help get more people unstuck through transitioning to a nomadic lifestyle. Add your email to get special access to private AMA sessions, pre-release products and other VIP shiz.