Building a Location-Independent Business While Traveling With Remote Year

by Aug 10, 2017

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In the first Pairs Well With… videocast from Lisbon, Portugal, I sat down for a chat with the amazing Carin to talk all things nomadic, including what it’s like to start a location-independent business while traveling with Remote Year, how to break your own boundaries, what it feels like to take a chance on yourself, and how we’ve become Macgyver-esqu in our laundry skills since departing the US as digital nomads.

After a fifteen-year marketing career centered on strategic storytelling, content creation, and brand amplification, Carin threw her conventional 8-5 lifestyle out the window and traded it in for a remote one.

She’s one of the most amazing people I’ve ever met and I’m thrilled to have gotten to travel with her for six-months.

Read of Carin’s adventures and learn about her content services for startups, small businesses, and entrepreneurs at

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Complete Video Transcript:

{00:01} Carin

Hi guys! Maybe the 3rd time’s a charm here. Maybe my laptop didn’t like it, but we are back. So, thank you for everybody that is joining us today. Kate and I are live in Lisbon. I am Carin, I am the founder and front woman of Pairs Well With a story telling business a social media strategist that helps business, entrepreneur, and other small businesses get off the ground and work on their social strategy. So, thanks for joining today.

So, I am with Kate Bagoy, who is on this crazy wild journey I am on traveling around the world. She has been a great collaborative partner this year. We spend a lot of time and working together. I brought Kate out because I think she is a great guest on this video cast to talk about inspiration, life, and how to reach your goals and dreams. So, you want to share a little bit of your back story?

{01.26} Kate

Sure! Hi, everyone! I am Kate Bagoy. I am a business coach and a business strategist. Also, a former user experience designer & a lifestyle designer. I think I was no longer going to settle for a mediocre life about 5 years ago. At that time I was struggling a lot with my drinking. So, I quit drinking and I am sort of on this trajectory on creating this life I love. that has brought me all around the world. At the time I was living in Portland and since then I have been across the country to Savannah, GA, where I call home, and I was just starting to get settled there when I decided to get crazy and join Remote Year and I have been doing that for the past 6 months. Now I am departing from Remote Year for my own thing, which is kind of exciting. In the meanwhile, I am getting to help women grow businesses and that was my #1 dream.

{02:07} Carin

Kate is a great source of inspiration for all of in the group. She has a lot of tips on how to lead your most authentic life, how to focus on the ideal client, how to make that move from corporate America to entrepreneurially endeavors. Do you want to share a little bit about your story about what was your jump off point was to leave corporate America, the cubicle farm you talk about, to starting your own business?

{02:14} Kate

Sure. So, I have left corporate America a couple of times. But, I think the more dramatic and impactful one for me was in 2008. I had started my career with a really great company. I was my dream job when I started. In about 5 years I was at a point where I didn’t know exactly what I wanted to do, but if I kept doing this I was going to kill myself or kill somebody else, and so it was time to go. So, I quit without a plan. Now, I call it taking a leap of faith and that is what that really was. I was burnt out and said, screw this. I cannot do this anymore.” , and “I don’t know what I will do, but it is not this.”. It was one of the best decision I have ever made. It was hard, it was challenging, it was one of the first times I initially started running my own business as a home-business working as a freelance designer and it was an absolute disaster. Because, I didn’t know what I was doing. I would scramble for any type of work that would come my way. I would take any client that would pay attention to me. So, I earned, I was basically competing on dollar amount instead of the value I could provide. But, it led me to a point where I went back to school and I got my Master’s in Business Administration and moved to Silicon Valley to work for another start-up there. Again, that was another disaster and it was an example to me for not listening to my “gut”. I took that job even though everything in my heart and in my soul told me, “this is not the place for you.” and I took it anyway. That is what happens when you are in your “head”. You do things because it looks great on the resume. Because somebody else tells you are making the right move and mean while you know it is going to be a disaster.

{04:21} Carin

You start to feel that nagging in your heart and your gut. You try to like, you know, you try to survive. It is a game of survival and ultimately you want to be able to do something. It is hard for a lot of people. I think there are a ton of people that go through life that are sitting at their jobs, regardless of what they do, that are finding themselves wanting to do something different. They find themselves looking over their shoulders consistently but, they don’t know how to take that first move. Whether it be a confidence thing or a financial thing. What advice would you give people about that first step they should take to move into new endeavors?

{04:59} Kate

The number 1 thing is to start listening to your heart and not your head. I tell my client’s all the time to put your hand on your heart, get quiet, and listen to the “quiet voice”. The “loud voice”, the one that tells you, “you are not good enough”, “that this is crazy”, “that your mother will never approve”. You know the one that says, “you are going to die alone being eating by cats.” like that is your brain. Your brain is designed to help you survive. When you listen to your brain you often make choice, actually, you make trade offs, that is what we will call that. So, listening to your heart is number 1.

Number 2 is making a decision. That is the key to action. Making the commitment to making a decision. You don’t have to know everything that has to come next. But, you can say, “I am going to quit this job.”, “this doesn’t deserve me.”, and put it in a timeline and say, “I will quit my job in 2 months and I will have a business lined up.” or”I will have a new job.” or whatever. But, make that committed decision.

{05:42} Carin

I think a lot of people make that committed decision and they keep pushing it out, pushing it out, and pushing it out. And, they are like, “Well, it is going to there.”, All you do, I am going to tell you first hand, is if you keep pushing it out and it is still there, you are just dragging your feet. Rip the freaking band-aid people and make a move. Because honestly, I probably sat at my shit job a lot longer than I needed to and I was like, “Look at this blissful life.”. It is awesome! There is nothing better. I didn’t think I was asking for a lot. My main goal are having financial freedom, time flexibility, and ultimately I want to work during my best working hours. I don’t want to be told you have to be here between 3:32 and 3:48 am. That is just not how my brain works. For some people it does. I am not knocking the people that have that lifestyle. But, they just need a little more creativity. That is is just one of those things where you have to make the move. I think that if you have that rub pulled out from under you, tell me if I am on the right page, you are forced to think differently because you don’t have that safety net. You are proficient, you are more sufficient, you’re more perfected and you are like, “Alright, I am going to figure it out”.

{07:08} Kate

Yeah, absolutely! It has been referred to us as a “hunger”. It is like a hunger, and another thing is “burning the boats”. There is an old story and probably a lot of you hear of it. I don’t remember the exact person, so please forgive me for botching it. So, basically, it was a military maneuver. They were going to take this island. This captain, they all knew they were out numbered, out manned, and most likely going to die on this island. And so what did the captain say to do? Burn the boats because we are not getting out of here alive. That is the only chance they had winning because of all those guys being so hungry for survival that they have to win and beat the other army to steal their boats.

So, that is what happens when you quit a job without a plan. Like joining up for something crazy like Remote Year. Not knowing how you are going to make a living. So, you have to listen to your gut and to your heart to see if that is meant for you the answers will come. You have to make that committed decision. Yeah, when you say, “I am going to quit my job at some point”, that is not a committed decision. Like, I actually have my clients create a contract with themselves at sometimes. Like, if they are particularly known for putting things off and I make them write a contract. Like, “I keep a goal that promised to X, Y, or Z by X date.”, and have it be really detailed and specific. Then you can back design your path as well.

That is something I do with people. We look at the vision of the life you want to create in the further and then figure out how to get there. That vision drives you forward instead of the fear of, “Oh! How am I going to eat tomorrow?”.

{08:48} Carin

I can say that Kate and I did a… I did a coaching session with Kate late last week or the week before. I have to say it was really nice because I had a sounding board. I was like, “Ok, bounce some ideas with me because this is where I think I am going with my business.”. That helps stream line what I was doing and my type of thinking. So, ultimately there is value in that person that has got that creative business mind that I think I have as well.

So, talk to me about what it is like to build a business on the road. I do it too, but it is different in everybody’s business.

{09:26} Kate

Yeah! As you know it is a challenge.

{09:40} Carin

What are you talking about?

{09:41} Kate

You know. We had a really good laugh last week when we had coffee. I was like, “Dude, I spent more time looking for Q-tips this week than I did working on my business.”

{09:39} Carin

And I am still looking for trash bags.

{09:50} Kate

She is still looking for trash bags. These are little idiosyncrasies that we find in cities all around the world. We get kind of caught in the day to day living stuff. So, that can be challenging. We never know when the internet is going to work when traveling. We have days like, I can’t seem to feed myself very well here in Lisbon, I just seem to always find the restaurant that is closed.

Aside from that, once you have some tools in place, it is actually really liberating. Because, like you said, I can work when it suits me. It suits my biological schedule and my creativity schedule. One of my biggest pet-peeves when we are working for anyone, even if it is jobs that I love, is like working from 8 – 5 because that is just what you do. If I don’t have 9 hours to work then I shouldn’t be in a cubicle. In fact, there have been many studies that show that people are most effective in shorter bursts. Like a good 4 hour workday is really solid. That is a really solid makerspace to put your head down and get some real quality work done.

So, I love being able to do that when I am on the road. I am personally inspired by travel. I have always have been. So, being in a new city really brings that creativity for me. So, that has been really helpful with my business. Also, it is about learning the tools that work for you. So, in my business, I am able to use Calendly, which allows me to book calls or video calls with my clients or potential clients. It also calculates time-zone issues for me. I love to use Zoom meetings and things like that. So, using those tools is really important.

Other than that it is really about the hustle. The biggest challenge with that is this Remote Year is budgeting the time between wanting to enjoy the lifestyle and wanting to grow my business. Because I think like you, my business is more than just a paycheck. This is part of my mission in life is to help other women and to inspire women to travel and live their life with purpose. So, that is really important to me and that means I have other trade offs that I have to let go of. That means I have to be really guarded with my time and sometimes other people don’t understand that.

{12:12} Carin

Time is precious. It allows to get stuff done, it allows us to make money, and it allows us to network. What would you say besides time is the other biggest drive in success?

{12:40} Kate

I think having a vision is really important. It so easy for an entrepreneur or a small business owner to get so caught up the day to day and the busy. We become addicted to the busy. I do this, my task list is where my ideas go to die. I am serious, I have had so many great ideas over the years and I put them on my tasks list and it is just a hot mess. When I become overloaded when I become scared, and when I go into feelings of self-doubt or self-worth I become busy and I will pick things out of my to-do box that really doesn’t matter. In the long run, this stuff is not going to move the needle, to use one of those awful cliche sayings. But, when I focus on the vision and I focus on the goal which to inspire others and to educate other. Then I can take special actions towards that and then I can say, “what is my next step?” and I do more powerful things. So, I think vision is very very critical.

{14:01} Carin

I agree. How would you guys… I know it took me awhile like my vision was here and then it was there. Last week I went through this moment of a Post-It moment and I had to take over my room with Post-Its. I was like this is so stupid. So, I was trying to get organized and streamlined because I will do this thing where I will do all these mundane tasks to keep busy and act like I am being productive. But, like you said, I am not doing anything to move the needle. So, it is very important to make sure you are prioritizing the things that will do the best for yourself, your business, your kids, and for everything you do in your life and having some sort of strategy behind that.

So, let’s switch gears a bit… What questions do you guys have so far? Feel free to shoot us some questions. Things like, what is it like being on the road? What is it like to catch a catfish with your hands in Vietnam? Um you know, Thai food poisoning for days? Things like those questions.

Oh yeah! So we are sitting here right before we get started and I look over at Kate’s computer. It has this little highlight that says, “I microwave my pants”. I am like, “What up on your computer?” She said, “Awesome! Can I hear the story?” And, I still don’t have the full story, so I am still curious, so go for it.

{15:03} Kate

It is just one of those little things that you have to deal with on the road. So, what you have experienced, you sort of getting used to it after awhile you are on a long term travel. And you tend to usually forget how it is unusual that you are used to things not working. Today what I realized was the one thing I really miss from home, more than my friends and more than my favorite places, is my laundry room. Because this morning I really wanted to go to the gym and my pants were still wet and I practically live in a basement and hadn’t air dry after 18 hours, I had to microwave my workout pants in an effort to have some gear to go to the gym. So, when you have a 20 piece wardrobe you don’t have extras like that. Which means I either go to the gym in jeans or I just don’t go to the gym.

{15:55} Carin

Usually, that means you end up in all black. That means most of your wardrobe is black.

{16:05} Kate

Yeah, so that means that is one of those little Nomad things. That was the starting of the post and I will kind of go on to other things I have learned in my Remote Year. Which, who I was talking to about last week is what we have learned on this trip and what this trip is kind of about. For me, I think this journey was learning how to live without.

{16:33} Carin

Agreed! So, the question from Kathryn says, ” What business have you worked on recently remotely that you have run into roadblocks that make you feel like you would approach differently now that you know different things?” But, would you approach it now differently?

{17:02} Kate

Absolutely! That is the benefit of hindsight. That is true if we knew now what we knew then we would do things differently. From a business standpoint … I started my own business right around the same time I started Remote Year. I abandon a lucrative business with doing that. Because I am an all in kind of person or an in the moment kind of person. But, in hindsight when I think of the timing and facing the challenges while on the road I probably would have kept a little bit of design work. That way I was a little more financially sound and so concerned about where the money was going to come from.

{17:30} Carin

Kristina had a question. What business opportunities are you missing out on by being abroad?

I guess the easy answer to that one would be stability, right? I have been in the game for almost 15 years now and being able to pick up a… whether it be a freelance job or I could have moved into a different role in Minneapolis or get a different job I think. There are probably other marketing jobs I could have gotten into but I felt like the timing was right and even as resistant I was to leave my job I was being pushed by the universe. Kind of like, “Nope, you are done here.” Moving on, so it was just timing. I had been planning on it for a very long time and longed for it for awhile. I was like we are going to do this. No matter if we sink or swim and no safety net we are going to do this no matter what. I think it is funny when people say, “Hey, how is the vacation?” I wish I could a vacation for a year. It makes my nostrils flare. I am like, “Nope. I am not on vacation.” It’s not like one of those who worked more hours or.. I have people like, that are watching this podcast, that can actually work 8 to 12 hours for free. It is just how we want to structure that work time. But, most of us are out here working very hard, trying to build something great or something with a purpose or something sustainable on the other side. That way we don’t have to go back to what Kate calls the “cubicle farm”.

{19:15} Kate

Some of us have to take care of what we do that is very creative. Like sometimes I have taken business meetings in alleyways in Asia. Because like you screw up the Time Zone on your calendar or your tuk tuk breaks down or whatever. You just don’t know what is going to happen.

{19:39} Carin

Like, some of us where the Time Zone changed, So I would have to get up at 2 or 3 am. I would get up at 2 and get ready and tail it to the office space and make sure I looked like I was ready for whatever. Because some of them were video interviews or whatever. You just learn to adapt, you are like, “alright, this is a new one for me.”

{19:48) Kate

Back to the previous question about what we have missed out on by being abroad? For my stand point, the way that I have built businesses in the past is being a part of the community and that has been challenging with the short amount of time that we have in each of these cities. So that has been learning different ways of learning on how to get involved and finding community online instead of actually finding local communities. I think that is just something we have to work through as Nomads if we want to continue this lifestyle. So, I am looking up new Meet Ups I can attend in a new city where I will want to meet some new local people to increase my networking or I attend a lot of conferences that way I can meet new people.

{20:40} Carin

Totally! There has been a lot of good ones this month too. So, I think it when you get involved in the local community you realize all the potential there is out there. This month I got involved with a group, Lean in Lisbon, a woman entrepreneurial group and during another even with them on Tuesday. You really kind of go, this stuff like that happens all over the globe and that is your chance to take those great opportunities as you want to and form those bonds.

We have another question from Kristina. How do you remain so positive during surprise cleanses, dog bites, Malaria, and other freak accidents?

I will be the first to say that I apparently have a problem walking and it is when I am sober. I wiped out, rolled, slid, and tumbled down some flights of stairs in Belgrade. I was like, “oh my god, is my phone ok? I don’t have money for a new phone right now.” “Did I lose any teeth? No, we are all good right here.” No, you got to think it is ok and it was just a moment. You all have had those days or those moments where you’re not feeling well and you need space. That is a hard thing with this group and like there is 60 of us and you’re like, “Can I just get a moment?” Right? And so, having your space or taking that space is a big thing. But, you have to let it out however you need to and take a step back and really be able to go, “Ok! A positive event is taking place and we are going out there.” I think for me it is having space.

{21:41} Kate

It is the space. I think for me it is… I start my day with gratitude and I try to return to gratitude at any giving point. Or at least I try to. So, in the morning, I have an actual morning routine where it allows me to stay focused throughout the day. And that includes writing some papers for you all that have seen the Artist Way and I also have an app called 5 Minute Journaling that I use for the 3 things I am grateful for, the 3 things I can make great and an incantation. When you are in gratitude it is really hard to be angry, to be upset, or to be anything else. I have to be honest when there were days in Asia where I had guiardia or when I thought I where I might die from rabies that after being bitten by a dog and getting the wrong treatment. And the best I could do in gratitude was at least I was still breathing. But, I still came up with 3 things I could be grateful for and that allows me to keep moving.

{22:49} Carin

So I see it says strength and lots of positivity from you both is so uplifting. Thanks, Mom. Yeah, it was my aunt and she says, “Thank you both for the adaptability and flexibility in your endeavors. I think those are qualities that everyone needs being so far away from home.

Thanks, Aunt Kris! So, what is the next… So, unfortunately, Kate is leaving the group after this month. She is going to continue to focus on her own endeavors on her coaching business. So, what do the next couple of months look like for you?

{23:27} Kate

The next couple of months looks pretty exciting for me. It is weird, but as much as I love my remote European family, and I really do love you guys and I am going to miss you dearly. I am really looking forward to new adventures and having the freedom. It is kind of accelerating to think that I can go wherever I want. Right now I am going to Barcelona which is a city that I just meant just a week ago and we had a fast love affair and it just captured my heart. I just love it there and put my head down to do work for about 6 weeks. Then I am going to the UK where I have a number of friends and where it feels like home. Then I don’t know. Yeah, probably find a place for the winter because I don’t love winters. And continue to work with awesome women, continue to grow, and help inspire others to travel. Because that is part of my soul.

{24:24} Carin

Oh! I love that. Before we get ready to go, is there a good challenge you can leave this group with? Like something you give them to think about or challenge them with? Something that will better or enrich their lives over the next week?

{24:48} Kate

I think the biggest challenge I can give anyone is letting go of things that embarrass you. Learn to love it. It is the number one thing I have adapted in my life that allows me to live in gratitude and grace every day. And you can start really small. Start by looking at your closet and those pair pants you haven’t worn in 5 years, just toss it. Get rid of anything that is isn’t pleasing you or serving you. And just move to bigger things like relationships, jobs, and cars.

{25:11} Carin

I always hear people complaining about their jobs, that is just the big one, I am like, “Get rid of it and find a new one”.

{25:26} Kate

That’s it! Stop complaining and get a new one.

{25:30} Carin

Just remember people, you have got skills.

So, what is next for me? Well, this is very exciting but I just pulled the trigger the other day and I just shared this with Kate just a second ago, I am going to Africa on Saturday. I just booked a trip to Africa. I am going to spend 4 days in Merica and do some cooking, and some maybe camel riding. I don’t know but there is going to be some pretty cool stuff. I will probably go take a Turkish bath and I am going to live in ??? for a couple days. So, I am really excited to go to Africa. It has been on my list for a very long time. This will be my sixth continent. So, that is 6 continents in 6 months. We will see that gets me and I will meet the rest of the group in Bog. My ultimate goal is too hot off 7 continents. I know it sounds a little lofty and a little aggressive. But, we will figure that out later. The living in Minnesota is close enough to live in Antartica so it is cheaper I am sure, but we will see when we get there. That will give me a little time.

{26:42} Kate

Maybe you will meet a hot scientist.

{24:46} Carin

Maybe, that is a possibility. I would like to be a penguin mom there. I want to thank you guys for tuning in and I hope to be able to have more opportunities to have these in each city I am in. If not twice with some very interesting speakers. Go to my Pairs Well With page and there is a link about Kate to learn more about her and sign up for a free no obligation consultation session. She is wonderful. So, check out her page and like my Facebook page so you can get all the upcoming things.


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Hey, I’m Kate! I’m a designer, digital nomad and founder of Six Figure Freelancers – I love to help talented tech pros start businesses.

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