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Ep. 143: How this former attorney left the American dream to become a remote travel writer.

In this week’s episode, I speak with Alana who is a Chicago-based attorney turned travel writer and founder of Course Charted, a source for slow and sustainable travel. 

As a child, Alana fled Kiev after the Chernobyl disaster to eventually move to the United States. She learned to be entrepreneurial when she left her homeland with just a handful of suitcase and eventually became a lawyer to follow the American dream. 

However, this changed when she realized that the typical American Dream was not for her and left to become a travel writer and remote entrepreneur. 

Listen on to find out how Alana left the American dream to pursue her personal freedom.


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Listen Below:

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Transcription:

Debbie:

Hey everyone, thank you so much for joining us. I’m so excited to be here with Alana. Hey Alana, how are you?

Alana:

Hey Debbie, I’m good. Thanks so much for having me on today.

Debbie:

I’m so excited for you to be here. Can you tell us a little bit more about you and why you live an offbeat life?

Alana:

Yes. So I think you kind of look back on my life trajectory. It would seem very on beat for a long time. I sort of had the typical immigrant child, overachiever experience when I first came to America. I think your yourself came from the Philippines, right? So you sort of had that similar experience growing up.

Debbie:

Yeah. Absolutely.

Alana:

Where you’re encouraged to go to school, go to college, go to grad school, get a job and there’s a certain handful of “acceptable professions for immigrants”. I think you know what I’m talking about. My friends that have also immigrated, joke around that lawyer, doctor, engineer I think is up there. So, my life looked a lot like that. It was very much framed both by parental and societal expectations as far as what I should be doing. And I was kind of following that ’till I went to high school to college, to law school to affirm job, and everything was sort of flowing in that direction.

I left with very substantial school loans as I think I know a lot of young people out there do, especially in America. It is very prohibitive I think to even think about creative professions when you leave school because it’s so expensive. And a creative professional sort of not in my mind for a very long time until I found myself, kind of extremely unhappy.

Having this sort of Groundhog-type day where you start living the same day over and over and there wasn’t like any particular “aha!” moment. I think a lot of creative say that there was like a big turning point in their life or like something sparked in them then, all of a sudden, they started pursuing a creative profession. I think for me it was more like a constellation of events that came together and made me sort of like question my life, question why I was doing the things that I was doing and why I was still in a profession that was consistently making me unhappy and unfulfilled. I think one of the things that sort of, maybe it wasn’t a changer of my life, but it was sort of a kind of made me reevaluate for a moment was when my grandfather passed away.

He was a sort of constant, very important figure in my life. He pretty much helped raise me when my parents came to America. They were working multiple jobs and it was sort of me and my grandpa for a really long time. And when he passed, it sort of brought the question of mortality and what am I doing with my life more to the forefront of my mind. It didn’t make me change anything at that moment, but it got me thinking in terms of when he was looking back on his life, how did he feel and what must have been important to him at that time? What was a comfort to him? And when I look back on my life in that way it sort of made what I was doing feel very unimportant, it felt very unsatisfying.

The work that I was doing, the things that I had learned. I think I did feel a passion for the learning aspect, but I didn’t really feel like I was touching anyone’s life. I didn’t feel like at the end of the day I could look back on that day or that month or that year and feel fulfilled by the work that I had done. So that sort of made me take a look around at the people at my firm as well in the kind of life that they were living, whether or not they seemed happy. I think it’s no secret that the profession of law is undoubtedly one of the unhappiest. I think they’ve done happiness studies on lawyers and they’re routinely just like abysmal figures. There’s a lot of alcoholism and mental health illness in the law profession.

I think that has a lot to do with the way that people practice law in America. It’s not a problem with the substance of the work. I think you can do really great work as an attorney but I think the firm culture can be very toxic, especially if there is a part of you that’s creative, there’s a part of you that wants more personal human connection with people. I don’t think that that type of life is conducive to that. So I think all of those things got me down the path where I was thinking about whether there was a way out of this the same path that I’d been on for a very long time and I started having conversations with my husband who I am extremely, extremely lucky for. I mean, he was instantly supportive and he said like, “Hey, I know you’ve been working for this but that does not mean that it’s your future.”

He was very supportive to be focusing on what makes me happy. He asked me that question many times and at first, I couldn’t answer it because I didn’t even imagine that there was a possibility where I could combine my professional background and education with a creative outlet. But he didn’t stop asking that question. He kept pushing me to really try to think about what would make me happy. And ultimately he encouraged me to take the leap and leave firm life to start trying to pursue things that were more creative.

And I think, for me, travel was a big part of that. My life had started out with that big move to the United States. And then I think that like risk-taking creative jump in, part of me had been dormant for such a long time that it wasn’t until I left firm life that it was like awakened and then I could pursue that.

Debbie:

Yeah, that’s a great husband there. That’s a great partner because a lot of times we kind of put ourself in a position like you had mentioned where we come from an immigrant family and we just followed that path because that’s what is expected of us for a lot of people, even if you’re not an immigrant family, especially since you went to school for all of those years and it’s just really tough to transition out of that and maybe take yourself out of a financial situation that becomes harder for you and your significant other as well.

So that was a really risky but also really bold decision for you to be able to do. Now, when you finally decided to do this and obviously your partner was with you, your husband was with you on this a hundred percent. How did you prepare for this big change, right? Because I’m sure you’ve talked about financials and how you’re going to move on, what you’re going to be doing after this. Was there an actual kind of decision making? Like did you actually plan this out or was it just something that you leaped into?

Alana:

I’m definitely a planner, so it’s not in my personality to like fully leave, even when I’m leaving I feel like it’s more of like little tiny steps into the leap so, I definitely planned. One of my priorities was to get into a position where I could pay off my school loans. So that was very important.

I felt like the student loans are definitely a burden and if one is in a position to try to stick it out in a job that, even if it’s making you unhappy, I think if you start thinking about leaving it may still make sense to stay for a little while and get to a good position where you can pay off your student loans and also create sort of a savings cushion for yourself because that sort of takes some of the pressure off of making those moves.

My husband and I are fairly frugal people, to begin with. So, we definitely had a talk about finances and things like that and living within our means. And then just figuring out how me being able to pursue something else would fit within a new life for us.

Debbie:

How did you decide what platform to actually go into, right? Because you knew you wanted to go into the travel aspect of it and you wanted to do something more creative but why did you decide to do a travel blog rather than like a YouTube channel or something else?

Alana:

Right. So it actually sort of came upon me organically. It actually started with social media first. That was an outlet for my photography, for dabbling, and travel writing kind of learning to write like a human being again. I spent so long writing for judges and other professionals in the legal space, so writing Instagram captions, stories, and just connecting with people on a personal level.

That was a really important first step. And it was something that got me even more excited and passionate about photography. When I shared my images and people said like, “Oh wow! Where is that? It was like some little gem, like the hidden place that I found and I felt at the time, these are insignificant things but people got really excited about it and that got me even more excited to share that type of content.

So it was actually kind of ironic that it was social media of all things that really got me excited again about travel photography and travel writing. And it was the community that inspired me to kind of keep working on the photography and the content that I was putting out there. I constantly got comments asking me like, “Oh, do you have a write up about this place? Is there more information about it?” And the more questions that I got, the more I could tell that I needed to create a space where I wasn’t, sort of, limited by the character limits of Instagram or Twitter where I could like really share something deeper about the travel experiences that I was experiencing and that other people wanted to know more about. And that’s what led me to start CourseCharted.com.

Debbie:

It’s really interesting because you were able to take your knowledge already and also help people out as a lawyer and you were able to take it into something more creative. And you started this website which is really great. So it’s not like you completely took yourself off from being a lawyer, you’re still using it now. And one of the things that we’re actually going to talk about for our extended interview is how as a creative, you can create these contracts before you sign anything with brands.

And that’s one of the things that has been able to help you, which is really incredible because as creatives we don’t really think about that. So I think you’ve done a really great job transitioning and also putting together things that have been your expertise to something that you also love to do right now.

Alana:

Thanks, Debbie. Yeah, definitely.

Debbie:

Now, what about when you finally left your nine to five as a lawyer? We all have this moment, I’m not sure you have it, but I had it, that “what now?” moment after leaving and you kind of realize that you finally did it. What was yours like?

Alana:

Oh, 100%. It’s terrifying, I mean, it’s still terrifying, like leaving the security of a constant paycheck and a secure job is very difficult. It’s definitely not without its challenges. Every day that you do a creative pursuit like from starting a website (which is what I did), photography, travel, writing, things like that, nothing is guaranteed. And when you’re working for yourself, everything is, “I knew completely.” If you’re working in the corporate sector, you, sort of, have that support system. But as a solo entrepreneur, everything falls on you and that can be very hard. I’m sure you know all about that. You have to wear a lot of hats and you have to be willing to learn a lot of things.

You have to always be open to learning something new to hearing feedback – that’s a huge thing. You have to always be open to people giving you feedback but also encouraging people to give you feedback. So you have to become a really good listener and a constant learner because when I started doing this, I knew nothing about starting your own website. I knew nothing about coding, I knew nothing about literally anything in that field.

So it was becoming a student again, just in a different sense, and learning all about it. And it just doesn’t stop being terrifying. Even chatting with you today, it’s really putting myself out there and it’s very scary because even though I’ve spoken in front of judges countless times but talking about myself is something that still kind of intimidates me and terrifies me.

And honestly, I would rather flip this interview around and start asking you dozens of questions about you because that’s sort of my comfort zone. But I’m trying to everyday embrace the fact that I’m stepping outside of my comfort zone is the way to go, It’s the way forward.

Debbie:

Absolutely. I definitely get that feeling of “what now?” and then it’s another issue, right? You finally left the thing that you didn’t want to do with your life, but then what on earth are you doing? There are so many questions in your head, even when you’re actually creating income from it.

There’s like imposter syndrome. If you’re actually doing what’s best for your company, for yourself or your family, there are so many things that are going on in your head. That’s why I tell people all the time, “If you have an issue, it doesn’t stop just because you left your nine to five. There are other issues, but it’s just the other thing, if that’s really what you want to do, you’re going to have an issue, either way, so you might as well do something that you love and have an issue with that, right?”

Alana:

Exactly. If you’re doing what you’re passionate about and the issues are fulfilling in a way. Do you know what I mean? Like when you encounter a problem and it’s kind of a pain in the butt at that moment but then when you get past that you just feel like this immense kind of rush from it, and you feel like now you can really like push forward towards something that you really care about. I mean, I think that’s the most important thing that you’re pushing towards something that matters to you.

Debbie:

You know at the end of the day we’re going to be miserable if we don’t do what we want to do, I know, for a lot of people, that’s really tough to do, especially if you have a lot of responsibilities. But I’m sure you can do something here and there to get yourself closer to that.

I tell people all the time, “Just do one thing that’ll get you closer because it’s not just about all or nothing, you don’t have to quit today and all of a sudden that’s what you’re doing and you’re struggling. That’s not something that you want to do especially if you have a family. And if you’re in debt, it’s definitely not sustainable. But doing something, even one thing every day will get you closer to that. And if you are just persistent, it’ll get you there. So it’s not about just leaving, it’s about doing something.”

Alana:

Definitely.

Debbie:

Now, you have gone through all of these different things with your journey, what has been the biggest setback that you had encountered? Even right now as an entrepreneur, what is that and how do you usually get over it?

Alana:

It’s definitely my perfectionist tendencies and I know that that is like the worst interview response you can ever give, right? Like if you go into a job interview and they ask you what your biggest weaknesses and you’re like, “I just try to be really perfect.” That is a terrible answer. But I mean in this case, this is 100% true about me, I’m a perfectionist in a very like type A personality. Maybe that’s why I went to law school in the first place but I won’t go into like the psychology of the law student. But I think there is like this type A part of my brain that tells me, “Oh, you don’t know enough so you shouldn’t make this decision.” You need to learn more, right? But you can literally do that forever and never make a decision.

So for me to keep moving forward towards my goals, I’m still working on this, become comfortable with being uncomfortable and making decisions with imperfect information. I feel like that’s going to be and always struggle for me to do that, but it’s something that I’m working on.

If there was one thing that I would tell my past self, it would be to launch Course Charted sooner because I literally agonized over this website for such a long time, with this like my imaginings in my head of what it needs to be like, right? This kind of like perfection and, gradually, I understood that when you’re running a website it will never be perfect – there’s really no such thing.

There will always be tweaks along the way and you may as well put it out there and start getting feedback. So I think that’s the mentality that I’m trying to bring into 2020, like put it out there, get the feedback and then change if you need to.

Debbie:

Yeah, I really believe that’s true. I think we’ve all agonized with that, especially as creatives. And that was one of the biggest mistakes that I also made when I first started out my other businesses is I agonized on what it looked like. And another thing that I didn’t do was actually focus on creating income from it and making it sustainable.

And it was just all about the look and how it’s going to do this and that. But, at the end of the day. It’s like you said, it’s never going to be perfect and you just have to put it out there. But, a lot of us are very type A, especially as entrepreneurs. So that’s really hard.

Alana:

Right! Very hard. Constant struggle.

Debbie:

Yeah. Now, when you finally are starting this company, and obviously we all want to make this more sustainable, so we great income from this, how were you able to land your first client?

Alana:

I think that working is really huge. This is something where law school and doing the type of work that I did in the legal field really helped me. In law school we even had a seminar about networking and the importance of talking to people and just asking them, “Hey, how are you? What challenges are you facing? What can make your life easier?” Just talking to the people around you, people that you meet, in the line at a coffee shop people, you meet on the street, in the subway, just chat with people and you would be surprised of how many connections and friends and just like wonderful people you can meet. And you can be a value to them and they can be a value to you and it’s really a beautiful thing.

So I think that’s probably the most important thing is not to think of it in terms of like, “Oh, I’m trying to land a client.” I think to think of it in terms of trying to connect to someone and I want to learn about what problem they have that they need to solve. And that’s sort of what led me to start thinking about combining my legal expertise and my creative passions to help creators that are constantly facing these questions of should I brand myself? What does it mean to brand myself? How do I protect my photography from being ripped off? How do I protect my writing from being ripped off? There are so many issues in this space that I, as a creator and my friends as creators, have faced that got me thinking about potential solutions that could make their lives easier.

So yeah, that’s my biggest tip is just talk to people, network, talk to people and think of it as forming a connection rather than trying to land a client.

Debbie:

Yeah. And you made it really great for yourself because you really found people’s pain points. And that’s one of the things that we learn in business. It’s like business one-on-one is to find people’s issues, problems and learn how to solve that. And that’s your business right there, especially if your issues sit in solving that. So that’s a really great way of doing it.

Alana:

For sure. And I know there are ping points because I felt them too. It’s like I felt the pain of, seeing my photo show up on a company’s website and I’m like, “Hmm. We’ve never even spoken. How do you have my photograph?” And I’m like, “What do you do in that case?” Luckily with my background, I know the steps that you need to take to make sure that you’re protecting your work and that if a company wants that value, then they go through the proper ways of getting that. Yeah, so definitely useful.

Debbie:

Now, Alana. What are some of the best resources that you’ve used to start your website and maybe something that would make your task a lot easier when you were creating it?

Alana:

So my hosting platform and totally unsponsored, but I really do love them, they’ve been really helpful. I host with SiteGround and they’ve answered every bogus weird question that I’ve had about my website and they’ve been really, really amazing. If you get a good theme developer that is also very helpful.

There are some people that are very engaged in the themes that they develop and they’re willing to ask the question to answer your questions and that’s who you should go with because if you don’t have that coding tech background, I think those can be invaluable resources. As well as doing some kind of basic sort of coding tutorials. I mean, what’s so amazing right now in this age: the internet, and YouTube. You can literally learn pretty much anything. I think that you want to learn from YouTube.

I’ve done like the repairs in my house for YouTube, I’ve figured out how to do things to my car off of YouTube. It’s just crazy and you can do the same thing with whatever it is that you’re working on in the travel space. I think there are a lot of resources out there. I know Udemy and all sorts of type of lessons, Academy type streaming services are out there and I haven’t utilized them enough to be honest. But the information is out there. I think it’s more about just kind of exploring your resources.

Debbie:

I absolutely agree with you on that one. YouTube is a lifesaver and we can find so many things there. Well for me, one of the things that have been really painful as an entrepreneur when I first started, when I created my site, was finding the perfect domain name that’s already not taken. It took me weeks and sometimes like when I started a new website, it would even take me months because I want it to be perfect.

I’ve brainstormed so much and it just gets so frustrating, especially when you look online and it’s already registered. I just can’t take it. That’s why I’m so glad that I’m actually partnered with Hover.com because they have over 300 domain name extensions to choose from which is so helpful because no matter what type of brand you want to build, they have a domain name for you and the best part is they also offer technical support to answer any of your questions.

As you said, it’s really important to have that because we all have those frustrating moments and having a helping hand is always a major bonus for all of us because I’m always so confused with anything technical. So if you guys want to know more about it, make sure to visit Hover.com/theoffbeatlife to get 10% off all new purchases and find the perfect domain name for your business, which has been so helpful for me. I’ve been cranking my brain, just finding new names for new businesses and when I have clients too. So it’s been super helpful.

Alana:

Yeah, that’s essential.

Debbie:

And that’s another thing is type A people, right? We need that perfect name all the time and it’s like, “Oh my gosh, somebody else has it.” And you had to keep going over and over again.

Alana:

Yes. But have you ever tried making it offer?

Debbie:

Oh, I haven’t done that yet. Have you done that, Alana?

Alana:

I haven’t. Luckily the name that I wanted was available but there were a few that I was kicking around and I did look at some of the pricing, so I did consider it.

Debbie:

Yeah, that’s also another great business to have, right? is to sell those domain names. So that’s another way for you to use Hover as well is to look up some really great names and maybe sell them and start your business a different one.

Alana:

Yeah. And I think some definitely people do that. You could tell that some people are squatting some very nice looking domain names.

Debbie:

Exactly. Now, going back to when you first started your business, how much money did you actually save before you became an entrepreneur and how did you make that last?

Alana:

I don’t remember what the actual amount was in my savings. I think my focus was so much on my law school loans, like college loans, that I was really focused on being debt-free, which was really important to me. I did have money in savings. There wasn’t one particular dollar amount that I was going forward, I’m like, “Okay, now I feel safe.” Because you’re never going to feel like,” Oh, okay, this is a safe decision to leave the corporate world.” But I was thinking about when I’m traveling, how am I spending? How am I budgeting?

My husband and I are sort of like that, we both like to track expenses and I think that’s really important to kind of know where your money is going. I promise you that if you start tracking expenses, you will find all sorts of like miscellaneous nonsense that you spend money on.

And it’s not until that’s salient where you can do something about it, right? So sometimes you have to just like be confronted with the numbers. And my husband and I have gotten really good at that over time. We’re also kind of like the extreme couponers of travel. So, I have an entire section on CourseCharted.com called travel smarter, which I am dedicated to the art of value travel. And I want to like focus on the term “value travel” because it doesn’t necessarily mean settling for the cheapest option. I know a lot of travelers out there are kind of they’re beyond the hostel life.

I’ve done hostels successfully and I’ve had great experiences in hostels but sometimes you want something different and you would be surprised when you start focusing on like the cost and the benefit of what you’re getting, which is what value travel is, that you can get some really great accommodations for the price of like getting an individual room at a hostel.

So yeah, I’ve dedicated this entire section so that I have like an outlet to share with others like this art of sort of hacking the travel space and finding ways to travel very inexpensively or sometimes free based on like points and miles and maximizing that because there are really a lot of ways to do it if you dedicate a little bit of time to it.

Debbie:

Yeah, I love those types of tips and they’re so useful. It allows you to really afford travel when you don’t have a lot of budget for it, which most of us, we don’t.

Alana:

Yes. Or, I mean, if you want some of your budget to go elsewhere, like eating and things like that. Everyone’s got to eat so you can’t just spend money on travel, unfortunately, right?

Debbie:

I know and I love food. So yeah, most of my money definitely goes to food.

Alana:

Yeah. I can’t blame you, we are sort of eating out people. We’ve kind of gonna handle on them more, sort of save the eating out for when we’re traveling. I try to cook at home as much as possible and that’s like a great way to budget too.

Debbie:

Now, let’s fast forward to 50 years from now and you’re looking back at your life. What legacy would you like to leave and what do you want to be remembered for?

Alana:

I want to be remembered for democratizing the legal field and that’s like a weird term but what I mean by that is I think right now the legal field for most people is sort of this like black box, right? Like when you have an issue, you hire attorneys, you don’t really know what they do, they use big fancy words and then they charge you a lot of money. And that’s sort of how it goes. You either have to spend a lot of money as an entrepreneur or you have to go it alone and kind of take a chance and see what happens.

What I’m trying to do is to carve this middle ground where I take the legal knowledge and the background that I have and I use it to make legal concepts both understandable and something that can empower creators in the travel space or small businesses to do a lot of this kind of work and this planning themselves, right?

Whereas normally they would spend thousands of dollars for something that actually does not take that much time and they could probably do themselves. I feel like a lot of people just don’t know the difference because the legal field is so murky, they just don’t know like, “which things can I handle myself?” versus “what do I need an attorney for?” And I want to help people find that sweet spot and empower them with that knowledge so they can do a lot of the work themselves. And I think it would make entrepreneurship and creative work a lot more accessible for people if they weren’t faced with having to spend so much money just to get their business off the ground.

Debbie:

Yeah. That’s a really great way of making that impact especially, again, that’s another pain point that a lot of us creatives have. So I love that legacy that you want to leave.

Alana:

Thank you.

Debbie:

What are you working on currently that is really exciting for you?

Alana:

So I’m actually heading to Thailand next week. I’m getting very excited to flood the Instagram feed with some photos of warm places. For the longest time, I’ve been sharing like all of these wintery wonderland shots from Northern Sweden including shots of the Northern lights, which was amazing. But I think it’s time to kind of switch up the cold, especially since I’m here in Chicago right now and we just had a huge snowfall for a warmer climate.

So Thailand will be wonderful I think. And I also have a project with a tourism board coming up and another one with the hotel that I can’t really chat about yet. But as soon as I’m able to disclose things, I always put them on Instagram stories at Alana in Wonderland and also on Twitter – @coursecharted (same as the website). So you will hear it there first.

Debbie:

Perfect. Well, thank you so much, Alana, for speaking with us today. I really appreciate all the knowledge that you gave us.

Alana:

It was my pleasure, Debbie. Thank you so much for having me. And if you want to reach me or anyone else wants to reach me, please head to CourseCharted.com and get in touch with me there or Instagram or Twitter.

Debbie:

Awesome. We’ll make sure to follow along your journey there.

Alana:

Thank you. And I’m sure you’ll link all this up, right?

Debbie:

Yes.

Alana:

Great.

GET THE EXTENDED INTERVIEW WHERE ALANA SHARES CONTRACTING TIPS FOR CREATIVES WHO ARE PARTNERING WITH COMPANIES.


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Show Credits:

Audio Engineer: Ben Smith


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