top of page
Post: Blog2_Post

A Story About Overcoming Fear with Alyssa Dotson

girl smiling because she overcame fear and wasn't scared to take big risks


For the very first guest interview of The Goodbye July Podcast, I'm excited to have Alyssa Dotson on the show. Alyssa and I met in El Salvador and, after she became a client, she then became a friend.

As I got to know her, I got to understand her story, and I found it to be inspiring.

In her early twenties, Alyssa faced a health scare that helped her vow to live - truly live - her life... and she has.

In the last 2 years alone, she's moved abroad solo (twice!), is learning how to surf and skateboard, and recently got her financial sh*t together so she could calmly rebound from a layoff she was afraid would happen, and ultimately did.

She's currently living here in El Salvador where she surfs, skates, and explores her creative side through art and music.

I am so excited to bring her onto the show today so you can hear her story.


[JT] Alyssa, I'm so glad to have you here. I'm excited you're my first guest! We have become good friends here in El Salvador and I'm so happy to have you on the show. I know I've sent you some questions in advance, so we're just going to start from the top.

Could you tell the audience a little about yourself and what you've been up to the last couple of years?

[AD] Thank you so much for having me. The last couple of years have been a whirlwind; life has brought me to this beautiful place, El Salvador, and it's like Disney World. I never expected to be here, but I was living the "normal" life in the suburbs in North Carolina, I'd been in a long-term relationship for 5 years and I was working in the pharmaceutical industry when I started dealing with a lot of health issues and stress. I was 25 years old and already tired of the rat race and knew I wanted a lot more.

I went on my first-ever solo trip for my 25th birthday 2 years ago to San Diego and that's where I stood up on a surfboard for the first time and I said, "Okay, this is my personality now," and decided I was going to move to San Diego. A couple of months later, I had plans to do that, and then I got this crazy opportunity to go do hair modeling in Italy.

A couple of weeks before I was supposed to go to San Diego, I canceled that and decided I'm not going to work right now; I'm going to take some time off to heal from the health issues I've been dealing with. I had a good amount of money saved so I booked a one-way flight to Italy and left my relationship and started this whole adventure.

In a way, it was an easy decision because I was fed up with the way things were going and so bored, but I think I was also at a point where I felt like I had nothing to lose. So I got to Italy; I landed with all my stuff - 4 huge pieces of luggage - and I just figured it out. I had pretty much no plan, I just knew I was going to this town called Cortona and that I had an apartment waiting for me from this hairstylist. I hadn't seen it, he just told me he had an apartment waiting for me, he said I could babysit for him, and that we were going to do hair modeling. And I said, "Cool!" and a week later I was there.

Even just landing and then taking four different trains to get to this small town in Italy was crazy and a lot more happened in the 5 months I was there, but it was a huge confidence boost, as challenging as it was because I thought, "Wow, I really did that, all on my own." I felt so capable of myself for the first time. I had this elated confidence and a big ego boost when I got back from that experience even though no solo travel or travel in general moving in general to another country ever goes perfectly, I feel like I learned a lot.

After I got back to the States, I wanted to move to San Diego again. I set up an apartment and got a job because I had $500 to my name. I met a few people while I was traveling that were digital nomads and, although I'd never heard of the concept before, it inspired me. So I came home and set my intention: I'm going to get a remote job in tech, and I'm going to move to San Diego and surf. Those were my 2 things.

And I wasn't worried; I had a deep sense of faith that it was going to work out. I was sitting in my parents' house with $500 and started coaching gymnastics for a bit while I applied for jobs and it just so happened that I got the first job I applied for at a fully-remote company. I set up a sublet in San Diego and booked a flight there. And then, about 3 days before my flight, the girl I was going to be subletting from decided to rent the apartment to someone else. And I thought to myself, "Dang, San Diego just isn't meant to be."

That same day I just happened to be scrolling on Facebook in a group I'm part of called Girls Who Can't Surf Good and a girl posted saying she was going to El Salvador for a few days next and asking if anyone wanted to go. And I thought, "Well, I'm not going to San Diego anymore." And something in me just told me to do it. I hadn't planned on coming to Central America; it never crossed my mind, it was so random. But it was my birthday and I was bummed about not going to San Diego and I thought, "You know what, I should do this."

It was a really cheap flight, I think I paid $75. Two other girls had responded to the post: one was in Charleston, South Carolina and the other girl plus the one who made the post were in Florida, and I was in North Carolina. So I drove to meet the girl in Charleston, and the two of us drove together to Florida - we were up all night - and, as soon as we got to Florida, we went to the airport and flew to El Salvador. It was just for 3 days, but that trip just immediately made me feel very connected to El Salvador.

The surfing didn't go so well - there's a reason I'm in the Girls Who Can't Surf Good group - but it made me really determined and made me want to come back and improve my surfing here, so I started the job that I got a couple of weeks after that trip and, since it was fully remote, I decided to just keep coming back to El Salvador. So I came back again in September and worked and, on that trip, I found a place long-term to stay for October and November. And I just kept coming back - something about this place just really feels like home, so here I am.


[JT] That's awesome. It's so cool because, as I said at the beginning of this, I knew parts of your story, but I hadn't heard the full extent of it. I knew you went to Italy to do hair modeling, and you'd mentioned San Diego a couple of times, and of course, I knew you came to El Salvador in the end, but what I hadn't heard was all the details.

Especially what stood out to me is how quickly you made many of the decisions, and I think that's really cool because I'm somebody who probably overthinks decisions before making them; I don't trust my gut. To me, it sounds like you had a gut feeling and you were trusting your gut, which is great because that's something else I wanted to discuss with you which is: you've moved abroad solo twice, and it sounds like you did both pretty quickly, so I wanted to understand what the emotional journey was for you.

It sounds like it was a gut instinct, but maybe you could talk more about that and how that felt.

[AD] The first time was definitely a shock to everyone, even me. I had gone to Italy a few years before for a family wedding (I'm half Italian), and the hair stylist for that wedding fell in love with my hair. This was right after I graduated college in 2018, and he mentioned a few times, "Come back and model for me."

I didn't take it seriously at first; I was very much thinking, "I want to go back to the States and work my job in the field I got my degree in," which was exercise science; I was working as a physical therapy assistant at the time. The stylist and I stayed in contact on Instagram, but nothing serious.

One day I was sitting in my cube at work and something told me to reach out and check on him to see how he and his family were doing, and his response was, "When are you coming back to Italy? Are you going to come model for me?" and I'd already put in my 2 weeks at that job and the plan was San Diego, but I thought, "You know what, this person's saying I have an apartment and a job and things set up for me, and this is a once in a lifetime opportunity. I have to do it."

I started telling everyone I was moving to Italy before I even had a flight or any details, but because I told everyone I felt like, "Well, now I have to do it." And it didn't really feel real until I was doing it. I was telling people, "I'm moving to Italy, and I'm going to be a hair model," but it didn't register until I booked the flight, and was going to the airport and I thought, "Am I actually doing this? This is insane."

I had, to me, so much money (I had $10,000 saved) and I got there and my rent was ~$400 and I thought, "Wow, I can just live forever!" I didn't check my bank account the whole time I was there and just did whatever I wanted. It was amazing. It was freeing, but it was also very emotionally challenging. I had just left a 5-year relationship and had just moved to a country where I didn't know anyone and was in a town with only 400 people which ended up having so much small-town drama.

I was like the new shiny American in town, and it was the middle of winter. I got there just before Thanksgiving, so not the best time to move to a small mountain town in Italy, but a unique experience nonetheless. But yeah, I just started telling people I was going to do it and then I was like, "Well, I guess I have to do it."


[JT] Yeah, that's what I was going to pick up on out of everything you just said. I've read and experienced something similar, where if you feel like there's a hard decision to make, and you have a bit of the gut feeling of, "OK, this is what I think I need to do," if you start saying it before you've even 100% committed to the decision, not only does it add a sense of accountability, but you're also affirming it to yourself.

And it sounds like that's what you did, which is great.

Italy sounds like the more emotionally challenging move since it was your first time, you were leaving a relationship and had some health issues going on, but I'm curious what it was like then when you came to El Salvador. Was it like, "OK. I've done this before, I know what I'm doing now"? What was that like?

[AD} El Salvador was way different. Again, it was super unplanned and random, but I knew it was a small town so I thought, "OK I'm going to another small town in a foreign country, I know how to conduct myself there." And I did come with a group of people the first time, so that was another way to ease into it.

One of the girls I came with had been here before. I think I was a little traumatized to step back into traveling again completely on my own, so I'm glad I did come with a few people even just for 3 days, which was super quick, but it helped me feel comfortable to come back by myself.

But it was a very different mindset because I was like, "Been there, done that." But my family was really scared, and I too had some fears because El Salvador sounds sketchy and I'm really glad I pushed through that because I really battled for a few days when I started considering coming on this trip. I thought, "Am I really going to do this?" I was really nervous about it being dangerous, the people, and I'd never been to Central America - and that was the only part I was really nervous about, it wasn't the travel or the surfing, or where I was going to stay; it was: is this a safe place to come?

And then as soon as I got here, that went away. I mean, I felt less safe in Italy sometimes. I actually got robbed in Italy twice, and I've never been robbed here or even felt like I was going to get robbed here.

[JT] Wow! Okay, that's interesting. We had the same experience coming to El Salvador the first time - we landed at night and we were so scared driving from the airport to our Airbnb, but I feel the same way. Honestly, in some places in the US when I'm back home, I feel more unsafe than I do here, and we've also been targeted for robbery in Barcelona where a kid ran up to Cory while we were biking and tried to grab the watch off his wrist.

So, yeah, I'm glad to be in a place where we can both feel safe, which is an interesting learning because, like you've experienced, when you think of or search "El Salvador" you're going to get all this horrifying, scary stuff so it's amazing you were able to push through that.


Now, you touched on the finances, and I want to talk a bit more about that because I think a lot of people struggle to do things they want or live their dreams for fear of money. So maybe you can talk a little more about the decision to move abroad from a financial perspective - how did you plan for that, what were the different steps you took and, if there was any financial fear, how did you work through that and decide: "I can do this, and everything is going to be fine"?

[AD] With Italy, there was no plan. Luckily, I've always been mindful of saving money and I've never been a frivolous big spender, so I think that's something that set me up well. It's just an intrinsic habit I have with money, which is that I save most of my money and I don't buy unnecessary stuff. But I also didn't live in a way where I felt like I was not buying everything I needed or wanted.

But I think the way I grew up and thought about money allowed me to set myself up without consciously thinking about it because, obviously, I wasn't planning on quitting my job and moving out of the country, so when I went to look at my finances, I was like, "Wow, I have $10,000."

Also, people my age don't really talk about money, so I didn't have a scale of whether that was a lot of money or a normal amount, or if I was doing well or what, but I knew my rent was going to be about $400 and, just doing the quick math on that, I felt like I'd be fine for awhile. It wasn't anything I felt anxious about. I was just like, "OK, I have $10,000. Cool."

I will say, though, that I had no idea how long I was going to be there so that made me nervous before I went, but I thought, "Well, even if I just go for a month and come back, or even 3 months like a study abroad," - there was no plan on how long I was going to be there, I just knew I needed to go see what the opportunity was and I figured if worse comes to worst, I'd just buy a flight home in a month and think, "Well, I tried it," and just go back to my parents' house.

I'm really lucky in that sense, as well: I can always go home. And I know a lot of people don't have that option. But, for me, I know if worse comes to worst and I have $0 in the bank, I have a roof over my head and I have food, and that's a huge blessing and comfort. If every single thing goes wrong, my basic needs are met. So I think having that security has helped make me not be so anxious about money.

But, again, in the Italy timeframe mindset, I was not really thinking about money. I didn't check my bank account the whole time I was there, mainly because I didn't have Wi-Fi or data - my sim card didn't work. So I was very disconnected which, in a way, was what I wanted because, when I was in the States before I went, I just wanted everyone to leave me alone and to get away. And then I got to this place in the middle of the mountains in Tuscany and my phone literally did not work.

I had to go to a coffee shop, connect to the shitty Wi-Fi, and then I could maybe make one phone call a day, but if I was inside my place, which I usually was because it was inter so I was inside my apartment alone a lot - nothing. I just read a lot of books and I'd download podcasts to listen to, and that's it.

That's the other reason I think I saved so much money: I wasn't really out exploring as much as I thought I would the first couple of months. I just got there and chilled for a few months. I would go to the salon and do that work, but it took me a few months to adjust to being there and being alone before I started going out and doing things, so that saved me a lot of money, too.


This time, with El Salvador, I came here working a fully-remote job with a good salary and having money coming in, and that was a year ago. About a month ago, I got let go from that job. And my mind was in the place of thinking about my finances a lot more this time around because when I got back from Italy, as I said, I had $500 to my name. So I went from $10,000 to $500, and when I got home and looked at that, reality hit and I thought, "OK, I need to do something."

So I got a part-time job, and I was living at home, and my parents didn't charge me rent, which was amazing. And it worked out that I was able to immediately get this remote job and get money coming in regularly again, but I knew going into this last job for the last year - I knew even going into it that corporate wasn't going to be for me. And no, looking back, I think the job served its purpose of getting me to El Salvador and allowing me to live this lifestyle I know I want.

So, again, I went back right back into saving mode and putting all my money away. Other than flights, I was staying in hostels and cheap places until I got my apartment in December that I'm living in now - it's pretty much just a habit. I always go with the cheapest or middle-of-the-road option, I don't stay in hotels really, I do hostels and book cheaper flights, etc.

Unless it was necessary spending like food, I didn't start spending a lot of money so I was able to build up my savings pretty quickly in the last year even though I've been traveling back and forth to the States a lot, it wasn't a big impact since the cost of living here is relatively less.


Being more mindful of my money this time around and knowing that I didn't want to be at this job forever since I pretty much knew in the first week that it wasn't going to work out and I was just trying to make it a year with the company so I could save up. About 6 months into it is when I met you and I knew I needed to start planning to either quit my job or get fired because I could tell there was tension and they weren't happy with me traveling so much.

It was such a relief when I did end up getting let go and I was so grateful for the time I spent getting my money organized with you because I was thinking if I had to do that in the month right after getting let go there would have been so much panic because of how the banking system is so antiquated and all the stuff we dealt with together when working to fund my HYSA (high-yield savings account).

But knowing that I already had this money set aside for this specific situation and we had done the math on my living expenses here, I was just like, "Whew. I'm fine. This isn't a perfect situation, but I planned for it." And that was the biggest weight off my shoulders. So I'm really grateful for that because it's hard to do alone. It's like, you know you need to do it and you know you need to get organized, but having someone to hold your hand through it is like - that was just like the biggest deal for me.

And it just seems very serendipitous the way this all worked out because I was just hanging out at the beach one day and I was talking to Cory and said, "I just need help organizing my money," and he goes, "My wife does that." It was so perfect.

Because I knew - I knew I hated that job and I was going to quit or get fired and it was perfect how it worked out. So thank you.


[JT] It means a lot to hear that and, I'm glad you were willing to share that story because, in the end, it's not about the money at all. It's not about how much money you're making, what you have, this or that. At least for me, and I know it's the same for you, it's about peace of mind and being prepared for situations that aren't expected or aren't ideal.

And I haven't been let go from a job, but that was always a personal fear that I had. But I knew that because I had an emergency fund saved in a high-yield savings account (HYSA) which usually gives you a much higher interest rate than you'd get at your traditional bank - that helped because I felt prepared to deal with that situation if it ever happened.

It's neat to see this play out in real life because this is exactly what that's for and, with you, it's so cool to see you go through a situation that so many of us are fearful of and say that it was a relief rather than something that causes you panic.

[AD] I think I was already working with you at the time, but I was at a work conference in February and I was crying in the hotel because I was so miserable and my friend told me something that really clicked. She said, "Alyssa, is this the dream?" And I said, "No." And she goes, "Well, then don't worry about it. This job isn't for you, and all you can do is prepare for whatever your dream is."

And I knew my dream was to be in El Salvador and to be surfing because I love being here - that's the dream. So I needed to do what it took to prepare for that; this job is not the dream.

At that moment I felt very conflicted. It was like, "Do I quit?" I just had no idea what to do because I didn't want to quit the job without a plan, but it was also sucking the life out of me. Now I just ask myself when I'm stressed about things or feel like I have a big decision to make: "Is this the dream?" and then I make the decision that is the dream, or if I have to make the decision that's not the dream and I still have to tolerate it a little longer, then I know it's not forever.

And I think with money, too, a lot of people don't agree with this, but I'm under the impression that I can always make the money back, but time and happiness are much more valuable. And I know that's a really privileged place to come from but, again, it doesn't matter exactly how much you're making if you can have that mindset then just be prepared to choose yourself and your dream over a corporate job or being part of this rat race in the states that people think they have to be part of.

You really don't have to; there are so many other options.


[JT] I think that's really important, and you've told me that before, and I love it: the concept of, "Is this the dream?" Because, to your point, I think few of us stop to ask, "Is this what I want to do?" I definitely didn't. I was in corporate for 10 years and I didn't ask that until the very end and it wasn't until I was so miserable that I was finally like, "I have to plan for something else."

So it's great that you have a friend in your life who would ask you that and it's now a mantra you and others can use (I'm going to adopt it!).

As for your corporate job, I think it served its purpose; it was a stepping stone for you. I think some of us might be in jobs that are stepping stones for us. But I think what's important about what you just said is to know whether it's a forever thing, or a stepping stone on your way to getting somewhere else.

And another thing you said earlier that I wanted to bring up is thinking about the worst-case scenario because that's something I've learned to do and it's helped. Whenever I'm freaking out, I've taught myself to pause and think, "What is the worst thing that could happen?" For me - and, again, it does come from a place of privilege - but for me and Cory, if we lost everything, we could go live with our parents.

And that's the worst-case scenario. And, again, I know that's not the case for everyone, but I think for a lot of people who listen to the show, that's likely the situation. So it helps to think about that.

And if your worst-case scenario is worse than that, and that's the reality you have to deal with, it's still good to ask the question because acknowledging the reality helps you figure out what you need to do. But it can help squash the fear a lot of times if you can just know head-on, "This is my worst-case scenario and these are the things I can do to either avoid that or plan for that."

But I love that quote, "Is this the dream?" and also thinking about, "OK, I want to try this scary thing and, if this doesn't work out, here's the worst possible scenario for me" - because, many times, it's not as bad as we might think.

Now, I'm so glad you brought up being let go because that was a big fear of mine and I'm sure it's a fear for others listening, as well, and I'm glad that it's going so well for you and I know we talked earlier about your new schedule of surfing and skating and doing some part-time work for a surf company here, which I love. I mean, you are living your dream.


The last question I have for you is: What's next for you, financially, work-wise, life-wise? I know you have your emergency fund so you don't have to be in a rush, which is such a beautiful thing. But what is next for you, and what advice would you leave listeners who struggle to find the courage to take risks that they know deep down that they should?

[AD] Who the hell knows! I feel like my life is so random sometimes but, again, this feels like home and I don't even like thinking about leaving; thinking about leaving El Salvador makes me anxious. So right now the plan is to stay here; I'm still very focused on surfing. I had this idea in my mind of "one year of surf progress" and how amazing that was going to be and, it's taking a lot longer than I expected. It's the hardest thing I've ever done, but it's the most rewarding.

It's so much deeper than the athletic side of it, for me: building this relationship with the ocean and working through dropping your ego and surrendering to the ocean. And that's my lesson with surfing and it's just going to take as long as it's going to take.

I've also started skating a bit, too, because it's big-wave season right now so I can't always be out in the ocean, but I like to skate and that helps with the surfing. I also started doing some part-time marketing work for a surf company; I met the owners on my second trip to El Salvador and that felt very aligned. We'd stayed in contact and I told him I lost my job and he said, "Well, great. I need some help with marketing." So that was a very easy transition and it keeps some cash coming in, and that eases my mind a bit.

I really am living the dream: I'm surfing, I'm skating, I live in a beautiful place at the beach, and I'm still doing some work. And I'm just able to focus on what I want, and I know what I want is to not work a corporate job, so I feel like also the blessing with knowing how much you want something is when you're up against a wall, it's going to force you to make it happen to yourself.

Because, yeah, worst case scenario I go home and my basic needs are met, but I want to maintain the life I have here, so I know I'll figure out how to do that in a way that works for me. So that's exciting. I've been able to explore a lot more of my creative side here so I think there are some things to come with that: content, art, etc.


The advice I'd leave is, again, "Is this the dream?" And I think that even though things are scary and uncomfortable, for me, it's like, would I rather be uncomfortable working a job I don't like where the work seems pointless, or go after what I really, really, really want? Either way, there's going to be some discomfort.

Especially coming from the background of dealing with all my health problems and almost dying and being completely miserable for 5 years from age 20-25 because of it... I think going through that at that age, I feel like I missed out on a lot of my early twenties. So I think that's changed my mindset a lot because now I think: I have the ability to surf, and I have the ability to be physically active and be healthy and I want to take advantage of that for as long as I can. So I am not going to sit at a job that I hate and be miserable when I've already been miserable for 5 years. I'm just not.

So I think coming from that place, as well, like while you're young and have the opportunity to do stuff like this, it's a dishonor of to yourself to not fulfill that. I always go back to that, as well. I was miserable for long enough, so even if I run out of all my money, I'm going to have fun and use my body and live my life. And I know I'm going to make it work because that's who I am.

So I would just say, ask yourself, "Is this the dream?" and try to make the decision that honors that.

[JT] I love that so much and sometimes what comes up for me is, as Americans, there's this whole narrative about if you work hard enough and long enough, one day, you get to retire, and then you get to live the dream.

But the reality is, you don't have to wait until you're 60 years old. And who knows if you'll live that long? We could get hit by a car walking across the street later today. You don't know what will happen, and you don't know what your life situation will be at that point.

But you know how you are today, you know you have today, and it's cool when you realize that, and you realize you don't have to wait to do cool stuff. You can do it right now. It's a matter of overcoming fear.


Want to get your hands on the finance tool I used with Alyssa to organize her finances? Grab it here!

Want to follow along with Alyssa's journey? You can find her on Instagram and TikTok.



The Monthly Financial Organization Tool I Swear By


bottom of page