When Sarah Waldbuesser stood in her windowless office writing reports that perhaps one person would read, she confronted a question that unsettles many high achievers: Why aren’t I happy? She had the career credentials that supposedly guaranteed fulfillment—a law degree, a master’s in public health, and a position working in global health that combined her passions for travel and making a difference in the world. She lived in an exciting city, had great friends, and got paid to travel internationally. By every external measure, she had arrived at her destination.
Yet something fundamental was missing.
Her story illuminates a truth many professionals discover too late—that career happiness cannot be reverse-engineered from achievements alone. The degrees, the impressive job titles, and even work that aligns with your stated values don’t automatically produce satisfaction if the daily reality doesn’t match your deeper needs for autonomy, flexibility, and genuine engagement.
What followed was not a simple resignation letter or a pivot to another traditional job. Instead, in 2012, at age 32, Sarah quit her position, cashed in her 401k, and flew to the Philippines to meet strangers she knew only through a podcast. Her decision launched a thirteen-year journey through digital nomadism, entrepreneurial ventures, and ultimately building two successful online legal businesses that serve coaches and entrepreneurs worldwide.
The Dream Job That Wasn’t
Sarah’s path to discontentment was paved with impressive credentials and seemingly smart choices. After graduating from law school, she started at a mid-sized law firm in Washington D.C. Within six months, she knew partnership wasn’t for her. “I had no desire to be a partner in a law firm,” Sarah said. “I didn’t want to work a thousand hours a week. I didn’t want to track my time in 15 minute increments.”
Rather than staying in a situation that clearly didn’t fit, she pursued what seemed like a better alternative. She earned her master’s in public health, thinking the combination of legal expertise and public health could lead to meaningful work in women’s health or global health. She spent nearly a year living in India and then landed a position at a think tank that appeared to check every box.
“I was helping other countries develop their disease surveillance systems through a legal document called the International Health Regulations,” Sarah explained. “I got to travel to Africa and the Middle East and Asia and this whole world of travel was opening up.”
On paper, it was perfect. In practice, the reality was stark. “I got to travel for less than a third of the time,” she said. “And the other two thirds of the time I was writing reports in a windowless office that maybe one person was actually reading.”
The disconnect between the job’s promise and its daily execution created a crisis of meaning. She had done everything right, invested seven years in education and training, chosen a profession rooted in service to humanity, and still found herself asking the question that haunts so many professionals: Why aren’t I happy?
The Analytical Approach to a Life-Changing Decision
Sarah didn’t make her decision impulsively. As someone trained in legal analysis and risk assessment, she approached the question of leaving her career with characteristic thoroughness. “I did what I do best, which is journaled and talked things through and researched other potential career paths,” she said.
But traditional career research wasn’t revealing satisfying alternatives. The breakthrough came from an unexpected source—a podcast called The Tropical MBA. “This guy was talking about how he had quit his job and was living in the Philippines and had an online business,” Sarah recalled. “I was like, what is this? This is not a career I’ve ever heard of.”
The podcast introduced her to the concept of location independence, a movement that was just beginning in the years before Covid made remote work mainstream. She discovered Tim Ferriss’s “The Four Hour Work Week” and began exploring what was possible beyond traditional employment structures.
“What I wanted to do was I wanted to travel,” Sarah said. “I wanted to kind of have that freedom and flexibility and not have to, like, take vacation when I wanted to go do something.”
She found herself listening to podcasts constantly, absorbing stories of people who had created businesses that allowed them to work from anywhere. When the hosts of The Tropical MBA announced they were offering a business course in the Philippines, Sarah made a decision that would have seemed reckless to many of her colleagues: she signed up.
“I had no idea what I was going to do, what it was going to be like,” she admitted. But the draw was powerful enough to overcome the uncertainty.
Navigating the Reactions of Others
Walking away from a prestigious career generates opinions. Sarah encountered the full spectrum of reactions from friends, family, and colleagues—from support to skepticism to outright concern.
“There’s a percentage of people that, you know, fully supported me,” Sarah said. “There’s a percentage of people that kind of thought I was a little bit crazy but was supportive. And then there’s a percentage of people, and this is not surprising, these are more like parents or, you know, parents, friends that were kind of like, what are you doing with your life?”
Her family’s initial response reflected their concern for her security and well-being. But an important conversation with her grandmother shifted her perspective. “I was talking to my grandma probably right before I left, and she was like, you’ve got to do you. You know, like, you’ve got to. Like, you only have one life to live. Go experience it,” Sarah recalled.
The validation from someone of her grandmother’s generation—someone who understood the value of both security and authentic living—gave Sarah permission to trust her own instincts.
She developed a pragmatic approach to handling external opinions. “I tried to always just, you know, listen to people, but ultimately knew that I had to do what was right for me,” she said. “And then you have to find your people. You have to find the people that get you.”
This last point proved crucial. Finding community among other digital nomads and entrepreneurs provided the support and accountability that made the transition sustainable.
The Reality Behind the Instagram Fantasy
Sarah’s journey through digital nomadism included extended periods in Thailand, Vietnam, Croatia, and Germany. She built community through nomad organizations and conferences. But she’s direct about the disconnect between the appealing image of location independence and its actual challenges.
“There is a but there,” Sarah said emphatically when discussing the outcomes of her choices. “It is not easy. I know the Internet might paste a picture of it being easy, but when you are solely responsible for your income, there’s a lot of pressure that comes with that.”
The early years involved significant financial insecurity. After the Philippines, she returned to Washington D.C. and temporarily moved back in with her parents while pursuing consulting work and part-time jobs. “I was just in survival mode for a while, trying to figure things out,” she said.
Her first business idea—Bootstrap Lawyer, offering legal courses and templates—didn’t gain traction. She tried e-commerce. Nothing was working smoothly or quickly. The freedom she sought came with the anxiety of unstable income and the isolation that often accompanies travel.
“Even in the past 10 years where I’ve had a successful business, I’ve still been like, should I go get a job?” Sarah admitted. “And then every time I even start to look at a job, I’m just like, oh no, this won’t work.”
The path to success was neither linear nor glamorous. It required persistence through uncertainty, financial stress, and the loneliness that can accompany breaking from traditional structures.
Building Something That Actually Fits
Sarah’s breakthrough came when she circled back to her legal expertise, but on entirely different terms. She launched Destination Legal, it is a template shop providing contracts for online business owners, coaches, service providers, and entrepreneurs who needed legal documents but couldn’t afford custom legal work.
“I had been selling to online business owners and realized that they needed template contracts,” she explained. The business aligned her legal training with the needs of the community she’d become part of, and it finally gained traction.
A decade later, she has expanded to include Twist Law, a trademark law firm focusing primarily on online coaches. She’s married, has two young children, and has achieved the flexibility she originally sought. “If there’s a sick day, it’s not skin off my back,” she said. “I don’t have to maneuver schedules.”
But she’s unequivocal about who this lifestyle suits. “It’s not for everyone,” Sarah said. “I have friends that look at me and my life and they’re like, you do you, but I would never do that. You are crazy.”
The key insight is fit, not superiority. “I think there’s plenty of online business owners that have gone back to a traditional job and been very happy there,” she said. “I think it’s just all about who you are and kind of how you want to live your life.”
The Courage to Question Success
Thirteen years after leaving her dream job, Sarah has built successful businesses, found her partner, started a family, and maintained the location independence she originally sought. Her journey validates the risk she took while simultaneously demolishing any romantic notions about how challenging that path actually was.
Sarah’s grandmother was right: you only have one life to live. But living it authentically requires more than identifying what you don’t want. It demands the willingness to experiment, to fail, to feel uncomfortable, and to build something that actually fits who you are rather than who you thought you should be.
The windowless office where Sarah wrote reports that almost no one read is far behind her now. In its place is a business that serves her clients, supports her family, and allows her to design her days according to her own values. That’s not just a better job—it’s a fundamentally different relationship with work itself.
This article was inspired by an interview with Sarah Waldbuesser and Amy Stone on The Art of Imperfect Adulting podcast. https://imperfect-adulting.captivate.fm/listen https://www.youtube.com/@imperfectadulting
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Big Law to Entrepreneur: Interview transcript Sarah Waldbuesser with Amy Stone | The Art of Imperfect Adulting | December 2025
Amy Stone [00:00:05]:
Sarah Sarah Waldbuesser. Welcome to the art of imperfect adulting. I’m happy you’re here today. Are you ready for a fun chat?
Sarah Sarah Waldbuesser [00:00:12]:
I am. Thank you so much for having me.
Amy Stone [00:00:15]:
Yes, ma’. Am. I start all my conversations with the same question. People sometimes wonder why, but I’m curious to know what part of the world you’re in.
Sarah Sarah Waldbuesser [00:00:23]:
It should be a simple question. I’ll give you the answer for today. Next month it might be different. Currently in my hometown of Saint. Saint Louis, Missouri.
Amy Stone [00:00:32]:
Okay, so when you say hometown, that’s your childhood, like where you grew, you claim as your grow up spot.
Sarah Sarah Waldbuesser [00:00:39]:
Correct. Correct.
Amy Stone [00:00:40]:
That is a wonderful answer. Home of the arch. One of the. So I went in the arch first as a kid. Like I have some family in the Midwest. Then I took my kids back on a trip. That is a wild experience still to this day. To go up in that little egg shaped thing in there.
Sarah Sarah Waldbuesser [00:00:55]:
It really is. I did it as a child as well. We would go with school, but I don’t think I would do it now. I think as I’ve gotten old, I’ve gotten way more claustrophobic. And you know that elevator is very, you can’t call it elevator, whatever it is, is very small.
Amy Stone [00:01:11]:
Yeah, no, I agree. And it is different when you’re a kid and the space is smaller. So I. It’s one of those things that it’s like going back to your elementary school and like, oh my gosh, the desks are so small. No, we’re bigger. We’re bigger.
Sarah Sarah Waldbuesser [00:01:23]:
Exactly. I need to get my kids up there, but I’ll probably send my husband up with them.
Amy Stone [00:01:28]:
That’s a perfectly reasonable response. All right, next warmup question. What is one way that you like to recognize or honor something that you feel is worthy of celebration?
Sarah Sarah Waldbuesser [00:01:39]:
So I would say right now it’s with verbal excitement. Clapping. So we have a first grader who is having his first math test and first spelling test. And so when he’s been doing great, we’ve just been over the top, excited with high fives and congratulations. And that’s amazing to really, you know, get that into his brain that he’s doing a great job.
Amy Stone [00:02:04]:
Yeah. Try and convince him that he’s enjoying the process of being. Being tested. Yeah, I’m going to put a pin in that to follow up in 5 or 10 years, see how it’s stuck. Anyway, could, could. It does for some kids so very much. Today we’re going to talk about something really a lot of fun. I think once upon a time, a long Time ago, you quit your job, cashed in your 401k and flew to the Philippines to meet some STR that you knew through a podcast. That’s a story. That’s a story. And I have a lot of questions. I’m dying to learn more about this. My first question is actually, how long ago did you do this?
Sarah Sarah Waldbuesser [00:02:42]:
So that was in 2012. So going on 13 years ago now.
Amy Stone [00:02:51]:
All right, so more than a decade ago.
Sarah Sarah Waldbuesser [00:02:53]:
More than a decade. I was 32 at the time, giving away my age, which is fine.
Amy Stone [00:02:59]:
We should be allowed to state and celebrate and be celebrated for all the anniversaries of our life. So that’s my opinion. Even though it is still really commonly accepted that you don’t ask people their age. I ask people their age all the time because I’m super curious.
Sarah Sarah Waldbuesser [00:03:16]:
Yeah, I’m over it. I’m over it.
Amy Stone [00:03:19]:
There you go. All right, so I have tons of questions. I’m going to try and be patient and lay the story out in an interesting and compelling way for the audience. You described the job that you had at the beginning of this process as a dream job. Tell us a little bit more about what the job was that you had that you walked away from.
Sarah Sarah Waldbuesser [00:03:39]:
Yeah. So I’m an attorney by trade and I started my career at a mid sized law firm in Washington D.C. that was not the dream job. That was the job after law school that I got and was happy to have a job being paid. When I was 25, within about six months, I knew I had no desire to be a partner in a law firm. I didn’t want to work a thousand hours a week. I didn’t want to, you know, I didn’t enjoy tracking my time in 15 minute increments. And I was just like, this is not for me. So I started looking around thinking, what else could I do for a hot second? You know, I’ve always had a huge passion for travel and, you know, wanting to make a difference in the world. And for a hot second I thought I might join the Peace Corps. I didn’t end up doing that. What I did instead was go back for my master’s in public health and, you know, through the combination of legal and public health, thought I could, you know, work in women’s health or global health. And so that’s what I ended up doing, working in global health. I spent almost a year living in India. I came back to the US Then and was working for a think tank at my supposed dream job, which was helping. It’s interesting. This was Way, way before pre Covid. But what I was doing was actually helping other countries develop their disease surveillance systems through a legal document called the International Health Regulations. We were funded by the government and so I got to go to all these other places around the world. So I got to travel to Africa and the Middle east and Asia and this whole world of travel was opening up, which was a huge passion. I was like, wow, get paid to travel. This sounds amazing. The problem was, is that I was, you know, yes, I got to travel for, let’s say, less than a third of the time. And the other two thirds of the time I was writing reports in a windowless office that, you know, maybe one person was actually reading. And so, you know, I had this kind of, I don’t want to say full on crisis, but it was just like, I’m living in Washington D.C. this amazing city. I have great girlfriends. You know, I was in a group of, of single girlfriends at the time. Maybe a couple married, but all pre kids and it was great. I got to walk to and from work every day, had this travel and I was just like, why aren’t I happy? Why aren’t I happy?
Amy Stone [00:06:04]:
That is really interesting. All right, so there’s a lot to unpack there because when I tell stories that people are sharing about walking away from a job, there is a difference in walking away from a job that is, you know, an entry level starter job. Like when my kids were in middle school and high school, they were, you know, lifeguards and bag packers at the grocery store. Walking away from that job or a job that you do that is, you know, is, is very different from walking away from a career, a job or a profession that you have invested seven years for. Law school, right? Undergrad and law school, six, seven years in training and then you went back and got a master’ that you had really put some deep thought into how you could use your talents, what mark you wanted to leave on the world. You chose a profession that, while funded by the government, is based in service towards humanity. NGOs for disease tracking, which I gotta say sounds very analytical, but. So that’s a big deal to walk away from something that you’ve put that much effort into. And I just want to honor the fact that this is not you walking away from flipping burgers at Wendy’s, which is an absolutely legitimate job and everybody should be proud of every job they do. But there is a difference.
Sarah Sarah Waldbuesser [00:07:31]:
Yeah, yeah, absolutely. This, this, it was not taken lightly. And you know, yes, I had tons of student loan debt and I had, you know, a six figure job and I was still walking away into complete unknown, you know. And you can guess how my parents and friends all reacted to this.
Amy Stone [00:07:51]:
That is a very common question that I ask. And I am very curious. First of all, when you like I’m very curious what the people in your, in your community and your circle thought about it when you made this announcement. But let’s back, let’s lead up to that. And so when was this Sounds like it was a very abrupt change when it actually happened. But it also sounds to me like a lot of planning went into making the decision. And something that I will say about the people I’ve met. I did not go to law school, but of all the people I’ve met who have gone to law school, there one of the strengths that they have is in analyzing things and making decisions. So I’m going to go out on a limb here and really think that you carefully and thoughtfully went through this decision at some point. What’s the first time that you remember being having the conscious thought, like, all right, I’m ready to burn all this down.
Sarah Sarah Waldbuesser [00:08:42]:
So I would say it was actually, you’re right, it was a good six to eight months before that. I remember distinctly sitting on the living room floor. I was in, you know, a basement apartment in D.C. so not a lot of light there. I had a notepad and I was somewhat journaling, like, what do I want? What do I want? Like, what is really going on here? Why am I so unhappy? What’s wrong with me? You know, I had all these people around me in careers and everyone was kind of content to go along. And I was like, what’s going on here? And you know, I dug into, I think, you know, I was reading the books, what color is my parachute? Like these kinds of things. And I was just like, I want to travel. I want to have freedom. I want to be able to work from anywhere, whether it’s Starbucks down the street or a cafe in Thailand. And it all came down to I just wanted freedom and flexibility. I didn’t want to have to report to anyone at 9am every single Monday. And that led to starting to Google travel. Get paid to travel, travel while you work. And you know, back then I knew I could be, I could work on a cruise ship like a travel agent, but none of that stuff was going to suffice it for me. Right. As a high achieving attorney who had a certain style, I had become accustomed to living, needed to make a certain amount and all of that. And I stumbled across this podcast and it was started by two guys and they were running what was called an online business. They were running a business from their computer, living in Bali. And it was like a giant light bulb had gone off. Like, what is this? I didn’t know people could do this. You know, they at the time had an e commerce store. I think they were like selling cat furniture and things like that. And I started listening to them. They had a show where they interviewed other entrepreneurs, online business owners. I started listening to it every day on my walk to and from work in D.C. and you know, it was six or seven months into that where they offered this two week course on an island in the Philippines on how to start your online business. And you know, that is when it all kind of came together. I was like, I have to do this, I just have to do this.
Amy Stone [00:11:13]:
So I was giggling there in the middle and trying to not seem disrespectful. But when you said that they were running an e commerce company selling cat furniture, it did make me chuckle. Not because I think that that’s not legitimate, but because the truth of some of the most successful businesses are these very, very niche things. One of the first, when I was in my 20s, I met somebody who had a very lavish lifestyle. And their business, which was this, before online commerce was they made shoes for nurses. It was the whole business, whole business. That was my first introduction to how something so specific can be very, very productive. So this is before one of the pieces of this story is this was truly before the remote work sort of revolution came with lockdown. And so one of the components of this is that you did not have as much awareness that you could be location independent. And so it sounds to me that location independence was the driver you really, really, really wanted to not have to be in a physical office as designated by somebody else. Does that sound accurate?
Sarah Sarah Waldbuesser [00:12:22]:
Absolutely. And this was when the four hour work week by Tim Ferriss had like just come out, right? Oh yeah, yeah, right. This was like the very beginning of that revolution and it was really Covid that sent it skyrocketing. But a lot of took place in those years between and yeah, that’s correct. Independence. Because what I realized when I was traveling for work, I was going to these amazing. You know, I was in Nairobi and Tanzania and Manila and Bangkok, but I was working, I really.
Amy Stone [00:12:53]:
You were seeing the inside of an.
Sarah Sarah Waldbuesser [00:12:55]:
Office of a hotel. Yeah, exactly. I didn’t get to fully experience. Now I tried my best. Each work trip I tried to build in a day. And you Know, but if you’ve been to Bangkok, how much can you see in a day? Right. And so I wanted to be able to travel where I wanted, when I wanted. And it seemed like these people were doing that, and they were doing it pretty cheaply. So it was very intriguing to me.
Amy Stone [00:13:20]:
As you were making this decision, was there any part of your thought process that was tied to what I’ll call sunk cost of the work you had put in for. For your law degree and your master’s? So you mentioned that, you know, you had a standard of living that you had become accustomed to, but was there any sort of thought that you were putting in that was like, I’ve got all these degrees, you know, I need to continue to put them to work, Like, I can’t release it?
Sarah Sarah Waldbuesser [00:13:47]:
So there was that thought. But also, my dad is an entrepreneur. He built and sold a business. And if there’s one thing he ingrained in me, and, you know, I still don’t know if this is true, but it’s certainly been a driving factor for me, which is if you enjoy what you’re doing, you never work a day in your life. And so I wasn’t gonna let the fact that I had a law degree or a master stop me from figuring out how to enjoy my life. I just. I wasn’t gonna sit and be miserable for the next 40 years. I just wasn’t going to do it.
Amy Stone [00:14:20]:
So I think that that’s a great sentiment, and I want to go a little deeper on that because I think that’s really interesting, so. Because sometimes people, they push back on that idea that if you like what you’re doing, it’s not actually work. And another phrase that people will sometimes use is the idea of, like, eat the frog first, right? And do the value of doing the unpleasant thing. This whole concept of deferred joy in terms of some sort of future payoff. And it is. I think it is hard for people who have not experienced it. But if you enjoy the frog, then it’s not a burden to eat the frog. That’s the thing that gets lost in that, is that if you enjoy whatever it is that is the grind of what you’re doing, then it’s just joy. It doesn’t feel like grind. And that’s true whether it’s sweeping the kitchen floor or painting the Sistine Chapel. And so for everybody. So I just wanted to say, I think that’s good. So this means you had representation in your life growing up of somebody who had leaned into their own decisions as an Entrepreneur. And you had an example of that. That’s helpful. That’s very, very helpful. And that really watching him do that and give you that advice, you had the ability at some level to validate your own decision. Like, I thought I was going to like this, but I’m going to change my mind.
Sarah Sarah Waldbuesser [00:15:40]:
Yeah, exactly. I have always been one of those people, and I know many people are not like this, who I was never going to put off happiness for retirement because I know no one is guaranteed to live that long. Right. Like, I just. And, you know, my husband and I are different. And this part, this is partly to my detriment that I do live too much in the moment and potentially don’t plan enough for the future. And are, you know, I’m working on this now, but I’ve always been like, instant gratification. It’s hard for me to put off things. You know, I would fail the marshmallow test. And so that’s something I am still working on as an adult for sure. But yet it led to many, many amazing experiences which I would never take back.
Amy Stone [00:16:28]:
So, you know, what’s interesting is that there’s a team of researchers who redid the marshmallow test in the late. I think it’s the late 1990s, but somebody else should look it up and double check it. I used to know this, like, by. By scratch. And it’s one of those things in the field of psychology from, like, the 50s and 60s that has kind of been updated to be like, hey, your initial premise was not complete enough. Because what they looked at was they looked at factors that the kids asked to make that decision, what they were going into it with, and how that impacted how they made the decision. So to just. Just radically oversimplify this and, you know, be super reductionist, if you go into the marshmallow test and you’re hungry, you’re more likely to take the marshmallow and not wait. So the marshmallow test is a test that is designed to support the idea of deferred joy and pleasure and tie it to success in life. So they asked kids like, hey, here’ a marshmallow. I’m going to leave the room. If you can wait until I get back, I’ll give you two marshmallows. And then the result was that the kids who were willing to wait, they. They were more likely to be, you know, boss and as adults. And then later on, people were, you know, people were like, well, I don’t know if that’s fair because I might take the I kind of would take. I don’t know how much I trust you. Maybe I would take the marshmallow. Does that mean I’m going to be a failure for life? But I think that that’s really interesting. And I too, would. I too, would fail the marshmallow test in many things. I think it throws into the discussion. I think it’s a worthy conversation for all of us to have about the implied agreement and the promise of modern day life and how much we agree with it. Does happiness just happen as a result? Just by chance, if we follow the rules that other people present, we go to school, we get the degree, we do the job, we buy the house, we get the family. Does happiness just happen or do we have to create it and be intentional about it? This question for everybody, right? And you’re a person who’s interested in creating it right now. All right, so you flew around the world to meet in person what are basically strangers. Yeah. You like, but you may have felt like you knew them a little bit because they’d been jabbering in your ear for several months. There’s like, people feel like they know podcast. So it’s. Here’s where I’m going to ask you what the people in your life thought about this decision. So when you did this, you cashed out and you did this, what did your co workers, your family, your social circle, what did people around you think about this?
Sarah Sarah Waldbuesser [00:19:01]:
So it wasn’t totally out of character. Okay, so I had. I had gone and lived in India, right? I had, you know, applied to the Peace Corps and decided, you know, at the last minute not to go. I had, you know, I had studied abroad in high school and college. Like, this wasn’t like, I had never left the country and was like, just going, like, this was a little bit part of my character. And so, you know, I think my parents were very concerned, right? Like, what is happening? I had some friends that were like, that’s amazing. Like, how cool is that Good for you? And others who were like, why are you doing this? Why can’t you just be happy? You know, I had a conversation with a friend who was miserable in her job 9 to 5, but loved the rest of her life and was just like, this is how it is. I’m gonna work to live, not live to work. And that just was not my philosophy. And so, you know, I think I would say friends, who knows what was said beyond my ears. But again, I think those that really knew me and knew who I was were supportive and kind of like, Enjoyed the show. Right. Got out their popcorn, like, listen, see how this is gonna go? And then others were just like, that’s crazy. That’s not for me. Right. That’s not something I would ever do. And, you know, it was, we can get into what happened over the next several years, but it was certainly not all roses. For sure. Like, this was a tough decision.
Amy Stone [00:20:38]:
So was there any. So you are an independent thinker and you have done this and this didn’t feel to you maybe like it was outside of your charact. I want to give you a chance to sort of reflect on what was the impact of the people around you and the feedback they gave you about this decision. Like, did it feel supportive sometimes? Were you able to ignore or not feel pressured by people who offered a contrarian opinion? And I asked this not in evaluation of the decision you made, but for people who are listening, who are trying to make a decision in their life and they’re maybe feel buffeted by the opinions that come from the peanut gallery.
Sarah Sarah Waldbuesser [00:21:20]:
Yeah, I think I have always felt a little bit different. Different than my siblings, different than my friends from high school, different than my friends around me in D.C. and listening to this podcast and hearing all these stories, I felt like I had found my people, people that I could relate to, aspire to be. And so I am a firm believer of surround yourself with people who are doing things you want to be doing. And I just knew that wasn’t I. You know, I love my friends to this day. They’re still best friends, but we’re different and we want different things in life. And so I have. My parents have always taught me not to be too concerned about what other people think. And my parents also, maybe to their detriment, always taught me to live my own life right. Like it’s nobody else’s life.
Amy Stone [00:22:11]:
So you were able then to hear the things that people were saying to you and just honor them as somebody else’s opinion, but not feel pressured to change your mind. Okay, so those are my words, not yours, but that’s what I took from that. So that is very good. Okay, so let’s talk about the original dream and motivation that you had that was pushing you to go to the Philippines. So before you left, you’d listen to this podcast and you were motivated to chase this. You found you saw this group of people as potentially like minded people who are going to introduce you into a new intentional way of living that was aligned with you. Let’s talk a little bit about what the dream looked like before you Left. And then we’ll talk about what it became and how it actually happened.
Sarah Sarah Waldbuesser [00:22:56]:
Yeah, so part of the program that I had signed up for was you got to hop on a Zoom call with these dudes and talk about, okay, well, what’s the business you’re going to build? Right. This was about, I’m going to build this business, it’s going to make me a lot of money right away, and then I’m going to sell it and be a millionaire. In, in a sentence. That was the dream. Right?
Amy Stone [00:23:16]:
Okay.
Sarah Sarah Waldbuesser [00:23:17]:
And so I spent time before I left thinking, well, what type of online business am I going to have? And I, you know, everything from E commerce, drop shipping, what can I sell, what do I like to do? And, you know, this. The, the guy on the call, you know, who I’m also still friends with today, was like, well, why don’t you do legal? Like, why you’re a lawyer, why don’t you have a leg business? And, you know, this was way back online, Legal attorneys was just not a thing. How are we going to do this? You know, obviously there’s state rules and what kind of law could you even practice online? And frankly, I didn’t like being a lawyer, so why would I do that? But he wasn’t wrong. And so I kind of was like, okay, I can see this. There was one or two other attorneys that I could look to. So I decided to kind of dive into that. And my first business, which didn’t last long, was called the Bootstrap Lawyer, which was helping, you know, start LLCs and, you know, do web policies and things like that. And interestingly, I did end up building a legal business, but not until three or four years later. I had to go through some mountains in life and in my own mind before I settled on that in a way that I enjoyed. But, but to answer your question, you know, the, the goal was to build a successful business and eventually sell it.
Amy Stone [00:24:42]:
All right, that is very, very clear. And that conversation is such a core. I have been in many of those conversations in the same position. You were in my own experience that, that question about what is it that you already know how to do that you can turn into an experience based business. That is a very, very core beginning point where a lot of business coaches begin. And.
Sarah Sarah Waldbuesser [00:25:07]:
Absolutely.
Amy Stone [00:25:08]:
And then the flaw in it, it’s not a flaw, but where it sometimes doesn’t work is exactly what you highlighted. And it’s like, well, but if I hate the thing, do I actually want to build something else on it? And that question, the Answer is different for everybody. Like, I know plenty of people who’ve built businesses and they are willing to make. Make that. That separation which you highlighted before, which is like, I’m willing to do this thing that I don’t love because it gives me a lifestyle I love. So. All right. So was the trip to the Philippines as you expected? You fly, you go. Was the two week experience what you thought it would be?
Sarah Sarah Waldbuesser [00:25:44]:
I don’t know that I had too many expectations. I had a pretty open mind about it, but it for sure was life changing. I learned skills during that time period that I use still that served me well. I met people there that, you know, became friends and mentors and coaches and, you know, I got to experience a part of the world I hadn’t been to before. So. And I left with a website and the beginnings of a business. So I would say for sure it met those expectations.
Amy Stone [00:26:17]:
That is amazing. All right, so let’s talk about what happens next. So you have the beginnings of a business. Do you come home after the two weeks? Do you come back to D.C. after the two weeks?
Sarah Sarah Waldbuesser [00:26:27]:
I did. I came back to D.C. and decided I was moving to Bali.
Amy Stone [00:26:31]:
Okay, all right, so.
Sarah Sarah Waldbuesser [00:26:33]:
Which did not happen. But that was, that was what. That was what the decision was.
Amy Stone [00:26:38]:
All right, so you come back to D.C. you say, I’m moving to Bali. You don’t move to Bali. What do you do?
Sarah Sarah Waldbuesser [00:26:43]:
I move back in with my parents.
Amy Stone [00:26:45]:
You move back in with your parents. At this point you’re single?
Sarah Sarah Waldbuesser [00:26:49]:
Yes, I’m single. I decided to leave D.C. and I was like, I’m going to go to Bali. But then I’m like, I have. I really don’t have money. I didn’t do this with a huge savings. I was scraping by and I was like, I need to feel a little bit more secure in finances before I, like, buy a plane ticket to Bali. And so I started looking for some additional income. So for one day, I was going to be a virtual court reporter. That did not work. For one day, I did one catering job that did not work. And so, you know, my parents, who are so supportive, you know, allowed me to come home for, you know, a hot minute and just figure out what I was going to do next. So what I actually started doing was some consulting for my dad, who had started a whole second business, and I started doing some consulting for him. And then I also started doing some consulting for my previous employer in D.C. i had run into a boss in a coffee shop before I left. They needed some help. They were okay with me doing it remotely. And so I was like, great, at least I will have some income to pay my bills and figure out my next steps. And so I was trying to get this bootstrap lawyer off the ground, wasn’t working that well and my parents were wanting me to apply to quote unquote, real jobs, which I did, I did for a few months, applied to some jobs. You know, one was going to be based in Paris, one was going to be in Madagascar, I still had that and you know, didn’t fortunately or unfortunately get any of those. And after about eight months there of still listening to the podcast, still being connected to these other digital nomad location, you know, location independent entrepreneurs, I, I realized that I needed to be around them. I needed to be around them. That was what needed to happen. And so I had enough money to slink by and I bought a one way ticket to Thailand. And so that was the next chapter where I was a digital nomad for almost two years, started another business, but that was kind of, that quite rocky in between of like, what am I doing? And then finally being like, if I’m really going to make this happen, I need to be in Thailand surrounded by other digital nomads.
Amy Stone [00:29:17]:
So there’s a lot in there, right? So one of the things that I think I hear you saying is that you were working really hard to hold on to this vision of a dream of what you wanted to create, but that the latter or the steps of how you were going to do it and what it would look like was unclear, unlearned new stuff you didn’t know how to do yet. And that does make it hard to do things right. When you don’t know where the tomatoes are in the grocery store, they’re hard to find. And so, and then the other thing that I heard you say, which I want to lean into and give you a chance to talk about a little bit more, is the importance and the value of surrounding yourself with people who are, who are already doing the thing that you’re trying to do. Because that is something that I think can be. Some people portray it as like it’s a requirement to do new things. I’m not sure that that’s quite it, but I do think it’s a huge accelerator if you can find it, to changing if you want to step into a new, you know, hobby, whether it’s knitting or CrossFit or running, if you surround yourself with people who are already doing that thing, it begins to feel more natural. But talk about why you felt like that was something that would be helpful for you and how it worked out.
Sarah Sarah Waldbuesser [00:30:30]:
So since coming back from the Philippines, I had gotten together with three, was it three other women, one of whom was on the island with me. And we brought in two other women and had a weekly call talking about building our business. And that was so helpful to just have those conversations, have someone, you know, that knew what you were up to. And it was also trying to do something. And so I knew that if I were actually in person with groups of people that that momentum would continue to build. And I just knew being back in St. Louis at the time and surrounded by, you know, friends that were here that were in the nine to five and all of that, that it would just be, you know, as you said, just be very slow. And you know, my dad actually really supported this move because he, he could see that this is what I wanted. And he agreed that, you know, being around other people would open up opportunities that you wouldn’t otherwise have. And that was absolutely, absolutely true.
Amy Stone [00:31:35]:
So it’s interesting because I think that sometimes, sometimes this idea of going to the place where there’s like minded people is really, really well supported. Right. I’ll give you the example of business school. Like go to business school, nobody questions like, is that a good move? Right. But if you want to move to California and try and be an actor, you might get pushback. Like, right. If you want to move to New York and try and be like on Broadway or move to Thailand and be a digital entrepreneur, those are examples where not everybody quite might get it. So I think that you had a good support group and I appreciate you sharing that experience. All right, so you’re digital nomad for two years working on starting your own business. Were you in Thailand most of the time or what kind of place places did you go and how long did you stay in the places?
Sarah Sarah Waldbuesser [00:32:23]:
Yeah, so I was in Thailand for about five months and then I was in Vietnam for a couple months. Then I was in Croatia for a month. I was in Germany for a month. You know, during this time I was still doing some consulting. So I did get to kind of travel to Egypt in Jordan and was still doing that side of things. I had shut down the bootstrap lawyer, started a dropship e commerce store for eco friendly furniture. And you know, not that it wasn’t working, but certainly these consulting gigs were, was what was paying the bills. And I did this, I would say for two years, just about two years. And at this point I was coming up on 35 and still single and I wanted to find a partner, I wanted to get married, I wanted to have kids. And it’s hard to do that when you’re traveling all the time. And because you meet someone and they’re there for a week or a month and it’s great, but then what? Right. So I decided at that point that I needed to. And also when you’re traveling full time, your mind is always on what’s the next place and where am I going to live and what am I going to do. So focusing on business is quite difficult. And so I knew at this point that I needed to come back to the US and figure out life and what is this business really going to be. I need to be stable enough to meet someone. And so at that point I decided to come back to the US and pick Chicago as the place I was going to go.
Amy Stone [00:33:54]:
So that’s really interesting. It’s one of the things that I’m talking to people a lot with the nomadic idea and the dream of nomadic and then the reality of some of the things that happen when you are traveling frequently and there’s so many levels of this. There’s like fast travel, then there’s like the slow thing, which what you were doing is more what they would call slow because you’re staying in places for a month, maybe more. Right. But the reality of the, the struggle with setting up an in person community and social support while being a nomad is definitely something that I think that people talk about these days, you know, because you, you, you may or may not have an ability or access to an in person community. And there’s a lot of like research or thought, thinking about the connection between in person community and relationships and happiness, which was a driver for what you were chasing.
Sarah Sarah Waldbuesser [00:34:47]:
Yeah. And you know, one of the pieces I haven’t mentioned, which was amazing to have, is that these two guys that started this podcast also started a community where every year in Thailand they would have a big conference, you know, 200, 300 people. Now it’s up to 600, I think, each year. And they would have hubs around the world. So if other people were in the community, you could match. So when I was in Thailand and I was with a group of 20 to 30 people, and then 10 of us decided to go to Vietnam. When I was in Vietnam, you know, that group of people decided to go to Germany. And so that really, you know, there were some places I was by myself and some places had that community, which was really helpful and a big part of, I think, what made that okay If I was just by myself the whole time, I don’t think I would have have lasted that long.
Amy Stone [00:35:41]:
And I think that that’s something that I’m seeing in more modern places and a spot where technology and remote connection really facilitates that happening across a lot of different things. So you. This was connected, this community was connected through this one education group, which was. Which is amazing. But I’ve seen that also in people who are looking at RV lifestyle, where you’ll have meetups for, like. Like, it’s like, you know, affiliation through, like, what kind of car you drive, you know, which. But it’s like, it’s a way to foster, like, community along with the location independence, which I think is easier than it has ever been before because you can log 100%.
Sarah Sarah Waldbuesser [00:36:23]:
Yeah.
Amy Stone [00:36:23]:
To a group of 10,000 people and be like, who’s in West Des Moines today? You know, and find that that’s really. That’s really impressive. All right, so you say it was not all rainbows and unicorns making it happen. What would you say today than a decade later? What is what. What has changed in your life as a result of this could be a massive question. So it may not be a good question. What has changed in your life as a result of making this one big decision to log out of your job, cash things in, and follow your dream as encouraged by a stranger on a podcast.
Sarah Sarah Waldbuesser [00:37:00]:
Yeah, well, I’ve never logged back in, so, you know, I’ve never been back to a nine to five. And now, now I can say today I have had a successful business for a decade. I’ve made over $2 million through that, and it’s allowed me the freedom to travel. Just this past year, we spent abroad with our two kids and a dog. We lived in three different countries. So I moved back to Chicago and really got focused. I found the coaching world, which. Another piece that I haven’t mentioned is while in Thailand and Vietnam, I was meeting all these online business owners who once they found out was a. I was a lawyer, they wanted help. They wanted me to draft a contract, do a trademark. I need a privacy policy. And so I, you know, fought it for a while, a good two years. I fought doing the legal. I thought I was going to be a health coach and then a business coach. Finally, I just gave in. You know, I was. I was out of money. My dad was sending me law firm contact tax in Chicago. You need to figure this out. And I did. And so I just dove straight in. That’s when I started my company, Destination Legal. And within I think six months of that, had my first 10k month. And so I think, you know, the story has that kind of happy ending because I let myself go through the process of, do I want to do E commerce, do I want to do this, do I want to do that? And then really realizing I do have this skill that people need, I can offer it in a different way. And now I get to help mostly women, mostly coaches bring their gifts and goodness out into the world. And I. My vehicle is legal. Do I love talking about contracts and privacy policies all day? No. Do I love what they do for people? Yes. Do I love what my business has afforded me? Yes. And so, you know, I did meet my husband in Chicago and we had two kids and. And again, like, just went on this big travel adventure. So had I not taken this move and jumped and gone to the Philippines, I don’t know where I would be today. And some of my best friends I met in Thailand 10 years ago, they’re from Australia, and I still see them a couple times a year. And it really was the impetus for all of us. This.
Amy Stone [00:39:22]:
So when you were in Chicago looking and you had opened your mind to dating and you had it on your vision board to attract a partner, was I just. This is such a personal question. You can totally tell me to buzz off the. Were you like, Were you like, listen, non negotiable. You have to be open to this travel, nomadic lifestyle.
Sarah Sarah Waldbuesser [00:39:42]:
You know, I w. I was, but not initially. I started having some dates with people that were like, in these stable nine to five jobs. And I was just like, I don’t know that this is going to work, work. And I. It kind of narrowed down people, really. I needed someone that had an interest in travel. So on my first date with my husband, it was different because a week later he was going to Italy, he was talking about going to Vietnam. He was in real estate, which I knew was a bit more flexible. And he, you know, I. One of my favorite places is Turkey, and he had been to Turkey, so. So there was definitely that openness. I don’t think he knew what he was signing up for, for real. But certainly I knew that I needed someone that was not a traditional nine to fiver.
Amy Stone [00:40:32]:
Right. And I think that that’s really interesting. It wasn’t just a conversation you had. You looked for evidence that he was already living that life, he was already traveling, and so that was a match. I think that’s really important. All right, so online business can actually be kind of a divisive topic, is one of these weird things. Like, some people are big fans, other people are critical of some of the corners of what they believe to be online business. I think there’s an argument to be made in 2025 that all businesses are online businesses, even if they have a brick and mortar but that’s, you know, totally here nor there. Would you say that you are glad that you have made. That you made this shift from brick and mortar service and law to online business?
Sarah Sarah Waldbuesser [00:41:19]:
I am glad. But. There is a but there, right? It is not easy. It is not. I know the Internet might paste a picture of it being easy, but when you are solely responsible for your income, there’s a lot of pressure that comes with that. A lot of people would much prefer to just know they have a stable income, know they have a 9 to 5 to go to, and are not risk averse. I have friends that look at me and my life and they’re like, like, you. Do you. But you are. I would never do that. You are crazy. Right? And there have been down moments even in the past 10 years where, you know, I’ve had a successful business and still been like, should I go get a job? And then every time I even start to look at a job, I’m just like, oh, no, this won’t work because I know my income potential versus what you could get at a job. And the freedom and flexibility once you have, it is very hard to think about trading in. Right. Like, I have two young kids now. Like, if, if there’s a sick day, it does. It’s not skin off my back. Right. Like, I don’t. It’s not a big deal. Like, I don’t have to maneuver schedules and, and things like that. So the freedom and flexibility have definitely been worth it. But it is, it is not an easy road and it’s not for everyone. I think there’s plenty of online business owners that have gone back to a traditional job and been very happy that there. Right. I think it’s just all about who you are and kind of how you want to live your life.
Amy Stone [00:42:46]:
You mentioned risk averseness. I think that lawyers are mostly not big risk takers, A lot of them, because they’re mostly in the business of helping people mitigate risk. Right. To understand and mitigate exposure. But would you say that this. So you’ve done this very risky thing, so you obviously have some appetite for risk. Does it translate into the other corners of your life? Like, do you. Are you a risk taker in terms of like, physical adventure? In terms of like, all kind of things or is it just within your career decisions?
Sarah Sarah Waldbuesser [00:43:17]:
So I did go skydiving on my 35th birthday. I think I draw the line at bungee jumping. I have no desire to do that. So I have run a marathon. Right. So I definitely have adventurous spirit in other ways as well.
Amy Stone [00:43:35]:
That is a beautiful answer. I love it. I want to give you a chance to talk directly to the audience more about. You mentioned the name of your company, but I want you to, to tell people directly what you do and how they can find you on the interwebs after they listen or watch the interview.
Sarah Sarah Waldbuesser [00:43:50]:
Yeah, absolutely. So my, my first company was Destination Legal, which I’ve had for now 10 years. And that is a legal template shop for other online business owners to find their contracts. So online coaches, health coaches, business coaches, career coaches, service providers, VAs online business managers. There’s people hosting retreats, in person events. So it is kind of a one stop shop for those legal documents that you need. And then I also just in the past couple years branched off. I had been offering trademark services under that as well, have now separated that out and have a separate trademark law firm called Twist Law and am also now expanding, but also kind of narrowing my legal focus to really helping online coaches. And you can find me on Instagram at the Legit Coach. That’s probably the best kind of place to hear about what’s going on and how you can work with me. But really, you know, the template contracts and offering registered trademarks are the two primary ways that I help people in the online space. And some brick and mortars, because brick and mortars need trademarks as well. But I would say for sure, 90% of my clients are online business owners.
Amy Stone [00:44:59]:
That is spectacular. I want to thank you for sharing. Are you ready for the final three questions, Sarah?
Sarah Sarah Waldbuesser [00:45:07]:
Yes. Let’s do it.
Amy Stone [00:45:08]:
All right, so this is a podcast. You’re a guest on my podcast. You were inspired by listening to a podcast to make this decision. What are some other podcasts that you would recommend if you, if I was to ask you, hey, what’s a podcast I should listen to? What would you recommend, Sarah?
Sarah Sarah Waldbuesser [00:45:22]:
Oh, gosh. So there’s a few. One of my favorite women and one of my coaches just started a podcast called called Hot, Rich and Free, and she lives in Thailand. And if you want someone to kind of bring you to the edge and challenge your beliefs, that is one I would definitely go to. And then I’m gonna call out the one that did it all for me. They still publish podcasts every Thursday. It’s called the tmba, the Tropical mba. And they just continue to bring so much value that if you have any interest. Interest in online business. I think I’ve been interviewed on there at least three times over the past, you know, 13 years. They just bring a ton. A ton of value. So. So those are two that I would call out.
Amy Stone [00:46:08]:
That’s great. I’m glad. I didn’t know if you wanted to shout them out directly or not because you were sort of, like, crediting them with.
Sarah Sarah Waldbuesser [00:46:15]:
Yes, I. I shout them out. I shout them out. Dan Andrews is. Is amazing. He’s one of the. The head guys. And if anyone, if you have, you know, if you own an online business and want a community, check out the Dynamite Circle. That’s the community of business owners that I still belong to to this day.
Amy Stone [00:46:33]:
So in the hot, rich and free. That title reminds me of one of the scenes from the comedy. Oh, my goodness, why am I Spacing the name Airplane? Where she’s like. Where she’s like, I take my coffee. I like my coffee like I like my men is the lead up to the joke. I don’t know why that reminded me of that. They’re not actually related, but if they inspired each other, then that. That is super funny. But that’s where my mind went. Okay, next question. What is something that people do that annoys you that you’re willing to share.
Sarah Sarah Waldbuesser [00:47:01]:
Publicly with the world, borrow and steal contracts from other people? So this is rampant in the online space?
Amy Stone [00:47:09]:
Yes.
Sarah Sarah Waldbuesser [00:47:10]:
Like someone will sign up for a coaching program and then just take that coach’s contract and use it as their own, which is copyright infringement. But also, we have no idea where that coach got their contract. People will Google and try to piece something together. So I would say you can already tell my voice is getting a little heated, but that is something that bothers.
Amy Stone [00:47:30]:
Me for sure, 100%. And it’s so much easier to do these days than it was like in the 1970s. Yes, exactly.
Sarah Sarah Waldbuesser [00:47:38]:
Right, exactly. Whereas I was a handful of the first, there are now dozens and dozens of online template shops run by attorneys where you know you’re getting a contract that has been drafted and will work for your business.
Amy Stone [00:47:53]:
Absolutely. All right, so this question. Let’s use St. Louis as you could choose St. Louis or Chicago. If I came to visit you in your hometown. Choose your hometown, whatever it might be, and we wanted to go out for a really nice meal, where would you suggest that we go out to eat?
Sarah Sarah Waldbuesser [00:48:11]:
I will. I will call out St. Louis, since, you know, Chicago has no shortage of recommendations. St. Louis has a really amazing food scene, which I don’t think people realize. I’m gonna call out a French restaurant called Brasherie Niche, which has been around for, you know, a very long time. We just went there a couple weeks ago for my mom’s birthday. It is great food, great scene, not too expensive, and just a fun place to celebrate any occasion.
Amy Stone [00:48:38]:
I love it. Thank you so much for sharing. That is it. Sarah Wallbuster, thank you for being a wonderful guest today on the art of imperfect adulting.
Sarah Sarah Waldbuesser [00:48:48]:
Thank you so much. This was a great chat.