Digital Nomadism Unveiled: Dorothy's Leap from Freelancer to Agency Founder

Hey Nomads, welcome to Digital Nomad Stories, the podcast. My name is Anne Claessen and, together with my co-host, Kendra Hasse, we interview digital nomads. Why? Because we want to share stories of how they did it. We talk about remote work, online business, location and dependency, freelancing, travel and, of course, the digital nomad lifestyle. Do you want to know more about us and access all previous episodes? Visit digitalnomadsdories. co. Alright, let's go into today's episode. Hey, hey, nomads, welcome to a brand new episode. Today I'm here with Dorothy Ilson. She is the co-founder of the Gig. The Gig is a digital media company that helps freelancers acquire and profit from high income online skills in seven minutes a day through their flagship newsletter, and you're probably, when you're here, you're probably interested in the digital nomad life and making money online, location independent, so I'm super excited to have Dorothy on the show today to talk about freelancing. Dorothy, welcome.

Thank you for having me.

I'm so excited to be here. So, Dorothy, where are you right now? Where in the world are you?

I am in Chicago so that is my home base, but my husband and I we both work remote and we definitely love to take advantage of that. So we just got home from a few weeks in Iceland and so definitely we try to make travel as big a part of our year as possible.

Cool, very cool. How was Iceland?

Oh my gosh. I've been blessed to take some cool trips, and Iceland was far and away my favorite trip that I've ever been on and if you have not been, 10 out of 10 recommend. We spent almost three weeks there and it was so magical.

Cool, very cool, but I always go to the sunny places. It just I always choose for chasing summer like it always has to be sunny. So Iceland is never, never makes it the top of the list, but it sounds really good what you said.

You shake it up, do some ice cave some do some different, it would definitely be different for me.

So, dorothy, tell me, when did your digital Nomad life start?

Yes, to make a long story short started in 2017. I had been working for a startup for about three and a half years and was really really fortunate in that job to have a lot of flexibility, a lot of autonomy. I could work remote when I needed to, and so when I decided to leave that company, I started interviewing around at different, different places and I was finding a lot of opportunities, but nowhere that wasn't going to make me be in an office in Chicago five days a week, and that was just not. I didn't want to go backwards in terms of the degree of control and freedom I felt in my life, and so I decided to all right, let's see if I can figure out a way to make money on my own, and started that kind of journey of exploration and eventually led to freelancing and ultimately, that morphed into the agency and now the gig.

Yeah, very cool. So why is it so important for you to be location independent and not having to go into the office?

Yeah, for me it's really about I'm a self admitted control freak. I don't want to have someone dictating to me like where I need to be and when, and like having that level of control over my life was the most important thing to me. But at the same time, I had this vision of what I want my life to look like in terms of how I want to be able to travel, where I want to live, what I want to be able to do, and I knew that in order to fulfill that vision, I also needed an income that was going to allow me to do that. And so we often think of things in these either or these like trade offs, right. And so I really asked myself the question of okay, how can I both be location independent, have the degree of flexibility and autonomy that I want to have in my life and also make more money than I ever could have dreamed of making in a nine to five? So that was really the goal for me was like how do I get both of these things?

Yeah, I love that. When I started working remotely, or when I even thought about working remotely, I thought that I had to make a trade off between the freedom or the career. I thought you cannot have both, but you totally can, and I love that you just shared that and that you already knew that, because I really had to figure that out. So how did that exploration phase, what did that look like for you? Did you try a bunch of different things, like took a million different courses, and was that the exploration, or did you have more of a like step-by-step approach of how you eventually started your freelance career?

Yeah, it was messy, let me tell you. I had left my job, I was not building this on the side while I kind of maintained my nine to five, and I had jumped in feet first and I really didn't know what I was going to do. You know, I had skills, I had worked in marketing at this company that I'd been at, but I didn't really know how to translate that into, like, all right, what can I actually get people like hire me to do for them on my own? And so the first several months I was renting my apartment out on Airbnb to pay my rent and buy myself some time, like literally sleeping at, staying at my now husband's house, staying with friends, but my parents like just trying to figure out how to buy myself time and was really just dabbling in a lot of different things and getting nowhere right. So about four months into this, I was honestly nearing the end of my rope. I was like all right, I got to figure out a way to make money here. And my former boss actually he gave me a call one day and said, hey, like I've got this ticket to this three day workshop on Facebook ads and I can't go. Do you want the ticket. And so you know, I said, absolutely sure, so I go to this workshop. It was in Madison, wisconsin, and it was this three day intensive on Facebook ads and I really, you know, I'd worked in marketing but I had never run ads, so this was totally new to me. And yet I knew like, all right, I'm very data driven, I like numbers. I kind of just had this feeling in my gut of gosh, I think that I could be good at this. And at the end of that three day workshop, the person putting it on he was pitching his kind of year long coaching program and it was $30,000. I was broke. I was literally like renting out my apartment on Airbnb, like living off of my credit cards. I had no money. And day two he, at the end of it, he pitched and he gave out his cell phone number and he said, hey, if anyone has questions about the program tonight, feel free to give me a call. I'm sitting there in my hotel that night and I'm thinking like gosh, like I just I really think this could be the thing. So I give him a call and I'm trying to dance around the question of like, how likely do you think it is that I could like really make this work and get clients. And he saw straight through me and he said to me like word for word if you do not have the money for the program, I do not recommend that you join. I'm like totally get it. Thanks so much. Hang up the phone. I immediately called my old boss who had given me the ticket and I was like I'm doing it, so show it up the next day, put the first like $6,000 payment on a credit card and literally just backed myself into a corner and said, all right, I'm going to figure this out Like I'm going to give this everything I've got. And the last several months before that I'd been dabbling, but this was really my moment of I'm going to go all in and I had to. I was on the hook for $30,000. I was like I've got to make this work. And so I knew that I was the kind of person where, if my back's against the wall, like I'm going to fight. And that's what I did.

Wow, yeah, oh, my God, so brave. That is insane, do you think? Do you think that could work for everyone, like, when people are listening now should they also invest? I don't know $30,000 or whatever it is. Should everyone just go all in and invest? Or like, how do you see that?

Yeah, so it is certainly not like blanket advice that I would give. I think self-awareness is really important. Right Again, like I'm the type of person where I was like I know, like I am going to, I'm going to do whatever it takes and I'm very, like, energized by that type of pressure. And that's not to say let me be clear I had many sobbing on the floor of my office, you know moments of what did I do? This is never going to work, like I'm crazy. But I pushed through those moments and I knew that I would do that. It would also I'd be remiss if I didn't say that but also came from this, in a certain sense, this place of privilege of knowing that if things, if shit really hit the fan, I could go sleep on my pain, my parents couch for a couple months or whatever I needed to do. Like I figured it's really important to work through what is the worst case scenario. And so often I think we build up in our minds like this kind of hypothetical this is so scary, like I, like this could go so badly. But we never actually work out like okay, how badly could it go? And so for me, like if I kind of played that out, it's okay. If this really doesn't work, what's going to happen? All right, I'm going to have this debt. I'm going to have credit card debt, I'm going to need to go get a job and I'm probably going to have to either sleep on my parents couch or stay with a friend or, like you know whatever, like I'm going to have to kind of get myself out of this, but like I'm going to have to go get a job and pay this money back. And that was honestly like not nearly as scary as just. I think when you're vague about it and you're just thinking, god, so risky, it's so risky. There's a lot of power in getting comfortable with the worst case scenario, and when you make peace with the actual worst case scenario, then it allows you to be so much more brave in moving forward because you have nothing to lose.

Yeah, yeah, and something needs to change to make a big change. Right, if you don't do anything, if you don't take any action, then nothing will change. So you will keep dabbling and maybe find something, maybe you don't. So how did it work out, like in that year of coaching? Did you like bake back your investment or did your freelance career take off from that moment? Or can you talk more about where you went from there?

Yeah, totally. Again, like this is certainly not blanket advice for everyone, but for me, hiring that mentor was 100% the right decision because he was, like he was really like one of the biggest names in Facebook advertising and so he really held my hand over that year and taught me from the ground up how to get results from people and so that he gave me the confidence to. It was almost like like I was able to like borrow his belief, like maybe I didn't have a ton of belief in myself, but I certainly had belief in him and that allowed me to kind of have the confidence to go out and get my first couple of clients and know that I was going to be able to get them results. Because I was literally like on zoom with him every week, screen sharing and my client's accounts, and like he was literally like teaching me from the ground up this is how you deliver on this promise that you made, and so that allowed me you know it was, I believe, my third, maybe my fourth month that I hit my first $10,000 month and that eclipsed what I had been making at my nine to five at the startup before that. Again, like I was really in this place where I was like I was ready to hustle and like I was ready to do whatever it took. And yeah, within those first few months I was able to get my first few clients, eclipse what I'd been making previously and very quickly paid off that $30,000. And then, over that first year of actually working with this coach, built a really strong freelancing business. And it was a little scary like once that ended and I was like all right, I'm taking off the training wheels, I got to go at my own. But I had learned I had really learned how to deliver, how to do this, how to do it at a very high level, and so by the time that year ended, I was very confident in my skills and my ability to go out and do it on my own for other people.

Yeah, and when did you decide to change into an agency model?

Yeah. So it was really, first of all, like I love freelancing. I mean everything that we do at the gig is about teaching freelancers how to build a business that can give them more freedom, more income, really profit from these types of what we call high income online skills, so things like ads, copywriting, graphic design and after about two and a half years of freelancing on my own, I was in this place where it was like okay, like this is amazing, I'm making more money than I, you know, thought that I could make. I have all the freedom, I can travel, I have this location, independence, I can do what I want. But I was in this place of I want to buy some of my time back. I want to be able to travel and not necessarily have to be spending so many hours at my computer working on these trips. And that was really what prompted me to start growing a team, to start getting help. And I think also, it was this understanding of okay, they're the things that I'm really good at, but then there are things that I'm not so good at, and there are people out there who can do these things better than I can. And, for example, like one of my earliest hires was a copywriter who is now actually my co-founder in the gig, jim Hamilton, and he is a phenomenally talented copywriter. Before he started freelancing writing copy, he was actually a massage therapist, so he also had this. I don't want to do this. I want location, independence. I want to make money online, but he's a phenomenally talented and skilled copywriter. So when he joined arms with me, all of a sudden, the results that I was getting from my clients were better than ever, because I'd been writing the copy, and that wasn't my strong suit. It was a couple of factors that really came together in that sense.

Yeah, I love that. I did exactly the same. I also started freelancing. I work in podcasting, right. So it's podcast production all day, every day. And I also realized at some point like, okay, I'm good at some parts of this, but there are also some parts that I'm just not really good at. I also don't enjoy it. I was procrastinating Like so much of some of these tasks. So I think hiring a team is awesome, like I'm so glad I made that change in my business at some point, and I think it's so interesting to hear you say like exactly the same reasons to build a team. So that's so interesting. And I think also, once you've been freelancing for a while, I feel like it's very important to know what needs to happen. So, for example, if my copywriter gets sick, I can write the show notes of show notes, of podcasts. I could do it. It might not be like the result might not be as good as what she can do, but we can still get it done. And also like, if, like, something happens, let's say, with my editor, I can edit the podcast. I think that's super, super important. So, yeah, I think it's really it's a great way to build a business like that to freelance, first get older skills and also see what you're good at Because maybe you're good at something that you wouldn't even expect and just trying out all these different things that you said. And how much did you travel during those years of freelancing? And then, when you build out your team and you had the agency, did you also travel a lot more or further away, or how was that?

Yeah. So I definitely traveled a lot. I think for me, like I was having so much fun building the business, like I got into this and I realized, man, like I love this, this energizes me, and so a lot of my travel, honestly in those for several years, was related to the business. Like I was going to events, I was joining masterminds, I was traveling with other business owners and that gave me so many incredible experiences and it was really like in the last couple of years, I had this epiphany of gosh, like I'm like I feel like I'm traveling all the time, I'm going lots of places, but I need to do more trips that are just like for fun, and so that's really what prompted me to do that with more intention. Right, because it's so easy for your calendar, like I feel every year, like around like June or July, I have this moment of looking at the calendar for the following year and thinking, my gosh, it's already full, and for me, I'm now being so much more intentional about putting the, the trips that are really just for me, like putting those on the calendar first and then building everything else around that, and so that's how my husband and I doing these two, three weeks in Iceland. That only happens if you are intentional about setting aside that time and protecting it Exactly.

And now you also run the gig right. When did you start the gig exactly and how did that happen? What's the origin story?

Yes, Jim and I, we launched the gig gosh in March of 2022. And really it was born out of this passion that we both have for freelancing as this entry point into entrepreneurship, because I think people often think that to start a business, it has to be like okay, I have this skill and now I'm going to go offer it and do it for other people and make a business out of that. But for a lot of people, the skill doesn't come first. It's the desire for the lifestyle, the results, the location independence, like that piece comes first. And then you're trying to back into okay, how can I make that happen? Like, how can I get this location independence without this kind of bullseye thing in mind of like, all right, this is like the service that I can offer, like the way that I can do that. And I think what's really incredible about the way that freelancing and remote work have exploded and gone from the fringe to the mainstream in the last few years is the opportunity is greater now than it's ever been before. So we really wanted to offer people a resource to be able to first of all understand all right, what are like? What are these high income skills that can give me this lifestyle that I'm looking for and how do I acquire those skills? And then, how do I actually build a business? Right, because there's the the skill of actually what you do copywriting, graphic design, running ads but then there's the skill of building a business and getting clients and pricing yourself and figuring out your taxes and like y'all these are things that you don't think about. So we're really looking to be that free resource for people to be able to get that understanding and that knowledge.

Yeah, very cool, and I think it's so cool that you really make this learning curve a little bit less steep. I think because you just share what you've learned in the end those years of freelancing, building an agency and working online and working and traveling so I think it's really a shortcut when you're looking at transitioning into a freelance career. I think this is just such an important, valuable shortcut that you can take. What would you say is your number one advice for new freelancers? Like someone who has no experience freelancing at all whatsoever, what's like the biggest do or don't?

Yeah. So there's a few things that I would say. First is you need to pick a direction, pick a skill that is going to meet the criteria for what you're ultimately looking to create. Really, this comes down to a few things. So the first is we really think of three criteria that defines what we call like a high income skill. So the first is that it gives you leverage to earn more, and this is really about being able to charge flat fee versus hourly. So, to give you an example, if you get paid $50 an hour, it's going to take you 100 hours to earn $5,000. But if you can charge $5,000 for an entire project and get it done in 35 hours, you just shot up your effective hourly rate to $142 per hour. So that's really important because there's so many remote jobs that can give you location independence of doing customer support for a company or different things. But if you don't have the leverage to charge project rates, then you're always going to be capped by the amount of time that you spend. The second criteria, and certainly the most important for everyone listening to this show, is that it can be done from anywhere. I think location independence is definitely one of the biggest reasons that people are interested in freelancing. And then the third criteria is proximity to the sale, and this is something really key to kind of understand. So proximity to the sale is really about the ability for clients to trace sales revenue profits directly back to your work. Now I'll give you a couple examples of what this could look like. So maybe it's that subscribers read an ad that you wrote, or sales come from a page that you designed, or even prospects speak to you on the phone before signing up. This is really what allows you to go out and justify these high rates, because you're able to really paint this very clear picture of how the work that you do is going to lead to more sales, more profits for your clients.

I love that. I think that's such a great tip, and I've never heard this criteria before in all the Star Free Lansing resources that I've seen. So I think this is so smart, because I think the idea of, okay, well, you just start freelancing and you just increase your rates as you go, yes, but I also think for many skills there is a certain maximum that you can charge and then above that, people are not going to pay it. And what you just saw, if you can just say, listen, this is the amount of sales that I got your business, this is what I charge. It's an investment, it's not a cost For the client. They will get more out of it than the money that they pay you.

So it's important and you will continue to expand your mindset around this as you press forward. Because when I first started, so for me my skill that I picked was paid ads right, and so when I first started I was charging anywhere from $2,500 to $5,000 a month to manage someone's ad account, and to me at the time that felt massive. That is so much money. I had to pay me that every month to do this for them. And then, as I kept going, as I ultimately built the agency, I had this really just mind boggling moment. This was about a year ago where we now in the agency we build clients based on how much ad spend that we're managing for them. And as we started working with kind of bigger and bigger clients that were spending more and more, I had this limiting belief of at one time like our rate chart capped out at $20,000 a month, because in my mind I was like no one's ever going to pay more than like $20,000 a month. That's insane. Who's even going to pay that? And we had this kind of capped rate structure where it was like all right, anything you're spending more than X, this is the fee and it doesn't go out from there. But then I had this moment of realization, like a mentor said to me, what happens when you're working with a client who's spending a million dollars a month? You're still gonna charge them that same rate. And so we shifted our rate structure, we uncapped it and the first time I had a client who literally, like we spent I think it was like about half a million dollars for them in a month on their ads they paid us $50,000 for that work in one single month. That's an entire salary. And so it's so I love what you said because it's so powerful to understand that. Okay, to me, like them, paying that, like that seemed insane, but to them they made millions of dollars off of that work, like they probably made $2 million in sales, right? So to pay us $50,000 to do that for them, like it's a clink in the bucket. So you really need to shift away from this idea of trading time for money and figure out how you can get leverage, because the more you can do that, the more you can both have this location independence, but you can also like really enjoy it and do it, have the lifestyle that you wanna have, without kind of these artificial caps that you may put on yourself because of what you think that people will pay.

Yeah, exactly, absolutely. I love this. Do you have any other tips for people who are already freelancing and they're looking to increase their freelance income?

Yeah, so you know, I would say that it's really about getting the right clients, and, for me, I'm a huge believer in the freelance platforms that are out there. My favorite is Upwork. It's one of the biggest and one of the ones that people are probably most familiar with and, honestly, like that client that I mentioned that spent $50,000 with us in a month I got that client from Upwork probably two and a half years before that, and I've had many of our best and biggest clients that came from that platform, and I think often people think that the clients who are on these freelance job boards are like these, like crappy, like low paying clients, and that is really not the case. But what is true is that the best clients on those platforms they use the platform in different ways, and so it's important to understand how to position yourself on those platforms in order to attract the types of clients that you really want to work with. And so actually I would love can I give a gift to your audience? Yeah, please. So we have this training that we actually sell through the gig, which is really a. It's like a 40 minute video training on my five step process on how to land great clients on Upwork and this is applicable, like it's really designed in mind for someone who has a brand new profile. You know you don't need to have a ton of reviews and like testimonials built up to follow this process. So we sell this through the gig, but I would love to give it to your audience for free. If you go to it'sthegigio backslash C, backslash VIP If you opt in there for the gig, you'll get the free newsletter and we'll also send you that training.

Very cool. Thank you so much. I think that's gonna be huge when you're looking to go into freelancing. Yeah, definitely use all the tips that Dorothy gave you in that video. I think it's really interesting. There's people who hate Upwork and there's people who love it. I feel like there's no in between, and you're obviously someone who loves it. So I feel like it's just that you know how to use it, and maybe people who couldn't make it work for them, maybe they just don't know how to use it or didn't figure it out yet. So I think this is a huge resource. Thank you so much for sharing that with us. Absolutely, it's my pleasure. Dorothy, do you have any other trips, anything exciting, coming up in your business at the gig? Can you share a little bit more about the near future for you?

Yes, oh, the most exciting thing for me right now is I'm actually putting a brief pause on travel because we are bringing a puppy home on Monday.

Yes, that's the best reason ever, so that's the most exciting thing.

Yeah, so that's the most exciting thing in my world right now. Super excited about that. But yeah, I think next on the bucket list we had so much fun in Iceland. We really wanna do like Norway, sweden, like Explorers, scandinavia, and then I would say like next highest on my bucket list is New Zealand. So that is. We actually literally have that trip all planned out. I think we're gonna do it at the end of this year and spend about a month over there. Yeah, that's what's next for me Cool, very cool.

That's all very exciting, especially the puppy, thank you. Great reason to pause travel for a puppy. I would do exactly the same, so that's super exciting. Are there any other places where we can go to follow you, follow your travels? Do you have any social media channels that you wanna share?

I am. It's so funny for someone who built their career off of running social media ads. I am like pretty dark on social media, but I do post a lot of stories of I ride horses, so you can see lots of horse content on my Instagram. So, yeah, you can find me at Dorothy Ilson on Instagram. You can find me on LinkedIn, like I would love to connect and network and meet people who are listening to this show, so you can find me on Instagram or LinkedIn. And then, of course, you can find the gig at thegigio and I can get that free resource.

Kite Awesome. Well, make sure to link all of those the free resource and also LinkedIn and Instagram in the show notes. So go to the description below and click all the links. Connect with Dorothy. And, yeah, make sure to check out the gig because it's awesome. I already did my research before this recording this episode and it looks awesome. I'm subscribed. I'm like I went through all the resources. I'm an expert now as well. Dorothy, thank you so much for coming on the show and for sharing your freelancing tips and wisdom with us today and, yeah, good luck with your puppy also, Kite-.

Thank you and I appreciate you having me.

It's been a lot of fun, kite and that's it for today. Thank you so much for listening. I appreciate it very, very much. I would appreciate it even more if you could leave a review on Apple Podcasts for me. That way, more people can find this podcast, more people can hear the inspiring stories that we're sharing, and the more people we can impact for the better. So, thank you so much if you are going to leave a review, I really appreciate you and I will see you in the next episode.