Ep. 302: How This Freelance Guru Helps Others Create Freedom Through Gig Work with Dorothy Hollabaugh
In this episode, I speak with Dorothy who is the Founder of Needle’s Eye Media, and the Co-Founder CEO of The Gig, a digital media company that helps freelancers acquire and profit from high-income online skills.
In 2017 Dorothy began freelancing and quickly fell in love with the freedom, flexibility, and uncapped income it provided.
She is on a mission to curate the most important freelance content & tips and give it to you in a fun, entertaining, and easy-to-digest format that you can consume in 7 minutes or less. Her goal is to help others build their own profitable, fulfilling, and recession-proof business as a freelancer.
Listen on to find out how Dorothy has been able to help others create freedom though gig work.
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Transcription:
Debbie:
Hey everyone! Thank you so much for being here.
I am so excited to be with my guest today. I’m here with Dorothy.
Hi, Dorothy! How are you?
Dorothy:
I’m good, Debbie, thank you for having me.
Debbie:
Thank you so much for being here. I am really excited to talk to you today.
Can you tell us more about you and why you live an offbeat life?
Dorothy:
Absolutely!
So, I am definitely someone who has always really just craved the sense of control over my life and really what I wanted to create and for a long time, I had this very, kind of stereotypical society driven view around what success looks like in a career and that led me to study Finance and Accounting and so you know, I was really going after this type of big, kind of, corporate, city career and it was during my final year of school where I realized, “Gosh, I’m doing this for all the wrong reasons.”, you know? I am doing this because of status, because of the salary, and I think that it was to help me to obtain and it really was, you know, it really wasn’t aligned with what was actually going to make me happy and fulfilled as a human and so you know, I was kind of facing down this path that I had worked so hard to set myself up on to get this, quote-unquote, “successful career”, and then realize that I don’t even want it.
And so I ended up essentially giving up my job offer that I had secured heading into my senior year, and moved to Chicago, not knowing how things were going to unfold and ended up working at a startup for 3 years and I left that company and went off on my own, and since then it’s really shown me just how fun life can be when you really open up all the possibilities and recognize that we can create our lives anyway that we want them, we just have to have the courage to make that leap and do it.
Debbie:
Yeah and I think that’s the hardest part is really figuring out how to get to that point where you can leave something that’s really familiar to you or you think and feel is stable and then taking that first step to do that, how did you get that courage, I guess to leave something that was what most people think is like the start of your American Dream, right? Because this freelancing and well, now after the pandemic, remote work is seen as more stable, but before when we used to tell people that, they were like, “Oh my gosh, you’re crazy! How are you going to live and afford anything?”.
Dorothy:
Yeah and honestly, I was stubborn and I was naive and that really worked in my favor at the time, you know, I’ve gotten really fortunate that the startup I work for here in Chicago, it was a small scrappy team, that business went on to be acquired in a multiple figure acquisition so it ended, you know really this big company but I was their fourth team member and on the first few years of that company when I worked there, we were very non traditional, you know, it really did look like, you know, kind of like the start up that you imagine, you know, where, there’s not a lot of structure, where we’re kind of flying by the seat of our pants and I had a lot of freedom and a lot of autonomy in that role and even though I did have a boss and yeah, we had an office, I did feel like I had that control that I wanted, you know, I was able to say, “Hey I’m going to take this three-week trip and work remote while I do it.”, and when I decided that I was going to leave that company, I did not want to go backwards in terms of the degree of flexibility and control that I felt I had in my life at that time and so the idea of working for a company that was going to make me be in Chicago, in an office, 5 days a week, it was really a non-starter for me and so as I was interviewing and talking to different people and looking at opportunities, I was finding opportunities but they weren’t going to give me that. And so it was really just this bet that I had to make on myself, of you know, “Okay, I’m going to try to figure out something that I can do on my own.”, and it really came down to confidence that if it didn’t work out, that wasn’t going to be the end of the world, you know?
And I think this is something like if you’re sitting in, you know, a 9 to 5 job or you’re afraid to make that leap, it’s really powerful to actually play out the worst case scenario. So really ask yourself, “If I try, what is the worst thing that can happen?”.
And for me, I was confident that I could get a job within 4 weeks, 6 weeks, whatever. You know, if sh%t really hit the fan and I had no other options and that was the position I was already in – was needing to go look for a job and so in my mind, it was actually very low risk because it’s like, “Okay, I can try this and either it’s going to work out.”, or, I’m going to go back sitting in the same position I’m in right now, and that was definitely something that made me more confident and comfortable, taking the chance.
Debbie:
Yeah and for somebody who always wants something more, something that they feel like they can really grow into, looking at the life that you have right now is most of the time worse than the unknown, because at least, you know, if you try something new, like you mentioned, Dorothy, you can always go back to where you were but if you never try, you never know. And then there’s always going to be that “what if?”, and regret, you know? And we get old very quickly and very fast and you don’t want to go down that route and just be miserable because you didn’t try something that you always wanted to do.
So once you finally took that leap, you left your job. What did you decide to do that allowed you to make this sustainable for yourself?
Dorothy:
Yeah so, you know, honestly, I really floundered for several months trying to figure out what I was going to do. How am I actually going to make money on my own? I was trying so many different things and none of them really panning out.
And so about 4 months into this process, you know, I was renting my apartment out on AirBnB to pay my rent, to buy myself more time and my former boss from that start up, you know, he actually called me up and said, “Hey, I have this ticket to a Facebook Ads workshop and I can’t go, would you like the ticket? And so, I ended up going to this three-day workshop in Madison Wisconsin, which was really, it was really the thing that clicked, you know, I had actually seen the startup that I worked for, they went from zero to 10 million in annual revenue, in a large part off the back of Facebook Ads.
And so I had seen that happen, you know, I understood the power of paid media but it was not something that I had direct experience in and I was in this place where I knew that I was very analytical, I was very data driven and as I was going through this, you know, this 3 days, I just thought to myself, “Alright, I really think that this is something I could be very good at and I’m really running out of options here.”, you know, nothing else was really panning out, so at the end of that 3 days, the person putting on the workshop who was really at the time one of the biggest names in the space, he was promoting his year long, coaching and mentorship program and at the time, I was broke, I was living off of my credit cards, you know, trying to figure out something to do and I really just felt this, just this feeling in my gut that this was something I could make happen and so, you know, against probably better judgment, I ended up taking a leap and I joined that coaching program, really I had no idea how I was going to pay for it or what I was going to do and just backed myself into a corner where it was like, “Alright, I’ve got to figure this out.”, you know, I’m on the hook for this now and within the first 3 months, I got my first couple of clients, you know, I had this coach really holding my hand and helping me to deliver on those promises and get them results and yeah, within 3 months I had substantially exceeded my salary from that job that I had left so that was really the start of my freelancing career.
Debbie:
And that’s amazing that you actually had that help that you needed because I think for a lot of people the reason why we don’t succeed faster than we think is because we don’t ask for help, right? We think, “Okay, I want to save money.”, or even like we’re too stubborn to ask for help because we think we can do it all on our own and you asking for that help, do you feel like that changed a lot of the trajectory of your business and what you’re able to do and you actually creating income from doing this?
Dorothy:
Oh without question. If I hadn’t done that, I really don’t believe that there’s any way that I would have figured it out on my own. I think I would have ended up having to go get a more traditional job because I think that if you’re in a position where you are working a 9 to 5 and you want to start freelancing to create this opportunity for yourself, you can do that alongside your job, and you’ll build that up slowly and acquire, get paid to acquire those skills as a freelancer, you know, work with small clients, build up your confidence and you know, your skill set and then going full time when you’re ready to make that leap and you have that all figured out. I wasn’t in that position, I was, I did not have my job anymore, I was on my own and I had to figure out a way to short cut that learning process because otherwise I couldn’t afford to sustain myself for much longer, and so making that decision, it allowed me to shortcut what would have otherwise been a very long and painful process of figuring out how to do it the right way out and how to do it successfully.
And so, for me, having someone hold my hand in that way was really exactly what I needed to make it happen.
Debbie:
Yeah and I hear this sometimes too from people like, “Oh, I don’t want to spend the money because it’s too expensive”, or, “I don’t know if it’s really going to work.”, and personally, I’ve spent a lot of money on coaching, on courses, that like 80% of them didn’t go how I thought it would be but like the 20% that did, you would pay like, I say this all the time, like there was one course where I paid like $1,000 just for the two minute or even a minute of that course that I really needed and I knew everything else except for that one thing and it was worth that thousand dollars for those two minutes because that’s the missing piece that you need.
So even if you just need like a minute of what they’re going to say and it helps you click it’s worth the money that you’re giving or, you know, because of all of the things that you’re actually learning it from it and it may even take you like years and years to figure that out for yourself.
Dorothy:
Yeah, I mean finding the right person is really important. I’ve also had coaching relationships that didn’t go the way that I wanted but I’ve had far more that have pushed me forward in ways that just wouldn’t have happened otherwise, I think that it’s important to have self awareness so I knew that I am a person that my back is against the wall and I’m going to fight and I was so committed to figure it out and make it happen for myself that I knew that if I was able to figure out how to invest in the right support, that I would do whatever it took to be successful.
So, you know, at the time it was terrifying. In fact, the second night of that workshop, the person putting it on gave out his cellphone number and said, “Hey, if you have any questions about the program, give me a call tonight.”, and I called him and was basically trying to dance around the question of, “Hey, how likely do you think it is that I could actually get clients and be good at this and make this work?”, and he saw straight through me and you know, said at point blank, “If you do not have the money for the program, I do not recommend that you join.”, and I’m like, “Okay, got it, got it, thank you so much. Totally, totally understand.”. I hang up that call and immediately rang up my old boss that gave me the ticket and said, “I’m doing it, I’m taking the leap”, and you know what, the next morning, I put that first $6,000 payment down on my credit card and it was really just this blind fate, this stubbornness of knowing that I was going to do whatever it took to make this happen and if you are going to, you know, I’d say what I did was the hard route of you know, going all in, all at one time and really kind of you know, walk into the fire that way, but I had the self awareness to know that, you know, that was the type of scenario where I would rise and figure it out.
Debbie:
Yeah and that is really exciting but also nerve-wracking at the same time because it’s not money that is just like it comes from trees, you know, you work really hard for that, especially for somebody who left their job that’s money that you need to live. So, taking that and having blind faith is a huge step for you, but obviously it worked out because you worked very hard and it got you to clients that you needed to make the income that you needed to have.
Dorothy:
Exactly and I mean it’s definitely, you know, I think if you’re sitting in a position where you do have a job that, you know, you’re able to build up some freelancing income on the side, you know, while you’re still at your full time job and you know, make that leap, it’s you know, it’s, again, about self-awareness, some people are really lit up by the idea of the way that I did it, and that story motivates them and inspires them and there’s some people who hear a story like that and they’re like, “Oh my gosh, that sounds terrifying.”, and there’s no right or wrong path, I was sort of forced into the, I would say, the harder path, by circumstances I happened to be in but it doesn’t need to be that way, so I think it’s just really, again, designing your life and creating it in the way that you want it and doing it in a way that feels elegant to you.
Debbie:
Absolutely and that’s the beauty about this is that you can have a life that you create for yourself and not something that you were led to so it’s more being proactive with what you’re doing now. So for you now, Dorothy, is this still what you’re doing? I know you have an advertising agency, is this what you ended up doing? Is this something that you really knew you wanted to do long term in terms of that, how did you make sure you kept on building your clients and making this into a full fledged agency instead of being a solopreneur?
Dorothy:
It was really just a natural evolution so I started taking on, you know, Facebook advertising clients and really worked on my own doing that for I would say the first 2 and a half year and loved it in many ways, you know, I was able to travel, I was able to have that complete control over my schedule and with what I was doing and who I was working with but I didn’t love the work, if that makes sense. It was one of those things where I was good at it but it wasn’t something that really lit me up but I kept pressing forward and then I got to this place where I really needed help and so I basically ended up, in 2019, brought on my first team member to support me, it was a contractor at that time and what I realized was, as I found help, I started to enjoy what I was doing day to day, more and more and I realized I loved being an operator, I loved managing a business, right? Which is very different from kind of the nitty gritty of being inside of running ads, like those are two very different skill sets and so that eventually turned into me hiring my first full time person and I realized if we needed to expand, you know, I had, my skill set was in Facebook ads but we needed to be able to run traffic for our clients on YouTube and you know on at the time, Snapchat and Pinterest and so that really led to me growing the team and you know, bringing out people who had more experience that I did and could do it even better than I could and that allowed me to really elevate into this role of CEO and manage the business and that really turned it into something that I truly loved and both had the control and freedom and flexibility but also really loved what I was doing day to day.
Debbie:
Yeah and it’s a totally different thing but I mean, if you think about it this way, there’s just some people that thrive doing the actual work and there are certain people that like to actually do the operation, manage all of that and that’s what you’re talking about, Dorothy, but how did you make that transition because that’s another ball game, right? It’s like first, you’re on your own and then you hire somebody and it may sound really great but then also like training somebody, finding the right people, making sure that they’re there for a long time because if you’re giving them all of these different skills, like how did you make sure that that all went exactly, I guess, to plan? I mean, you know, not everything goes to plan, but how did you make sure that that worked out for you and to build an even bigger team for yourself?
Dorothy:
Trial and error and messing up a ton and learning and figuring out and pressing forward, you know, it definitely wasn’t something that went entirely to plan, I started by bringing on two, basically interns, actually, they, you know, I met some people who are studying marketing and in my mind I was thinking, “Okay, great, I can train them to do some of the things on the back end”, and that went well and then you realize that training someone often takes way more time than actually executing it yourself and so it was really why I hired my first full time person at the end of 2019 that I started to be able to lean in to that transition to becoming more the operator of the business and it was really a 2 and a half year process, from the end of 2019 to present day, I mean now, we are a team of 5 and we’re a 7 figure agency and it really looks the way that, if i could’ve sat back at the time a few years ago and just envisioned like my absolutely dream of how this business could look, it would be exactly where we sist right now which is such a beautiful thing but it was messy to get there so I think it’s really this ongoing journey of making mistakes and learning from them and figuring it out, you know, it’s never going to unfold exactly the way you imagine but you just need to keep the focus on the end result of what you’re looking to achieve and take a live action of every step of the journey.
Debbie:
Yeah, absolutely and I think also having again, having that faith, that things will work out, especially when everything is messy, and you’re making mistakes, you know, and just understanding that this is kind of like the hard part of it and it gets better cause sometimes it doesn’t feel like it.
Dorothy:
Yeah and having faith, I mean it gives you the courage to make bold moves and I think that is really a lesson that has shown up for me time and time again in a really powerful way because as a small business, you often don’t have the luxury of training someone up often, if you’re just really busy and you need help now, you need someone who can step in and really do the job from day 1 and ideally do it even better than you could and so, it’s interesting to talk about how some people love being the operator and some people love really executing on the work itself and my now business partner, that was really his story, as he started getting help and building a team, I loved my work more and more and he hated that transition, he was like, “This sucks, this is pulling me away from what I love”, which is the marketing and the strategy and what I’m doing for clients day in and day out and so when he and I met, it was just, we immediately clicked and it was so clear that there was so much synergy there between the two of us, though he had offers on the table from agencies far bigger than mine who were offering him twice the salary that I could pay him at that point and so I ended up literally, the day after I met him, on Zoom, I booked a 6:30AM flight to Washington D.C. to meet him in person and to convince him to work for me since I knew I couldn’t match those other offers, you know, just on salary and making bold moves like that has really served me well and that was the catalyst to really the most, you know, substantial growth that we’ve had in the agency.
Debbie:
Yeah and that’s something that most people wouldn’t really do, right? And that’s what you really did, it showed that person they’re important and they would really mean something to your business, if they decided to work for you, which is pretty incredible that somebody did that when you’re trying to decide what you’re going to do, you know?
It’s kind of like those romance, like movies. Like, “They took the time to see me and these other people didn’t, so I’m going to choose you.”.
Dorothy:
And it’s funny but that was exactly what it was for him because he was someone who was, loyalty was very important to him and he wanted somewhere where he could really make an impact and he told me later that when I said that i was jumping on the plane to come talk to him and have that conversation in person, he knew that he was going to say yes, almost regardless of what I put in front of him and so I think, having the courage to trust your gut in those instances when it’s, like, you know, my gut was just screaming at me, you know, I’ve got to do something and I’ve got to do something big and that really played out in a great way.
Debbie:
Yeah, and I love that, that’s such a great story to tell people about how you found each other and how you were able to create this business together and how you were just, in sync in that sense. So, Dorothy, I know you also own, you’re also the CEO of The Gig, can you tell us more about that as well?
Dorothy:
Absolutely, yes so, freelancing really was my ticket into an offbeat life, into having this control and really being able to create my life in the image that I wanted and I’m very passionate about the opportunity that freelancing imposes for people to do the same thing, you know, whether your goal is to have a business with a team or if you are someone who wants to just be a solopreneur and live this lifestyle of travel and freedom and opportunity and so, we started The Gig, my co-founder and I, we started it really to help people acquire and profit from these high income online skills that have so much opportunity today, so you know, things like advertising, things like copywriting, graphic design, you know, web development, there are so many opportunities for people who are in the position that I was in where I didn’t have the skill set, like I have never managed a Facebook ad, when I decided, “Alright, I’m going to start freelancing in this, I’m going to figure out how to do this.”, and so it’s an opportunity to really get paid to learn and build up this income, either on the side or you know, full time from the start and I’m really passionate about helping other people do that so you know, through The Gig, we publish a free daily email newsletter to help people start this freelancing journey and do it in the right way and short cut these mistakes.
Debbie:
Yeah and I love that you’re able to do this and teach people all of these high income skills that they can do as a freelancer, they can do from anywhere because most of the time when we leave school, a lot of the things that we learn, really is not as helpful as we think or maybe it’s just the tip of it and it’s really when you find the right mentor or you learn something from maybe a current job or you really try to go out there and try to figure it out that you do find something so I definitely think we need something like what you’re doing, Dorothy, because otherwise, it’s just floundering around, just trying to figure out what works for you, I mean, obviously that’s not always a bad thing, that’s how we figure out where we want to be but having people who have gone through it and kind of showing you the way to figure it out is so helpful and like what happened to you when you found a mentor, it allowed you to go a lot faster than it would be if you just did it on your own.
Dorothy:
Exactly and you know it probably doesn’t matter, kind of what your situation is right now, you really just have to have the commitment to do it, I mean my co-founder, Jim, he was a massage therapist and was making you know, something like $35,000 a year and you know, really just did not like the path that he was heading down and so he decided to start learning copywriting and now, fast forward to a couple of years and he makes 6 figures as copywriter and has again that same level of control and just freedom in his life that he wanted, so you know, there’s so many opportunities out there, this is a space that has really exploded, you know, since the pandemic and so the opportunity now is greater than it, certainly greater than when I started and really greater than it’s ever been.
Debbie:
Absolutely. There’s just a lot of opportunities out there that are just honestly emerging and still growing so we don’t even know where it’s going to lead and what else is going to come from it and I love that.
So, Dorothy, let’s fast forward to maybe 40 to 50 years from now and you’re looking back at your life, what legacy would you like to leave and what do you want to be remembered for?
Dorothy:
Hmm, I love that question, you know, I really believe that the purpose of life is to find what brings us joy and to really do things that light us up and support other people and doing that as well, you know, I think there’s so much fulfillment that comes from helping other people and pouring into others and I really just, I’ so grateful that I stumbled onto this path because when I think back to what my life would’ve looked like if I had gone forward with that accounting job, you know, it’s just, it would be so different and it would really be of so far away from this life that created and that I really love and so if I can help other people to do that for themselves and to really design a life with intention to live an offbeat life and really do the things that light them up and bring them joy, that is the greatest gift that I can give myself from the standpoint of fulfillment and legacy, so, that’s really what we’re trying to do with The Gig, is to help people take back control and create a life that they love and so, if I can help some people do that, for the next coming years and decades, that is something that I would really love.
Debbie:
That is amazing and I am so grateful that you’re doing that because I’m sure there’s going to be a lot of people who will really get something from that. I wish I had when I first began like 5, 6 years ago, that would’ve been super helpful but I’m glad that it’s being out there right now, so thank you for that, Dorothy and thank you for joining us today. For our listeners who want to learn more about you, where can they find you?
Dorothy:
Absolutely so you can find me on Instagram, @dorothyillson. I would love, if anyone is interested in freelancing or want to explore this, I would love to give a gift to your audience, we actually have 2 guides, maybe helpful for you, depending on where you are with your journey, if you are really just trying to figure out what you could do to start freelancing and build this income on the side and start to move away from your 9 to 5, whatever it might be, if you opt in to The Gig, we send everyone who opts in this High Income Skill Guide which goes through the different skills that have the most opportunity today so you can start to figure out which is best for you and then we also have a video training that I did on my exact step by step process on how to get clients on Upwork.
So if you already know what you’re doing and if you’re ready to start taking that step and look for clients, I would love to share that training, so you can get both of those at thegig.io/vip and if you opt in there for the newsletter, you’ll get both of those delivered straight to your inbox.
Debbie:
Perfect! We love that, Dorothy, that’s definitely going to be super helpful for all of us. Thank you so much for sharing your journey with us, we really appreciate you.
Dorothy:
Thank you for having me, it was a lot of fun.
Listen to Dorothy’s extended interview where she talks to us about how to create a recession proof business as a freelancer.
What you’ll find:
Expert tips and valuable advice on how to create a recession proof business as a freelancer.
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