Episode 155: From job security to career freedom: how freelancing can protect your future – with Dorothy Illson of The Gig

Quitting your job and becoming a freelancer can sound risky, but freelancing and having multiple clients can actually insulate you against a downturn and make you more recession-proof than when you’re an employee.

Freelancer and advertising agency owner Dorothy Illson (Hollabaugh at the time of recording) talks about the advantages and disadvantages of being a freelancer instead of an employee, how freelancing can make you recession-proof, and the different skills you need to become a freelancer.

She explains how freelancing can generate uncapped income, the flexibility and control that freelancing brings, and why anyone can become a freelancer no matter what career they are in.

Today’s guest

Dorothy Illson of The Gig

Website: The Gig

Instagram: The Gig

Twitter: The Gig

TikTok: The Gig

LinkedIn: Dorothy Hollabaugh

Dorothy Illson is the founder of Needle’s Eye Media, a digital advertising agency for data-driven businesses looking to scale, as well as co-founder and 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.  After generating more than $1 million in freelance fees, she pivoted that experience into a results-driven paid traffic agency that spends millions of dollars each year on behalf of its clients.

Now through The Gig, Dorothy is on a mission to curate the most important freelance content and tips and give it to you in a fun, entertaining and easy-to-digest format that you can consume in seven minutes or less.  Her goal is to help others build their own profitable, fulfilling and recession-proof business as a freelancer.

What you’ll learn in this episode

  • [1:43] How Dorothy learned about the business world.
  • [3:16] Why Dorothy became a freelancer and started her own agency.
  • [4:48] How people responded to Dorothy leaving a prestigious career path.
  • [7:06] What ‘freelancing’ means.
  • [8:42] The advantages of being a freelancer instead of an employee.
  • [10:29] The disadvantages of being a freelancer.
  • [11:45] The increased control freelancers have.
  • [13:45] How being a freelancer can make you recession-proof.
  • [16:55] How freelancers can pivot into different niches.
  • [20:40] The best high-income jobs for freelancers.
  • [24:30] How to build freelancing skills.
  • [27:48] How to find your first freelance clients.
  • [29:35] How new freelancers can compete against a global labour pool.
  • [31:48] How to compete against experienced freelancers.
  • [33:18] How long it takes to transition from employee to freelancer.
  • [35:39] The overarching skills all freelancers need.
  • [37:14] How to build the sales skills that are necessary as a freelancer.
  • [39:24] How to know how much to charge as a freelancer.

Resources mentioned in this episode

Please note that some of these are affiliate links and we may get a small commission in the event that you make a purchase.  This helps us to cover our expenses and is at no additional cost to you.

Episode 155: From job security to career freedom: how freelancing can protect your future - with Dorothy Illson of The Gig

Jeremy Cline 0:00
Quitting your job and becoming a freelancer may sound like it's pretty risky. But what if I was to tell you that, actually, it can be a great way of insulating yourself against a recession or an economic downturn? By having multiple clients, can you make yourself more recession-proof, not less? That's what we're going to be talking about in this week's episode. I'm Jeremy Cline, and this is Change Work Life.

Jeremy Cline 0:40
Hello, and welcome to Change Work Life, where we're all about beating the Sunday evening blues and enjoying Mondays again. If you want to know how you can enjoy a more satisfying and fulfilling working life, you're in the right place. When we're in an economic downturn, probably the last thing you're thinking of is quitting your job and becoming self-employed. But could becoming a freelancer, in fact, be the safer option? When you have greater control over your time, who you work for and how much you get paid, can you become more recession-proof, not less, than when you're an employee? That's what we're discussing this week with my guest, Dorothy Hollabaugh. Dorothy started freelancing in 2017, and used her experience to found a digital advertising agency. She's co-founder of digital media company The Gig, through which she helps freelancers build their own profitable fulfilling and recession-proof businesses. Dorothy, welcome to the podcast.

Dorothy Hollabaugh 1:35
Thank you so much for having me.

Jeremy Cline 1:36
Why don't you start by telling us a bit more about The Gig and why you started it?

Dorothy Hollabaugh 1:41
Absolutely. So, The Gig really evolved out of reflection on my own career journey over the last five years or so. I had a very twisty, turny type of path, I thought that I was going to be an accountant, that was the plan all through school. And then really, right as I was graduating, I realised that I was going into accounting for all of the wrong reasons. I was not excited about it, it was really just to kind of tick the box of what I thought success meant. And I basically decided to jump ship and give up the job offer that I've worked my butt off to land, and ended up going to work for a start-up here in Chicago instead. And this was a very early-stage start-up, I was their fourth employee, they were brand new. And I worked there for just under four years and saw that company go from zero to 10 million in annual revenue, they ultimately went on to sell for multiple nine figures. And it was really an unbelievable educational experience, and kind of what it looks like to scale a business from the ground up. Even though I had studied finance and accounting, a lot of my role at that company, I mean, in a start-up like that, everyone wears a lot of hats, and I wore a lot of marketing hats, that was really my primary focus. And so, when I left that job, I've just gotten very spoiled. And having my first role out of school be something where I had so much flexibility, so much autonomy, I could work remote when I wanted to, before that was a common thing, and I really wasn't willing to give up the level of autonomy and control that I felt I had in that job, and go work somewhere that was going to make me be in an office five days a week in Chicago. And so, that was really how this idea was born of trying to do something on my own. Why don't I see if I can make money without getting a normal job? And I'd always had a little bit of an entrepreneurial bug, I had a vision that eventually I might want to start a business, but I didn't think I was going to do it at 25. Right? So, that decision to, let's just try, let's just see if I can make this happen, it ultimately turned into the start of my journey as a freelancer. I freelanced by myself running Facebook advertising for clients for about two and a half years, and then started hiring, and that morphed into what is today a seven-figure agency. So, the idea of The Gig was really about how do we help that person who's sitting where I was almost six years ago, who is looking to create more freedom, create more flexibility in their lives, have that uncapped income, how can we help them to do that more effectively, faster, and really kind of avoid a lot of the common pitfalls and mistakes?

Jeremy Cline 4:34
I've got to ask, I mean, accountancy has a reputation possibly for being a bit dull, but it is quite prestigious. I mean, what was the reaction of your friends and family when you said, 'No, I'm not going to be an accountant, I'm going to go and work for this four-man start-up'?

Dorothy Hollabaugh 4:49
They thought I was nuts. Yeah, I mean, my parents, as you can imagine, were not thrilled. My friends were supportive, but definitely thought that I was a little bit crazy. And I think it really came down to, I didn't know what I wanted to do, but I knew I didn't want to do that. And really what had happened was, I had stumbled into the world of personal development and really just started to expand my mindset on what was possible for me, and for the very first time, I asked myself the question, is accounting just going to make me money, or is it going to make me happy? And that, I felt, was a resounding no. And so, in terms of kind of what people thought, I think the general chorus I was hearing at the time was, it's so risky, it's so risky. And I'd really love to kind of flip that on its head for people, especially if you are sitting in a position like I was, where I needed to go find a new job. And I was fortunate that I was pretty confident that I could get a job quickly if things really hit the fan and I needed a job in the next four weeks, I was confident that I could get some sort of job, even if it wasn't what I ultimately wanted, I could get something that could pay my rent temporarily. So, really, whereas everyone was saying it's so risky to try to do something on your own, I thought, 'Well, what's the risk?' I try to do something on my own, either it works, or it doesn't work, and then I have to, what, go look for a job? Which was exactly the situation that I was already in. So, I think that exercise of playing out, okay, what is the worst-case scenario, if I try, that can be very freeing, when you realise it's not quite as scary as you may be built up in your head.

Jeremy Cline 6:34
In 150+ episodes of the podcast, I don't think anyone's come on and said, 'Is this something that's going to make me money or make me happy?' But that's such a beautifully pithy way of putting it. I absolutely love that.

Dorothy Hollabaugh 6:46
Yeah. And to be clear on that, too, it's not, 'Is it going to make me money OR is it going to make me happy?', it's, 'Is it going to do both?' Because I think, often we can get into this place of feeling like we have to choose. And I think that's unfortunate.

Jeremy Cline 7:02
Let's start at the beginning. How would you define freelancing?

Dorothy Hollabaugh 7:08
I mean, freelancing is really when you are being contracted by companies, by business owners to do work on a contract basis. So, they are not hiring you as an employee, they are hiring you for a specific project or on retainer to month after month complete the same task for them. So, you're not working for just one boss, one company, you have several different companies that you are contracting with, making up your total income.

Jeremy Cline 7:39
And is there anything that looks like freelancing, that perhaps you wouldn't define it that way? So, you often hear of people leaving companies and then going back to them as consultants, and it turns out they're actually doing pretty much exactly the same job, just on a different basis. I mean, does that count as freelancing? Or is that something a bit different?

Dorothy Hollabaugh 7:59
I believe it does, because what they're doing then is they are perhaps doing the same thing they were doing for that company when they were an employee, but now that they are not an employee, they have the option to go and do that for two other companies at the same time, and they have the ability to dictate the terms and dictate the rate. And if that company doesn't like those terms or doesn't like that rate, well, then they can look for clients that do. So, it's really about the flexibility and the control, to really kind of dictate how it's going to go, and choose clients that are aligned with that vision.

Jeremy Cline 8:37
And just expanding on that, I know we've touched on this, but can you talk to the advantages of being a freelancer versus being an employee?

Dorothy Hollabaugh 8:46
Absolutely. I think it definitely takes a certain type of person and personality to really love freelancing. I can talk about the other side of this coin, but really, what attracts most people is this idea of flexibility and control, really having true freedom in your life, in terms of who you work with, when you work with them, how you work with them, and what you get paid. And that was something that I was especially attracted to. I mean, I'm definitely someone who is motivated financially, I really can't stand the idea that what I can earn is arbitrarily capped by somebody. And so, I think the desire to earn more is definitely, I would say, a massive motivator for people, and then, the desire to have flexibility to travel, to work remotely, and to really set their schedule, and fit work into their life in the way that feels elegant and feels good to that individual person. So, I think it's the uncapped income, it's the freedom and the flexibility to decide your schedule, to pick your clients. If you don't like a particular client, if you don't like working with someone, you can't fire your boss very easily, right? You pretty much have to go pick a new job. But you can very easily fire a freelancing client that isn't showing you respect or treating you the way that you want to be treated. So, I think those are probably the biggest things.

Jeremy Cline 10:21
And turning to the other side of the coin, what are the disadvantages of freelancing when compared with being an employee?

Dorothy Hollabaugh 10:29
Yeah. So, there is such a gift to being in control, but then it also means that you are in control. Right? So, it means that no one is handing you that project on a silver platter, you have to go out and get it. And that's something that some people are very good at and enjoy doing, and then there's other people where that terrifies them and are like, 'I would hate to be kind of in charge of knowing where my next pay check is from.' So, it really is a thing about self-awareness and kind of understanding who you are and if that's something that is going to light you up and really motivate you, or if it's something that, frankly, you have no interest in, and you prefer that stability to the potential that comes with the uncapped income, the control, all of those things.

Jeremy Cline 11:22
And this idea of freelancing, being a route to uncapped income, that's something that's, I think, going to be new to a lot of people, quite surprising, this idea that, hang on, what, you mean I'm not just limited to earning $50,000, $80,000, pretty much the sky's the limit.

Dorothy Hollabaugh 11:41
Exactly. Yeah. I mean, it's something where, I think often, back to that idea of control and really understanding where the power is in terms of what's going to happen to you, we often think about a traditional job as being that stable, secure option, but really, your boss, or your boss's boss, or someone who doesn't even know you can wake up one day and decide that you no longer have a job. And so, I think there is this really kind of beautiful power that comes in the ability to choose your own clients and set your own rates and know that there isn't any person who can tell you that you don't have work, you don't have income, you don't have a job. And then, as you gain more experience, and as you become more established as a freelancer, your ability to charge more, your ability to hire, to leverage your time and get help, that is really what allows you to be able to make as much as you ultimately choose. And that's definitely been my experience, it did not take long, I would say probably three months into my freelancing journey, if you will, I had well eclipsed what I was making at that start-up.

Jeremy Cline 13:07
As we record this, there's a certain amount of economic uncertainty in the world, will we go into recession, won't we go into recession, if so, how long, how deep, that kind of thing. You've already touched on how an employee might be vulnerable in a recession, in that they might be employee of the month, but if the company is looking to cut 10% of its workforce, then they can be one of those people quite easily. Flipping that on its head though, how might being a freelancer make you recession-proof, presumably in an economic downturn, when companies are spending less on freelancers in the same way that they're cutting down costs with employees?

Dorothy Hollabaugh 13:56
Right, that's a great question. And I think, if you can grasp this concept, it is so powerful. Because first, it's important to understand that, in a recession, a recession or any type of economic downturn typically does not hit all sectors of the market or all industries equally. Right? Usually, there's some industries, some large sectors of the market that are hit really, really hard. And then, there's other areas of the market that may actually be doing very well. So, for example, COVID, I think, is a perfect illustration of this, where companies that were positioned to support remote work or these different types of tools, Zoom, for example, that we're talking on now, absolutely skyrocketed during the pandemic. And so, what is really cool about freelancing is, as a freelancer, you are typically choosing what we call a high-income skill. So, that's how we describe it at The Gig. And these are really skills that allow you to help businesses make money, and for you to get compensated for that. So, things like copywriting, things like managing, advertising, graphic design, sales, all of these things are skills that can be applied in many, many different ways. So, if you think about recession, and say that you're a mortgage broker in a recession, where housing is hit really, really hard, like we're seeing right now, trying to pivot your career and go into something that isn't related to housing, it's like trying to turn a cruise ship, right? It's going to be slow, it's going to take a lot of energy, a lot of work. But if you are a freelancer, say you are a copywriter, and you have been working with companies in the real-estate industry, writing copy for them, and all of a sudden, that same recession hits the market, well, you are a copywriter. So, instead of having to kind of turn this massive cruise ship, it's like you're in a speedboat, and you can pivot and go apply that same skill that you already have to a company that is thriving during that time. So, it's really about your ability to not have to change what you do. All you have to change is who you are doing it for. And we saw this in my agency, when COVID hit, we had a couple of clients, our bigger clients, who were advertising events. And they shut down over night. So, we lost, I think it was 40% of our revenue in the week following COVID really hitting. But within three weeks after that, we had more than replaced that revenue with new clients that were thriving. I mean, ecommerce was huge at that time. So, it's really about this idea of, don't change what you do, just change who you're doing it for.

Jeremy Cline 16:53
That leads on to quite an interesting question about finding your niche, because there's a lot of talk about being known as the person who helps dot-dot-dot. So, you might be the copywriter who specialises in writing copy for the hotel industry, or for, I don't know, car sales or something like that. So, if you are, say, the copywriter to the hotel industry, and then hotels are taking a complete battering, how do you kind of pivot when you've developed such a strong brand and reputation in one particular area?

Dorothy Hollabaugh 17:36
It's a great question. I think there's a couple different ways to approach that. So, first to kind of share a personal example, the way that I always approached that, approached niching down in terms of my work as Facebook advertising that I really started in, was that I didn't specify what type of company I was working for, I made all of my positioning about the attributes of those companies. So, because I come from this finance and accounting background, I'm very analytical, I'm very much a numbers person. And so, I really position everything around, I help data driven companies to profitably scale their customer acquisition. And obviously, there's a lot more that kind of went into that. But I really worked with a variety of different types of clients for really the first two years. I worked with a car dealership, I worked with ecommerce brands, I worked with digital product sellers. And that was really an incredible way to kind of hone my skills and figure out what I liked and what I was drawn to, and ultimately, digital products ended up being what is now kind of the niche of our agency, but we don't necessarily kind of close the door to other types of businesses, if they do kind of fit the core criteria that we are really looking for. But if you are someone who has really branded yourself, I mean, niching down is incredibly powerful, and it's something that I really, really recommend to people, because it helps you to get traction, it helps you do attract clients. But in the freelancing world, there are these marketplaces, like Upwork, for example, that's definitely my favourite one, where you have all of these different people who are posting, who have a need right now, that they are looking to hire and fill. So, if your niche is real estate, and all of a sudden, real estate companies aren't hiring, then the thing that I would recommend to do is go to these freelancing platforms, like Upwork, where you can really just be presented with a sea of people, all of whom are looking to hire right now, and you can really look to get some small projects with people in other industries and start to build up from there. And honestly, it's not as hard as that may sound, because if you're a great copywriter, you're a great copywriter. And what makes you a great copywriter isn't so much your knowledge of real estate, it's your knowledge of human psychology and persuasion and how to craft copy in a way that is going to be compelling and is going to inspire action. And typically, it's the same thing with advertising an ad account, what makes you good at that really has nothing to do with the niche that you maybe have focused on from a marketing standpoint.

Jeremy Cline 20:33
Okay. Let's go back to basics a little bit and talk to the person who's maybe just taking their first tentative steps, or maybe they've just found out about freelancing as a thing, what jobs are particularly well suited to freelancing?

Dorothy Hollabaugh 20:50
So, at The Gig, we talk about these high-income skills. And there are a couple of criteria that I feel are very important in order for something to be a great opportunity as a freelancer. And the first one is that it gives you leverage to earn more. So, this is what we're talking about with this uncapped income potential. And this is really about charging flat fees, versus hourly. So, I'll give you an example to kind of illustrate this. If you start freelancing, and you're getting paid $50 an hour, it's going to take you 100 hours to earn $5,000. And there's nothing you can do about that. That's exactly how much you're going to make. But if you charge $5,000 for an entire project, and you can get it done in 35 hours, then your effective hourly rate has just shot up to $142 an hour. So, that is really what the key is to having that uncapped income and being able to earn more, it's charging these project rates. So, that's the first criteria, you need to be able to charge your clients in that way. The second criteria is that it can be done from anywhere. Now, this might not be important to some people, but I think for a lot of people who are interested in freelancing, that is something that is very attractive, it's that flexibility, it's that opportunity to travel, to work from anywhere you want. And then, the third criterion of these high-income skills is proximity to the sale. And here's what I mean by this. It's about your clients having the ability to trace sales, revenue, profits, directly back to your work. So, to give you some examples of this, maybe you're a graphic designer, and sales are coming from a page that you designed, or subscribers are reading an ad that you wrote and posted on Facebook, or you're doing high ticket sales, and a prospect is literally speaking to you on the phone before signing up. These are all things where it becomes possible to really measure your results and the impact that you're having on a company. And this can get very, very powerful. Right? Because it might be absolutely, I'll give you an example from our agency, we have a client whose bill, like their retainer with us this month, is going to be $50,000. And when I first started freelancing, it was incomprehensible to me that anyone would pay anybody $50,000 in a single month, to manage their ad account or do something like that for them. But if they're making a million dollars in profit from that work, they will be glad to pay you $50,000. Now, that's an extreme example, obviously, it took a long time to kind of get to that place. But the concept stands. When clients are making money, and they can really trace that back to what you're doing, it becomes very simple to justify your rate. So, those are the types of skills that you want to focus on.

Jeremy Cline 23:57
I'm hearing people in my head who are thinking, 'Oh, well, it's clearly not for me then, because I'm in a profession where it doesn't have any or all of those characteristics that you've just described.' What are some of the ways that someone can perhaps be creative in terms of starting freelancing, but starting from a place where it doesn't seem as though they're in a profession or a job which necessarily lends itself, it doesn't have those characteristics? So, I don't know, maybe someone's a teacher, maybe someone's a doctor or a nurse, something like that. How might someone like that approach this?

Dorothy Hollabaugh 24:38
Right. So, that's where I was. When I left that start-up, I had been exposed to advertising, but they had agencies that ran their ad accounts. I had nothing to do with that. And so, when I decided to try to do something on my own, I had absolutely no idea what that was going to be. And it was a process of probably about four months, where I didn't really have savings built up, so I was renting my apartment out on Airbnb to pay my rent and buy myself some time, staying with friends, like literally doing whatever I could to just buy time to figure out what I wanted to do. And I had never run a Facebook ad in my life, I'd never done anything with that. But about four months into really kind of floundering and trying to figure out what I could do to make money, I was invited to this Facebook ads workshop, my former boss had a ticket to this three-day event, and he couldn't go, and he offered me the ticket. And it was really one of those things where I was like, you know, okay, I know that I'm analytical, right, I know that I am good with numbers, I know that I like data, I think this is something that I could be good at. So, when I started freelancing, I really had no experience directly in that skill. And so, when you're a beginner at, insert skill here, what you're typically going to be doing when you start is you're going to be working with beginner business owners, who can't afford to go spend a tonne of money to hire an expert, and so, they will be interested in really partnering with you and betting on someone who's saying, 'Hey, I'm new in this, I've been studying, I've been working on developing this skill, and my rates reflect that level of experience, but I'm going to work harder for you than anyone else will, I'm committed to this.' And that's really what it was for me in the beginning. I was finding clients who were willing to take a bet on me, and then, I was working day in and day out to study and practice my chosen skill. So, say you're a teacher, and maybe you're an English teacher, and you like to write, but you've never done copywriting. My co-founder, I'll say, he was a massage therapist, and copywriting was what he chose. So, it doesn't need to be an English teacher, it could be anyone. You can get a programme, like, for example, there's a course out there called Copy Hour, where every single day you're handwriting a proven sales letter to build that muscle memory and those skills and understand persuasion and copywriting. If you're doing paid ads, maybe you're literally looking at ads in your Facebook feed and studying what are they doing, adding the ones that capture your attention to a swipe file. Graphic design, maybe you're creating a mock Instagram story for one of your favourite brands. So, it's really just about choosing what you think is most appealing to you, practising, studying, starting to take on small projects, small clients, and then figuring out is this aligned, do I enjoy this, and either pushing forward or potentially trying something else.

Jeremy Cline 27:44
And if you're starting out, where do you find this first client?

Dorothy Hollabaugh 27:48
Yeah, so Upwork is by far my favourite freelancing platform, it's where I got started, and where, honestly, my agency still gets clients from Upwork today. To kind of set the stage for someone who may not be familiar, Upwork is a freelancing platform where businesses or entrepreneurs who need something done, they are able to go and post a job, and then freelancers can submit proposals for that work. And there are over five million client accounts on Upwork, and over 100,000 open postings every day. So, what I started doing when I was brand new was, I just took, it was really only about half an hour a day, I would say, where I had my saved searches set up for kind of the keywords around Facebook ads and paid traffic, and I would just scroll through the posts of listings that hit those searches, and submit proposals for anything that seemed aligned. And that process of going through all the open postings, submitting proposals, using my template that I created, I would personalise it for each one, that took about half an hour a day. And like I said, it was within three months that I was able to eclipse my income from my previous job. And so, even if you're brand new, this is something that's really powerful. And we actually have a step-by-step training that goes into my exact process, my five-step process that I follow to get clients from Upwork and help people who are brand new to freelancing, brand new to the platform to do it, too. And so, we produce content like that in The Gig, and I think Upwork is really the best place to start for really a variety of reasons.

Jeremy Cline 29:33
Two potential objections, which I'm interested to hear you address. One is that with a platform like Upwork, you are competing against people who may be somewhere with a much lower cost of living, and so they can charge less and still make good money for where they are. So, if you're doing this as a newbie in a place with a higher cost of living, like the US, like the UK, then it's tough to compete against that, and also, you're competing against people who have already got the star ratings, because they're already there, and you're starting, and you've got no reputation, nothing behind you. So, it's that chicken and egg situation where people can hire you. So, can you address those two points?

Dorothy Hollabaugh 30:21
Yeah. So, first, to the location question, if you're in the United States, there's actually a toggle that you can flip on in your searches for US only. So, these are clients that have specified in their job posting that they are looking for a freelancer located in the United States. And if you're in the UK, or you're in Australia, or wherever you are, there are a lot of people who want to work with someone who is in their time zone, they don't have to worry about potential communication barriers or any sort of other factors. And so, there really is such an abundance of opportunity on these platforms, that really has never been an issue for me. There are people who are looking for the cheapest possible way to get it done, and honestly, those probably aren't the clients that you want. You want someone who's looking for quality, someone who's looking for other things than just the cheapest, right? And so, there's this meme that I see circulated on the internet every so often about freelancing, where it's like, the $500 client is the one who's asking you, 'All right, how are you going to change my life? What are your guarantees? How are you going to revolutionise my business?' And the $10,000 client is the one that says, 'Hey, wire sent.' It's the higher paying clients that are often a lot more enjoyable and simple to work with. So, that's one thing I'd say. And then, the reality is that everyone starts brand new on the platform, and the way that you build up to get those star ratings, to get that Top Rated badge on your profile, is by taking smaller jobs, executing at a high level, and then, really making a personal appeal to that client to post a good review for you. And this is something that I did, I mean, our Upwork training is really for someone who is brand new, doesn't have a profile on Upwork. And to give you another example, my husband, actually, he recently decided to start freelancing, doing podcast production. Right? So, he's been managing his own podcast for some time, and he thought, you know, hey, I enjoy this editing, I can do this for other people. So, about two months ago, he started on Upwork with a brand-new profile. He now has seven recurring clients for podcast editing. So, this is something that is very doable, really, as a result of just volume of opportunity that exists on these platforms.

Jeremy Cline 32:46
Someone who's looking to go from employee to freelancer, it's going to be a transition of sort. At one end, it could be, quit your job, go into freelancing 100%, with no kind of runway between. At the other end, you allow yourself a bit of time where you're doing both. What factors can influence the speed of transition? And allied to that, how can you make that transition faster if that's what you want to do?

Dorothy Hollabaugh 33:18
I think this comes down to self-awareness, similar to something that I shared earlier. Are you the type of person where you thrive under pressure, and you're really going to rise to that, or are you someone who would really prefer to take a slower route and have a little bit more stability and security in the way you make that transition? So, for me, I had left my job, I did not have a pay check, like I said, I was literally running my apartment on Airbnb to buy myself time and get my rent paid. And so, I didn't have the luxury of doing it the slow way. And so, for me, I'm the type of person where you put my back against the wall, I'm going to, I'm going to fight, I'm going to make something happen. And so, that really worked for me, to kind of have this high pressure, okay, I've got to do this, and I've got to do this now and make it work. But I would say, for the vast majority of people, I wouldn't recommend that. If that's your situation, then let's go, it's very possible. But if you have the opportunity to start to do this on your nights and weekends and start to build, especially if you don't have the existing skillset, right? So, I probably chose, I mean, I chose the hard path, right? I actually ended up hiring a coach to kind of help me learn this skill faster, which was another reason I had to make it work, because I was on the hook to pay for this coach. When I put the first payment on a credit card, and I was like, 'All right, I've got to do this.' So, I really, really rose to that pressure. But if you're someone who has a full-time job that you can tolerate, that you can take the next six months to build that skill, do that daily practice an hour every evening before you go to bed and start to build up those smaller projects and build that reputation on a platform like Upwork, that is definitely the kind of the smoother way to get started, I would say.

Jeremy Cline 33:20
I guess when you move into freelancing, there's going to be the thing that you do, whether it's copywriting, video editing, whatever it might be. There are presumably other skills, though, that it would be helpful to master as a freelancer, which are outside of whatever it is that you're doing. And those might be skills that you wouldn't need as an employee. Can you talk to what those skills might be?

Dorothy Hollabaugh 35:39
Yes, I love this question. Because this is a huge focus for us with our content in our daily email newsletter, because you're right, there is what you do, but then, there are all of the skills that go into being a business owner, because that's really what you are now, right? So, how do you handle your taxes? How do you price yourself? How do you handle a client who isn't treating you well? How do you kind of filter and qualify people and package your services? All these different things that really aren't about the kind of core competence of the skill, they're about how to sell that skill, how to work with clients, and how to be a business owner. And then, I think the other side of it is how to work for yourself, because that really is a skill on its own as well. How do you kind of create structure where there is none? How do you work effectively as a solopreneur? So, these are all absolutely things that are necessary to be mastering at the same time you're mastering the core skill, which is why we make it such a big focus of our content in our email newsletter.

Jeremy Cline 36:51
And if you're someone who likes the idea of freelancing but doesn't like the idea of some of these skills, maybe selling yourself or that kind of thing, there's someone who just want to do the job, they don't really want to get into self-promotion, or whatever, does that automatically rule someone out of doing this, or are there other ways that you can approach this?

Dorothy Hollabaugh 37:15
To be honest with you, if you really hate that, if you really hate sales, if you really hate kind of talking to people and putting your offer out there, it's going to be much harder. That is going to be a challenge that you're going to have to overcome. What I would say is that not everyone likes that stuff in the beginning, not everyone feels competent at those things in the beginning. So, I think, for a lot of people, it's the fear of what that might feel like, or what that might look like, that is really behind that emotion. And once you actually start, once you actually kind of get yourself in the trenches, what you realise is that, sales is a value exchange. Right? And as you continue to hone these skills and get better and better at what you do, you get to this place where you know that you can help this person on the other end of the phone, that you're looking at over Zoom, you have something that can create this result that they are looking for. And so, once you have that confidence, which really just comes from putting in the reps, it becomes much more comfortable to sell, because you're not just kind of shamelessly self-promoting, you're offering someone the solution to a problem that they have raised their hand and said, 'I have this problem, please help me.' Right? So, it's a different mindset. I think a lot of it is just really understanding, you're working as hard on your mindset as you are on your business. So, that, I would say, is the majority of people. If you're someone who genuinely, you're like, 'Nope, it's not a mindset issue, it's not, it's not a practice and confidence thing, I hate this', then freelancing probably isn't for you. And I think that self-awareness is really important, regardless of kind of what field you're going into or that you're in currently.

Jeremy Cline 39:12
You touched on this briefly, but with any anyone who's starting their own business or going freelancing, I see this question come up all the time. How do you know what to charge?

Dorothy Hollabaugh 39:24
That is a loaded question, right? I think it is really important to do what you can to make connections in the industry or in the skill that you're working in. Right? So, if you are getting started as a copywriter, we kind of use this example, meet other copywriters, join, I recently came across a wonderful woman, Amy, who has this group on Facebook called the Copywriting Girls Club, and everyone in that Facebook group are female copywriters looking to grow their freelancing businesses. So, that, I would say, is the first thing, is trying to find community of other people who are freelancing in the same skill that you are. Upwork has these community boards where you can find these things. And see what other people are charging. Go on Upwork, create a client profile, and do a search for what you're looking to do, and see what other people are charging, what those kinds of ranges are. And so, when I started, it was really this function of, okay, I want to charge something reasonable enough that it's reflective of my skillset, but I think it's critical to realise that you are far more likely to under-price yourself than over price yourself. So, do that research, my opinion is, take whatever price comes to you intuitively from that process, add 50% and try to start there.

Jeremy Cline 40:52
Okay, so you mentioned your own course, which I'll definitely put a link to that in the show notes. In terms of other resources which have either particularly helped you in your freelancing journey or which you routinely recommend to other people, what comes to mind that listeners might want to take a look at?

Dorothy Hollabaugh 41:11
I love that question. I would say podcasts have been a massive part of my development as a freelancer and just my journey as an entrepreneur. Because filling your mind with positive propaganda, for lack of a better term, is really, really critical to forging forward when things are hard, right? And so, one podcast that has been incredibly impactful for me is The Chris Harder Show. I stumbled upon that podcast when I was first getting started. And it's all about money, mindset and entrepreneurship. And now, fast forward to the present day, I'm actually in Chris Harder's mastermind group, which has just been revolutionary for my business. But his podcast, I listened to it for years before I ever met Chris, and that is a resource that I would definitely recommend to anyone getting started.

Jeremy Cline 42:02
And where can people find you? Where would you like them to go?

Dorothy Hollabaugh 42:05
Yes, so you can find us at thegig.io, we publish a daily email newsletter that is completely free, that is filled with tips on how to work with clients, how to work for yourself, how to land clients, and how to grow your specific skill. So, the first two skills that we're starting with are copywriting and paid ads, where we're actually going to be introducing separate newsletters for those skills specifically, but the core newsletter is applicable to anyone freelancing in any type of online skill. And I mentioned earlier that training on how to get clients from Upwork, my step-by-step process, I would love to give that to your audience for free, and they can get that at https://www.thegig.io/c/vip. When you opt in for the newsletter there, I will send that course straight to your inbox.

Jeremy Cline 42:55
Fantastic. Well, as always, links to those in the show notes. Dorothy, all I can say is thank you so much for coming on the podcast and sharing your knowledge.

Dorothy Hollabaugh 43:03
Thank you, it was a lot of fun. I appreciate you having me.

Jeremy Cline 43:06
Okay, hope you enjoyed that interview with Dorothy Hollabaugh of The Gig. One thing I liked about this conversation was that Dorothy is pretty clear on what sort of skills she thinks are well-suited for freelancing. She talks about these high-income skills, the skills for which clients are going to pay you well. But that doesn't necessarily stop you from starting out as a beginner. Her suggestion was, you can begin with beginners. You start that way, you build up your skills, you build up your reputation, and that way you can move to working with bigger clients. I also loved how Dorothy said that, make me money or make me happy isn't necessarily a choice you have to make, you can have both. Freelancing isn't necessarily the only way you can do it, but a lot of people seem to limit themselves with the belief that it's either one or the other. The show notes are, as always, on the website at changeworklife.com/155, that's changeworkllife.com/155, for a full transcript, summary of everything we talked about, and links to the resources that Dorothy mentioned. And if freelancing is something you're thinking about, but you're not sure whether it's right for you, or even what skill you'd like to offer, then that's something that I might be able to help you with. One of the things I do with my coaching clients is go through their work history and pick out the skills which they're really, really good at, and also which they quite enjoy doing. And it's led to some really interesting places. I've recently been working with a client who was working in IT for a large company, where he's now exploring the fashion industry. If you'd like to find out more about how I might be able to help you, then visit changeworklife.com/coaching, that's changedworklife.com/coaching. And if you'd like to arrange a chat with me, there's a button there where you can set that up. One of the advantages of freelancing, which Dorothy mentioned, is the possibility of working from anywhere, the digital nomad lifestyle, which we've talked about on the podcast before. But one thing we haven't addressed is how you can do that when you've got children. If you've got kids who are school age or younger, how realistic is it to take them away with you to a foreign country, so that you can work elsewhere? How do you look after them? How do you make sure that they're being educated, that they're socialising? Well, in two weeks' time, that's exactly what we're going to be talking about. So, make sure you've subscribed to the podcast if you haven't already. And I can't wait to see you in two weeks' time for that episode. Cheers. Bye.

Thank you for listening!

If you have any questions or comments, please fill out the form on the Contact page.

I would be so grateful if you’d: