It's never easy, but it can be simpler than we want to make it. We love to overcomplicate these things. I know I talk to a lot of people who believe they need to have a fully fleshed out website, and I've got to have all this professional experience. And if I didn't major in English, I can't do this. And my answer to that is I don't have a website. I didn't graduate from college, and I get paid a lot of money to write email sequences for clients. So like you don't need all the things that people think that you need. You can start and you can do it. And it's not necessarily going to be easy, but it can be fairly simple once you understand the process. We always hear the big names in the gig economy. Companies that deliver on-demand experience to consumers like Uber, Grubhub and TaskRabbit, and those who focus on business customers, Upwork, Fiverr and TurboTax Live. But rarely do we get to hear the stories of the people who provide the services on these platforms. Why do they choose to freelance? How do they get started? And what's changed over the past two years? I was fortunate enough to meet my next guest, Abby Prett, when she spoke at the Upwork kickoff three years ago. Her personal journey remains an inspiration for me to this day. Hey, welcome to the show. Thank you so much for having me. This is so exciting. We were just talking, I can't believe it's been three years. Crazy, crazy. Like time is a social construct, you know? I want to talk to you about freelancing in general. In your talks, you talk about freelancing as a lifestyle choice. That seems to be something that's all over the news now. Like I took a pandemic when we met before the pandemic. Talk to me about how your work became a lifestyle choice. Yeah, it was pretty simple actually. I had a baby 23 years ago, my first one. The idea of putting on pants that required zippers and buttons was not a lifestyle choice that I wanted to make. And then beyond the whole getting dressed thing, the whole point of leaving my baby with somebody else so that I could go and work to make the money to pay for her to be with somebody else. That just did not sit well with me. So freelancing as a lifestyle choice, it was really, I mean, I call myself an inherently lazy person. I wanted to be able to stay on my couch and get paid. So freelancing became the way to do that. You think I'm kidding. I'm not kidding. Like these were my thought processes as a 23 year old new mother. No, I just think you were ahead of the curve because everybody's sort of saying the same thing. Right. Yes. You talk about turning personal struggle into opportunity. And I know it wasn't always easy. So you had your first child at 23, which is not a baby anymore. Tell me about the journey because I think one of the things that a lot of people believe is that it's easy that, hey, once you get started, you get a couple of clients or, you know, even if you get a job, life isn't easy. Right. Tell me about your journey of it. Sure. Like I said, I started freelancing when I had the first baby and then I had a whole bunch more children. I have five all told. And one that was juggling. There was a lot of needing to be many things to many different people. So I was mom. I was wife. I was freelancer for clients. And my third child was born with special needs. It took a while before we knew everything that was wrong. And my fifth child also has some like minor special needs that we don't really even focus on in our house because we're obsessed with the third child. And the third child also had cancer at one point, which threw a wrench into everything. So there's a lot of juggling. There's a lot of having to be all things to all people and needing to make the decision that you can't be all things to all people and you have to pick the parts that you're going to focus on and the parts that you're going to let go. And that's going to change on a daily basis and over the years. And for me, freelancing let me lean into my own desire to not do the same thing all the time. My tendency to be easily bored by things. It let me move from project to project and it let me manage client work in the time that I did have available. Let me scale up and down as I wanted to. And to your point about is it easy? It's never easy, but it can be simpler than we want to make it. We love to overcomplicate these things. I know I talk to a lot of people who believe they need to have a fully fleshed out website. And I've got to have all this professional experience. And if I didn't major in English, I can't do this. And my answer to that is I don't have a website. I didn't graduate from college and I get paid a lot of money to write email sequences for clients. So like you don't need all the things that people think that you need. You can start and you can do it. And it's not necessarily going to be easy, but it can be fairly simple once you understand the process. I think that's inspiring about your story. One of the many, sorry, one of the many things that's inspiring about your story. I was just rereading the article we published three years ago, and it just I had the same feeling as when you were on stage speaking. People think that freelancers are doing work for small companies, just small businesses. Tell me your experience because you've worked with some pretty significant brands. And so when you hear the story of a mother of five who has a special needs child who is inherently lazy, but doing amazing work for some big brands, it kind of blows my mind a bit. Yeah, just go ahead and tell me the story. So when I started back in the dark ages, we didn't have Google as a search engine. We had Alta Vista and that was super helpful. And the place that I looked for a lot of my first freelance writing jobs was Craigslist. I would not say that I necessarily recommend that today because I think Craigslist has changed a little bit in the past 20 years. But back then you could still find some fairly decent freelance writing jobs. And you'd be surprised, but a lot of big companies at the time were putting out calls for writers on these sites. So I wound up writing a lot of courses, internal training and compliance materials for big companies like Toyota, eBay, that kind of thing. And I remember on one of my first calls with one of these clients, they were like, OK, well, Abby, you're the expert in online compliance training for corporations. And I was like, this is probably a bad time to tell them that I did not understand any of the words in that sentence. Like, I have no idea what we're doing. But that's really what freelancing is. I think in general, building a business is people doing things for the first time and not being afraid to ask questions and say, well, what's a great outcome going to look like for you? What is going to make you thrilled when I deliver it in three weeks? What do you want the deliverable to look like? And being OK with asking questions and being very genuinely curious. I tell people at times when I'm writing on topics where I don't know anything about the topic, I will just say to them, OK, I don't know anything about this. So you have to explain it to me really, really clearly. And then I can write about it for other people who also don't know anything about it and they're going to understand it clearly. So I'm never afraid to ask questions and to maybe look a little bit foolish. And I don't think of it as looking foolish. I think of it as I'm getting the information that I need to do a great job on this piece. It was interesting when you were talking about asking, like, what is the goal? What is the outcome you want? That's something that I'd never experienced in corporate America. I never did because no one would ask the call. You just do work like, hey, this executive would like to see this. OK, let's go and do that. And it's one of the refreshing things that I get by working with freelancers who bring a diversity of skills and thought to every project, whether they've done it a bunch of times, they've done it for a bunch of different clients, like you said. We hear a lot in the news about remote working. Freelancers are like what we've been doing this the whole time. So it's welcome to the party. What are some of the hardest parts for you when you think about trying to build culture and just going day to day? Right. So I think that there is something that sometimes can get lost when you don't have those water cooler interactions. But I absolutely think that there are great ways to replicate that online. I think that being very clear with freelancers about expectations, I think that working with freelancers who have solid processes in place can be very helpful. I think that if you are working with freelancers, remembering that they're not your employees and that they're not hearing everything that happens inside the company on a day to day basis and just keeping them in the loop. And it can be in the easiest ways. It can be with text. It can be with email. It can be in a Slack channel, just having conversations. I think that if you remember that there's a human on the other end of the screen and spend a little bit of time just talking, getting to know people at the beginning of almost every call I have with clients, we spend maybe 90 to 120 seconds just, you know, what's going on, what's happening. And often the stories that come up in that minute and a half, again, I create content for people. So that comes out in all sorts of ways that we can then use in the stuff that I'm doing for them. I work with a lot of people who have personal brands at this point, right? So those stories are what make them approachable and what make other people love them and want to work with them and hire them. And so when they tell me, oh, yeah, my kid had a swim team and I literally watched her not stay in her own lane. Like I literally watched her lose the race because she was so busy watching the kids next to her and how they were passing her. And we can turn that into an amazing business story that resonates with people and everybody's like, oh, my God, yeah, my kid does that. Wait, hold on. I do that, you know? I was about to say my daughter Sidney was going to ask you a question at the end of this episode. Almost lost the race because she kept looking on both sides to see if she was going to win. So it's a relatable story. You talked about process. And I think one of the things that people don't realize is that when you work with seasoned freelancers, they respect their time. Go back to inherently lazy. Like they respect their time. How do you use automation in our process to scale and run what you do? Yeah, I think that it's being really smart about automation and where you can use it without losing the human touch. So a great example for me is as I was building my own online course business in the beginning, it was just me, right? And I answered all the email and I happen to be really good at email marketing. So when I would encourage people to hit reply to my emails, many people would reply to the email and I wanted to respond to all of those people. But if I spent all day answering email, I wouldn't get a lot else done. So I found a text expander tool and I don't use like the big fancy name one. I use the one that was $4.99 for a lifetime license made by like a guy in a room and provides no tech support, but it works. And a text expander, if you're not familiar, you just type a few characters and it spits out entire paragraphs. It can do whole pages worth of text. And through the text expander shortcuts that I created, I was able to personalize email responses to a lot of people, but do it very quickly, like with just a two or three keystrokes. I could have an email that says, wow, I'm so excited that you're starting your journey in freelance writing. Here are some things that I recommend. Like it would just spit that out and I could personalize it and make tweaks to it on the fly and get through it really quickly. So automation tools like that let you grow and scale without losing the personal touch. I rely a lot on zappier automations to move things from Google Forms to Slack so that I can be on top of things without having to constantly check in a lot of different places. So I look for ways that I can use automation to speed things up for me without creating like an impersonal feeling experience for the person on the other end. I think the idea of working efficiently when you were talking about the text expander, I'm like, I could have saved so much of my time in 25 years. Oh, yeah. Of big tech. Just have a text expander like $4 could have saved me eight months of my entire life looking back. You know, you talk a lot about bucking trends and doing what makes you happy and it sounds easy to do that. I mean, it's a great sentence. You know, there's a bunch of clickbait articles saying, hey, you know, you should be find your purpose. You'll never work a day in your life and that sort of stuff. And a bunch of people, by the way, selling courses that say they'll take you to the promised land. When you say you're bucking trends and trying to do it actually makes you happy. What does that really mean? Yeah. So when I say it, I mean, I hate meetings. And so I don't work with clients who require me to come to meetings. Like the way I schedule my process with clients is when I'm handling content for them, we have one call a month and that's our content call. And it's a conversation. It's not a meeting. There's not seven people in it. It's me and the person I'm talking to. And we're having a conversation and we're laughing and we're enjoying ourselves and it's over in an hour. And I designed my business specifically to avoid the things that I don't like. Like one of the reasons that I don't work with many corporate clients these days is because I could not stand the process involved in having seven people review a document and not having any one clear owner of the project. So that it was very difficult for me to, you know, nobody could tell me, well, what is the goal here? What are we trying to do? There were like seven people who would give seven different answers. And that made me crazy. Some people thrive in that more corporate environment and love working with corporate clients. And I think that's awesome. I knew for me, it made me unhappy. So I built a business that doesn't require me to do that. I built a business that lets me live in my basement and not have to like go out in the world and talk to people on a day to day basis. Like for a long time, when cell phones became a thing and like wireless internet was new and whatever, we were all excited. Because we could go anywhere and keep working. And that's a very cool stage to go through. And I think that when you do build a business, you go through that stage of like, yeah, I can go on vacation and also work. I'm now in the stage where I'm like, oh, actually I can go on vacation and not take my laptop. Like I can be disconnected. I've built a business that can run even when I'm not sitting at the desk. That certainly doesn't happen overnight. But when I talk about bucking trends, like I'm not looking to make a specific amount of money. I don't care about labels on things. I don't like, OK, you're sitting in a shoe closet. A lot of people care about shoes. I own a pair of sandals and I own a pair of sneakers. And in the winter, I own a pair of shoes that are not sandals. So this is this is a professional podcasting shoe closet. There's a whole story on my argument with my wife about how I need the closet, which has the best acoustics. Acoustics, absolutely. I totally get it. But like, I'm not a shoe person. Like I don't care. I know a lot of people who will spend a lot of money on shoes and bags and whatever. That is not who I am. My clothes all come from Target. So I built a life that makes me happy and it's not necessarily something that would make anyone else happy. To me, it's super important to be able to go for a walk every day with my husband so that we can get away from our five children for a few minutes. But also have some time to process our days together. To me, it's really important that if my son is playing piano upstairs, that I can stop what I'm doing and just go upstairs and sit and listen to him play for 45 minutes and enjoy myself. If they've released a new season of Stranger Things, I want to know that I can block off two days to sit and watch it because somebody decided that the final episode should be two and a half hours. I don't know what that was about. I want to know that I can do those things. And here's like a crazy example, right? So my son with minor special needs, the minor special needs in our family is my child who is born with only one ear. So we're going to the States for a month for surgery that's going to build him a brand new right ear with a functioning ear canal. So he'll have binaural hearing. So I guess it is kind of a big deal. But in our house, it became very secondary to his brother who had more significant special needs. And I can go for six weeks to America. And yes, part of the time I'll be working and my business will be running. And part of the time I will absolutely not be working. Like when my kid is having 10 hour surgery, I will not be working that day. I'll be there and I'll be present. And when he's recovering and when he needs that one on one time with mom and dad, like we can do that. We've created a life that allows that. And that to me is incredibly exciting. I think the thing that resonates most with me about your story is that you have decided and thought about it. You're living deliberately. And I'll speak for myself. There for most of my career, I didn't think deliberately. I didn't think about how I wanted to live. And there was a wonderful woman who is on a previous episode of this podcast and Sidney asked her, what should I be when I grow up? And her answer was think about how you want to live. And so now I don't ask my children anymore, you know, what you want to be or what you should be. I say, how do you want to live? And I think that was for me, even like when she said it, I'm like, wait, where were you when I was, you know, 30 years old? That would have been really helpful. But in fact, some of those powerful advice. I want to get just a couple of thoughts, because there's a lot of people who listen to this podcast and want to start engaging with freelancers have thought about engaging with freelancers, but are still don't know how because it's a new way of working, which is why I wrote the book. Gig mindset. Give just quickly your top five tips for working with a freelancer. So if there's somebody out there who wants to work with someone who doesn't like meetings, who's in the basement or somewhere around the world, we're top five tips from Adam on working with freelancers. Go. OK. And tip number one, your freelancer has a zone of genius. There's something that they do really, really well. Let them do that thing and don't try to force them to do what you might think is related, but that might actually be very far outside of their zone of genius. They are probably telling you very clearly, I do this and I don't do that. So believe them when they tell you that and there's like a method to their madness. You know where that comes from? Because staffing agencies place people and if the business changes, it's hard to get a new person because you've signed along. So they're just used to saying, Hey, Abby, you're right. Hey, do you mind coding this page for me? It's not really hard. And I'm sure you can figure it out. OK. Totally. Number two, tip number two is give people what they need in order to be successful. Like we said earlier, freelancers aren't in your office day to day. They're not part of your organization. They're not necessarily getting CC'd on all the emails going back and forth. And that is a good thing. I'm not saying that you should start to do that. But most times they'll ask you for the things that they need, like access to files, information about programs, whatever. Let them have the things that they need. Don't assume that they're just going to magically know them. Nobody can read your mind unless you tell them what's on your mind. And stop using email. Also, yeah, move to Slack and Slack, communicate transparently, hypertransparenly. It just makes everything easier and reduces meetings to. Yes. Tip number three, respect the process. We've talked a little bit about processes. The best freelancers have done what they are doing, like the thing that you've hired them to do. They've done it before. They know exactly what they're doing and they have a set process. They'll tell you what that process is and then they'll walk you through it. And if you let them guide you through the process rather than saying, oh, well, we've always done it this way. Well, how's that working out for you? Right? Like if it were going so well, would you have brought me in and paid me this money? Probably not. So let me show you my process because I know that it works and it works really well. Tip number four. All right. This is going to sound a little crazy because we've said we hate meetings, right? But front load on the meetings and then let people do their work. It's to start a project by telling the freelancer all of the information that they're going to need in order to be successful. They can't do the work by magic in the air. You've got to tell them what are the deliverables? What's the timeline? What are the expectations? What's communication going to look like? All of the things that go into a successful project. Generally, when I do this with clients, it's a two hour kickoff call at the beginning, but we don't ever have to. It's like when you start working out after not having worked out for a long time and like afterwards, you're like, oh my God, I hated that. It was so horrible. But you don't have to do that again. Like you do that at the beginning of the project and then everything else goes smoothly all the way through. Tip number five. You have feedback so that your freelancer can incorporate it going forward. I think of this because I'm a mom, like when my kids would come to me and say like, oh, I want spaghetti. So I can make spaghetti and that's fine. It's going to take me 10 minutes. It's going to take me like two and a half hours and a really messy kitchen to teach my kid how to make spaghetti. But then I never have to make the spaghetti again. So having taught all of my children to be self sufficient and cook for themselves like, yes, I've worked myself out of a job and I am OK with not having to be the person who makes the spaghetti. Like it's so much easier for you to if you get something from your freelancer and you're like, oh, here's a thing that like they it's not necessarily wrong, but it's not the way you wanted it or maybe it is wrong or maybe there's something that needs to be changed. Tweet, it's super easy to go in and make those changes yourself. Don't do that because you're setting yourself up to always be the person who makes the spaghetti. If you teach the freelancer one time and you say to them, hey, here's my feedback on this. Let's incorporate this going forward. A good freelancer will take that on and will make those adjustments moving forward and you'll save yourself a lot of time and a lot of frustration in the long run. That is some great advice. Now, I want to do my favorite part of the show, which is a question from my daughter, Sydney. Love it. I have a question. What advice will you give your kids when they start looking for jobs? Sydney, my oldest daughter is 23 and she actually has her first job right now. And even before she went and got this job, when she started talking about going to college, I said, are you sure you want to do that? Maybe you just want to take an online course instead. And her father said, that's a terrible idea. So we disagree on those things and those are conversations that we have to have. But the advice that I give my kids is think about what makes you happy. Is this job going to get you there? Now, my oldest daughter wants to be a writer. Surprise, surprise. But she wants to write novels. She wants to write books. So the job that she has right now is a job that she can do using very little of her brain power so that she can save her energy and her effort for working on her novel. And that's a conscious choice that she's making. And I fully support that choice. It's a job that pays her well. She's making good money and she doesn't care about advancing in that job. I'm on board with this. My I have five kids and they have different needs. So I'm going to give them all slightly different advice because they're individual humans. But for the ones of them who are more creative and who want to do something for themselves and follow perhaps a non-traditional path, I absolutely encourage that. And I really believe that they can do amazing things and I will be their biggest cheerleader for that. Some of my kids, it's much more suited to having a regular job and going to an office and getting paid a regular salary. And that's fine. I don't have an issue with that if that's what makes them happy. First and foremost, I want my kids to be happy because that's what I want for them. And I know that if they're doing something that they love and that lights them up and that fills them with joy, that their lives are going to be better. That's great advice. And that's one of the things I love about doing the segment on the show is that Sydney gets to hear a bunch of different people besides dad give her advice or answer her questions. So thank you very much. Thank you for being on the show. Somebody wants to learn more about the work you're doing. How do they get in touch with you? Yeah. So you can find me at successfulfreelancemom.com. I am also pretty much the only Abbey parrots on the internet. So I am very Googleable, very findable and extremely responsive. And we'll put all your links in the show notes. Abbey, thank you so much. It's been a long time, but I really enjoyed catching up. Thank you so much for having me.
