EP. 002

How to find out if you’re right for freelancing

Not everyone is cut out to freelance—and that’s okay. In this episode, Paul and Kaleigh talk about the factors to consider when you’re thinking about freelancing as well as some of the characteristics and qualities that help people be successful freelancers.

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Kaleigh Moore: So, Paul, one of the questions I hear a lot from the people that I talk to who are curious about freelancing is, how do you know if you’re right for a freelance type of career? If they’re switching from maybe a full-time job that’s really secure and stable, or maybe it’s somebody without a job, how do you figure out if you’re going to like the freelance path? What’s your experience with that?

Paul Jarvis: Yeah, Kaleigh, I love this question, because I also get this question a lot. I think I have a bit of a counterintuitive approach to how I think about this question, because I think a lot of times people that aren’t freelancers think that passion is the biggest thing, like I’m so passionate about writing or design or development that I want to do this as a job. I actually think that passion is the worst reason to get into freelancing, if that is the only reason. So I think being passionate is totally cool, like be as passionate as your bad-self, but I think that that is not the main factor.

I mean, for me, I wasn’t passionate about web design at all. I wasn’t passionate about writing when I started doing that. I wasn’t passionate about any of those things. Once I started doing those things, then I started to get passionate. So I think there’s two things here that I want to cover with my answer to that. It’s like the longest answer ever, but bear with me.
I think the first thing for figuring out if freelancing is right for you is if you have the skill, the core skill, before you take the leap to freelance. I think it would be really hard to become a freelance writer if you aren’t already skilled at writing, or it would be really hard to be a freelance designer if you didn’t already have design shops. You need to be good at what you do in order to start that.

I think the second thing is, and this as well is a bit counterintuitive too, like air quote “internet advice for thought leaders”, but the second thing I think is that it makes sense and it seems smart to test the leap to freelancing with a smaller jump into it first, so not going, like, walking into your boss’s office and flipping them the bird and being like, “See you later, suckers.”

Kaleigh Moore: Byeeeeee!

Paul Jarvis: Yeah, I don’t think that would work. I have no experience with this, this is just folk knowledge at this point, but I think being able to test the leave … It’s just like if you’re learning how to dive, right? You’re not going to climb up to that ridiculously scary 30 foot board that the Olympic divers jump from, you’re going to start at jumping from the edge of the pool into, like, six inches or 32 centimeters … I don’t even know what the conversion is, I suck at that.

But so I think being able to test your leap … All of the freelancers that I know that have been freelancing for more than a couple of years, like they found a long-term cadence to freelancing, didn’t just jump into it willy-nilly. They all kind of like, “Okay, I’m just going to do a bit of freelancing in the evenings or on the weekends, or I’m going to see if I can get some flex time with my job or see if I can go down to four days a week to start.”

So I think that more important than passion, the most long-winded answer ever, is that you need to have the skill first, and there are other skills that we can talk about after, but you need to have the core skill first, and you need to test the leap before you just be like, “Hey, I’m a full-time freelancer.” Just try it a bit first and see how that fits.

Kaleigh Moore: I’m so glad you said that, because you just totally validated my own path to freelancing.

Paul Jarvis: Yes. Let’s talk about that.

Kaleigh Moore: Yeah, so I had a full-time job, I was a PR person, it was a great job, loved the people that I worked with, but I had a lot of free time in that job, and so in the evenings I started looking for other things that I could do to keep busy. To be honest, I was working at a non-profit and so I wasn’t earning a ton of money either, so I was looking for a way to supplement my income, and I started doing things on the side. I started doing some social media work and some freelance writing work, just to kind of figure out what I liked most.

Eventually, after about six months, I was to a point where I was earning almost as much as I was at the full-time job, so I thought, “Okay, well, this is fairly secure.” I had a couple of retainers so it was regular recurring income that I was making, and so I said, “All right, well, I’ll give myself a timeline of 18 months and if this doesn’t work, then I’ll find another full-time job.”

But I had kind of a base for switching to the full-time freelance career path where I felt I have to have a plan, I have to have something in place where I feel secure enough to switch from this full-time job that has this lovely vacation time and healthcare and all these important things, to this much more risky type of career path where none of those things are guaranteed. I have to play the accountant and I have to know how to do all these business things that scare me.

So yeah, I totally agree with that. I think that the kind of starting on the side or just … People have free time. You don’t have to hustle, you don’t have to work yourself to death, but if you have a couple of extra hours in the evening or if you have a schedule that allows you to work in the afternoon, I think that that’s a great opportunity for people to test whether or not this freelance type thing might be a good idea.

Paul Jarvis: Yeah, I really like that. I’m glad that you basically have this story that validates what I said. That works out so well.

Kaleigh Moore: Absolutely.

Paul Jarvis: We didn’t even plan that.

Kaleigh Moore: It did work!

Paul Jarvis: So you brought up just briefly, and I really want to dive into this a bit more, ’cause I think it’s really important, the idea of an auxiliary skillset, because I think when you’re a freelancer … So when you work for a business, you just have to be really good at the job that you do specifically, because other people in the business take care of all the other things, but when you freelance you have to take care of all the things. You have to wear all the hats, or the touques if you’re in … Do you know what a touque is?

Kaleigh Moore: We call it a touque because we love that word.

Paul Jarvis: Okay, good. ‘Cause some Americans are like, what’s a touque? A touque is a beanie, like a winter hat. I was just testing your American-ess there for a second.

Kaleigh Moore: Yes, I passed.

Paul Jarvis: Yes, exactly. So I think the part of being a freelancer and part of thinking if freelancing is right for you, and it’s funny, we’re talking like freelancing I don’t think is right for everybody, and this comes as a shock to people because we teach a course on freelancing, but I don’t think freelancing is right for every single person, because I think sometimes some people can thrive better in an environment where they’re so hyper focused.

I think that thing here is that there’s so many other skills that you need to develop when you’re freelancing, right? Do you want to get into some of those other things that you need to do?

Kaleigh Moore: I kind of touched on them earlier. When you’re a freelancer, it feels like it’s all rainbows and unicorns. You have this flexible schedule and you can do whatever you want, work when you want, and that’s true, but you also have to do some things that are really hard and kind of sucky. If you’re not a numbers person, like me, things like doing your taxes and bookkeeping, those are really intimidating and hard. So in my case, I found that hiring that out to somebody else that’s better at it than me made a lot of sense. I also found that getting some processes and systems in place that made those things simpler was a huge lifesaver for me.

For example, the Creative Class Contract. I was always worried about protecting myself as a business owner and, “Oh my gosh, what if something goes wrong and somebody wants to sue me and take my house away and take my car and all these things that I have associated with my own name?” And so having those things in place that make things simpler and less stressful was really smart for me.

But if that’s not something you’re comfortable doing, or you don’t feel like you can, then freelancing probably doesn’t make a lot of sense. You really have to self-direct a lot of those efforts and that can be hard for some people to do.

Paul Jarvis: I’m so not a numbers or accounting person either, so hiring a good accountant and bookkeeper, and one that understands the type of freelancing you do I think is really important, because I’ve probably had … I feel like I’m Spinal Tap and my accountant is the drummer, where I’ve had so many accountants, and the reason why I settled on the one that I currently have is because they understand the type of business that I have and they understand it. Doing taxes and giving the government your money isn’t cut and dry. It would be so nice if it was just like, “You made X, you owe X,” then everybody could do it. It would take five minutes. And this is my dream world. Doesn’t work like that.

Kaleigh Moore: Yes, that would be so nice.

Paul Jarvis: The way I think about it is that my accountant should save me more money than he’s charging me. So if I pay my accountant two grand, he has to save me at least two grand on my taxes. And I don’t even know if this is a legit assumption, but this is the assumption for me and it ends up working out where they always save me more money than I’m paying them, so I feel like it’s a wash.

Same with lawyers, same with a few other things like that where it’s just really good to have someone. Like, clients are hiring you because you’re an expert at what you do. It kind of makes sense that you hire experts, especially when it comes to legal and accounting, that do what they know how to do for your business.

Kaleigh Moore: Absolutely. I think a lot of people put those things on themselves and then they get really stressed about it and they either throw their hands up and say, “I can’t do this,” or it leads to other problems down the road, so I think just knowing that that’s an option and you can do that is the first step.

But, I mean, there are other things you have to think about too when you’re validating the freelance path, and I think another one of those questions is, the people that you want to work for, that you want to hire you, do they have money to do that and do you know those types of people and are they willing to pay for the services that you’re offering? I think that those are three other questions that you have to really consider when you’re thinking about this.

Paul Jarvis: Oh my goodness, yes. So I have a story from my buddy, Justin Jackson, who I’m in a Mastermind group with. He was either telling me personally, or it was an episode of his podcast, I don’t remember which, but anyways, he was saying that he knows this person who really wanted to develop websites for realtors. Seems like, okay, realtors probably have some money, that like probably a check mark there.

But then Justin kind of got into it with him and he was like, “Well, do you know any realtors?” And the guy was like, “No.” And he was like, “Well, do you attend realtor conferences or events, ’cause there are lots of those,” and he’s like, “No.” And he’s like, “Well, how are you going to find these people? How are you going to build a contact list with this people?” And he was like, “Well, I haven’t really thought of that yet.” And I think that sometimes we get so enamored with this idea of I want to work for myself. It’s a valid dream to have, you and I do this.

But I think we can lose sight of, okay, what do we have, how can we sell that and to whom, and do we know who these people are? Do we know the people that we want to have as clients? Do we have contacts, do we have ways to make these people contacts? And I think when you freelance, that’s kind of the elephant in the room with a lot of … Especially with creative freelancers is that you have to sell. You don’t have to be crazy hustling all the time, but you have to be able to position yourself in a way that people want to give you money for the work that you do.

Kaleigh Moore: Yeah, and they have to have that money to give you, too. I came from a non-profit background so initially I felt out the idea of working with non-profits, but then I thought about it for about five seconds and I was like, oh, right, they’re always resource strapped. They don’t have a lot of money to hire out freelancers a lot of the time, so that’s almost setting myself up to fail, because I’m trying to target this niche that is really struggling to have financial resources to hire people for the type of work that I do.

So I think that that’s a question you have to think about too is, do you have the right connections to get a foot in the door with this world that you’re trying to enter, and do they have the money to pay you for the stuff you want to do for them?

Paul Jarvis: Totally, because I think that that’s definitely really important that you know the answers. If you don’t know the answers to these things, maybe hang on a sec, find the answers to those things and even it’s just talk with you.

Kaleigh Moore: Yeah, do some market research.

Paul Jarvis: Exactly. And I mean a lot of … and I know because I’ve taught creative class for several years … is that people shy away from the like … They’re like, “I’m game for all of the things you teach,” and then their one lesson I’m like, “Okay, here’s where you talk to people,” and they’re like, “Okay, I’m out.”

Kaleigh Moore: Right.

Paul Jarvis: If you’re freelancing, even if you’re super introverted, like I’m super introverted, you still have to find a way to be able to talk to people, because a lot of freelancing, regardless of the type of freelancing you do, involves communicating with other people. You can’t just be that designer at an agency who the PM or the creative director does all the client managing, client wrangling, and they’re just like, “Hey, here’s the work you have to do,” and like, “Go to it.” You have to be the one who’s talking to the people. I mean, that’s really a massive thing when you’re thinking like, “Should I freelance with people?”

Kaleigh Moore: Yeah, and like you said with being introverted, thanks to the internet you don’t have to go to a million conferences or networking events, or whatever it might be, that’s intimidating or not suited to the type of person that you are. You can do a lot of things online that really kind of accomplish the same goals.

I know that’s something you and I both do, and it’s really just a matter of putting yourself out there and taking that first step and then it gets easier the more you do those types of things. But, by all means, you can stay at home in your pajamas and do those types of activities. It’s totally doable.

Paul Jarvis: I’m in my pajamas right now.

Kaleigh Moore: Same.
Paul Jarvis: … ’cause why not, right?
Kaleigh Moore: Team Pajama.

Paul Jarvis: Yay! Weren’t we going to do something wearing Hawaiian shirts as well?

Kaleigh Moore: Oh, we were.

Paul Jarvis: Well I think that’s the good thing about working for yourself is you can wear whatever you want most of the time, unless you’re doing a video call then you should be dressed all the way, because you never know if you have to get up and move something in the back and then it’s like, “Uh-oh.”

Kaleigh Moore: I’ve made that mistake before, that’s for sure.

Paul Jarvis: Oh, so have I. So it’s important to be professional when you need to be professional.
Kaleigh Moore: That’s right.
Paul Jarvis: Is there anything else in this?

Kaleigh Moore: I think the final question is just a matter of really taking a hard look at the type of person you are. Are you the type of person that can be motivated to do the work on your own and not be pushed by somebody else to do the things that you need to do?

So for me, I’m a pre-crastinator. I work ahead of schedule on a lot of things. I don’t put anything to the last minute. It’s drives me crazy. You don’t have to be like that to be successful as a freelancer, but I think you have to be motivated to do a lot of things that either make you uncomfortable, or that you feel like are hard or scary. You have to be the type of person that’s really going to follow through on those types of things, ’cause that’s such a huge part of freelancing.

Paul Jarvis: Yeah, I’m really glad you brought that up ’cause that’s a super important point. I don’t have an alarm. I haven’t needed an alarm for 20 years, but I still get up at five or six in the morning and get to work, because I know that I work best early in the morning and so I wake up.

But I think the flip side to that is that you don’t have to be working all the time to be a good freelancer, a successful freelancer. If you have that internal motivation and that internal drive to get the work done, I’m exactly the same way. If I don’t work ahead of schedule for everything that I do, I get so stressed out and I’d…

Kaleigh Moore: Same.

Paul Jarvis: … be like a wreck. But, still, there’s some days where I’m like, “I’m just going to go for a hike today,” or like a show just came on on Netflix. There’s 12 hours that I’m not going to be working. But the majority of the time, I’m getting stuff done, I know you’re getting stuff done, so I think that that’s really important.

Kaleigh Moore: Yeah, and one last question: If you were thinking about going into freelancing, what would you recommend that somebody have in savings, kind of as a buffer for the first six months or the first year of freelancing? Do you have a recommendation?

Paul Jarvis: Yes and no. I think it depends. I think you have to find … and I’m such a cheapskate. I think it’s called minimalism now. That makes it sound way cooler.

Kaleigh Moore: Trendy now.

Paul Jarvis: It is. Hashtag trends. So yeah, I try to live as far below my means as is comfortable. I think that that’s really helped me with freelancing. I’ve never gone into debt for work. I mean, luckily a lot of types of freelancing only really requires a computer and an internet connection, and then sometimes I’ll go by six, seven years without upgrading a computer, just because you don’t really need to.

So I think figuring out the least you need to live a comfortable life means that you can have a much bigger runway. If you’ve saved up $10,000 and you need $8,000 to live each month, then having a one-month runway would be, like, one month and … See? Math is just not my strong suit … a month and a tiny bit to live off of, whereas if you have $10,000 saved up and your life makes it so that you only have to spend $2,000 a month, you’ve got a five month runway, so that makes lot of sense.

So I think for me, I feel the most comfortable when I have six months in savings, because I never know what’s going … Even I’ve been doing this for so long and when I was doing a ton of freelancing I was at a waiting list and still in the back of my mind was like, “What if everything goes away?” So I would always try to have six months of savings so I could have the minimum amount of necessities covered, just in case everything went to crap. How about you?

Kaleigh Moore: I feel the same way. I’m a super saver so I think six months is just a good rule for life to have six months worth of savings, because even if you’re not freelancing, things could go wrong and you might need that money, so I think that having that is really wise.

I’m the same way, too. I live in a small house, my husband and I don’t have a lot of fancy things. We travel a lot; that’s a priority for us, but I wouldn’t go out and buy a super brand new expensive car if I was getting ready to freelance.

You have to also think about your life decisions and how they line up with what you’re trying to do career-wise too. I think that that’s just a common sense kind of thing. So yeah, I think six months of savings makes a lot of sense and I think it’s just a good rule to live by also.

Paul Jarvis: Yeah, and I’m excited, because the next episode is going to be all about budgeting when your income isn’t specific. So this is kind of like a lead up to that, ’cause there’s so much more that I want to talk to you and everybody else about with that, so I think this is a good place to say, see you later everybody and thank you for listening.

Enjoy this podcast? Check out our course that teaches you the business of freelancing, the Creative Class.


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