The realities of freelancing (and luck vs. talent)
Inspired by a Twitter thread, this episode takes a deep dive into the realities of freelancing and looks at how both luck and talent impact the freelance journey in a major way.
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Kaleigh: So you shared a thread of tweets with me a while ago from AJ on twitter and it was kind of discussing how timing and luck play in to freelancing and how it makes things a little bit rosy colored I guess. It can distort the reality of freelancing for some.
Essentially he was talking about how you can see this people freelancing online and it looks so amazing, and so somebody will reach out to him and say, “I’m going to quit my stable 9:00 to 5:00 job with health care and benefits and I’m going to build a kick ass web app and it’s going to be easy.” Essentially I think is the gist of this tweet and how there is a lot going on behind the scenes with all of this, so I kind of want to dive in to that and talk about some of the realities of freelancing and how there is a lot goes on behind the scenes. Like how you really need to know what freelancing is like? I know you have a lot of feels about this, I’m going to let you kick it off.
Paul: And that’s why you wrote in the notes that I have the feels about this, so yeah AJ is an interesting guy. Like nobody even knows this guy’s name, and he uses the Johnny Mnemonic avatar. I have talked to him for years and I have no idea. I know that he lives in Nashville and that is it. He does well he runs this service called CARRDO and he’d run a HTML 5 up in Pixelarity. He has done fairly well and I guess and I see the same. I get emails from people because I’m like the freelancing person, “Oh you’ve inspired me to quit my job.” And I’m like, “No, wait hold on a second.” Because I think that is not as easy as that. I think that there is for one I think it is possible if you want to quit your job and be a freelancer, I’m not going to stop anybody from doing that.
But I also think that there is more than just like the rainbows and butterflies are working for yourself like it is hard work. And we talk about in the starting episode. It is sometimes it is hard to start. You have to pitch yourself constantly to get work. You have to be good at business as well or you need to learn how to become good at business. There is so much that has to be done and I’m like when I look at my own transition from like working for an agency to freelancing.
It wasn’t that big of a risk for me, like I still live at home with my parents. If freelancing had completely flopped I could still have a home cook meal and a roof over my head. There was no risk for me. I live in Canada so I have health care. Most of the Americans that I talked to that work for themselves that is their biggest concern is being able to afford health care or to be able to afford it even if they have insurance if something goes wrong and they still have to pay out of pocket for things that just worth it, just like they got the wrong ambulance to the hospital, or the wrong anesthesiologist that isn’t covered by their health care. It’s scary stuff, so it is not all like just sitting on a beach in Bali with a laptop, sand and laptops don’t mix.
Kaleigh: Let’s just get that out of the table right now. It is not realistic.
Paul: So even with like me jumping from just doing freelancing, doing more product stuff like the only reason I could do that is because I’ve been doing freelancing for probably 14 or 15 years at the time. I begin on saving money so I had savings like I would never just jump in to something cold turkey. While I think it is possible I wouldn’t do that because to me that feels like too big of a risk and I don’t even have kids or dependents, or I don’t have a lot of stress on my life. I live in a first world where a lot of things are taking care of for me that I don’t even need to think about.
I think that people see the one aspect of somebody else, like somebody’s success like AJ success and they think that is all there is. They think it is like a one dimension where there is nothing else that’s happening behind the scene and he does a good job of like getting into that. I kind of get into that myself but what are your feels on people just wanting to quit their job and jump head first into freelancing?
Kaleigh: So I have two thoughts on this. So my personal experience was that I started doing it on the side, I had a full time job, and I was like a very stapes and I’m still am, and a very stable relationship but I had a home like a lot of the big ticket items were taken care of for me, so I think that helped provide a lot of stability. And you know I had the free time to do the stuff on the side and to focus on it and really kind of get things up and running fairly quickly. So for me that made a lot of sense to start on the side and then slowly transition in.
Now, I will say that the one instance where I could see somebody wanting to quit their job and jump in with both feet is just kind of cold turkey as if you have the type of job that is so time and mind consuming that when you get home at the end of the day, you have no energy, and no inspiration, and no motivation to do anything else, a total brain drain for you.
Now, in that situation if you have to quit the job and you give yourself a short runway of I’m going to give this a six months to try this new thing. I can see it in that situation, especially if you have the stability of a partner who helps support you or you are not making a major life changes right now. You are in a fairly stable life stage, that I could finally see it.
Paul: Or you can save the money for that.
Kaleigh: Yeah, right or you’ve been saving strategically for that six months of test period for a while. I could see it in that situation. Personally for me I also started on the side and transition slowly and so, there is a lot of stability that played to my advantage and I think that was a huge part of my success. I don’t want to discount that and again that is something that I don’t talk about a whole lot because it is kind of a behind the scenes thing that you wouldn’t normally know or understand otherwise.
Paul: Yeah, like I started freelancing when I lived with my parents. It is not just something that comes up but it is not something that anybody’s ever asked me either, which is why I like having this show with you because we get to talk about these sorts of things.
Kaleigh: So what are the some of the other not so talked about realities of freelancing?
Paul: I guess we’ve talked about it before but it is kind of lonely to work for yourself at home especially if your partner has a full time job and they are out of the house and they get home and just want to be in the house and you’ve been in the house all day. You are just like let’s go do something because I’m so crazy.
Kaleigh: Hangout with me.
Paul: Exactly, that definitely can play into it. I don’t know, like I think that you also have to look at it in terms of like the grass is always greener. If you work for somebody else, you will always going to think you are working for yourself as better, just like I don’t want to freelance instead of going back to working full time for somebody which I don’t think that is a bad thing.
I guess it just depends on where you are at and what kind of what is working and what is not. And I think the other thing is something that AJ can really get in to is a lot of the people that you think are successful, are successful because they are really got lucky. Yeah they might have skills, they may have done some pretty smart things but you don’t know how is something going to work out until you try it. I didn’t know that I would be a freelancer for 20 years when I started. I was just like whatever I’ll just going to try this thing and see.
Same with products, I didn’t think that I would have five books with another book on the way when I wrote my first book. I was just let’s try this book thing and I didn’t know if it’s going to work out. But like I could look back and say this were like the 10 Strategies I have for becoming… and like I do that voices as well. Here is how to become a best-selling author. It was like I just lucked out so many times for those things to happen.
And I also think the other part of that is that, I advise I think that is always warped by time and hind sight in our own like very subjective views of experiences but I also think that some of the things that had worked for me have definitely worked for me because I’m a dude, I’m white, I live in a first world country. Like I get to play life on easy mode for the majority of things, so I could work just as hard as somebody else and get a lot further with like my career my freelancing or whatever just because of some things of I have no control of. I just happen to be a dude and I just happen to be white and happen lived in Canada, so I think that part of it too where it is like it is easier for me and it sucks that it is and it shouldn’t be but I also know that that is the case in a lot of the time and also luck like I said.
Kaleigh: Yeah, that is just part of it. And I mean there are other, I wouldn’t say unpleasant but not so great things about freelancing that people don’t talk about a lot of the time.
Paul: Like what?
Kaleigh: I mean you have to do hard stuff all the time, you really have to be self-motivated and push yourself to make difficult calls and to do the work that you are supposed to do with nobody there to tell you to do it. We talked about that before and last seasons as well, you have to be a self-starter, you have to be okay with pushing yourself to do these things. You don’t have the sure fire income every month a lot of the time freelancing is variable come months to months, so you have to deal with the amount of risk associated with that.
The other hand of that is that you know when it comes to freelancing a lot of the time if the economy shifts or a business models change, freelance expenses are one of the first things to go in budget scale tight. And so for me like all of a sudden we have a major recession again and all of this SAS company shut down or cut back way off in your marketing efforts because people weren’t buying things anymore, I would really be in an awful place because people will stop hiring me.
I mean, I would be one of the first people to go as far as where money was being spent. Again, there is a lot of risk that feels uncomfortable and feels scary and it’s just part of it.
Paul: And they know that not every corporate job is like this but I do know people who have corporate jobs that slack off way more than I would be able to and still make money. That is also just a matter of how work works. Like if you have to be in an office for eight hours a day and you only have four hours of work, you get it done you sit there and nothing else to do, so why wouldn’t you watch cat videos on Youtube. I would do that. I would 100% do that. But when you are freelancing, you have to, the other thing is like vacations. How many freelancers get paid vacations, I guess it is a total of zero.
Kaleigh: Yeah, none.
Paul: So in order to take vacations which I think can be good even if it’s just like a whatever millennials call them, staycation, where you just stay at home and don’t work, which doesn’t cost nearly as much. You still have to make the money to cover that. Even like taking time off like during Christmas, like if you need to make money in the last two weeks of December it is really hard to get clients and get work and get feedback or get like emails from people, same with the summer. I always find that it is difficult to move projects quickly in the summer because people take vacations and they take pay vacations at companies.
But at the same token I always try to budget in for like the amount I need to make a year where I’m not working 52 weeks of the year because I think that if I’m in the place where I can take time off I don’t want to beat myself up about it and I only say that because I do beat myself up about it. If I’m not working sometimes because that is the other thing like if you are not working if it is a nice stay out, if you just want to be out in your garden.
Like, “Oh I should be working. I should be making money.” And it’s like sometimes you need to recharge the batteries, sometimes it can be more creative and more productive if you just take a break and then get back to it but it is hard. It is literally hard for me to do that sometimes when I know I have work to do, when I know that work is going to make me money, it is hard to be like I’ll just walk away from this for a little bit.
Kaleigh: That is very hard to do. So that makes me think then, you know we talked about some of the ways that you and I both transition in freelancing kind of minimize the risk. When would you not risk starting a freelance career? Like what would be a scenario or a stipulation that would keep you from jumping into freelancing? If you are starting over from scratch?
Paul: Yeah so and we talked about this in the scratch episode a little bit but like if I couldn’t find a hand full of people to hire me for the job I wanted to do, while I was still working full time, even if I didn’t take on the work I just asked would you hire me for this? Yes or no? If I couldn’t find anybody to do that I’ll probably reconsider what I was thinking of doing which is at that point it’s easy because you don’t have a business, you don’t have to pivot some massive business, you just have to change your idea to something else for the majority of the time.
If I had a serious illness and I needed the medical coverage of the business that I was working at, I don’t think I’ll move. I have a preexisting condition and my insurance sucks but it doesn’t suck enough for to it’s worth like ridiculously expensive, like I need a lot of drugs for my asthma but it’s not ridiculous in order to pay for those things where I live. That would be another thing. If I couldn’t save up a healthy enough runway to make the leap I don’t think I would have the guts to do it. If I had nothing saved I don’t think I could quit a full time job that was paying me regularly.
I mean that could be different for everybody but for me personally I know me and I know I couldn’t do it unless I had like at least, because you are making a guess. It doesn’t matter how talented or skilled you are, you are making a guess when you start freelancing you see if it’s going to pay off or not. So if freelancing worked out, great. If the freelancing didn’t work out unless I had a good answer to that I wouldn’t do it.
Kaleigh: I think that makes a lot of sense. The only thing that I would really add to that is if you didn’t have a support system in place of people either family or friends or a partner who is on board of what you are trying to do that would make it really difficult if you are just getting started because there is so much risk, there is so much stress and anxiety when you are trying something new, just experience something new.
When it is related directly to your income and how you can provide for yourself, it really do need a network of people that you can turn to and like talk through the difficult things of it and that can support you if you have kind of slow start to things and that can help walk you through the difficult parts of freelancing. Like, “Oh no I quit my job and now I’m super lonely” or all of a sudden, “I have a lot on my plate and I’m really stressed out and I don’t have anybody that I can talk to about it.”
Like that kind of recipe for disaster I feel like, so making sure that you have a network of people you can turn to and that are on board with what you are doing and they kind of cheer you along and support you through that I think again something people don’t really talk about but really important.
Paul: Yeah and I guess the other thing that I would add to that because there is definitely a few things is that willingness to learn how to do and run a business quickly because if you are working full time for somebody, you are doing that job that just your skills set because there are other people in the company that take care of HR, and finance and accounting and payroll.
When you work for yourself you are all those people. You are the person, and I think a lot of times new freelancers misjudge how much time is spent on the business versus how much time you spent doing the work that you are paid to do. And for a lot of the people I talk to, it is like about half. Like half of their day is emailing with clients or communicating or looking for work or writing invoices. All of that I can’t even think of all the things, there are so many things. And then the other half, if you are lucky I get three hours a day or four hours a day to writing and design, I’m like this is the best day ever because I have like three hours to do that job.
And even when the only job I had was freelance web design. If I had three or four hours a day to do that I would be like yes this is so good because most other days it would be like I have calls to do. I have like proposals to write, I have like people to follow up with, people to contact to see if they know anybody that needs to do the work, I have emails to send, I have people to connect with on the socials just like keep in touch with. There are so many things.
Kaleigh: Yeah, all of those things takes time. I feel like this is a really important episode and I hope that we are able to share the initial Twitter thread because it is a really good one, it’s a great perspective for anybody whose thinking about living a very stable job, about the realities of freelancing. I’m sure we will link to that in the notes.
Paul: Yeah, and this will be in the transcript now so when one of us will see that and link to AJ’s Twitter thread. And yeah, just to reinforce I’m not saying that people shouldn’t quit their full time job to freelance like obviously we did. I’m just saying like there is ways to mitigate the risks so it’s not I would never want to be in a do or die situation with work. I don’t want anybody else to be in that situation because like I want people to freelance long term and stable, because I don’t think working for a company is more or less stable than working for yourself.
There is things that you have to do in each scenario to make it stable. And I think if you are always in a do or die situation, it is stressful and it’s straining. And the other thing is, it is harder to pitch when you need, like it is much harder and there is some psychology element to it too. Like if I know that I would like to work with this client and obviously this is going to help me meet my goals for the month if I get this project then get that money. That is very different than like if I don’t get this client I don’t know how I’m going to pay rent or eat. It is really hard to pitch in that situation and it is really hard to be compelling because people.
It’s weird like people can sense desperation and the more you can do to make sure that you are not in a point where that exist in your life the easier it will be. I don’t know what the psychology is for people not wanting to hire people when it’s just like do or die versus like I would love to work with you and this is obviously going to help me get the work I need to pay my bills, but if this doesn’t work out I’ll find something else as opposed to like it’s this or nothing. It is a hard, it is a stressful situation to be in.
Kaleigh: It is, very stressful.
Paul: Yeah, cool. I think that is all I had to say, is that all you had to say?
Kaleigh: Yeah, that’s about it for this one.
Paul: Cool.Posted in Creative Class, the freelancer podcast · See more articles
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