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Dann—What does freelancing mean to you? I mean, what do you think when you hear that word, “freelance”?
Ash—[▶] So, when I say that I'm a freelancer, or when I used to say I was a freelancer, to me it meant a lot about controlling my own schedule and feeling like I could determine the projects I actually wanted to work on. So, there is this feeling when you're working somewhere that you definitely have power over what you're doing, but at the same time, you do have to go where your call of duty was. And there is some of that as a freelancer, but I think as you get older and as you form a better network, you can kind of pick and choose projects as is interesting, and you can start to work off of potential, rather than just need. So, you can see a project that ... I mean, I had a bunch where someone might have said like, "Oh, this is not an interesting project," but for me personally, I was like, "Oh, this is really interesting. Like we can probably make something out of this."
Dann—What was it like when you were getting started? What made you want to even try freelancing?
Ash—[▶] When I started freelancing, the main thing that I wanted to figure out was how I liked to do things. I think, especially...I went to design school. You know, was in school all my life doing things the way the teacher told me and everything, and at some point, working full time, I realized, you know, I don't even know when I like to get up in the morning or how I necessarily wanna work. So, freelancing was a great opportunity for me to kind of figure out my own rhythms of how I like to work and, you know, do I need to take big breaks and not be at the prey of like meeting schedules or so on. So, that was a big freedom for me.
Dann—Totally. I think that’s a great approach. But why freelance and not doing full-time work?
Ash—[▶] I was freelancing instead of doing full-time work because I had a lot of other projects on the back burner that I wanted to explore doing more as my primary projects than doing work for clients. So, I was writing my books. I was like teaching myself to paint and doing all these like, I call them like prairie woman activities. I was learning to read, knitting a bunch, planting a lot of plants. So, um, I kind of wanted to get back to my creative roots in some way, and that was like part of the exploration.
Dann—What do you think it takes to become a freelancer? Not necessarily a successful one, but to just become one in general.
Ash—[▶] To be a freelancer, there's the ethereal things and then there's the practical things. So practically, it helps to be really organized. Uh, for me personally, like it doesn't bother me to go and do receipts or write down every expense I have. That's like definitely an important part of it. Uh, for the ethereal things, I think you constantly have to be telling yourself, you know, "This is what to do next." You have to be very self motivating, because there really is less of the cheddar waiting for you, where you're like, "Oh, (laughs), if I don't do this, X person on my team is going to get mad." A lot of the success really hinges on you doing it because you think you should do it.
Dann—Do you need to know business in order to become a freelancer?
Ash—[▶] I think you definitely need to know a little bit about business to not be stressed out while freelancing. I've seen a lot of people freelance who don't know anything about business, (laughs), and either they learn it on the job ...I mean, the first time I went freelance, I was like 23 or 24, and I didn't know anybody, and I was just like, "I'm just gonna do this because it seems like something I could do right now," and it was definitely scary. Like you don't know what to charge. You don't know things like how to make the client pay you if they forgot to pay you, like how to check in gracefully and so on.
Um, and I think that it can be hard if you don't have a financial cushion, so I advise all new freelancers, I'm like:
Before you go freelance, make sure you have like 6 months.
and even that like starts to feel like kind of scary, because you don't ... There's always that feeling, like you don't know when the next job is coming. Even if you've had steady work for years, everyone I've talked to who has been freelancing forever is like, "I don't know, maybe it'll dry up next month." No one knows, (laughs). And so, you have to be kind of comfortable with that risk, but you can definitely defray the risk by saving up for it beforehand. And so that kind of alleviates business things, (laughs).
Dann—Do you think you can make a lot of money freelancing?
Ash—[▶] You can definitely make a lot of money freelancing. I would say, if you worked as much freelancing as you worked full time, you could make double, and I think that's always surprising, but the problem with the freelance money is when you get that check at your full time job, you're like, "All right, cool. Put that in my bank account." When you're freelancing, we're like, "All right, well X percent goes away immediately, and I have to go put that in a place where it's safe but not out of reach to pay my quarterly taxes," so there is this mental tension where like the money is like, you get this like fat check that you would not get full time, but then you're like, "I don't get to keep any of this," (laughs).
Dann—I always thought pricing was the hardest part when I got started, over time it ‘s not that it becomes easier but you just get more comfortably with it. What do you think about pricing? How do you charge clients?
Ash—[▶] Pricing's such a dark art, (laughs). Uh, the way that I would do it actually vary. I would charge people hourly if there wasn't much direction in the project, so if it wasn't well scoped, cause that tends to just spiral out of control. And that's okay, that's part of the process, but you don't wanna be stuck at the end of the day being, holding zero dollars, (laughs). So, uh, if it was not a well scoped project, I would charge hourly. Most people I would charge by project. Um, if I was coming in 3 days a week or something, I would charge by week.
When I was first starting out, I was terrified to charge anyone money. That's one of the things I think is hardest for designers who may not be totally business facing, (laughs), is, uh, you know, I was working at an agency before I went freelance the first time, so literally someone else was doing the pricing. I like didn't even see it, except by accident once. And so, when I first went freelance, that was kind of my guide. I was like, "They're charging X dollars for me, so I'll just charge a little less than that to be competitive," and uh, that was back when I was young and was terrified to charge anyone money.
Then, as I got older, I heard this piece of advice. I forget who gave it to me. And they said, "If you don't laugh a little to yourself when you're charging, you're charging too little." Like that should be your metric, is like, "Okay, this is like too, it's like, this is like a ridiculous sum," and then it's like, that's probably around the right level.
If you don’t laugh a little to yourself when you’re charging, you’re charging too little.
It is funny because even after years of freelancing, you would talk to some clients nd say like, "This sum, I'll give you a little off cause you're, you know, younger or something." And they're like, "That's the most ridiculous sum I've ever heard." And then other clients, you charge them and you're like, you do the same thing where you're like, "I'm a little busy or something, and so I'm not gonna, I'm just gonna charge you a little extra to see if it's really worth your time," and then they'll come back and be like, "Sure." And so there's no like, there's really no predictable things people are people I think
Dann—You always hear you have to be good at selling your work as freelancer, let alone as a creative in general. What are your thoughts? Do you need to be a good sales person when freelancing?
Ash—[▶] It certainly doesn't hurt to be a good salesman if you're freelancing, (laughs). But I don't think you necessarily need that. I know a lot of people who are just really good at their craft. Come in, do their project, say as little to the client as they can, and they leave and the client's like, "Wow that was amazing." And then she's like, "That's just what I do," (laughs). You can be any type, but it definitely helps. It's not gonna hurt you to be good with people, (laughs).
Dann—How do you promote yourself? How do you get all that work?
Ash—[▶] To promote myself, I was relying pretty much entirely on word of mouth and friends of friends. There was a big difference from when I first went freelance and I didn't know anybody to the jobs I was able to get after I'd been in the industry for awhile, worked at a couple full time companies. There were a lot of people who had left and were starting other startups or friends of friends who were starting startups. So, that was like the easiest way to get work. There were still a couple of people who had come in through my website, but uh, it tended to be the projects that I was interested in were friends of friends.
I think Twitter was probably a pretty big platform for me, just people who had been following me for awhile and, uh, were interested in working with me, or um, who just found me through there. But honestly, I did not get a lot of work through Dribbble or Behance. I never, I've haven't gotten the really...I haven't sat down and been like, "All right, let me figure out my Dribbble platform and everything and get that going." It was just like another thing I like didn't really have time for, even though I knew a lot of people were getting work through there. But I just was like, "One more platform to manage," (laughs).
Dann—How do you still connect with people, when you’re all alone (sometimes) as a freelancer?
Ash—[▶] It's funny because in terms of isolation, I'm I guess fortunate in a freelance setting, where I'm very introverted, so I could look up...If I didn't have my dog, I probably wouldn't have left the house for weeks. But uh, it is a good question of how to stay in touch and keep growing and stay in tune with the network and everything. I have a couple of freelance friends who, uh, I would go out to lunch with. We'd kind of talk shop, maybe like co-work from their office, and for some of my clients, I [would go in and work a couple days a week, uh, just so we could really closely with the team and everything.
Dann—How much of an important role did San Francisco play in becoming a successful freelancer for you?
There's definitely an advantage to being in San Francisco. Just the density of work available, it's pretty easy, comparatively, to get work.
Ash—[▶] I think you can freelance anywhere, but I think there's definitely an advantage to being in San Francisco. Just the density of work available, it's pretty easy, comparatively, to get work. I can imagine it being a lot harder if everyone isn't ... Here, it's like everyone is like, "I need a designer right now. Like do you know anyone?" So, I get a lot of emails even now that I'm full time of people being like, "Do you know anyone who's still freelance? We need somebody like yesterday."
Dann—Haha, you’re like me. Sometimes I need a break and go full-time at a start-up and I’ve noticed you do the same thing. What made you go back full-time this time?
Ash—[▶] When I first went freelance this time around, I was convinced, I was like, "This is it. This is the end," (laughs). Never going to have another job.
Um, I think what made me move from freelance to full time was that I had this realization that full time, if you play it right, is basically having one client. And a lot of my art projects that I was just figuring out and just starting when I was freelancing were starting to pick up. You know, things were starting to have a life of their own. I felt a lot of direction on where I was going, where ... I was getting a lot of creative fulfillment out of freelancing, and nowadays it's, feels more like I'm getting creative fulfillment out of my art and my projects. And so it felt more like I should be dialing back the client work to do my like best creative work, uh, as art and so on.
So, cutting down to basically my job right now, it's like, I have one team that I work with. The paycheck comes in, so that's nice. All the taxes are already taken out, (laughs). And yeah, I just get to my art stuff without thinking about it, and then working with a team that I know is reliable, is good to work with. There's no contact switching, which is kind of nice.
Dann—Anything you’d like to say to other freelancers out there or anyone thinking about making the jump?
I think if it calls to you, if freelance calls to you, you have to try it at least once, just cause you don't wanna always wonder. The worst thing that can happen is you just don't like it, [and you can just get another job, and that's fine. But you won't always have this like fantasy of, uh, I don't know, (laughs), maybe you wanna have the fantasy of freelance just dangling lightly in front of your face forever, but yeah. I think it's a good mystery to plum, if you're curious.
