Poornima Vijayashanker

How to Prepare to Strike Out on Your Own and Pursue Your Creative Calling


Have you contemplated leaving the comforts of a company to strike out on your own to pursue a creative calling?

Perhaps you have an idea for a product or service. While there’s a strong pull to pursue it, hesitation maybe holding you back.

You’re worried about being good enough, attracting customers and clients, and how to make it all come together to find fulfillment, while at the same time tending to the practical side of things like paying the bills!

You’ve probably heard plenty of stories around striking out to build a startup, raise capital, and pursue a big idea. While that sounds exciting, you’re looking for an alternative approach…

Well, in today’s episode of FemgineerTV, we’re going to be tackling all these topics. To help us out, I’ve invited Jessica Hische, who is a letter, illustrator, and type designer.

Jessica began her career working for a design studio called HeadCase. She then went on to work for a prominent designer, Louise Fili, and eventually struck out on her own. Jessica has had notable clients like Wes Anderson, David Eggers, Tiffany Co, and Nike, just to name a few.

As you watch this episode, you’ll learn:

  • Steps you can take early in your career, such as how to reach out to people or companies you want to work for and learn from;
  • Why a day job can be immensely valuable and how to find one that is nurturing;
  • Why you don’t have to run a 10+ person design studio or a 100+ startup, and can be a solopreneur;
  • How to reconcile your client’s vision with your own creative desires;
  • How to get compensated fairly by conveying the price and value of your work;
  • Why learning tangential skills as a creative can be helpful when it comes to hiring; and
  • How to balance side projects and attract work with the day-to-day work that pays the bills.

Whether you’ve been in your career for 6 months or 6+ years, and have toyed with the idea of doing your own thing but weren’t sure how to set your own terms, this episode is for you!

For those of you who are interested in design and typography, check out Jessica’s latest book In Progress. We also talked about her popular post, “The Dark Art of Pricing,” which you can read here.

Listen to the episode on iTunes!

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How to Prepare to Strike Out on Your Own and Pursue Your Creative Calling: Transcript

Jessica Hische: You know I have a pair of cowboy boots and I bought them when I was Austin one time, of course. They were super fancy ones and I never wear them because I feel like such a nerd when I wear them because mine have little hearts.

Poornima Vijayashanker: Nice. I actually got these here, but it’s still the west.

Jessica Hische: You convinced me to bring them in.

Poornima Vijayashanker: Yeah, you should. I like to wear it with dresses because it’s my personality. I don’t like to be super feminine or super masculine. It’s kind of a nice mix. Yeah, it’s always a conversation starter everywhere I go.

Jessica Hische: I’ve had shoes go completely AWOL on me. I’ve owned them for years and then all of a sudden they’re like, “You know what, I know we were super comfortable and everything was cool. Fuck you, now you get blisters every second that you wear them.” I don’t understand it. It’s not like my feet grew or something.

Poornima Vijayashanker: Maybe you should take them back to the cobbler.

Jessica Hische: Maybe. I don’t have my cobbler. My husband works at Facebook so I send all my shoes to get fixed with him. I haven’t formed a shoe relationship here in the city.

Poornima Vijayashanker: Sure. Nice. Welcome to the 17th episode of Femgineer TV brought to you by Pivotal Tracker. I’m your host Poornima Vijayashanker, the founder of Femgineer. In this show, I invite innovators in tech. Together we debunk myths and misconceptions related to building products and companies in tech.

At some point in your careers, you might be tempted to leave the comforts of your company and strike out on your own. There’s that moment of hesitation where you might worry if you’re good enough, if people will actually want to be your clients, and how do you put it all together. Well, in today’s episode, we’re going to be talking with Jessica Hische, who is a freelance designer who focuses on lettering, illustration, and type design. Now Jessica has gone from working in a studio and transitioned to being a freelancer. She’s going to share a lot of her journey with all of you today. Thanks for joining us, Jessica.

Jessica Hische: Happy to be here.

Poornima Vijayashanker: Yeah, so I think I discovered your work while I was doing a google search on pricing and getting paid. I stumbled across your post on the dark art of pricing.

Jessica Hische: Indeed.

Poornima Vijayashanker: I loved it and we’re going to get into that in a little bit. Ever since then I’ve been quietly admiring your work. I’m really excited to be here. It’s a treat for me to be talking to you. Now I know you’ve worked with a lot of prominent clients and you do a lot of different work. Let’s go way back to the beginning. What did you want to be when you grew up?

Jessica Hische: Well, I always wanted to be an artist. I don’t really know what that meant. I was a kid that just loved to draw all day. I think part of the reason why I loved to draw all day is because I was easily given permission to do so. It is a quiet activity that keeps children occupied for many hours of the day, so my parents were like, “Yes, please continue down this path of being quiet in the corner and doing the artwork that you seem so in love with.” It wasn’t until I got to college that I really figured out how to turn that into a career. It was really not purposeful. I didn’t go to college intending to become a designer, because there are careers in design. I went to art school trying to pursue literally anything that had to do with art. I took sculpture classes, glass-blowing classes, painting classes. I really loved everything, but when I took my first design class is when I really felt like I sort of found the path that I wanted to follow. Just because it took a lot of the things that held me up a lot about just general art making and removed them so that the path became a lot easier.

For me being an 18-, 19-year-old in college, I didn’t feel like I could trust whatever opinions that I had to express in the world as being valid. I was like my life has been generally pretty normal. I don’t come from a crazy background. I don’t have an incredibly unique opinion to share with the world yet. Being able to work for clients—and in school it’s not for clients, it’s based on project briefs—was really freeing. It took down the wall of starting a project. That’s, I think, why I ended up in design and why I stuck with it, and why I enjoy it so much. I really like how collaborative it is, and how it’s about problem solving instead of about self expression.

Poornima Vijayashanker: Yeah, and why specifically lettering?

Jessica Hische: Well, lettering I did a bit of it in college just because my school was really hands on and encouraged a lot of exploration and bringing stuff from other disciplines into your work. I was like every other student that was super broke and couldn’t afford to buy fonts and so I drew my own fonts for projects a lot, and didn’t realize that was actually a profession unto itself. Actually not until a few years after college, when I was working for Louise Fili after I graduated. She does a ton of lettering for her projects and the people that work for her do a lot of lettering for the projects. Even then I always thought of it as I’m a designer that draws lettering as a part of my work. Not thinking that that was a field unto itself. I was doing a lot of illustration work on the side because I love illustration. I actually feel like if I understood the field of illustration more when I was younger, I probably would have ended up an illustrator rather than a designer. That’s really drawing all day with a purpose.

Poornima Vijayashanker: Right.

Jessica Hische: It’s it. I love that I have the design background because lettering is a really good marriage of the two. You use principles from typographic design but you’re drawing it custom as an illustrator would work. The whole process of working with clients and even just the process of creation is very similar to being an illustrator. It’s just you sit on this line between design and illustration.

Poornima Vijayashanker: Mm-hmm. You mentioned the opportunity that you got to work with Louise Fili and that’s great. For those of you out there who aren’t familiar, Louise has done a lot of design work for prominent brands like Good Housekeeping and Tiffany and Company. For our viewers out there who might just be graduating and thinking, “Wow! What a lucky break Jessica. How do I get such a lucky break?” I realized it wasn’t a lucky break. You actually did something to get that opportunity. Do you mind sharing the story of how you got it?

Jessica Hische: Yeah, it feels a little bit like a lucky break. This is what I tell students all the time when they reach out to me about, “How do you reach out to people that you want to work for and blah, blah, blah.” People can get really discouraged if they’re reaching out to people and then they get a lot of, “Sorry, we’re not hiring. Sorry, we’re not hiring.” What I always tell students and young designers is that if you’re interested in working somewhere, meet with them without immediately saying, “I really want you to hire me.” As people that are in any profession for a while know, if people really want you to work somewhere they will make room for you. You have to get in the door and get them to meet you first. Really in your super early career the thing that’s gonna get you a job is your attitude and professionalism and just seeming like someone that would be a good addition to a team. Rather than your work, because it’s clear that your work is early. There’s still a lot of room to grow.

Poornima Vijayashanker: Oh, yeah.

Jessica Hische: If you have a bad attitude, your potential employer would automatically know, “I don’t know how much this person is gonna grow under my tutelage.” When I ended up working for Louise, I wasn’t actually looking to work for her. I sent her one of my illustration promos just because I was such a super fan of hers. I sent it out to 250 people that were all in ad agencies and publishing houses trying to get trying to get freelance work. I got hardly any responses whatsoever except from Louise, who wrote me. I happen to send this promo to her while she was in this period looking for a new designer.

Poornima Vijayashanker: Oh, great.

Jessica Hische: She had not publicly advertised this position. A lot of small studios don’t do that. What they do first is try to exhaust their network of people that they know, or recommendations of people that they know. She had sort of worked through a lot of that, but was open to the opportunity of meeting new people. I had sent the promo along right at that time. She called me in for an interview. I was not 100% ready to upend my life and move to a new city. I was completely happy living in Philadelphia and thought that I was gonna be a freelance illustrator in Philadelphia.

It was scary to take the leap, but of course I had to do it. I idolized her at the time, too. It was an opportunity that felt like it came out of nowhere, but it’s not that did. It’s that I worked so, so hard when I was in college to try to make this portfolio that stood out from a lot of people. Then I was open to new opportunities and putting myself out there to people that didn’t need to be looking at my work, but I wanted to put my working in front of them.

Poornima Vijayashanker: Yeah. How do you think she influenced you, or how do you think she inspired you?

Jessica Hische: In so many different ways. One of the biggest influences that I think Louise had on me is just how to run a business that is in a high-stress environment. The job that I worked before working for her was a great studio in Philadelphia, called Head Case Design. It was run much more like how a freelancer would run their studio, where it’s just like, “Project time. We’re working on stuff whenever. This is a crazy book project. I guess we’re working until midnight tonight.” The schedules were a little airier. With Louise, she was super tight with clients. She would not schedule a meeting to show a presentation until after all the printouts were made. It sort of showed me that if you’re prepared and you take control of your calendar and your schedule, and not in a way that is abrasive to other people, but just in a way that sets up yourself for success that you can both be successful and not work 24 hours a day.

Poornima Vijayashanker: Oh, yeah. Definitely. While you were working for Louise you weren’t just working for Louise. You were also doing some freelancing, right?

Jessica Hische: Yeah, so before working for Louise I had sent out that promo and was really pursuing this freelance illustration work. Some of it started to trickle in, so when I started working for Louise, I asked her, “I know that you have a noncompete. I won’t do anything to work for your clients or pull clients away from you, but I do really want to do this freelance illustration on the side.” She was very understanding and said, “If someone comes to you and it’s clear that they’re coming to you and not coming to you because they want a cheaper me, then you’re welcome to do it.” When you work for someone that’s been in the industry for 20 years, not working for any of their clients can be really hard. She’s worked with every publisher and worked with every magazine.

We had a really good honest and open relationship about that. She said, “As long as this doesn’t interfere with the work that you’re doing for me, and that it doesn’t take away from the work that could’ve been coming to my studio, I’m completely fine with it.” I was just really open with her about it. The thing that made it very easy for me to do freelance illustration work on the side, there were a couple things.

I think it’s easier to do work after work if it’s really different from the work they’re doing during the day. If you’re doing insane engineering work during the day you don’t go home at night and do more insane engineering work because you burnout. It feels like one 16-hour workday rather than a 9-hour workday and a 7-hour workday. The illustration work was different enough for my design work that I felt like I was just going to a second job that was still really interesting when I was working at night. Then the other thing that really helped it is the fact that Louise did run such a tight ship with the studio. I was out of there every day by 6 pm. I could be really honest with my freelance clients and say, “Hey, I can’t do anything right now, but I’m going to be home in an hour and I can send you the final event.” If I was working in a different studio where the hours were more unpredictable, I think it would’ve been a lot harder to run the freelance work on the side.

Poornima Vijayashanker: Right. There weren’t those firefighting moments where you had to freak out and be like, “Oh my boss. I got to go answer her stuff. I can’t handle you.”

Jessica Hische: There still were firefighting moments, but not because of Louise, because of clients that couldn’t—sometimes you work with a client and they’re like, “But we need this at 2 pm.” I’m like, “You didn’t tell me that yesterday. You told me that you needed it by end of day and the end of day is not 2 pm.”

Poornima Vijayashanker: 2 pm some other time zone.

Jessica Hische: Some other time zone. I’m like, “You’re not in Europe. You’re in California. 2 pm is not end of your day.” I was living in New York at the time.

Poornima Vijayashanker: It sounds like you had a good thing with Louise. Why leave the comforts of company and strike out on your own?

Jessica Hische: Well, the schedule was really difficult to keep up with. I started working for Louise when I was 23. I worked for her for two and half years and kept up this schedule which is pretty much me working from nine in the morning until one in the morning most days. Then working at least one day over the weekend. I always knew that I wanted to be on my own just because I really liked having the autonomy to just take on the projects that you want to take on. Of course I was a young designer, too, that wanted the ownership over their work.

I think that’s one of the reasons why a lot of people look towards freelance work as being the ideal. When they’re young they just want to get the credit for what they’re working on. I think now in retrospect I can completely understand why someone would think that being freelance is the ultimate thing to do. When really if you have dreams of doing really big work or really grandiose projects, it’s not. It’s too difficult to do everything yourself, or to coordinate lots of outside help. Being at a company can be amazing. For me, it was really practical. It’s different to work at a small design studio in New York that’s focused on smaller niche clients, like restaurants and food packaging and things like that. My salary was not a Silicon Valley salary.

Poornima Vijayashanker: Sure.

Jessica Hische: At a certain point, my freelance work—I was earning more in my hours as a freelancer than I was in my hours working for the Louise. I could’ve been saying, “Awesome, that’s just double salary.” I really wanted to reclaim a little bit of my personal time back. It just was a clear indicator of, this is really, the ball is rolling and can roll with it, and now is the time to do it and feel safe about it.

Poornima Vijayashanker: Yeah, that’s a great transition where you had been working and moonlighting, and then decided, “OK, the freelance gigs are actually coming through and I have a sustainable business. Now I’m gonna leave my full-time position,” versus many of us who wake up one day and we’re like, “I hate working here. I want to quit. Oh, wait. I have no money in the bank. How am I going to make this happen?”

Jessica Hische: I think that one of the things that’s really important as a creative person or just anyone in general is to be really self-aware and staying in check with yourself and your emotions about the work that you’re doing, and doing what you can to maneuver your environment to make sure it’s ideal for you. I’m not the kind of person that says that everyone needs to quit their day job and do what they love. I don’t agree with that. I think the day jobs can be amazing. If you give up on them too quickly, you’re not exploring all the ways that you could be in that very nurturing environment, but optimize it for you.

To make a really weird comparison, I had a baby last year. In the process of literally having the baby, they said, “If you think that you’re gonna need an epidural, you can’t tell us when you’re past the point of no return. You have to tell us when you’re 80% away.” Just because there might be another surgery or whatever and they need to make sure they’re around. I think that it can be like that with your career where you can’t wait until you’re broken to fix everything. You have to be staying in check and staying on top of it. When you start feeling like things are not going the way it’s supposed to be, that’s when you need to be exploring other options. If you already made it to the desperation point, that’s when you’re gonna make really rash decisions, and when you’re gonna do things like quit your job with no other options out there.

Poornima Vijayashanker: Yeah, or no source of income and then you’re like, “Oh no. What am I gonna do next?”

Jessica Hische: Yeah, I think a lot of people that haven’t been able to pursue freelance careers well is because they’ve made it too far into their job to the “I hate my job, I need to completely change my life” point. Then they branch out on their own and it can take a while to kickstart a freelance career. Even as someone with a successful career, what I remind people all the time is it’s not a steady paycheck. Clients usually have contractually up to 90 days to pay you. Really they can kind of take longer than that before you start sending aggressive emails to them.

The work that you’re doing right now is not paying your bills right now. It’s paying your bills three to six months from now. That can be really scary if you go out on your own, have no other options, have no money saved, knowing that even if you’re insanely successful and have ten projects lined up right when you’re done you’re not gonna get paid for this project for a few months. I think that’s something to really keep in mind and that’s what you do have to be aware of, “Holy shit, I’m burning out. I need to figure out my next step. I need to start setting myself up so that that next step can not be super scary and can be actually doable.”

Poornima Vijayashanker: Yeah, let’s talk about how you came up with that pipeline of clients when you were transitioning. Did you have people that you established relationships with? Did you write a bunch of blog posts? How did that come about?

Jessica Hische: Well, for me as an illustrator it’s a little bit different than being a freelance designer or being a freelance anybody that has long-term relationships with people. I love illustration because the project timelines are generally a lot shorter. I get a lot of high turnover and I get to work on a lot of different kinds of projects. What I don’t get a lot usually is a ton of repeat clients. When clients hire me, they want me to do my specific thing for a specific project, but the next project they might want a completely different look. It kind of is about quantity and just making sure that your staying involved in the conversation and being involved in the communities. Whether that’s online or in person just making sure that you’re establishing these relationships with art directors, with designers, with other illustrators because work comes from word-of-mouth a lot of times.

I was also super involved just in the community online trying to post resources. I started doing public speaking after I had put out a personal project that people were interested in hearing the background of. That certainly brought in a lot of work. I think for most people, the thing that brings in the most work is just the relationships that you have with people. That’s why it’s important too that if you are planning to leave your job that you don’t burn a ton of bridges. A lot of times work can come that way. How many companies in the Bay Area do you know that hire people that have left the company as freelancers. It’s a very often thing.

Poornima Vijayashanker: It’s usually a first client sometimes.

Jessica Hische: Yeah, exactly. I think that it’s really important to think about that and to just know that any relationship that you’re building, even if it doesn’t seem like it, it’s a direct correlated relationship for this person who will literally give me a project. It could turn into something. With peers, too, it really works that way. If you think about how much work runoff people have, because if they’re like me, and I’m a freelancer that doesn’t plan to have a 10-person studio, there’s only so much work that I can take on. Then the work that I can’t take on clients very much appreciate it if I can refer them to someone that would be a good match for their project. Everybody has their five to ten people that they’ll send their run-off work to. You can start making those relationships while you still have a job.

Poornima Vijayashanker: Yeah, so why not the 10-person studio? Why stay by yourself?

Jessica Hische: For me, I still really like having the flexibility of being able to dictate my schedule. For now, especially I have a one-year-old daughter, and we’re sort of in the time of our lives where the flexibility of my career makes a huge difference for us being able to parent equally. If I had a full-time studio and suddenly had to take three days off work because my nanny called in sick or something, and didn’t have employees that I could trust 100% to be autonomous while I was gone, I think it would be really stressful. I still really like being able to work when the spirit moves me. Which of course I keep a really tight schedule especially because of childcare and things like that, but I like that if I have to work on a Saturday because of a Monday deadline, then I can take off on a Wednesday. If I was running my own studio, I wouldn’t really have that; I’d have to be the person running a tighter ship.

Poornima Vijayashanker: Right, you’d have to be more regimented and routine.

Jessica Hische: I’d have to be more regimented and routine. Also, too, any person that has been running their own studio or freelancing can tell you that a lot of the work that you do is not actually creating the work. It’s about managing your business. I think that if I were to start setting up a studio, the first move that most people do is to hire junior designers or people that can help make the work. When really that’s the opposite of what I want.

What I don’t want to do is hire other people to do the thing that I want to be doing so that I can do more managing. I think there could be a time in my life where I’m interested in doing more art direction and management. I certainly love teaching and I love mentoring and that kind of thing, so I do foresee that at some point in my life. I could want to run a studio. Right now, what I really want is more time to actually physically make stuff. The more people that I have working for me, the less time that I will have for that.

Poornima Vijayashanker: In a previous episode with Maria Molfino, we talked about creative freedom. It’s clear that you are practicing creative freedom. Has there ever been a time in your career where the criticism from a client, or a peer, or maybe even a mentor stung?

Jessica Hische: Absolutely. There’s always going to be, not haters because they’re not haters, they’re people with legitimate criticisms for you. I think that you have to engage with people, especially if they have something that you feel is legitimate criticism or something that’s way off base, too. I’ve had a couple of instances with people online where they said something really intense about me, but still at replied me. I’ve reached out to them to be like, “Hey, I’m sorry that you feel that way. What’s the deal? Can we talk about it?”

I think people are so used to behaving anonymously and not realizing that there’s people behind the people that they talk about. When they are confronted by it they’re like, “Oh, I was just talking out of my ass. I didn’t mean it or whatever.” Sometimes you do get legitimate criticism. The things to ask yourself are, “What’s this person’s intentions with giving me this criticism? Are they projecting?” That can definitely happen. Is this something that is an actual thing? Is this a more than one-time occurrence? Have I gotten similar feedback from other people? The first time that you get really hard criticism about something you can take it with a grain of salt. Pay attention to it but know that this could just be a subjective thing.

Poornima Vijayashanker: They’re blowing off steam. They’re having a bad day.

Jessica Hische: They’re blowing off steam. If you know that you have done that thing and they’re alerting you to it, that’s a different thing. If you start getting feedback that’s similar over and over again, then clearly there is something that you need to address. The feedback that I got from close friends early on was, “Whoa, whoa Jessica. Watch how much you celebrate these things that you’re working on. Maybe you’ll come off as being full of yourself.” I had to sort of look at that and go, “What kind of person is saying this to me? Oh, this person is a much more private person that doesn’t feel like it’s appropriate to say, ‘I’m so excited about this. Look at this thing I did.’” It depends if someone—it’s just not what they would do—says that versus it’s someone that would do that and they’re saying that. Then you could actually take that and say, “OK, maybe I was being a little braggy.”

Poornima Vijayashanker: That’s why you put the disclaimer of, “I’m a constant oversharer.”

Jessica Hische: Yeah, for sure. I think too, I think, that feedback early on influenced the kind of writing that I do on my site where I always try to make everything from my experience. I feel like it’s difficult to refute someone’s advice if they’re just speaking clearly about things that they have gone through or things that have worked for them, or have not worked for them, versus writing about empirical, “this is the way to do it.” I think that of course there are people out there that love writing that way and want to write the resource. I think because I’ve been a little self-conscious about expertise in general, just like…I’m 32 but, I feel like I’m still like a baby when it comes to having a career. I don’t want people that are 70 that have been doing this for this long to go, “Oh, honey …”

Poornima Vijayashanker: “Let me tell you.”

Jessica Hische: “Let me tell you what it’s like after you’ve been doing it for 40 years.” I think always approaching feedback and advice and things like that from my own personal perspective has helped me to share more. I feel less intimidated about the fact that whatever I’m sharing will be incorrect. It’s correct to how I was feeling at the time. Even with articles that I posted to my site and things like that if they’re viewed six years later I can at least say, “Well, that’s what it was like for me six years ago. That’s not my opinion now, but that’s what it was six years ago.

Poornima Vijayashanker: Nice. You’ve also worked with some prominent clients like Wes Anderson and Dave Eggers. Were you ever concerned that you couldn’t live up to what their vision was for their brand, or their book, or movie?

Jessica Hische: Both of those clients had very specific visions. One of the things that I think has worked in my relationship with the both of them…I’ve worked with Dave three or four times now. I just really like working with him. Wes was amazing to work with on the Moonrise Kingdom titles, but you have to really give yourself over to whatever it is that their vision is. I think that designers can have a difficult time knowing when to step in and say, “You should be trusting me to do this.” Versus when you tear down that wall and say, “I’m your hands, tell me what you need my hands to do.” I think because I trust both of them so implicitly with whatever vision that they have in their heads it’s easy for me to go, “OK, you don’t like that R let me change that R.” Versus, “I don’t know. Do we really need to talk about this R?”

I don’t want to have an argument with them if they have a really clear idea of what they want. What I’m always happy to push back on is when I get feedback that disagrees with how something should be drawn because of just the anatomy of type and that kind of thing. I always am very straightforward and say, “Technically we could do anything. You want me to make that R look like a unicorn? I can absolutely do that. Is it the correct way that that letter should be constructed? No. Based on the rest of these letter forms it no longer matches the rest of this.” Ultimately if I have to really get people to back off I’m like, “Nerds love writing really angry articles about these things. I’m not gonna say that they’re definitely going to, but there’s the possibility that some Fast Co. article, or some brand-new article, or whatever is going to premiere with a major criticism of this thing that is screwed up. What I don’t want to do is set you up for that to definitely happen.”

Poornima Vijayashanker: Oh, nice. You basically walk them through the consequences of their choice or their vision.

Jessica Hische: Yeah, exactly.

Poornima Vijayashanker: That’s smart. I never thought about it that way. That’s a good idea.

Jessica Hische: I think, too, I am really happy opening clients up to the process of doing what I do and trying to educate them about why decisions are made. I think that it helps them but it also helps me. I have to be very decisive about the things that I do because I know that they have to be backed up all the time. I don’t just make decisions because I feel like it. I make decisions because there’s a reason. Especially when it comes to doing logotype work and that kind of thing. I want them to be able to ask me about any single part of that letter form and for me to give them a reason, an actual reason of why it was drawn the way that it was. So that they can then say that to someone else or know that everything was thought through.

Poornima Vijayashanker: Aside from these consequences they might face, has there ever been a time where someone has come to you and had a vision that didn’t align with your own integrity?

Jessica Hische: Integrity stuff usually comes up much earlier on. Like if someone is trying to come to me and have me work on a project for a client who I don’t agree with—like tobacco companies would be a big one, or something like that. You just have to make decisions of “I don’t work for tobacco companies.” You can give legitimate reasons of why you don’t. I could say, “I don’t want to work for tobacco companies because I want to also work on children’s projects. I feel like there’s a major conflict of interest in working for those two different kinds of clients.” You could just not give a real reason and say, “Sorry, I don’t work for this.”

I don’t do work for churches because I’m not a religious person myself. I feel like there are certain industries where if you end up becoming a person that works for them there are assumptions made about the kind of person that you are. Not that religion is a bad thing all the time, but I don’t want people to make those automatic assumptions of me. It hardly ever comes up where there’s an integrity issue later in a project. It’s usually when people are initially hiring you.

Poornima Vijayashanker: I know another challenge that a lot of designers and engineers who are freelancers struggle with is getting people to compensate them fairly for the work that they do. It’s a topic I feel strongly about. I’ve written a number of things on, and as I was doing my research I stumbled across your post on the dark art of pricing. Can you share with us what your processes is for pricing, and how you convey that to your clients?

Jessica Hische: Sure, one of the things that I think is really important I think people learn over the course of their career is that having a contract and talking about pricing up front is incredibly important, as uncomfortable as the process can be. I think that one of the things that I have really learned is that while clients love being special, the thing that they don’t loving being special about is when it comes to pricing. They want to know that whatever you’re telling them is just the fact. It’s not a specific thing that you’re coming up with them. You’re giving them the price based on your own experience and what you would have told other people. Which is odd. It’s not odd, it makes total sense in the same way you wouldn’t want to go to a clothing store and have there been no labels on the clothes. Then you go up to the register and they go, “$20.” You’re like, “Oh my God. Is this $20 for me or is this for everybody?”

I think that being really up front and matter-of-fact about how you want to price things is really important. I think it’s important, too, to talk about it as this is what the value of the work is for me. You can justify it as much as you want. When it comes to doing logo work, for instance, I can say, “I only want to do one logo project at time. It takes me six to eight weeks minimally to work on a project, and because of that I need to charge X.” I could charge less if I was taking on more projects at a time, but then I couldn’t devote as much of myself to the clients. If people come to you, it’s nice to have those reasons of, “Hey, the reason why this is, is because of this.”

The other tactics are sort of I don’t price hourly. Part of that is because I don’t want clients to just be able to nitpick forever and bleed into other client work. My calendar can be really difficult to maneuver. Having everything priced per project really makes these clear deliverable dates and lets me know when something is probably going to be off the books. Then I can have a new project come on. Another reason why pricing hourly is really difficult for creatives is that people get extremely allergic to high hourly rates. Even though as a professional you’re probably a lot more efficient than you were as a young designer. Therefore it takes you way less time. Say it took you four hours to make a poster. You couldn’t charge someone $400 an hour to make that poster because you wanted to make over a thousand dollars on the poster. They would look at you like you were crazy.

Which is odd because lawyers easily charge that much, whatever. People expect there’s this horrible double standard where if you love your work you should be paid very little. Part of that is just jealousy from other people where they’re like you like, “You’re lucky enough that you’re doing what you like to do. Therefore you shouldn’t be paid how a lawyer is. Clearly they had to pay for tons of education and they don’t actually like their job half the time, whatever.

Poornima Vijayashanker: Really. I thought that was just an insurance policy so they avoid getting sued. Yeah.

Jessica Hische: Yeah, exactly. It’s really figuring out what works for you and also just talking to people around you. If you’re not competing directly with an individual on a project you can have very open conversations about pricing. If someone came to you and said, “Hey, I want you to design a website for me,” you could write every person you’ve ever met and ask them, “Hey, I’m going to be vague about the person because I don’t want to give with the client, but here’s the general brief. What would you charge for this?” You can have those conversations super candidly and I really encourage people to do it. Talk to a variety of people. Don’t just talk to your one friend. Your one friend might be under charging.

Poornima Vijayashanker: Yeah, that’s true.

Jessica Hische: Your one friend might be overcharging a lot because they have achieved some level of fame that you’re not at or yet something. It’s important to do that. The only time that you can’t have those conversation is if you and a friend are competing for the same project. That’s called price-fixing so you can’t talk about pricing with them until after you’ve both delivered your prices.

Poornima Vijayashanker: What about free?

Jessica Hische: Well, honestly I don’t work for free for real clients. I do work for free for charities. I do work for barter occasionally. For instance, I get free haircuts forever from my hairdresser because I did some logo work for her. It’s really pretty transparent usually when someone’s trying to get you to do work for free, but they actually do have a budget. Versus when they’re asking you to do something for free because they have zero dollars and want to bring you on as an investor in their project or whatever. There should be some exchange of something if that’s the circumstance.

Poornima Vijayashanker: Yes, even if you’re young and just getting started.

Jessica Hische: Even if you’re young and just getting started. You really need to establish a way to assign value to work. One of the ways that’s really great for doing that if you are clearly working with people with no budget, but you know want to work for free, is to send them a contract outlining what you should be paid. Then discounting it to what they’re offering to pay. Then they know that you’re giving them this special, one-time deal. Then also next time they come to you they shouldn’t expect that special one-time deal. When they recommend you to friends, those friends shouldn’t expect that one-time deal. That’s the real danger in pricing yourself very cheaply. If most of the work that comes to you is based on referrals—because that’s a lot of how work happens—you don’t want to be known as the person that works for $20 an hour because everyone is gonna say that. How many people have you my that when they talk about working with someone they’re like, “Oh my God, he was so inexpensive. He was so reasonable.”

Poornima Vijayashanker: Everybody says that. Right.

Jessica Hische: It’s the first thing that they say if it’s a thing that they feel they can share. If they felt like they were getting a discount they’re not going to say he was so reasonable. They’re going to say, “We had a special thing worked out and they won’t say that that’s available to everyone.”

Poornima Vijayashanker: Exactly. I think that’s also valuable for those of us who work for sweat equity. That contract of for some period of time. Then once that funding, or that first customer comes, it’s time to be valued for the work that you’ve done.

Jessica Hische: Exactly. That’s something that I think is really unique with working with startups and something that people in the Bay Area experience a lot more than in other areas of the world. I think, too, before I moved here if you think about working for someone for equity, you think, “Awesome. This could be a real payday.”

Poornima Vijayashanker: Except for when everybody around is offering equity.

Jessica Hische: Then realize that 95% of businesses fail. Then also of those 5% it might take six or seven years before you have the option to exercise those in stock that you were granted. If you never care about earning money and want to just roll the dice as a lottery ticket it’s a great thing to do. If you have the bandwidth in your life to do that, it’s absolutely a cool thing to do. Every now and then it does actually work. You might get a few thousand dollars or whatever. If you actually need to think about paying the bills, you need other ways to do it. One of the ways that I think designers and just people in general can do that is by taking a low fee and then having the additional payment be something that’s a little bit more ethereal. Like stock or something like that. I do that when it comes to working on greeting cards and things like that. I’ll get it a very low fee upfront and then get royalties later on the sales of the cards so that the ultimate payment ends up being what it should be. It just takes a bit to get there.

Poornima Vijayashanker: You’re more aligned as well.

Jessica Hische: Yeah, exactly.

Poornima Vijayashanker: Another one of my favorite talks is the one that you gave on learning tangential skills. Why is it important for designers or engineers to learn these tangential skills? Why not just focus and get better on your particular craft?

Jessica Hische: I think it’s important to stay involved in your direct industry for sure. Especially when it comes to stuff like engineering and coding. Everything moves so quickly. There’s new technologies and it’s important to sort of know what’s around you, so that you know what to use, and you know what to delegate out to, and things like that. I think learning all of the tangential fields around you too helps you understand, “If I’m not capable of doing X, I can go to this person to do it.” It’s really pretty often where you end up collaborating with people. Whether you’re the person that enlists it, or your client is the person that enlists it is another thing. It’s nice to know what other people are capable of doing, so that you can incorporate that into your thinking about the project. I think as a designer that focuses mostly on print and doesn’t do a ton of web stuff…I do web stuff for fun and I loved learning how to do development for my own projects. What it’s been really helpful with and why I encourage designers that don’t plan to do development as a part of their career, why I still encourage them to learn development, is because for one thing you can call bullshit on people when they say that something’s not possible. You say, “Absolutely that’s possible. If you personally are not capable of doing that that’s one thing. I know this is physically possible.” You can call people out when they are being lazy. Instead of saying, “That’s not in my skill set,” they’re saying, “That’s not a physical possibility.” The other thing is it really expands your mind about what you can do when it comes to designing. It either sets a limit, because you can say, “I really would love it if every headline on this page was custom blah, blah, blah.” But this is a scaling site and there’s going to be weekly articles. We don’t have the budget to hire someone every single week, so this has to be typeface. It could be something where you say, “I do want to have this be a crazy animated something. I know that this CSS animation exists so it’s not actually super crazy. It’s not gonna crash, the website is not JavaScript nonsense everywhere.” Maybe it actually is possible to have it have a little bit of animation fun going on.

Poornima Vijayashanker: Besides your design work, you have a lot of side projects. Side projects are great for creativity. How do you manage the overwhelm?

Jessica Hische: Well, I’m starting to get to the point where some of my side projects that I had set up a few years ago I need to start sailing away to other folks to handle. When I had started launching a lot of side projects, they weren’t always one-page, one-off, archivable projects. They were ongoing things. My daily job CAD project was an archivable project. I made 12 sets of alphabets and then could leave it up as an archive forever. All that I have to do is make sure that WordPress people don’t dig in and hack the shit out of it.

Other projects that I had set up as resources that were more amoebic and stuff like that, like Inker Linker, which is a resource for finding printers, the overhead now of managing that project years later has exceeded any possibility of me making money on it. I never made money. Now I’m at the point where I need to pass it off to someone. Side projects for me have always been a way to fill in the gaps of what I’m not doing with my client work. That’s why most of my side projects actually don’t have to do with doing lettering work.

I feel like I’m getting a lot of my actual artwork creation for fun out of my client work. What I’m not getting is writing, I’m not getting web development, I’m not getting general graphic design. A lot of the projects that I do on the side have to do with building community resources, doing a lot of writing, making things that are not lettering, because I’m getting paid to do that. There’s no need to continue doing that for fun.

Poornima Vijayashanker: Yeah, I know I love to speak, and teach, and write. I know you do a lot of it. I know why I love doing it. Why do you love doing it?

Jessica Hische: Well, there’s a bunch reasons. I get really, really excited when I see the excitement in someone else and I’ve been able to contribute to them finding their way in someway or another. I’m empathetic to the point where it’s almost a disorder. I feel like it’s really easy for me to put myself in the place of other people, and to know what it was like to be so intimidated to start something or to feel like it’s impossible to move your career forward.

I feel like everyone’s older sister where I want to be the person that shows them that it’s not actually impossible. I think that’s why when it comes to the do what you love stuff I’ve been in the much more practical camp of it. Rather than the “screw your day job that you hate.” I more of like the, “Well, you should talk to your boss and see about doing stuff that you like more.”

Poornima Vijayashanker: Right, as a first step.

Jessica Hische: As a first step. I really like giving people practical ways to move forward. I think that’s how I just am in general, too. I think that’s one of the reasons why I’ll probably never be some crazy startup founder of a life-changing thing. I’m not a person that relishes thinking about that big of picture. I really like thinking here and moving forward and growing naturally out. Rather than starting here and figuring out how to get there. I just use the skill that I have and insight that I have to try to help other people to do that.

Poornima Vijayashanker: Well, I think it’s too early to tell because there’s definitely no bottoms up and then top down. Yeah, we’ll see.

Jessica Hische: We’ll see.

Poornima Vijayashanker: You recently wrote a book called In Progress.

Jessica Hische: I did indeed.

Poornima Vijayashanker: Yes. Tell me why did you decide to write this book?

Jessica Hische: Well, there were a few reasons. For one thing, Chronicle approached me and said, “Hey, we think you should do a book. What kind of book do you want to do?” I said, “I don’t know. I know I should do a book, but I don’t know what kind of book that would be.” One of the things I talked about for a couple years, because I’ve had a few other publishers approach me about doing something, is that I definitely did not want to do a monograph. I feel like—

Poornima Vijayashanker: What’s that?

Jessica Hische: A monograph is a book of just an encapsulation of your work.

Poornima Vijayashanker: Oh, OK.

Jessica Hische: I just felt way too early in my career to put together a book that was like, “Here’s my life’s work.” I think you do that when you been working in the field for 20 years or when you feel like your career is about to take a really dramatic shift into a different kind of work and you want to put a little package around the stuff that was this part of your life. I was really self-conscious about putting together a book at age 30 that was that. Initially my thoughts were, “OK, everyone seems to freak about my sketches, when they get to see them, maybe we do a coffee-table book about showing the process of sketch to finish.” As I started working with them it turned into much more of a resource-driven book than I had initially planned. Part of that actually has to do with the contract of working with a publisher. In working with the publisher, you tell them, “I promise not to use this work in another book for X amount of time.”

Poornima Vijayashanker: Sure.

Jessica Hische: After spending four months going through contracts and trying to all get on the same page I was like, “Man this should probably be a bigger deal than I was initially thinking it was gonna be.” That was one of the things that drove it that way. Then thinking of it like this is a big deal that I’m putting a book out in the first place drove me to be like, “I want to make this as good, and as dense, and as helpful as it can be.”

It started as a 5,000- to 10,000-word, which is really just captions for the work, into a 30,000- to 40,000-word textbook light. I’m really, really psyched with how it turned out. What I find to be really nice about it now is that it puts together a lot of the things that I convey in workshops, and a lot of the things that I learned in taking type design courses and things like that. Rather than having people have to come to California to take workshop directly from me or feel like they need to learn from me in my physical space, which is only possible for so many people, I’m able to take that knowledge and make it a much easier to access thing for everybody. You don’t have to be in California to hear everything that I would tell you about how to create an early piece of lettering.

Poornima Vijayashanker: Very nice. It’s your own piece of Jessica at the convenience of wherever you are.

Jessica Hische: Yeah. The convenience of wherever Amazon Prime is.

Poornima Vijayashanker: Yeah, exactly. This is a lot of stuff. Lettering for other people’s books, and art, and then your own work. How are you balancing all this, and the speaking, and the teaching, with your design work?

Jessica Hische: It’s a constant evolving thing. Maybe a year or two ago I put together this ultra schedule as a post when I was trying to make really strict guidelines on my daily schedule. Which is very against my earlier statement of, “I love when I can just do what I wanted whenever.” One of the things that I think a lot of people struggle with when they become freelancers is this sudden complete erosion of a schedule makes it so that it can be really difficult to get work done unless you have so much work that you can’t not work.

I tend to be completely fine with my loosey-goosey schedule if I have so much work on my calendar that I feel like I’m almost being crushed under the weight of it. If I’m more reasonable about the work that I take on—and I do have caps my schedule, and I have the ability to leave room in case an interesting project comes along, that kind of thing—then if I don’t have a very tight schedule to go with I end up procrastinating on things. Every few months I sort of look at what my week is like. What are the things I’m spending too much time on? How can I take those things and make a smaller amount of time in my week to work on them?

I do a lot of self-assessment and self-checking of I’m spending too much time answering emails. I need to figure out how to spend less time doing that. I said “yes” to too many speaking engagements. I need to have better rules about what kind of speaking engagements I talked at. I think as someone that works for themselves and rely on people coming to me to say, “Here’s the work that you’re gonna be doing in the future.”

I think that it should also be on me to say, “Here’s the work that I want to be doing. How do I make sure that I leave room in my calendar to do that?” If I know that I can only do five speaking engagements in a year, now how do I actually just reach out to people and say I want to speak at your event rather than waiting for that right event to come to me? I think it’s a combination of waiting for the right thing to come along and making sure that you’re still being active and trying to line yourself up for success.

Poornima Vijayashanker: Any final thoughts that you’d like to share with our viewers out there today?

Jessica Hische: I think really I’ve said it a couple of times. It’s just really important to spend time thinking about what you want to do and what’s important to you. I think that other people out there are really good about offering advice all the time. You can’t spit and not hit someone that’s trying to tell you the ideal way to run your business, or the ideal way to do whatever. Just know that people get really excited to share their own success stories and things that have worked for them. That might work for you or might not work for you.

You have to sort of know what kind of person that you are and know what’s gonna make you happy. Rather than following prescriptive methods of what has made other people happy. I think the people that have the best careers and the people that are the happiest in their careers are people that have created careers around them based on their needs, and based on who they are and what they want to do. Rather than people that have fallen into line and got into a career that seemed like a pre-carved path.

Poornima Vijayashanker: That’s a good point. I know I certainly fit into that that latter camp of design your own career and design your own path.

Jessica Hische: What’s interesting is that it seems like the scariest path to take because there is no track record of success because you’ve invented your job. In the end, because you’re more malleable than people, that get into a more traditional ladder climbing kind of situation, the rug doesn’t get pulled out from under you quite as easily. I think that diversified the way that things come in. We didn’t talk about this very much, but I think that’s incredibly important and something that as an engineer within the web world is very easy to do. You can work on big projects, but you can also work on little teeny projects. I think that having the mix of those things is what really makes it so that you don’t have to worry if you’re one client goes out of business, because you have other things going on.

Poornima Vijayashanker: Yeah, you’ve got that diversification. Yeah, wonderful. Well, thank you so much for talking to us today Jessica.

Jessica Hische: Yeah. Thanks.

Poornima Vijayashanker: Yeah, it was wonderful.

Jessica Hische: It was great.

Poornima Vijayashanker: Thank you. Thanks to all you viewers for tuning in today and special thanks to our sponsor Pivotal Tracker for their help in producing this episode of Femgineer TV. If you’ve enjoyed this episode, then please share it with your friends, your teammates, and your boss. Subscribe to our YouTube channel to receive the next episode. I’ll catch you next time. This episode of Femgineer TV is brought to you by Pivotal Tracker—build better software faster.

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