1. When did you realise you wanted to be a designer?

I was sitting in a Calculus 2 class my freshman year of college studying to be an electrical engineer. I was one of those kids who really cared about getting good grades, and for the first time in my life, I wasn’t turning in homework or studying for tests. I just didn’t care.

Sitting there tuning out the Calc 2 professor, I realized I was pursuing engineering because it looked good on paper but I didn’t enjoy the work of it. I was good at it, but I got into engineering because I wanted to create. And I felt all I was learning to do was fix broken circuits—not create new things of my own.

I was playing in a crappy rock band at the time and spent all my time outside of class building a website for the band. It turned into a hobby. I really enjoyed that work, and I realized I was studying the wrong thing.

So I went into my engineering program advisor’s office and told him I wanted to switch majors to design. He gave me an odd look and pointed at a folder on his desk. “Those are scholarships for the top 5 freshman engineering students, and you are one of them. Do you still want to quit?” I said yes. His shoulders visibly sagged, and he probably thought I was nuts. I left feeling like I’d dodged a bullet. And I’ve felt that way ever since, 15 years and counting.

2. How did you get started and what was the biggest hurdle you overcame?

My design career began by teaching myself to code and build websites for fun. When I switched majors to design, I thought I had it made, but I quickly hit a major hurdle: I realized I was learning the wrong things in school.

Since my career began through teaching myself by trying to imitate the designers I found online, I had a really early idea of what kind of work I wanted to be doing. And when art professors tried to tell me design was a bad career track and that I should pursue fine art, or when graphic design classes didn’t even cover digital design (which was still relatively new back then), I decided that I’d have to learn that stuff on my own.

So I spent my summers during college reading programming books, building portfolio websites and blogs, and devouring anything I could find about web design. I started working with software called CafeLog (which later evolved into WordPress), Flash, HTML & CSS, got student copies of Adobe and Macromedia software, and just learned everything I could. Eventually I got a copy of a book called “Flash Math Creativity” which was endlessly inspiring and set me on a path to walk the line between code and design which I have enjoyed my entire career.

By the time I graduated, I landed a job in a local ad agency in Oklahoma City (the city where I went to college). It’s a college town with lots of competition because there are a lot of design graduates from several universities but not many design jobs. I won out against all the art majors at my school and got a coveted gig by teaching myself what I needed to learn. I felt really vindicated that I could achieve the kind of career I wanted in my own way.

3. What’s been your most successful way of getting clients?

I have never worked with a single client by finding them on a job board or freelancing site, believe it or not. I find all my clients through my network of peers & colleagues or by clients finding me because of my writing and products business. I’ve written a few books and built some software products, and I write about those experiences which tends to attract clients.

I know that I’m really fortunate and privileged to make this claim, but I really believe that many designers go about finding clients the wrong way. You can intentionally structure your business so that clients find you, instead of having to seek them out.

The other side to this is that I tend to keep clients for a very long time (I have a client I’ve been working with every month for over 3 years, for example), so I don’t need as many new leads as some other designers might.

4. How do you get clients to stay with you and use you for more work?

This is actually a much more complex question than some people might realize. It’s not a trick of structuring your projects, fees, or sales differently. Getting repeat work from the same clients is about a more fundamental approach to working with clients to get results for them.

Many designers see their services as providing a deliverable. But, clients don’t hire designers because they want a logo or a landing page design. They’re hiring us because they want that design to accomplish something for them, like earning sales, getting customers in the front door, etc.

When you think about your services like “Once I send the final draft, I’m done”, it’s harder to get repeat work. Because how many logos does one client need?

But when you see your services as a designer more from a design thinking or UX perspective, things totally change. Design Thinking & UX teach that designers should be doing more than making that final, shiny deliverable. And if you start working that way—towards measurable outcomes for clients—it becomes a lot easier to stay useful for the long term.

Specifically, long term work can include all kinds of things. Supporting regular marketing efforts like producing ad concepts or helping with product design so a client can launch a new feature every month. Doing this requires nosing into your clients’ businesses and paying attention to what they’re doing. It requires asking them about how their marketing is working and what their customer churn stats are. Helping them evaluate those aspects of the business, and helping them solve the challenges with design.

Some clients don’t need ongoing work of course. A local restaurant might need a logo, website, and menu design, and then they’re set for a few years. So, the other side to this is intentionally seeking out clients who might have ongoing needs. This is hard to tell without working with a client directly, so I use my first project with a client to learn more about them and look for ongoing opportunities. Sometimes there aren’t any, but you never find those opportunities if you don’t look. For more on this, check out my article on A List Apart and my article on retainers.

5. Do you ever have issues with clients paying late? How do you manage that?

It’s been many years since I’ve had an issue with a client paying up. (Now that I brag about that, I bet it will happen to me next week.)

Kidding aside, I think these issues are symptoms of a larger problem. Usually when a client isn’t paying, it’s because of a disagreement or misunderstanding. The client didn’t like the design, they changed their mind, or whatever. I think that getting paid on time requires being a stickler at every stage of your projects. Asking smart questions to vet clients before you start working for them, keeping the entire gig running smoothly, keeping clients informed, setting clear expectations, having a clear contract and project specs, delivering on time, and so on. All of these things lead to getting paid on time.

I actually have a client who pays me early, before I even send my invoices. It’s the holy grail! It’s amazing. But I think that happens because we have a great working relationship and he trusts me. I deliver good work on time, every time. He always knows what I’m working on and when he’ll hear from me next. Things like that take a lot of effort, but they make my life easier in the end—and they help ensure I get paid.

6. What does your typical work day look like?

Sorry to be a jerk about this question, but I don’t really have a typical workday and I don’t want one. If I wanted a boring 9-5 grind, I’d take a salary gig somewhere (no offense to people working salary gigs, this is just what’s right for me). I work for myself so that I can choose what I work on each day, and it’s an incredible privilege.

More specifically, I tend to dig into one subject matter and format of working at a time, almost like an informal sprint format. This lasts over longer periods rather than changing daily. So I’ll spend a week or two doing nothing but writing, then a week writing code, or another week designing. I do my best work when I can really dig into a problem and focus on it without any other distractions.

Setting up that kind of environment can be tricky (especially now that I have 2 young kids and I work in a home office), but I’ve found I am a lot happier, more productive, and more creative when I have control over what I do and get the chance to focus. I don’t think it would be possible at a salary gig, which is why, for now, I’m indie to the core.

As for daily schedule, my most productive days are when I can set up the right environment to focus. If I can get into the zone, I can do more in a 6-hour work day than two 8-hour days where I’m dealing with distractions. So, I tend to be one of those annoying people who answers emails late (as Chris knows, sorry Chris!), avoids setting up calls if possible, etc. Because it’s all about getting into the zone.

Clients get priority over everything else, and I sometimes break my rules for them when I won’t for others. But I’m still careful to only schedule calls in the afternoons so that I get focus time every morning when I have my most creative energy. I’m also lucky in that I can keep a relatively light client workload and get spare time to work on my products and writing. My preferences would be impossible if I needed eight billable hours per day.

7. Any piece of advice/wisdom that you’d like to give the readers at This Design Life?

The tug of war between client/user needs and my own creative ambitions is one point I’ve been thinking a lot about lately. I think designers often face this conflict of interest where we know how to make an awesome design, but it feels like we have to keep compromising for the sake of clients or users.

The UX movement can make this feel even worse—we’re being taught that the most prized quality of a designer is not our creative vision but our capacity for empathy. It feels like more than ever before, to be a designer, you have to sacrifice your own perspective. I think that’s a really difficult pill to swallow, even though the designers out there wearing empathy on their sleeves mean well.

Don’t get me wrong, I am a huge advocate of user research, but I think designers can reach a tipping point where we can forget that users are not design experts. So, to anyone out there struggling with this like I am, just a little encouragement: yes, user perspectives are important, but your perspective as a designer is important too. Yes, pay attention to users. But don’t stifle that creative voice either, because that’s where the great work comes from.


Jarrod Drysdale has been a professional designer since 2004, working independently since 2010. He is also a generalist writer, developer, marketer, researcher, and product maker. Jarrod has completed work for clients including Framer, Personal Capital, Bloomberg, Scottrade, Intuit, State Farm, McDonald’s, Kraft Foods, and New Line Cinema. He teaches design courses at Proximity School and writes a popular design newsletter.

Chris Green

Chris Green at This Design Life
Chris Green is a designer and marketer. He runs an agency called Calloway Green and is also the founder of This Design Life.

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