Five Rounds – Round Four


This week for Round 4 of 5 Rounds we’re talking to our experts about what’s the worst. Our three experts are:

Deanna Dionne, Creative Contractor
Jim Masie, Senior Graphic Designer at AmTrust Financial Services, Inc.
Chris Haas, Art Director at Flourish Agency

If you missed the first three rounds, read them here: Round 1 (the office), Round 2 (the work), Round 3 (the people).


DD: I find a new one. It’s just part of the business! I work with smaller companies, and sometimes I’ll have a client who wants a lot of work from me for several months, so I slow down on hunting for new clients. But oftentimes the smaller business can’t afford to keep coming to me indefinitely. Ideally I’ll have a medium-sized client or two that will have me on retainer while I also work on my jewelry business, and they support each other.

JM: For the most part we don’t lose clients; when we do… it’s because they’ve decided to outsource. We do perform an inquiry to see why they decided to not use us.

CH: We either are pretty bummed or pretty happy. Depends on the client.


DD: Well, it’s all on me. It’s best to play it smart and keep your business finances separate from your personal, but that can be difficult when so much is intertwined. I have found that contracts are helpful, not only to protect myself if things go sour with a client (which is generally always due to miscommunication) but to keep myself liable. The best thing is communication and being up-front and human about your mistakes. I’m honestly still working on that.

JM: My supervisor/marketing manager and I perform a Quality Assurance assessment. The idea is not to place fault, but to learn from our mistakes and figure out solutions to guard against future issues

CH: Nothing really. Unless it was a something that needed to be reprinted or reproduced, in that case, we would use an insurance claim.

DD: It can be difficult to not have steady finances. I also miss peer review from working with a team. But there are ways to get around these things as you grow. Charging your worth and going after larger clients who will have steady work for you and put you on retainer helps with finances. And you can create your own team by subcontracting on projects or getting feedback online.

JM: Office Politics. The strategies that people play to gain advantage for their project (to be worked on). Also, working with others who are unwilling to do their part (or go the extra mile).

CH: The clients. Sometimes they can be tough and hard to understand. Some will make decisions that defy logic and that is hard to get accustom to, especially coming from school where you get to make the majority of decisions about your projects and work.


DD: I’ve never considered working in an agency because I’ve heard it is constantly stressful with tight deadlines. As a freelancer, I set my own timetable.

JM: Depends on the role. From a manager’s perspective, not having people (and/or resources) you need to get the work done.

CH: The worst thing about freelance is maintaining client relationships and finding new work—design becomes only one area of the freelance role as you also have to maintain the day-to-day business. The worst part about being an in-house designer would probably be the lack of diversity in creative work. And second, most large corporations with in-house teams will outsource the best work to a large national agency.


DD: I work on my jewelry business, which I hope will become my main source of income (so, still work!). I like to set up coffee dates with friends and new acquaintances. I also volunteer with some community projects.

JM: Research. I’m big believer in continuing education; so I research new techniques, what other designers are creating, and the latest industry news on design, software and conferences.

CH: Play on the internet.


DD: In the beginning I’ll write up a proposal and contract. I try to keep track of my hours even if I’m not charging hourly, to make sure I’m charging correctly, and I usually send about 5 emails a day. Of course none of this is with physical paper– I only use paper for sketching designs, problem-solving, or illustration.

JM: Very little. I do write proposals for initiatives I am try to launch/implement.

CH: Close to zero.


DD: I don’t want it to seem like I’m holding their product ransom, but that’s basically it. I generally charge half up-front, and then I won’t send the final product until I get final payment. I’ll send screenshots and previews so they know what they’re paying for, of course. They are usually eager to get it and pay on time. I wouldn’t do it any other way. Sometimes, a client slows a project down (which slows payment), and that’s when it’s useful to have a contract with milestones spelled out. If you can’t get their feedback within a week, sending an invoice usually gets their attention.

JM: For in-house we do not charge our clients. As a freelancer, I charge a daily late fee, which starts accumulating 5 days past due. If they don’t pay, I usually just cut ties with the client. 9 times of 10 it’s not worth the legal effort (to force the client to pay). One safe guard (I require) is a deposit (50% of quoted amount) before I start on the project.

CH: Not something that creatives deal with at an agency.

By Kassey Sikora
Published November 21, 2017