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The Hobbyist Freelancer’s Process: Part 1

By April 13, 2015April 16th, 2015freelance, Uncategorized



Out of the many commissioned projects I worked on over the years, this is the first time enough of it has been done digitally that I have a fairly large amount of the process documented. It made sense then that I could use that as the basis for a helpful, step by step account of how I tend to work from beginning to end when tasked with creating something real from another’s wispy imagination. Specifically, Part 1 will focus on the iterative, client-driven design process of making a work of art designed for commercial use. Part 2 will focus on an artistic driven, step by step process of creating a digital work of art for use in advertising and promotion.

A few things to note before I begin. A few aspects make this a less than ideal project for an “objective” look at a freelancer’s process. The client was an old college roommate of mine, Michael Kelly, whose friendship allowed for a more easy going relationship right from the start, as well as a better understanding on what he was looking for in his artwork. While this might seem like the ability to have a headstart in the working relationship would be unique to this project alone, it also happens to be a valuable lesson for the beginner and hobbyist alike.

As an artist that has a full time job, and mostly does freelance work as a hobby, I find that the majority of the work I get is from family, or friends, or family and friends of friends and family. While having your own website and social media streams allow you to have your portfolio digitally available to the world at large, often times it is the people that are the most likely to see or know of you in real life that pay the most attention.

I’ve often felt that for every couple hundred people there are in a social circle, likely there will be one or two creative folks in there that are the go-tos if anyone ever needs anything made for them.

“Jeff is the painter in the family, I’ll give you his number.”

“Kelly has a bunch of photo equipment, I’m sure she’d love to photograph your bridal shower.”

And as someone that dabbles in freelance work, this is where the majority of the work comes from for right now. Word of mouth that passes from person to person about the quality of your work, as well as the working relationship you had with the client themselves. So while this project is a far cry from an anonymous client contacting me out of the blue because they have seen my work online and wish to commission something, I feel that it is a more realistic example for most beginning and hobbyist freelancer’s out there. And personally, I’m always in professional mode when it comes making art for someone else, so I’m confident that this is still an accurate look at my freelancer’s process.


Starting Out

Late last year, 2014, Michael got ahold of me to let me know that sometime down the line he was planning on taking his own hobby, guitar diddling, and taking it to the next level. A real band, complete with a band name, trip to the studio, an album release, live shows; the works. As such, he remembered liking the art he had always seen me making nearly a decade before, and was wondering if I’d like to help him in making a band logo, and possible down the line a banner of some sort. Having not had a good project to sink my teeth into for a while, I eagerly accepted.

By early December, the phone call finally came. He was set on the band name being Slow Train. Michael had always been a big Bob Dylan fan, and the band name seemed to fit his folk-rock sound very well. He said that having a train for the logo was what he was thinking, and if possible I should work the neck of a guitar into the smokestack of the train. I advised that if it was a logo he was thinking of, those would normally be very simple, graphic images that could be easily recognizable by people. After some quick searching on both our parts for famous band logos, he agreed with this note, and I said that I would get back to him with some random sketches so we could figure out a direction to take.

I remembered this process from my college graphic design classes as being the ‘horizontal’ stage, where I would try to come up with as wide a range of possible starting points as could potentially be allowed given the client’s instructions. Following this process would be the ‘vertical’ stage where I could iterate on whatever specific design Michael decided to go with while taking into account any further notes he provided me.

After the sketches were complete, I emailed them off to him with a few brief words.



I tried to hit a wide range of possible styles with the initial sketch, from a heavy line weighted graphic one to more pin or button themed designs. And as I noted in the email’s body to him,

“…also added my own idea with the snail shell thing.”

Normally at this stage of the process, when the client’s ideas are much less concrete and only exist in their mind, they are usually much more open to possible directions to take a project. So while 90% of the designs I submit are my honest take on what I feel they wanted me to produce, I always like to throw a curveball in there that is my own version of their seedling. Admitting that it is of your own design helps the client to not feel as if they were misunderstood in any way, and opens them to accepting that this is coming to them from the point of view of the creative artist that they hired.

Avoiding slighting a client while gently directing them towards a much better and more dynamic final image is always a delicate thing. Honesty and clarity helps, as does remembering that it is the client who needs to be happy with the final product and not you as the artist. But at the same time, they came to you because they like the visual voice that you have, and expect to see some of that in what you are making for them. Again, tricky. I normally find that a 70/30 split is where i end up. 70% exactly what the client had envisioned in their head, with me sprucing things up the final 30% using my intuitions as an artist to make alterations. While this ratio is going to vary wildly between clients and projects, I find this the average.

Within the same day, Michael had consulted with some of his fellow band members and wrote back

“The top one is the one we liked best, but it seems like the one right below it (both circled) is very similar. Whatever blend of those two styles you think might work best for what we’re doing w/ the logo.”


Narrowing Things Down

Having had Michael make his decision, I could now move into the “vertical” iterative process now. Since he liked the front-facing train so much, I could do some online research and find as many wildly different train faces as possible.


“Heres some different train fronts to choose from. The styles don’t vary too much from these from what I could find, so this is a good overview. To help you visualize what would make a good logo, ive included a simple line drawing of each and blacked out one as well. Wanted to give you some sense as to what the basics of the train design would be once it becomes more of a “designed” logo.
The blacked out ones are to help you see the overall shape of the train, as having one you like that is also easily recognizable is important. Let me know what ones you like and I can take it from there.
The next step after you choose one will prolly be finding out how simple/graphic you want it to be, and finally we’ll add some design flourishes if need be.”

I’ve included the entire email body here to show how I try and keep the client current with the thought process that has led me to outcome they are now seeing. Again, providing more information rather than less, as long as it doesn’t complicate things, goes a long way in making someone feel as though they are more a part of the process than they would be otherwise. Importantly, I specifically explain the inclusion of the line/blacked out drawings.

While a focus for me as a designer to look at the potential simplicity and “instantly-recognizable factor” of the image we were making, here I brought the client into a bit of the sausage-making process with me. While I probably could have explained it a bit better, I always try to put whatever big design decision is to be made at this point in the simplest wording possible, always trying to avoid using overly complicated artsy-design jargon. The client will have a better idea on the different factors that they should then consider in addition to simply preferring one image over another. The decision will now be an informed one.

This helps to prevent wasted effort down the line when a finalized image ends up being drab or poorly designed when you as the artist could have caught it many steps earlier. The client will then know the reasons behind design decisions and have a better understanding for the major decisions that have been made to this point, avoiding the feeling of drastic swerves from the idea they had in their head. The client will feel a partial ownership that the direction the design took because they will understand why and how it got there.

Next, a phone call was made and we talked about which train Michael ended up liking the most. He chose the initial design (far left sketch), as it was the first one that spoke to him and continued to be the loudest. During the call, I took notes.



This is always a helpful tip. Take notes while talking to a client. In addition, drawing in real time as well. It helps to capture that initial flame of inspiration when you first hear of a specific revision to be made, as well as a putting meandering ideas that you would like to try down as well.

During the conversation, I realized that Michael had responded to the working design we had so much that dropping the simplified graphic-image concept from the beginning was necessary in order to keep the soul of what he liked so much alive. This was going to be a much more detailed design, closer to a traditional drawing..

I asked whether Michael wanted it to remain highly detailed and photorealistic, or if he wanted some sort of stylization to the train. Considering the tone of his band, I suggested I could add a bit of a woodcut motif to help it feel closer to the western, cowboy fueled vibe I was getting from the whole design. Michael said that whatever I thought was best as the artist was fine with him. Having a good sense of what I was going to do, I let him know I thought I had enough information to get started on the near final design.

I made sure to let him know that because this was a logo that ideally would be used by a band in all sorts of ways (album, shirt, sticker, website, etc.) I was going to make sure it was done in Adobe Illustrator.A simple explanation that the vector graphics would allow for an almost limitless amount of size customization for whatever he may need it for was gratefully accepted. Again, allowing a bit of insight into what I was about to do, why I was doing it and why it would be the right choice for what he needed went a long way.

Final Steps


“…Here you go. A couple variations (outline, with train tracks, and an example of what it’d look like on another type of background). I haven’t done the extreme details yet in case you want to make changes.”

The most important thing I wrote in the body of the email was informing him as to what was actually different in the separate images.

Near the end of the project, once the fine details are being added it becomes hard to notice the changes being made unless you point them out to the client. I also included the picture on far right to give him an idea of how it would look placed on something other than a white background. In retrospect, I would probably have included a few separate items with the logo applied, a t shirt or as a bumper sticker to further help him visualize how the overall image will look used in it’s intended way.

“Initial thoughts are: I dig the smoke (I’ll pick one), undecided on the tracks yet, I’d like to see something on the train that shows it’s us – either an “S” and a “T” or something… – branding the guitar w/ it is a great idea, or maybe one letter on each flag maybe… will think about it.”

The return email shows what having a good client on the other end will get you. Very honest, informative and direct feedback, specifically pointing out their feelings on the choices that you have made.

An additional email and phone call from Michael helped to clarify things even further.


This is a good time for any artist to remind themselves that this is a commissioned piece of artwork. Someone is paying you to make something specifically designed for them that will, at the end of the process, be theirs to own and do as they want with. I feel that more traditional artists might scoff at the sight of someone drawing all over their design while the graphic designers out there will call that old hat. Coming from the fine arts side of things, decisions are always left up to the artist and the artist alone. If your art work sells, it is always with the intent of it being a singular work of art that was purchased to be maintained as-is and unaltered. With some commissioned pieces, this is absolutely the case. Clients may want nothing more than a unique piece of art made by your hand.

But with more commercial works, like this train design I made right here, it is best to view it as a collaborative effort that will never truly be yours. Once the final files are sent off, the client can erase, alter, color… do pretty much anything to it that they want before it ever sees the public eye. And you will have to be okay with that. It’s the nature of this particular beast.

The notes made here, in addition to the information Michael provided over the phone, were added into the next iteration of the drawing.


Another descriptive email was sent along with this one, outlining the differences found within each version. He wrote back with a few final notes, but for the most part it was a completed design.

“Looking great man! It’s so hard to decide between single and double rails! I love both, it’s cool how the single track is angled off now. But I think I want to go w/ double rail.
So I’m going with #3 except double rails instead of single.”

The return email provides a final example that giving the client even a few options to help them tailor the design to what they want leads to a not only a successful commission and a happy customer.

The last bit of advice Michael needed was where to find different fonts, as the finalization of the train drawing was coinciding with the release of his demo CD and he was looking to complete the cover art himself. This was important for me as one of the last things that he wanted added was a small ‘ST’ to where the logo of the guitar manufacturer would normally go on the head. After providing him with the link to Google fonts, he picked out half a dozen that he liked and asked for my opinion on them.

Whenever a client asks for my opinion on something that is creatively tangential to the actual thing I have been hired for, I don’t hesitate in offering a response. Clients often pull a “As long as you’re here!”, asking your professional opinion on other minor creative decisions they may need to make. As long as they are easy and few enough that it doesn’t feel like you are suddenly a full blown creative consultant, I always answer them. Sure I could probably nickel and dime someone over it, but I see it more as a goodwill gesture on ensuring that they will recommend that you are great to work with and go the extra mile to other potential clients.

“…As far as the font for the guitar goes I agree with you that the last one is the best looking.
I’ll add that in and do some final touch ups to the double tracks and have the mostly final design off to you.”

The font was chosen and after making the final few changes that were requested, I sent the completed image off to Michael.


I will send multiple versions of the final image in one large dump. These will vary by file size, anywhere from a small 292 x 776 pixel image for use on a website or facebook to a 4854 x 12912 pixel image for use in high quality prints for shirts or posters. I also send each size in a few different formats (.jpg, .png, .tif) so as to give them options when bringing the image to a production center. Additionally, when working in color, I also do a third variation of RGB and CMYK allowing for printing facilities to use the format that allows them to most accurately match the colors. Additionally, if the file size is too large to send through email, an external file hosting website that is easy to use and trustworthy (such as is a great solution. Simply upload the large file and send the unique download link off to the client for them to use at a later date.

Once the files are sent off, it’s time to send them an invoice detailing time spent on the project, as well as additional expenses involved. Once the payment and final email come in, the project is at last complete.

“This rocks!! It’s ready to go :D”

The second part will outline the latter half of this freelance project, the creation of a large banner for use by the band Slow Train. This project will show a much different type of commissioned artwork, one in which I am given a germinated idea and bring it to fruition mostly on my own.


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