Or Should You Ever Do Freelance for Friends and Family?
I will do a more expansive review for everything at the end of the year, but I wanted to write today about doing freelance work for friends and family. Now the old adage when it comes to working for friends and family is, “don’t.” There’s definitely merit to that but more often than not, I find that to be a pretty rare exception—at least on the basis of difficulty to work with, but I’ll break that down too.
My mom teaching her Sunday school class, early 90s
Truth be told, pretty much all beginner freelance is exclusively for friends and family when you start out. Realistically, no one else is going to hire you! While I certainly didn’t have a solid directional plan when I was younger, I knew that illustration was something that would figure into my adult career if even only tangentially. My mother recognized this and fostered that creativity by being my first and arguably only client for years if not decades. She was responsible for all the youth programs at our church and would ask me to draw giant “pages” for stories she would tell in Sunday school (Christian education geared for kids during or around church time). Now a mother’s admiration and love is hardly good justification for quality, but while she swore up and down my poster size drawings helped keep her kids attention, they were hardly good. However, they did enforce several very important things to me such as deadlines and keeping up with design trends (if only what cartoon characters were popular with a very specific demographic at the time). These “jobs” also helped me refine my ability, so while I’m thrilled no one outside of a very select few have ever seen them, they set things in motion.
This year, I was able to pay those things forward with more than a few friends and family, and I’d like to talk about how those experiences are still really important for experienced professionals and not just those starting out. Typically, you’re not getting a decent payday from friends and family because it will hopefully be important for you to maintain those relationships on a deeper level than just “Jane and Johnny Client,” but that doesn’t mean they can’t still have an impact on you and your career.
Now speaking of only getting hired by friends and family in the beginning, I was really excited to work with an old friend who arguably had one of, if not the most, influence on my career. Even before I started my education, John Lambert was one of the very first adults I ever knew that always treated me like an equal, never ever talking down to me as a child, but also taking a key role guiding and teaching me as well. I was even his ring bearer at his wedding!
He had started the Gramercy Brass of New York in 1982, so when I was starting to put together my portfolio, it was this prestigious organizational name that I exploited for my resume. John had me help with everything from building sets and stages to giving me the opportunity to create my very first print ad. When I went on an interview, it was almost exclusively the work I did for John that got me in the door. Now John will modestly tell you he was asking me because I was eager to help and only lived a few blocks away, but the reality is that he was the first person to set a standard of quality. I would have to develop multiple concepts, ensure overall print quality, and above all else—strive for something that actually looked somewhat professional. Now none of that early work is good, but it was the catalyst, so I was very excited and honored when he asked me to help with creating the Gramercy Brass’ 40th Anniversary Journal. I can’t say I did anything over the top or groundbreaking, but when you have a relationship that’s about as old as you are, there’s a freedom with candor and understanding that you just can’t manufacture with a client, even if you’ve known them for years. This is primarily because John isn’t just a dear friend, but someone I put on a pedestal for helping me get started.
Left to right: John & I at a Gramercy Brass Orchestra concert in August, 1997. The very bad—but also my very first—print ad for the orchestra’s newest album at the time, American Anthems (2001). The cover and a single page for the GBO’s 40th Anniversary Journal. And finally, two significantly older but wiser men still happy to work together.
One could argue that this could easily be seen as an obligation rather than a job, but neither of us saw it that way and I was so happy to get to work with him like this again. In so many ways, it felt like it was 1997 all over again, and I loved it.
The next project and “client” I want to mention is Lucas Ross. Now I’ve talked about Lucas and how great a guy he is ad nauseam in the past, and it’s possible because of all that adulation he reached out to me to help him with his newest live album, There Will Be Banjo. Again, taking on this job could be seen as the logical “thanks” for all the work Lucas did as the host for my documentary from earlier in the year, The Making of The Great Muppet Mural (which you should totally watch today!). But Lucas and I had that spark of a moment multiple times during the documentary where we really just enjoyed working and talking together. While my intentions were to do so much more for Lucas, he was gracious enough to take what he could get from me with several illustrations he then assembled together himself, but Lucas was also a great client as well as a friend with how we continued to communicate.
Lucas with the Oklahoma Opry and the album cover to the live album
You see, when your day job, freelance, and hobby are all the same thing—in my case, drawing—there’s a nuanced way of going about such a thing with equal respect and attention to all three. Lucas has somewhat of a similar understanding with his music, and so I not only felt comfortable being more open with him about everything from technique to personal concerns, but also letting him use and manipulate my illustrations however he wanted. Lucas was also the key person in helping me understand how I need to better manage and even understand my time (something I’ll most likely write about in the coming weeks or months), and I had no compunctions telling him this. My inside joke is that these things will help me to best work with (just) Lucas again soon, but my reality is Lucas really helped me understand myself better in that way, and I can guarantee that’s never something I would have recognized with “just another client.” (Thanks again for that, man!)
The last instance is a combination of working with both a childhood, lifelong friend and my dad. Now both of these men have known me not just longer than everyone else, but better than everyone too. Plus, both of them needed my talents with a much quicker turnaround (although to be fair, with my dad, it was my fault as I kept putting it off). I grew up with (now Major) Myron Smith as one of my closest best friends. As tiny children, we would play basketball and music together—both for fun and competitively—to which Myron would always always best me. As teenagers, we would go to the beach and the ice rink weekly where we would skate and talk to girls—I was only slightly more adept at these over Myron, so I’ll take my trophy on this one. Technically, what my dad asked was just an update on something I had already done in the past, but as I’ve mentioned numerous times as well, my dad is a big deal to me, so it goes without saying he didn’t have to twist my arm (just remind me constantly!).
So if John and Lucas were varying levels of circles, Myron and dad are on the inner most ones. There are cons to working with people that know you that well for that long, but there’s also a freedom to it as well. You can experiment and try out techniques you wouldn’t with other clients because those close friends and family sure aren’t going to take their business elsewhere. You will also find rationalizing your own choices easier as well, because like them, you’re locked into those relationships too.
left to right: Myron an I in the mid 90s, all grown up (June, 2022), and my dad and I at an art show displaying his work (May, 2010)
In the end, all of these “jobs” secure a more fundamental appeal, and that’s getting the chance to reconnect with them. Do you ever say yes or no right away when friends or family commission you? What type of layering does it add to old relationships? How likely are you to work with or for an old friend or close family member? I’d love to hear your thoughts here, Instagram, or Twitter!