First post today and hopefully one of many!
To be honest I’m not much of a blogger. I have very little stamina for longform writing. Last Spring though, I came across this blog from NY caricature artist Marty Macaluso, a veteran in live art since 1978(!!) who has been recording his experiences since 2001. I’ve sold art on and off since 2009, but only began live illustration as a service in Fall 2022. So to see someone survive the industry for so long (and through COVID) without burnout or bitterness, has been solid-enough proof that this path is valid, possible, that I’m not completely out of my mind when sketching with folks and thinking:
Is this real? I’m having too much fun . . . this can’t really be a job??
The best part is when I’ve finally sat in the event chair and the first person (always the bravest) decides to risk being stared at by a complete stranger. Then for a few minutes there’s nothing better in the world than getting to meet someone new, draw for a few minutes, and hopefully brighten their day with a simple sketch. As Marty put it over twenty years ago, all that matters is:
“The people had fun and I learned.”
Marty at an event in 2023 (quicksketch.com)
But it isn’t as if the work isn’t work.
It’s real, boring, sometimes frustrating sit at your desk for days drafting quotes, invoices, grants, data analysis, pitch decks, market research, deductions and quarterly taxes kind of work.
Though it is kind of fun in it’s own way, when it’s your own business.
There’s also the financial planning required to survive the slow periods, and I’m still navigating that panic. In all this too, Marty’s writing has been invaluable as a record of event patterns across the seasons, for insights on upcoming trends, tactics for crowd control or difficult client interactions, tricks of the trade, as well as the more general wear-and-tear to watch out for in a job where sitting is almost always the norm (but not necessarily — and he has tips for that too!).
Which brings me to the why for the blog. The drawing bit is easy. It’s the backend, all of these business arms of freelancing that can sometimes be a bit of a drag. Updating a portfolio may be useful long-term, but just doesn’t deliver the dopamine hit like I get from a live event. It can be easy to lose sight of how much progress has been made, what needs working on, and where I want to go. Because knowing me, I get bored. And while I can’t see myself ever wanting to not do live art, I know I also want to do something with it in a way that isn’t just transactional: Jenny goes out, money comes in, another face to post on the gram. It’s the people who make it all worth it, so the work has got to be more about them.
I’m still figuring out the format of how I want these posts to go. Unlike Marty, I don’t think I can commit to writing a regular record after each event. For one, I prefer not to tie any pictures directly to a specific time or place if possible — both for my personal privacy (photo shy) and guest safety. For another, I just don’t have enough gettupandgo in me at the moment, so I think quarterly is the pace that I can handle.
For now, I’ll finish things up with some stream-of-thought bullet lists. Maybe next quarter I’ll have something fancier to share, but it’s already 11am and I’m starving.
So to start:
2025 FIRST QUARTER SUMMARY
WHAT I’VE DONE
Guest Resources Page: if you or anyone you know is currently facing threats of domestic violence, deportation, eviction, discrimination, or other hardship, this page is up now and links to several non-profit organizations that may be able to help. Please feel free to pass it on if useful, or let me know if I should add anything.
Pause on Commission Work: starting January I’ve stopped taking on commissions. Nowadays I might draw something custom for clients on a feel-like-it basis, but for the most part I’m committed to personal projects.
WHAT I’M DOING
Incentive Programs: this year I’m hoping to redirect both the timing and type of gigs, specifically encouraging more early week/morning bookings and connecting with more local families for small community events. I already have one discount active towards this, and am researching what that might look like for marketing. The big events are still fun, but it’s the small groups where guests really come out of their shell and I love that!
Portfolio Refresh: nothing much to say for this one except it’s mind-numbingly boring and I’ve been avoiding it, but it’s so overdue. If only it were automated somehow . . .
PROJECTS IN THE PIPELINE
Find way to automate portfolio refresh process so people don’t have to read me whining about it anymore.
Find way to combine regular sketching practice with fundraisers. Plenty of artists do this to help raise for their preferred charities, so it’s probably just a matter of committing to a regular schedule (the hard part, for me).
Tutoring?: a far-down-the-line idea I’ve been considering and talked to a few clients about, but not sure how committed I am to building up that business arm yet. Would also like to get some formal teaching credits under my belt if I did add this service. But maybe some website freebies could be a good offering in the meantime? One of my favorite parts of events is when the kids share their own creative passions and what they’re working on, so it would be nice to somehow encourage that!
More language education: I LOVE languages and have a rough background in 2 (Spanish and Japanese), and would ideally like to have a rough background in at least 10. Another big event joy is being able to meet the guests where they’re at in the language where they’re most comfortable, so a long-term goal is to build on what I’ve got and expand it. The longest-term goal would be to then seek out gigs in countries where these languages are the main and in that way have a job truly without borders. Currently working on reading/writing for the following: Arabic, Yiddish, Ukrainian, Korean (but please don’t talk to me in these yet I’m absolutely at the beginning stages with the alphabets and the how-are-yous!) On second thought, please DO talk to me, sign to me, write to me, in whatever language you choose; I'm sure we can make ourselves understood! And if nothing else, we can always draw.
Dream Client BINGO card?: because what kind of Millennial would I be if I didn’t try to game-ify my goals.
And I think it’s about time to wrap this all up! Lunch is seriously calling me, not to mention all of these projects that I’ve now publicly committed to working on.
For any clients or potential clients who’ve now read this all through — thank you! If you’re Marty reading this — thank you more than I can ever possibly say! If you’re another artist reading this — don’t forget to pay your Estimated Taxes for Q1!
Until next quarter,
Jenny G.