Options, Goals, and a Midsummer Work Schedule

I’m making good headway on all sorts of things, and I’d like feedback as I decide between four options, (re)set short- and medium-term goals, and formalize (for myself) a work schedule for the rest of the summer.

Pretend you’re my manager and tell me what I need to do differently or better. (Don’t worry. I listen but often disregard directions.)



Tonight I’m sleeping on a lovely development studies researcher’s couch in Brighton. I met her on the Tube on the way to my last couchsurfing place. So technically you might say I am homeless and sleeping with strangers (but not like that). Not where I’d like to be after being in a new country for a whole month.

But actually, I am kicking butt. Here are five awesome things I have done in the past month:

1. Executed a transcontinental move alone with no job, partner, or place to go.

2. Done improv, stand-up comedy, and singing in public. With people watching and listening. On stages. Out loud. 

3. Started couchsurfing alone… Going with the flow of people and places, beginning to learn the lay of the land. Left and right and all. 

4. Painted in public. With people watching and questioning. On the Thames. 

5. Realized what is the one thing I have to do when I’m upset or destressing, on a deadline or have all the time in the world, or happy and can do anything in the world. The thing is painting. It is so hard for me to admit I Just want to paint. I don’t know anyone who makes a living as an artist, a visual artist, much less a painter. So I had concluded that was the wrong model, the wrong way of channeling the impulse.

But that skips a few steps. Like, ten years of trying. Giving the world half a chance to value me for what I do. Getting better at knowing what that is and doing it well. 

To be fair, I started exhibiting my paintings ten years ago. At my first opening, an unknown buyer (a woman, not a suitor) bought a 16” x 20” for almost $300. When I opened an Etsy store in May, I sold 9 paintings in 4 weeks (and then put the remainder in storage).

When I have taken my work to market, there has always been a market there for it. In the interim—the ten years since my first show—I didn’t take the work to market as much as I could’ve. Instead, I got discouraged on one hand, and distracted getting a PhD on the other. 

But I kept creating and getting better while writing a dissertation, some articles, a poetry book, and an album’s worth of songs… And anyway I think now I have to value myself and what I do enough to try again to give the world half a chance to value me for it.

Or, in business parlance, make my elevator pitch clear. Pitch my goods and services to the right markets in the right way. Be sure they see the value and know how to pay me for it. Clarify the call to action. All that jazz.

Meanwhile, I have now identified one very specific thing that I do as an artist and entrepreneur—painting. And one very specific logistical problem to just doing what I have to do—space. I need space where I can make a mess and store wet paintings. (It would also be great if I could sleep there.)

Since I honed my desire to be a jobbing artist and run my own business into this more specific desire, two specific and two general options for getting the space I need to do it have appeared or become clearer. I’d like feedback on those options, and on the goals and schedule I intend to implement once the space thing is at least settled for more than one night at a time.


Space Options  

1. The South Galleries—a lovely art gallery near London, in Maidstone. I could keep the gallery open and use the space to paint. If I could get good enough advice from online message boards about how to teach at the gallery’s school within the terms of my visa, I could do that too.

Pro: Right field, nice people, free space to paint and store paintings, opportunity to learn how galleries work and sell work in one, close enough to London to take the train in for open mics, gallery openings, pitching, meetings, plays.

Con: I might be too messy (I oil paint and generally end up covered in the stuff). It might be too far from London to optimize networking. I don’t know where I would sleep. So it doesn’t give me my own artist hermit-hole in which to create undisturbed, which might be more specifically what I need. Even though another awesome thing I’ve done lately is be out of my hermit-hole all the time when I used to only go out for work and orange juice.

2. Hacktivist collective on the Continent.

Pro: People I can talk with about my transparency activism and political philosophy, learn from about encryption and other infosec stuff I need to know for my germinating Portraits of Peace project, people who might like and know people who might like some of my relevant political art (e.g., the Too Big to Surveil series), probable opportunity to see more awesome Continental painting, learn more languages, do different public art experiments, sing at different open mics, and enjoy lower cost of living.

Con: I might be more isolated outside of a big city, in a country where I don’t speak the language, with a group I don’t really know (but trust). I might not be able to ship paintings as easily if I got an online painting business up and running again. 

3. East and outer London. These are the best areas for a London artist of no means to live. I could research studio and live-work space shares in these areas. I’ve banged around talking to people and trying to figure it out, but not approached this one thing like it’s my #1 job.

Pro: Big city market. Vibrant arts and culture scene. Lots of open mic, gallery opportunities. Busking is legal in public spaces. Probably tons of options I don’t know about here. Felt good enough about London to haul myself here. Must be for a good reason, right?

Con: Cost of living is high. The city is not known for being particularly forgiving. But I keep finding nice people and safe couches, so I can’t complain. No specific anchor of person or place. This is such a general option…

4. Brighton and surrounding areas. Ditto.

Pro: Largest number of working artists I’ve ever seen, from the railway station—where I talked with a nice corporate businessman-turned-small shopkeeper with the most beautiful cubist tattoo, and played and sang with a bunch of strangers on the horribly out of tune piano—to the beach and city center. This must be the Santa Fe of Britain.

Con: Smaller market, more supply of artists than demand for their work (such is an artist haven). No specific anchor of person or place. Less known about this one than London—starting over in terms of reorienting, beginning to learn lay of land. But it feels good, too. These options actually all feel good. But it’s a little hard to know exactly how I feel. I need to paint to know that.


Re-Setting Short and Medium-Term Goals 

My work schedules are typically not feasible. I keep making them anyway, attempting them, failing, remaking them… And stuff keeps getting done. Now with 80% less saturated fat and self-loathing!


6-7 AM exercise, eat

7-9 write 

9-11 sing

11-12 eat, email

12-5 paint

PM: target 3-5 open mics a week, singing my own songs plus some covers; online art business stuff


This schedule serves these short- and medium-term targets:

       Minimum 1 gallery pitch, opening, or new public art experiment a week—starting next week, so by July 15.

       100 paintings in a month à reopening active online store for ecommerce—by August 9.

       Secure space to create those paintings within a week—by July 15.

       Minimum 10 painting sales in a month—by August 9.

       (Re)Write, (re)illustrate, self-publish first two of the illustrated children’s book series Where the Wilde Thinks Are within two months—so by September 9. At least on Kindle and CreateSpace, maybe on other digital platforms too.

       The apocryphal album recorded in three months—by October 9.

       Have a pilot/beginnings of a portfolio for the Portraits of Peace series within one month—by August 9.

       Have a product of the series within 1 year—by July 9, 2016—in book form, or an online series that’s a fuller portfolio I can use to get freelance art jobs, pitch galleries, and do other stuff with I can’t even imagine just now. (E.g., there’s a field experimental component of the project incorporating some positive psych stuff like from Pennebaker’s work on expressive writing that I haven’t hashed out yet. I want to listen deeply and see what feels right in the context of people’s stories first.)


Money as a target and how I will make it:

       This is the thing I have always been bad at so much as thinking about as an artist. Let’s correct that error now. Again. Or blog trying.

       I’d like to pay off my attempted business launch/move debts and have money to make art and travel. Ideally I’d make something like $110k/year. But most businesses take years to turn a profit. So setting a short-term goal that’s specific feels really weird. Overly optimistic. But I have to get better at doing it or it’s not going to happen.

       There are six relatively immediate ways to monetize my art:

o   1. selling paintings online and in person, getting a better sense of my market and pitching to them better, 

o   2. making prints and postcards to sell at markets or openings, 

o   3. properly illustrating and self-publishing the Wilde Thinks children’s book series, 

o   4. teaching (although I start to worry about the visa issue with this—there has to be a way for people to legally teach in other countries as they travel, but I’m not sure how this all works and want to follow the rules), 

o   5. working on the Portraits of Peace peace-maker interview and painting series, perhaps starting with Syrian refugees or folks who have come back from the war in London (Eliot Higgins says he can try to get me in touch with some relevant folks to do a pilot/get started on this—I’m happy if other folks can too), and 

o   6. offer painting-photography portraits (combining techniques using a camera, a printer or access to one, photo transfer using acrylic gel medium, photos to canvas, and paint in combination with that—but this seems like something I’d need to build up a clientele in a place doing, like any other portrait photographer), 

Clearly formatting is not one of the things I will be getting paid for in this life. Also modeling. 

Just painting and selling the paintings online as best I can seems like the simplest, most obvious thing here. Re-launching an online oil painting store has got to be the most analogue, weird, inefficient way possible to be a digital nomad. But it’s what I think I have to try next.

I don’t know if I’m doing it all wrong, but this is what I’m doing. I want to be a jobbing artist, run my own successful business, and be loved. Just doing what I have to do as an artist in a space where I’m allowed to make a mess—but keep getting out plenty meeting nice people like I have been—seems like a good place to start.

Let me know what you think in the comments, via Facebook, or send me an email.