Bullish: How to Make Money as an Artsy-Artist Commie Pinko Weirdo, Part I

Have you ever read a “How to Get Ahead in Your Field in 90 Days or Less Using Negotiating Techniques/Mind Control/Fairy Dust” article or book and just sort of let the advice glance off, assuming that it doesn’t really apply to you because you don’t wear a suit and look like a businesslady stock photo?

I live on Wall Street, and once walked up out of the subway to see a movie being filmed on Wall Street. It was a Saturday, and all the besuited people were actors. It looked just like…well, a movie. Because everyone was very young and attractive, and also carrying briefcases — rich, shiny leather, or gleaming chrome. Briefcases. No one does that. Not even on Wall Street. This was some Platonic ideal of Wall Street, minus all the grumpy older men with bad skin and frowzy trenchcoats who try to cut the line at Starbucks.

Are you are imagining “business” exclusively the way it is portrayed in the movies, or — even better — the movies of your formative years? Like Wall Street or Boiler Room or even What Women Want (gross when it came out, and even grosser now, Mel Gibson). I have found myself doing this. For instance, certainly you’ve heard the advice to make friends with gatekeepers, to always be nice to the receptionist. It’s easy to see myself doing this on Mad Men. She has a beehive and a prim little suit and would like it if you sent flowers. But in real life, the person at the front desk is almost certainly a 23 year old who is always on Facebook. She is wearing leggings. So, yes, that is the person you are supposed to be nice to. (For the record, if I made less than $15 an hour, I would wear leggings too, just to stay sane.)

So, here are some thoughts about making money without becoming a Republican. Because we’re all in business, even those of us with neck tattoos.

Find a millionaire you don’t hate.

Many liberal-types say “rich person” the way we also say “racist.” This is probably not so good for you. Recently, a friend posted to Facebook Bernie Sanders’ speech in Congress about the widening rich-poor gap in America. Some Glenn Beck-loving yahoo posted some shit that went like this:

Excuse me, let me get this straight, if I’m fortuante enough to save some money through my hard work and good investments for children and grand children I’m suppose to just willingly give this to a country to let them sh.. on it and put it in a museum and call it art?

And — I wouldn’t recount a Facebook conversation unless something happened other than 50 smart people jumped all over this guy — a friend of a friend (a gay man in an artistic field) posted this:

OK, so I am a millionaire and guess what. My business continues to blossom and life is great. I get so many tax write offs I hardly pay any money to uncle sam. Are you making more money now than 2 years ago? I am. How are your investments? Mine are fabulous. Would I be willing to pay a couple percentage points more to dig us out of this mess? Absolutely. I have worked very hard for many years to accumulate what I have and am more than willing to do my part to help the 98% percent of the American population suffering.

That’s worth waving a fucking flag about, isn’t it? It is!


Liberals are probably more likely to hide, rather than brag about, their millionaire status. But there are actually totally awesome, ethical people out there who are rich. So, don’t hate rich people, because you’ll probably constantly undermine your own business, career, and negotiations in a million small ways. Hate assholes, some of whom are rich and some of whom are not.

Find a rich person you admire. They are out there, and in many cases the non-famous contingent of admirable rich people would really enjoy being acknowledged by someone like you — after all, it takes skill to make seven figures, and it’s the sort of skill you can’t talk freely about in most social situations.

If you’re lucky, you might end up with a mentor.

Get a real accountant.

If you have a natural aversion to this idea, I assure you that you can actually just wear your normal clothes to your accountant’s office and talk at great length about your burlesque-dancing career or your business making “This is what a feminist looks like” jock straps, etc. You don’t have to morph into a “person who has an accountant.” It’s just like how everybody should have a dentist.

To jump back a bit: If you are a lovable artsy weirdo, you are almost certainly self-employed, and hence are supposed to pay quarterly estimated tax. Filing your taxes four times a year? Personally, I think taxes should be on a less frequent schedule than Botox, thankyouverymuch.

If you also have a regular job, however, one incredible time-saving measure you can take is to have extra taxes taken out so you don’t have to pay quarterly estimated tax on your business. According to the IRS, you’re supposed to pay estimated tax if you expect to owe at least $1,000 at the end of the year after subtracting withholding and credits. So it’s not about your employment status, so much as just about the fact that, if you owe the government money, they want it sooner rather than later. You can pay this extra cash out of your regular job by taking 0 exemptions and/or electing to take out an extra dollar amount from each paycheck. From the IRS:

If you receive salaries and wages, you can avoid having to pay estimated tax by asking your employer to take more tax out of your earnings. To do this, file a new Form W-4 (PDF) with your employer. There is a special line on Form W-4 for you to enter the additional amount you want your employer to withhold.

If you’re not sure of how to do the math (if you make very little from your sideline, taking zero exemptions might be enough, but if you make half your income from your sideline, you would need to take a very large chunk of money out of your regular-job paychecks), an accountant will help you set this up.

Relatedley, if you’re using a home office for something that is generating income and you’re not confident enough to figure a home office deduction on your own, that would be a good time to hire an accountant. I had been filing my own taxes online (It’s so easy, you just fill out a form and they tell you pay a lot of money! Like a free whack to the head — it totally sucks, but it’s FREE, ACT NOW!) for years, when my BFF insisted I see her accountant. He asked if I worked at home. I said, “Most days, from about 8am to 3pm.” And he said, “Do you have a special area of the house where you do your work?” And I described the part with the desk and file cabinet and printer and bookcase full of 200 pounds of test prep books. And he said “Why are you not taking a home office deduction?” In my head I had some answer about how people who work at home had fax machines and took conference calls, and I never did those things, but I couldn’t say that because it was stupid, so I sort of shrugged and winced and hummed a little song while my accountant filled out my taxes for me and saved me thousands of dollars. (He also had me deduct the bookcase.) And this is why I have an accountant.

Warehouse Clearance Sale


I was raised with a pretty literal view of money — you make a certain number of dollars, you pay your bills, and then you have a certain number of dollars left to spend, so don’t go over. As I talked about in Social Class in the Office, a good test of social class is whether you’ve ever seen your parents shake hands (I never did growing up). If your parents don’t shake hands, they probably never say “It takes money to make money,” nor do they “manage wealth.” (If you were not raised among the wealthy, ask yourself if, deep down, you don’t maybe feel that investing is cheating. That would be a good view to get over.) In any case, if you were raised with a very literal time-for-dollars view of money, then you feel like a big fuckin’ bigshot when you give someone a $475 check in exchange for saving you $4,000.

You are networking, even if it involves Facebook and having sex.

When I ran a company in Virginia, I really did go to networking events (“The Chamber of Commerce will be having its September mixer at Goldstein Eye and Ear!”) in well-lit rooms where everyone shook hands and gave their thirty-second elevator pitches and politely exchanged business cards. These events are a really good way to meet salespeople.

Networking events are to networking as speed dating is to dating. Some people do meet the love of their life during an event where everyone wears a nametag, but that’s hardly all there is.

The first five or more years of my career, I had serious misconceptions about networking. I was the first person in my family to go to college, and when, four years later, I was running a small company and there was no magical nexus of powerful 40-year-old Dartmouth alums ready and willing to help me out, I assumed that the Ivy League just hadn’t stuck to me, that I was made of some kind of white-trash-Teflon that caused my hard-won education to slide right off.

It turns out, I was supposed to spend my college years making actual friends, and then waiting until they got old enough to have powerful jobs. Oops!

My point is, I do think that nearly all of the old-school networking advice still applies, even if business cards are now kind of lame and much of your networking takes place when you are drunk and sweaty. You are still supposed to be a little fake, by which I mean pretend to take an interest in things that you don’t really, and practice memorizing things you will want to be able to mention later. People you meet at Williamsburg loft parties where everyone wears retro roller skates and a costume still like it when you remember their birthdays and vote for their SXSW panels.

Come back next week for “How to Make Money as an Artsy-Artist Commie Pinko Weirdo, Part II”: how to break away from your peers in your industry, how to schedule creativity, and how to set prices for creative work.

originally published on The Gloss


Woman's hands holding coffee and the GetBullish Money Reset book on a cozy blanket

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