I’d like to live like a poor man with lots of money. (Pablo Picasso)

From Wikipedia – ‘A freelancer, freelance worker, or freelance is somebody who is self-employed and is not committed to a particular employer long-term’.

You might be represented by a company or an agency that resells your labor. Or, you may be completely independent... an 'Independent contractor’.

Art-related fields where freelancing is common include: advertising, publishing, film and TV production, photojournalism, web design, graphic design, and video production. And lots of local, state, and federal art jobs, like Montana artist Chuck Black winning the 2023 Duck Stamp contest. Here’s an interesting opportunity – did you know the Federal government has a large 50-year-old Art in Architecture program? It's run through the GSA -- the General Services Administration. And it is very easy for artists to apply online. Artists like painter Adam Cvijanovic, who added himself to the little-known federal registry of artists. When the government begins an architectural renovation of sufficient scope, it can grant one lucky artist a commission. Cvijanovic was chosen to make art for the military payroll Bean Center building project in 2011. Past recipients have included Alexander Calder (a big red metal sculpture in Chicago’s Federal Plaza) and James Turrell (neon lights on the façade of San Francisco’s Federal Building). Good New Yorker story here, thanks to my friend Rick in San Diego. He sent it to me just a few hours after I published this book online... and it only took a few minutes to update with the GSA information. You could NEVER do this with a print book!

How much do freelance artists make? Who knows? What kind of a freelancer? The folks you see painting store windows at Christmas – or a corporate logo designer meeting with clients on Wall Street? Or the whole range of skills in between, like an artist making graphics for small-business web pages? How much income? It’s an impossible question, that ultimately depends on your ability to sell into the top 10 prospects that you or your marketing folks have identified.

Sales are the lifeblood of business

There are thousands of books and videos on selling techniques. I prefer three – first, Secrets of Closing the Sale by Zig Ziglar, who sold more cars than anyone else, amazing numbers, and his story starts with giving out a zillion business cards to everyone he met. You can to. Second comes Way of the Wolf, by Jordan Belfort, played by Leonardo DiCaprio in a great Martin Scorsese movie, the Wolf of Wall Street. Belfort preaches ‘straight line selling’, where, after identifying real prospects and discarding time-wasters, you repeatedly attempt to close the sale at least four times in the first meeting, looping back again and again to add value and counter objections... while always trying to keep the customer ‘on the line’, without wandering off to talk about things not related to the sale. Check Belfort out on YouTube. Third comes a movie, Door to Door, starring William Macy as salesman Bill Porter. Now, we don’t do his kind of selling much anymore. But your takeaway from this film is to never give up. To keep trying to get the sale. Over the years, I’ve learned to take five tries to sell a valuble new client. Five meetings, and each time going back with a new approach to counter the ‘No’ from the previous try. Because there are only four reasons why a qualified prospect won’t buy –
1. They don’t trust you (at that first meeting, you only have 5 seconds to make a good first impression)
2. They don’t trust your company (counter with success stories from other companies that use your products)
3. They don’t trust your product (find out why, and counter with product specifics)
4. All the above are OK but the timing isn’t right yet (leave with an agreed-on callback date).

A qualified prospect, of course, is one who can actually make the order (sign the check!), who knows what you are selling and wants to hear how your product might fit in to their needs.

There are two types of sales. First are what we just discussed – sales to prospects you don’t know. People you never met before, usually. Now, research shows that someone has to know you for at least seven hours before they start trusting you. In many sales jobs, like selling cars, you just don’t have that time, so you’ll use Belfort’s straight-line techniques to close that sale NOW. But you can’t be too eager (desperate). Instead, it is calming to remember that there’s a law of averages. The best baseball batters only hit safely one out of three... a .333 average is excellent. And on that car lot, knowing that you certainly will ‘hit your average’ as the days go by is VERY helpful... it frees you to relax, to truly try to actually help the customer get what they want, even if it isn’t a car you are selling. And then something surprising happens – you double your sales overnight, just beacause you put your customers’ needs ahead of yours and your sales manager’s.

The second kind of sales is quite different. Here, you are selling to people you know. People who already trust you to represent your product accurately, without bogus selling pressure. Example? At Tetrahedron Corp., I sold high-tech dielectric spectrometers to aerospace companies. Rockwell had a problem with voids (holes) inside polyimide (plastic) B-1 bomber parts, and reached out to see if we could help, which led to rapid testing to see if in fact we could detect the voids, which then led to the order. That order led to further orders... and a referral to their friends at General Dynamics, who were having a similar issue with voids in Tomahawk cruise missile wings. Referrals are the sales sweet spot, the key to growth with new customers who come in prepared to like you and your product. See the Referrals section further along in this chapter.

What’s freelancing like? What are the real-life positives and negatives? Well, I’ll share my own experience, hoping that it gives a realistic picture of what you might run into, if you want to work for yourself.

Rollercoaster ride

Ran my own company for 15 years. Company? Well, um, not exactly. Just me. Never had the inclination, or the business skills, to hire enployees. Self-employed.

Made ads and brochures for clients in San Diego, from 1978 to 1993. On the surface, well, a success! 15 years! In reality, a real rollercoaster ride, wild monthly income swings, and always uncertainty about the future. Do you get used to that? Yes, you do. Do you become – different – from all the people around you, people with normal paycheck jobs? Yes, you do. In a good way – because after about a year, you know for the rest of your life that you can go out into the world and make a living. Concept, text and graphics, layout and production. Ads and brochures, newsletters, annual reports.


While I can’t give you an estimate for the average freelance artist, I can certainly share with you what I made. But it won’t be much help – up and down, no consistency. As little as $2,000 a month – as much as $8,000 (great money, back in the ‘80s). That’s gross income, not net after expenses.

Which brings up a problem: artists can have a very high net income, because we have few business costs – few deductions – which can lead to hassles with the IRS later. “What? I owe you how much? You’re kidding!”

Because, you see, I followed a classic business model that a friend in the garment center taught me, years before. We were out on 38th street, enjoying the hubbub, the clamor of Spanish from the Puerto Ricans pushing the clothes racks, and the Jewish guys who still, back then, spoke Yiddish.

“Wow,” Chaim said, turning to look at a passerby, “Sheyne meyde!

“What?” I asked. “What did you say?”

“Pretty girl,” he laughed. ‘For a shiksa. Jon, the way you start a business, you buy a piece of cloth... and you cut in in half and sell each piece for what you paid for the first cloth. That’s it. You don’t need no capital to start up. You don’t need no bank. Just work hard. An opgesheylt ey kumt nit glaykh in moyl arayn. A peeled egg doesn't come into your mouth by itself! Goyisher mazel! Good luck!”
(technically, “Good luck to a non-Jew [a goyim]).

And it was true. Take out a startup bank loan? Forget it. Began with about $500; went down to about $50 before I learned that you can never stop selling. That what you sell today is money one-to-two months later, like 60 days out... and if you don’t sell today, you won’t eat then. Hard lesson to learn. Hard at first. And work hard!

Learned to price by the job, not by the hour. And to never, ever go back on an estimate, once you’ve made it. But to have variable pricing – to charge rich customers a lot more than poor ones. Thick rug? Wood-panelled offices? Several secretaries? Pay me more for that brochure, a lot more, than a small high-tech startup operating out of a rundown building in an industrial area.

I learned, particularly in Scam Diego, to insist on payment in real money, not shares in the client’s company, or promises for future payment when the client’s ship came in. I’m not a factor; I’m not in the business of financing your business against your (possibly worthless) account receivables.

Also learned that many customers just don’t want to pay. Made an annual report for Scripps Seagrant, an oceanographic institution, part of the University of California. Gold-plate client, right? No. They – just like some large corporations – had a purposeful policy to delay bill payment as long as possible. And they got away with it because their suppliers, out of fear, put up with it. But one day I couldn’t wait any more, went into their accounting department and just started yelling at managers until they handwalked a check to get me out of there. Never sold to any government agency ever again.

The lessons you learn: that the only thing that can make you quit is you yourself. That it’s very hard to regularly save money. That you have to put aside for taxes. No 401K retirement plan, either. But I went through the early ‘80s recession in good shape; by then, I was selling ads and brochures to banks, real estate developers, and a few high-tech firms.

Sparrows in the field

Matthew 6:26 -- Look at the birds of the air: they neither sow nor reap nor gather into barns, and yet your heavenly Father feeds them.

At first, I had no idea where to get customers. But I learned that work, somehow, just kept coming in. How? Mostly from referrals. Where one client would help me get work from another. Sometimes these were linked companies. Ted Gildred owned Torrey Pines Bank in Solana Beach (logo, ink artwork, ads and brochures), and Gary, their marketing director, sent me over to see Jeff at Lomas Santa Fe Developers, another Gildred firm (ads and brochures).

Referrals – I made ads, brochures and a newsletter for Financial Profiles, a software company in Carlsbad. Good work, nice people. Ad, brochures, a newsletter. This led to a large full-color poster for a subsidiary company, which was selling a banking platform-automation program. And, Jim at FP knew Laura at nearby Counterpoint, where they made high-end $10,000 amplifiers for audio buffs... great ad work.

Referrals – my typesetter, Nova Graphics, was a locus for leads. David, the owner, was learning dBase programming, and one day I went with him to meet his customer Morris the lawyer, who was starting a new company called the Fax Group out of a cabana by the pool behind his house in Rancho Santa Fe. Great place to work! Press releases, Ventura Publisher development. Ended up as their marketing guy, a few years later. And Dave’s wife Sara sent me to see Andy, who ran Smartek Software – ads, CD packaging design, and a user manual.

Referrals – one day, Stan at Tetrahedron (ads, brochures, newsletter) introduced me to his friend Vince, who ran a silkscreen company making artificial stained-glass windows. Vince had a rich friend who bought an old Northern Pacific passenger railway car, and, as part of the restoration, had to re-create a 1940s glass panel with an etched NP route map. Made the art, hand-cut a large bumper-sticker-like mask, and pulled the squeegee – a hydrofluoric acid ‘ink’ project!

I’ve said that sales are the lifeblood of business, and, for me, referrals were the engine that drove sales. Make sure to ask your customers if they know anybody else you might help!

Made a great deal of money some months, a lot less in others. Never was able to even it out. One month you’d sell a pencil ad rough for $1200 ... pure profit! But the next month, you might be bogged down on an 8-page brochure, with a customer needing change after change. Remember – even though you bill for changes, you never make money on them.

These years coincided with a seismic shift from traditional artboard production to computer graphics. In 1978, I was experimenting with the first text-based microcomputers; by 1990, we were using Xerox Ventura Publisher to make camera-ready catalogs.

And I started losing customers. One day, out of the blue, Financial Profiles turned my newsletter work over to their secretary. “We just don’t need typesetting any more,” said my contact there, the marketing manager. “Jon, maybe you could teach Sharon how to use Ventura?” That was a wake-up call, even though I kept their ad and brochure work, and designed a large full-color poster for a banking platform automation product.

When there’s a technology revolution, you have to adjust. Just as the shark is about to eat you and your surfboard, you have to jump onto another board close by. As time went by, I found myself working harder and harder to get and keep customers, for less and less money. More and more businesses bought small computers and learned how to make their own marketing collateral... brochures and newsletters. But at least I had an ace in the hole – I’d started working with computers years before.

An Arabian computer

In 1980, I’d worked as a contractor doing marketing for Tetrahedron. Selling dielectric spectrometers to aerospace corporations, and making ads, brochures, and a newsletter. For about six months, juggling other customers on the side. Here, you work on the client’s premises, and everybody ignores all the IRS rules that define an independent contractor vs. an employee.

One day the owner got a contract to make a microcomputer that ran in Arabic. “Jon,” he said, “I want you to meet Mohammed. I want you both to run this project. We need to have one ready to show in 3 months. And I think we’ll hire a teacher from Cal to teach you both about computers, at night after work.” He did, we learned, and the project began. Decided to modify an Exidy Sorcerer, as it had a removable ROM cartridge that we could re-program with an Arabic version of BASIC.

I made the Arabic character set, with all of a 9 x 14 pixel grid to work with, not near enough for a lovely script-based-language that extends letters horizontally to indicate emphasis, and uses diacritical marks every time you turn around. Mohammed rewrote Exidy BASIC, and we shipped the first Abbas-1 units off to the Ministry of Defense in Saudi Arabia right on schedule.

Just like other early PC companies, we made ads and brochures with fake screenshots – marketing vaporware where you were betting that the product would become real by the time the orders came in. Abbas-1 morphed into a CPM-based Abbas-2, with a 100K disk drive. And we made a user manual, which wasn’t too important to me at the time, but helped land a job as a technical writer years later.

The project made money. We were first into the Middle East market – ahead of IBM – but it wasn’t smooth sailing. My Arabic character set came in from severe criticism from the Mutaween, the religious police in Saudi. There was no way, you see, to create proper-looking Koranic script on a text-based screen. Today, with Macs and Windows, it’s trivial – back then, impossible. Just imagine trying to program the calligraphy in the image below!

And we had to remake a brochure, where Mohammed was standing behind a secretary, teaching her to use Abbas. Oh, no... can’t have that! Men use computers, never women. Retook that picture fast, with the lady looking adoringly at my friend as he typed something on the keyboard.

Fax from your PC

Around 1990, went independent contractor again. This time for the Fax Group startup... which found investors and moved from Morrie’s poolhouse to an office suite in Del Mar. We invented a fax board that let you fax from your PC. Faxes were big in 1990, and I was amazed that I could fax highly-graphical pages right from Ventura. Sold a bunch of FaxPro I boards.

Came up with a good slogan – ‘See it, sign it, send it’ – made ads, brochures, and the retail package design. Learned a lot working with the rep from box-manufacturer Kent Landsberg, Making the outside design is the easy part! You also have to specify hotwire cut lines for special foam inserts, order anti-static plastic bags, and so on. And, I wrote another user manual. But then, as it goes all too often in high-tech, our next FaxPro II just didn’t work – it used a multilayer circuit board at at time when they were very hard to make. Over and out.


We went into another recession in 1993, and my wife watched me running around in circles. One day she said, “What would you do – if you could do anything you want?” And, for some reason, I blurted out, “You know, I’ve always wanted to sell cars!” And I did, for the best part of a year, a wonderful transition back into the world of normal jobs. Because you sell on commission, which I loved, but I also was part of a giant organization called Ford Motor Company, Lincoln-Mercury Division. Fun!

But after 11 months I really missed words and graphics. One day, I sold a baby-poop-brown (Mocha Frost) Tracer to a father, a safe first car for his teenage son. “It’s beautiful,” he said. “Don’t you think it’s the best-looking car you’ve ever seen?”

“Yes,” I replied. “Beautiful color!” Car salesmen all lie like mad, you know. “What do you do?” I asked.

“I’m a technical writer,” he said. “Great job. Mellow. And the pay’s pretty good.”

And that was true enough – his credit cleared in five minutes flat. And I remembered those user manuals I’d made. Aha! Went to a temp agency, then off to an interview, where two older guys asked “Can you draw?” What? “Sure!” I said. And they had me draw a camera lens, right then and there. And all my years of sketching, of drawing, paid off handsomely – I was hired on the spot and worked there for nine years, back in the system again.

RVs for artists – work anywhere

For many artists, working in your RV from anywhere is the Holy Grail. Most places, like in the cities and suburbs, there's cellular service. Easy to use your smartphone as a wifi hotspot. So much less expensive to live in your RV, than in an overpriced apartment! Small towns, too... anyplace with a public library or hospital to get that free signal. Now that covers 90% of where we usually go. But that 90% is only 10% of what's out there.

Most of America, it turns out, is off the grid. Particularly out West. Places like the Buffalo Gap National Grassland in South Dakota... imagine painting on a lovely spring day with a waving sea of sweet-smelling prairie grass all around, peaceful and quiet. The federal government owns about 50% of the land out here, free of charge for campers with few restrictions. Fine artists can create without frequent contact with their agents or customers, coming in to town now and then to stock up and get an internet signal. But it's not that easy for commercial artists, who may need constant communication with clients.

Enter Starlink, Elon Musk's satellite-based high speed internet connection. Two mobile plans -- basic at $150 per month, where you set up the receiver antenna whenever you stop (just point it at the sky), plus $600 for the hardware. Other plans from $250 a month up. As business expenses go, that's not much, and of course it is tax-deductible.

Beyond that, there's nothing stopping an RV from being the perfect art studio... certainly for most artists with drawings or paintings less than about 3' on a side. Acrylics? You have water. Oils? Carry some turpentine. And for digital work, you have all the power you need for that computer and rarely-used printer. RVs as an art studio? You bet. Possible now, practical, and if you like getting out in the middle of nowhere, absolutely perfect!

Home or on the road, you’ll have financial ups and downs, and learn more about people than you could ever imagine. Most of your work will come from referrals, and, soon enough, you’ll have more work than you can handle. And the work will vary in wonderfully unexpected ways. But one day you’ll want to be part of an organization again. And that’s where we go next – how to pick the right spot, for the next phase of your working life... after a short digression in the next chapter on Pencils vs. NFTs.

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