March 7, 2005

Independent Contractor

For some reason I get lots of email from people asking me about going out on their own and independent contracting. Well folks, I don’t mean to disappoint you, but I am just a few months into this now and I don’t have all the answers. I’ve been at agencies my entire career thus far and have picked up some helpful advice along the way. Most of my decisions were made on the scale of “things that make sense to me” or “things necessary to live” or a neurotic urge to be overly prepared and organized. I have made my decisions and come up with my own tactics for staying sane and hopefully clothed and fed. Time will only tell if this works out for me, or if I end up on the highway off-ramp selling half-sharpened pencils. This is just my advice from the questions I receive, take it with a sack of salt.

What steps/planning did it take to go out on your own?
First off, stay the hell in school. Completing an education can only aid you in your life and your career. If you are out of school, get a job or apprenticeship in the industry. Learn and make your mistakes in a low-threat environment from people who know more than you. The idea of starting your own company straight out of school might seem like a glamourous idea, but it is a staggering venture. There are more things that go into self-employment/business ownership than you might imagine, especially with things like school loans and debt to pay off.

Educate yourself because there is no sense going into this blindly. Get something like the Graphic Artists Guild Handbook because it’s chock full of business info, paperwork samples, and legal advice. You should read this anyway (or something like it), even if you don’t plan to be self-employed; there is a little something for everyone. If you can afford the luxury, hopefully on the side while employed, pick up some freelance work. Get a feel for dealing with clients, time, and personal management in a try-before-you-buy situation. This is a good way to get your feet wet while staying in relative safety (your regular salaried paycheck), but if you are having trouble with handling one side job, it could easily be a sign that you either may not be ready for this step, or you need to look again at your freelance scheme. This is also nice because if you are planning on going from a steady paycheck to contract work, you might be able to plan a few months ahead and stow some money away to make your first few months on your own a little less stressful. If possible, it’s ideal to get to the point where you can take on enough freelance work on the side that you are just about to lose your mind. Then resign and monetarily ease right into self employment.

Once out on your own, find yourself an accountant. Taxes are now your responsibility and you need to pony up quarterly instead of one a year. The accountant will cost a bit, but they are indispensable because it’s not something can afford to mess up. One of the greatest reasons for failure in contractual work comes from people either not paying their taxes or not paying them correctly. Open up a separate business checking acount, this makes it easier during tax time. Get business cards and letterheads if you like too, these are all things that make your business real to the outside world and make people take it (and you) seriously. If you walk into someone’s office with your phone number scribbled on a napkin, you may experience some backlash.

How do you get clients?
Start off small. I am easing into this and I promised myself I wouldn’t jump at every job that comes down the line. I think this is a very tough thing to do because it’s so easy to panic and get worried about paying bills and business fees. First consider the time, pay, and direction of the projects. Does this project get away from the markets I want to work for? Will the workload of this project kill me? Am I a good match with the client?

Strive to do the kind of work you want for the kind of people you want. It’s not always possible on every job. Sometimes you make exceptions and sometimes you just suck it up. The more experience you get with this, the easier it is to read what type of client you are dealing with. You will also get much better at learning how to assert yourself and ask for the things you want and need. What it comes down to is your preference and your tolerance. You will be as much of a whipping boy as you allow yourself to be.

How do you stay organized?
I already went into some of the methods I use last time, but the planning behind it was a bit different. After working at a few agencies I came up with my own way of keeping tabs on all my job related information. When I started out, I assigned all of my clients and jobs a number; clients started at 0001, and jobs started with 1000 while getting incremented each year (so this year started with 2000, next year will start with 3000, and so forth). I use these to organize everything from payments and invoices to archiving assets. Which brings up another good point, backup everything and do it often. I have a schedule set it iCal that yells at me to backup everything important, mail, jobs, prefs, etc. I am also in the habit of burning at least two CDs for job archival. This serves two purposes. First, I have a spare copy if anything happens to one. Second, I keep a binder full of the spare discs at a friend’s house in case one of my cats falls asleep with a cigarette and burns down my place. Never hurts to cover your ass.

Create some paperwork. Spend some time and write up contracts (or pay a lawyer to), invoices, and proposals templates. Every job starts with negotiation and these are the terms of that negotiation. They are also the last ditch means you have in protecting yourself from jobs that go south. Have a SIGNED CONTRACT and a decent percentage of the job fees up front (30-50%) before you start working. Especially if you don’t know the person/company. I think everyone will tell you this, and most people are still liable to go ahead with a project without a signed contract. I know I did, and it only takes one time getting burned before you get your head out of your ass. Keep signed hard copies of your contracts and make sure you clients have one too. You need to keep a paper trail for every job, every payment, everything. There are plenty of good examples in the GAG book and online.

How do you stay sane and keep writing? Time is money, right?!
One of the things I have noticed now that my home is also my office is that I have to be more aware of my schedule. When I worked around a lot of people, it was easy to know when to take breaks; everyone stands up to go to lunch, I stand up and go to lunch. Nowadays I can get lost in what I am working on and before I know it, 3 o’clock rolls around and I still haven’t eaten. Take time out to repay yourself for your work. I try to make a point of getting outside for a walk, even if it’s just to the bank or grocery store. Make some time each day to read, draw, or whatever; just get away from work. The point is, no one will tell you when it’s time to take a break and it’s easy enough to get overly responsible and become your own slave driver.

It’s tough staying motivated, especially when a pajama lunch order of sushi is just a phone call away from my front door. Make yourself comfortable and make your workspace conducive to creativity. Invest in a little slice of heaven like the Salton Hot Spot coffee warmer. The only one watching you, is you. You can wake up, or not. You can shower, or not. You can play Grand Theft Auto all day, or not. The biggest difference is, your bank accounts will dwindle. Responsibility, you evil bitch goddess.

A very wise man once told me: “Now that you are on your own, make a point of taking a shower, shaving, and leaving the house for at least a few minutes everyday. Because it’s easier than you think to see the clock hit 5 and realize you’ve been watching Law and Order reruns all day”. So very true.

Commentary (31):

1. monooso says… mar 7, 2005 | 4:45 am

2:34am? What was that you were saying about becoming your own slave driver ;) ?

2. Shane says… mar 7, 2005 | 8:08 am

Nice read Jason. Thanks for the valuable tips. Hehe, I’m tired of browsing your site and not posting anything (hehe I hate trolls).

3. Dan Mall says… mar 7, 2005 | 8:15 am

Aw, stay in school?! Thanks for nothing, Stan!

4. Ian says… mar 7, 2005 | 8:45 am

The second-to-last paragraph could not have reminded me more of The Sims instruction manual. I’m happy for you, Stan.

5. Chris Kavinsky says… mar 7, 2005 | 8:46 am

Good points Jason. As someone that’s in the same boat of just starting up going out on his own, I would have to agree with them all. I would also add — set realistic expectations, especially when it comes to time management. I think a lot of people, especially with little or no professional experience, don’t really understand how much time and work is necessary on the front end (planning, pitching to clients and developing ideas). It’s eye-opening when you realize how much time you need to effectively sell your skills and services, and also work and communicate with clients. I would suggest for people just starting out, get a job in an established company, learn all aspects of the business, and gradually work your way into doing your own start-up.

6. Phil says… mar 7, 2005 | 8:59 am

Thanks for the post!

If you don’t mind me asking, what were the psychological factors involved in going on your own? What things were you looking to happen, what things were you afraid of, and how much of each has been realized?

7. Jason Santa Maria says… mar 7, 2005 | 9:07 am

Phil: The main factor was, can I actually do this and make enough to eat, or will I have to go back to another staff job?

I was (and am) mainly looking to do what I love and make a living from it, on my own terms. It’s tough to gage real success just yet other than I have a roof over my head, but things have been going as planned so far. Get clients, make money, leave job, start business, rule world… getting there.

8. Wade Winningham says… mar 7, 2005 | 9:18 am

When I was working at home, Friday was movie day for me. I’d take off for a 1:00pm show to beat the crowd when any blockbusters opened up. This isn’t every week, but it is a nice break to the day. Go to the grocery store in the mid-afternoon, too.

9. Hans says… mar 7, 2005 | 9:43 am

Hi Jason, and thanks for the tips. I’m getting more and more into quitting my job and going at it full time on my own. I just don’t have the stomach for it, yet.

I would like to do some time in an agency first though, but as it appears, there aren’t that many jobs available (in Sweden at least). My main reason for not taking the step is the fact that I don’t really know how to get clients. The jobs I’ve done so far have been through contacts.

You really inspire me though, so it may not be long before the days of safety are over…

10. RJ Hampden says… mar 7, 2005 | 10:59 am

I like this:

How do you get clients?
Well, the question should be, How do I prevent a catastrophic loss of life as they pile up on my doorstep?


11. Mike D. says… mar 7, 2005 | 11:30 am

“Stay in school” is great advice, even Mr. T agrees, but there are some caveats:

1. Your degree itself will not do anything for you in the job world. The education behind it will help you become a better designer, but no designer gets hired (freelance or full-time) based primarily on their degree.

2. Use your time in school to network. It’s people who will ultimately get you jobs… not books. If you want to be hired strictly on your design skill, give that notion up right away. Your people skills and who you know matter just as much, if not more.

3. I wouldn’t strike out on my own until I had clients coming to me for work. Start out at a company, get your name out there a bit, and then break off on your own when you’re famous enough to where someone designs a virtual version of you and posts it on the internet.

12. Jason Rutherford says… mar 7, 2005 | 12:57 pm

Where were you with this information four years ago? I had to go and learn it all the hard way!

13. Matt Johnson says… mar 7, 2005 | 1:51 pm

I am with Mike Davidson on the “stay in school” advice.

The last two posts have motivated and inspired me so much, its amazing. Hope to hear more about being independent. I myself just signed a contract as an independent contractor. Thusfar, not too bad.

14. John Athayde says… mar 7, 2005 | 2:14 pm

The schedule was the most difficult thing to maintain when I was working from home, however it was also the best. I would wake up at 10am and be at work. Done. I would work through until dinner and then work after dinner.

This was all well and good for a while, but lethargy set in. I realized i needed to get on a better schedule and exercize. Without exercize it was just productivity hell. Distractions abound, and when you’re tired, they look really really nice.

So yeah, exercize. It makes you feel better. And your significant other will thank you for it as well.

15. Mike says… mar 7, 2005 | 4:22 pm

I’ve just moved into a new house that finally lets me have an office apart from the living room and it’s fantastic. The best part is that after the move I decided that with a new house/office comes a renewed drive to make my business better. These recent entries you’ve written, along with others like Doug Bowman, have been just what I’ve needed to start getting my head straight.

For that I say thank you. These may just be ramblings to you but they are gold to a guy like me.

16. Josh says… mar 7, 2005 | 6:29 pm

Yeah good read — Nice hints, too.

Doing angency work right now and I must say it is an ugly beetsh (sometimes)… on the other hand you learn good lessons, too…

But sometimes when the economy goes bad - like on my side of the world - it helps to have a regular check to get you over… :D

17. El Clinto says… mar 7, 2005 | 11:49 pm

Dude…that was nice to read…i need to get some paperwork (contracts) in order asap. And the whole “go outside” thing is much needed for me too..sometimes I feel like a vampire. Thanks for this man, and thanks to Jake for the link.

18. niff says… mar 8, 2005 | 8:49 am

do you think it will be as complicated for illustrators? =(

great post stan…very encouraging and honest.

Oh. i do have one thing to add—if staying in a REALLY expensive school, that you are going in debt for…maybe drop out and go somewhere cheaper…ha. save yourself from working your whole life to pay it off. sigh. =( great school none the less.)

19. helenjane says… mar 8, 2005 | 12:37 pm

I loved working from home, but went absolutely insane from lack of contact with actual humans.

I prefer working with other designers (even if that means physically travelling to an office every day) because I can learn so much from their technique, their tools, not to mention the handy programmer down the hall.

20. Mike Stenhouse says… mar 8, 2005 | 1:31 pm

There was a little article written about this in a mag over here in the UK: Ditch the day job… It manages to get across the biggest pitfalls as well as the benefits.

The best advice I’ve read so far is Mike D’s 3rd point (#11). Getting work is hard, especially if you’re only just starting out. If you can manage a year or two in the industry before trying it on your own you’ll find yourself at a big advantage. The experience you gain from working with people who know the industry will also help you no end.

Contracting offers a great in-between since you get a guarunteed wage for a month or two at a time and a bit of company while you work, but you maintain a degree of freedom. That’s not easy work to get though - you need experience and a bit of luck just to get through the door.

If you can make it though, freelancing is ace!

21. Philip says… mar 8, 2005 | 10:10 pm

A few questions…

With Google, tutorials online galore, beautiful websites, people with opensource mentality and who love to teach good coding online, plus books, what’s the point of going to school? Why can’t one learn online and save the cash for a rainy day? Is it simply that most people lack the discipline to do this from the comfort of their home with no pressure of homework and grades?

How do you get clients? I didn’t feel that you answered this. You answered “How do you handle clients and prospective jobs?” Now, obviously you have a lot of skill, the site speaks for itself, but do you go looking for jobs, handing out cards, talking to everyone, using Or are you getting clients because of the networking you did (as Mike D said) from school and your previous jobs?
This one is a biggie for me because a the route I’ve chosen for my life doesn’t currently allow me to go to school or hold down a multi-year job. I do a lot of travelling and my desire for freelancing is to have a laptop and roam the world.

Finally, contracts. Signed? When my client is 5 states away? As Mike D mentioned, “only dinosaurs still have fax machines” What is your method of contracts in the digital age?

I’d be super happy if you could clarify your points by answering these questions and hearing what any of the others here have to say in regards to this too.


22. Jason Santa Maria says… mar 8, 2005 | 10:45 pm

Philip: Great questions, let me see if I can clear a bit up:

Some people will disagree with me, but I say hell no. Book smarts are only half of the equation. You can read all the tutorials in the world, but it still won’t replace good old mentored, hands-on learning (assuming we are talking design). Aside from meeting people, learning how to deal with jobs in a emulated environment, and getting a variety of criticism from your peers; school gives you a groundwork to build upon. The pressure on homework and grades is a good thing. It doesn’t all of a sudden become easy once you graduate. Stress and pressure are day-to-day companions. I wouldn’t trade my education for my Amazon wishlist. No way, no how.

Mike D is partially right here. I ended up getting a job right out of school based on my work. The only people I knew at that time were people from school and they were all just as fresh as I was, so those connections didn’t mean much in terms of getting a job. Although, those contacts kind of incubate. Within 2-5 years time, everyone ends up somewhere, and everyone meets new people (including you). After a year or two in the business, you realize it does quickly become who you know. Work is still very important, but the difference between being talented at a bad firm and being talented at a good firm can hinge on that guy you sat next to in class sometimes.

You don’t need to go to school to get immersed in a network, quite the contrary, you will just need to do some more footwork for yourself. Every major city has a community of designers and artists, and there are always meet-and-greets going on. Find events online from sites like, then go and be a social butterfly.

As far as me getting clients, I took a slightly different route. I tried to get my name out there and promote myself with my site to hopefully attract work. I don’t have a huge list of my own clients. I work through other firms (who can get better clients and bigger jobs than I can on my own), and pepper it with my own clients. The best way to get work (in addition to meeting lots of people and immersing yourself) is to promote the hell out of yourself. Websites are a great and inexpensive way to do this, but you may need to look into other options dependent on what kind of work you want to get.

Well, Mike is half right again. Many freelancers and subcontractors can get by without a fax machine (I don’t have one), I dare say we are a minority on this one because many companies do still use them on a daily basis. Normally, I send the client a PDF or Word doc of the contract with instructions to print two and (snail) mail them back to me (with a down payment). After I receive it, I sign one, and mail it back to them. I have considered getting a fax machine or the prospect of using one of the many fax-to-email services that I have heard many promising things about. I also want to look into Acrobat. I remember it has some sort of digital signature feature (has anyone used this? does it hold up legally?). In the end, it’s entirely up to you, your preferences, and what you can get your clients to agree to.

23. Mike D. says… mar 8, 2005 | 11:17 pm

Ok, first of all, I am never partially right. I am always entirely correct in everything that I say, do, and think. This is the case even when I’m wrong.

Now that that’s out of the way…

In points 1 and 2, I said that it’s never your degree itself that will get you a job. No art director will say “Wow, this guy’s got an MFA from Art Center, I don’t even want to see his portfolio. Hire him!” The degree takes a back seat to the portfolio, the references, and the likeability of the individual. My point here was that if you are going to school because you want to be able to present a degree at an interview and get the job because of it, you’re on the wrong track. A degree is a nice thing to have, but it only supports your portfolio and networking… not the other way around.

I also said that generally people get people jobs, as opposed to design skills getting people jobs. There are obviously exceptions to this, but as Jason said, sometimes the difference between being at a good company and a bad company comes down to who you sat next to in class. I SOOOOOOOOOO did not want to believe this for the longest time, but it’s just true. Yes you can let your portfolio get you a job right out of college. If your portfolio is good, you’ll land somewhere. But how much better of a gig would you land if your classmate’s father’s doctor’s golf buddy was the head of Saatchi and Saatchi? That’s just the way the world works unfortunately. People who are widely connected do a lot better at almost everything in life.

Moral of the story: You can get by on talent alone, but you’ll just be getting by. Meet people. Be nice to people. It will all come back to you.

24. Mike D. says… mar 8, 2005 | 11:41 pm

And by the way, it should be noted that I knew of Jason and his excellent design work long before I met him personally in Vegas last year. Before that time, I referred exactly zero clients his way.

But after throwing down fifths with him at the Tabu in the MGM until sunrise, I now send business Jason’s way whenever I can.

Again, relationships.

25. Ryan Nichols says… mar 11, 2005 | 7:50 pm

Having just gone freelance myself, I’m curious what your plans are for getting more work. Any certain niche areas you have in mind? Ideas?

I’m planning on building a gigantic foam easel suit and standing out on the street coring waving a sign while dancing to R&B. I thought maybe you might have some ideas for other foam suits that will work well.

26. Jan Brasna says… mar 13, 2005 | 11:41 am

I’m currently in position of “independent business owner” :) and it’s the same + I have to manage a small team of people. All of this during studies.
It’s quite interesting, it teaches me a lot, but I have to have all this things you wrote in mind. Otherwise I’d have to convert to the highway/pencils plan :))

27. Frank says… mar 24, 2005 | 4:27 pm

“The main factor was, can I actually do this and make enough to eat, or will I have to go back to another staff job? I was (and am) mainly looking to do what I love and make a living from it, on my own terms.” - Jason

What a great discussion. We’ve been batting around the same questions at BLANK. Why is there such a large gap between passion and profession among designers? Can you make the jump to pursue your passion on your own terms and still eat? I went a little overboard with a post yesterday to the site and compared working for a corporation or agency like Little Red Riding Hood working for the wolf. I’d like to post your thoughts on B L A N K as a means to help others with your permission.

Keep up the good work.

28. Patrick says… mar 28, 2005 | 9:51 am

This was a very encouraging read. I’ve been secretly following the segments of your life that you choose to share here for a little over a month now and I’ve developed a great deal of respect for your ideas.

After reading this post a few weeks ago, I was inspired to head back to school in pursuit of an advanced degree while developing a greater freelance foundation. As always, thanks for sharing - especially the the tip about basecamp. Great stuff.

29. Damian says… apr 25, 2005 | 12:16 am

Thanks for these two posts. Both were helpful.

Our team has been going full time with our design studio over the last year, and learned a lot of these same trials and tribulations..

Just curious, what do you use for tracking your time? We’ve been using basecamp and the only thing it lacks as far as project management is just the time tracking.

30. Kevin says… jun 15, 2005 | 5:55 pm

Nice info Jason

I came across a great website that provides lots of information for independent contractors and freelancers. It’s called The Independent Contractor.

It’s a new approach and above anything else, there are good articles and tips available

I’m out

31. Ibragim73 says… nov 4, 2005 | 2:36 pm

Great site, nice design! what it is all about?