The Business Life of The Self-Employed Designer

In this article I’d like to give an overview of how I organize the logistic and business side of my life as a self-employed designer and illustrator. If you’re thinking about becoming self-employed (go for it!) this small guide might be helpful.

We’re Only In It For The Money

Well, sort of. It’s fair to say that we self-employed designers and illustrators love our job and that’s our primary reason for doing it but we are definitely trying to make a living out of this passion of ours.
Enter money, invoices, receipts, taxes.

I can handle many things but money isn’t one of them: I need an accountant to take care of my tax returns.
Every month I have to print out all my invoices, expenses and PayPal receipts, two copies each (one for my accountant and one for me), put them in a folder and bring them to my accountant. Done? Nope.
I have to remember to pay my rent, the Internet company, the accountant and the government every month. I always forget these things, putting myself in embarassing, unprofessional and potentially dangerous situations.
The solution? iCal.
Just set recurring alarms for all these events and let technology remind you of your chores. Any calendar application will do as long as its alarms pop up on your desktop even with the app closed.
I also set reminders for house chores (laundry, aquarium water changes, etc.).

It’s all in the name

A few months in my self-employment gig I started to have trouble finding files. Relying on search applications like Spotlight is crazy in my opinion: nothing beats a well organized folder tree.

I switched to the Mac to concentrate on creating things in my apps instead of managing files and taming the OS so I chose not to fight OS X’s default folders. I put my pictures in the Pictures folder, my movies in the Movies folder, my downloads in the Downloads folders…

One area where I can’t tolerate any type of external interference, though, is my work, both client and personal.
In the Documents folder I created one folder named Grafica. it contains only three folders: Materiali (graphic assets), Lavoro (“Work”) and Personali.


Assets and Dropbox

Materiali contains everything I might need to create graphics (brushes, icons, fonts, patterns, templates and textures) and it is an alias. Its real location is in the Dropbox folder.


I use the free edition of Dropbox which gives me 2.2 GB that I fill with graphic assets, app libraries (Little Snapper, TypeIt4Me, password database, serial numbers), scans of important receipts, my ID files (logo, avatars, business card, signature) and files I need to quickly share with people (in the Public folder).

Work folder

Lavoro contains my client work. Each job sits in its own folder, named with a code (year+3-digit progressive number) and a title.

job folders

Note how the list automatically goes from older (top) to newer job (bottom).

Each job folder contains the same set of folders (the skeleton) to organize the many files I produce each time.


Assets contains everything the client sends me to do the job (current company logo, mood boards, guidelines, app descriptions etc.).
Comps are the in-job deliverables that I use to show how the designs progress. They’re usually image files with the job name, content description and date in the upper left corner and my name and logo in the upper right corner. There’s a PSD and a JPG/PNG for each.
Quotes contains the estimates (I’ll have to pick a term sooner or later).
Ref contains all the reference files I collect, usually they’re the result of Google image searches.
The remaining folders are self-explanatory.

Naming files

I always name files according to this scheme:
project title_content_YYMMDD (ex. CapBrown_sketch_100916)
This way the most recent files are at the bottom of the list.

Keeping track of everything

I use Google Docs to keep track of every estimate and every invoice I create, in two separate files. I have bookmarks to these two files both in my work folder and in my browsers.


I have a separate folder for all the estimates I prepare. I move them to the Job>Estimates folder once they become jobs or leave them here if the job never materializes. Each estimate gets its own code, separate from the job code (it sounds messy but it works for me).
I record all my estimates in a spreadsheet for easy reference (click for full size).
I use InDesign templates for estimates and invoices. I could get by with a text editor but I want to have control over how these documents look. The only downside is that for each estimate and for each invoice I have an InDesign file and a PDF. Having a separate folder for each type of document eliminates the potential mess though.


Invoices must have unique codes. The government and your clients demand that. I don’t reference the job code in the estimate code but my invoice files always contain the project name as well as the issue date. Some jobs have multiple invoices so having a separate naming scheme works for me. I record each invoice in a Google Docs spreadsheet.
I’ve gone through several invoice designs, one of which was documented in a tutorial.
I have a blank InDesign template but it’s actually faster to open an existing invoice and edit the text.

Let’s go to the morgue

I think it’s hilarious that the place where creatives keep reference and inspirational material is called the morgue file.
I use LittleSnapper to collect images from the net. I just drag them from the browser to the app’s icon in the Dock and they get imported. I have images of animals, female and male faces (for portrait practice), color schemes, architecture, typography, caricatures, the usual stuff we all collect from FFFFOUND! and RSS.
When I’m in a rut it’s great to casually browse this library to find ideas for a new personal poster, a new illustrative style, shading techniques, interesting facial features, hair rendering etc.
I keep my LittleSnapper library file in the Dropbox folder. Admittedly these files are not vital but I have free space in my Dropbox account so why not use it?

Communication with clients

Having no local business, my only means of communication with clients is e-mail.
Contacts are initiated via the forms on my websites. Very rarely do I engage in Skype calls or chats because they take up too much time and they’re volatile. Get it in writing.

I couldn’t work without Gmail. I have several work addresses routed to one main Google Apps account.
Contrary to most other designers I get very little e-mail each day (I must suck) so I don’t need OS apps, notifications and advanced filtering. Nonetheless I make use of Gmail’s advanced features for better organization.
I mark as important all the conversations related to jobs. They are labeled Work and populate the Priority Inbox.
Starred messages sit in a separate inbox and refer to job requests that I have to respond to with an estimate.
Everything else sits in the Gen Pop inbox at the bottom of the list.
I add a star to an email to signify that I have to take an action (either reply or do some work and send it to the client).
I also have labels and filter set up for Work, Quote etc but they are not essential.
My inbox is small and not very active but it’s visually clear and ready in case traffic increases.

I have some canned responses set up but nowadays I mostly use TypeIt4Me to quickly compose e-mails. I have shortcuts for all my e-mail addresses (the Paypal one is the most important, never mess it up!) and standard replies to job inquiries.
All very necessary.

The community

My presence in the community has somewhat dwindled. I no longer publish tutorials and articles on design blogs nor do I publish content on Cute Little Factory.
(Un)fortunately client work has intensified its grip on my weekly schedule and frankly I’ve said everything I had to say about Photoshop and Illustrator in my published works. Creating new tutorials would only be repeating myself and I’m not going to do that.
The same goes for icon sets. The ones I’ve published have been successful but nowadays everybody is creating icons and I’m moving on to full blown illustration for my personal work.
I try to create and publish new work every week provided the idea and most importantly the execution come together. I’m expanding my skill set, learning new things every day and having lots of fun. Hopefully I’ll be able to get more illustration work in the future. That is my goal for the next to years.

I haven’t disappeared from the community though.
My Twitter usage is at its epitome thanks to the Mac app. My tweets are basically whatever crosses my mind during the short breaks between work sessions. I try to share my interests in music, languages and conspiracy theories. Follow someone else if you’re into design links. If you follow me, though, entertainment is guaranteed. I find this a more honest approach to tweeting than just restricting myself to design.

I am also on Dribbble, with which I have a love/hate relationship.
On the one hand it’s a phenomenal source of information about what’s going on among designers and a great place to check how other designers have approached similar jobs to the ones I’m working on at any given moment. Along with Iconfinder, Dribbble is essential to avoid inadvertently copying other people’s ideas.
On the other hand it’s a cesspool of copycats, a club where trends are started, graphic metaphors abused and banality and lack of talent glorified. It’s a big source of frustration, too, when my shots are ignored but others are unjustly (in my opinion) praised. Needless to say Dribbble also enforces the unhealthy concept of rockstar designer and the subsequent fanboy mentality that are steadily robbing our profession of honesty and levelheadedness.

Maintaining a presence in the design community is a must for me, though, since the only business I have comes from the Internet. Yes, that’s great and very scary at the same time.


Not only are our lives all but digital hence dangerously immaterial and ephemeral, we also live fragile times. We should probably back up our entire lives.
Short of hiring a professional tailor to make exact replicas of all my (probably) irreplaceable vintage clothes, a group of scientists to clone my fish etc. here is my backup scheme for digital files.
Time Machine backs up my 1 TB hard drive to an external 1 TB drive every hour.
Carbon Copy Cloner does the same to another 1 TB drive every three days.
I manually upload finished jobs (client and personal) to the Backup folder on my hosted server using Cyberduck.
My Dropbox use is described above.
Everything is free.

I’ve been thinking about using a paid online backup service like Backblaze but with hundreds of GB to upload and with my 1 Mb Internet connection I’m looking at weeks and weeks of continual upload…scary!
It’s probably a good idea to have a second online backup of everything.
All I have to do is collect and organize the mess I have on two additional external drives, find a place for their content on my computer and update all my backups. Boooring!


I’m sure I’ll devise more efficient ways to organize my business life as I go along but the system I explained in this article works really well right now. The folder structure and file naming scheme are especially effective.

I hope you found some of my tips helpful but ultimately you should come up with a system that works for you. That’s when you’ll start to really kick ass as a talented, successful self-employed designer, illustrator and artist.