Holly Gordon

Here’s an illustration I just finished as an homage to Greenport, NY. It’s a teeny tiny town at the very end of Long Island, and I’ve spent countless summers there in my Great Grandparent’s waterfront home.

The Other Stuff

here are two loosely categorized aspects of freelancing. The design part and the other stuff. The design part is your cake. The other stuff is your frosting. Like peas and carrots, Ren and Stimpy and Rock and Roll, you just can’t make one part work without the other.

Because I was so shocked at how much time and effort the other stuff encompasses, I figure it’s a good thing to lay down, right off the bat, before it’s too late. When I first started freelancing, I didn’t realize just how many roles I would have to play. I call myself a designer for simplicity’s sake, but I’m also an accountant, receptionist and marketing manager. Roughly half of my time is spent taking care of billing, answering emails, keeping track of hours, managing my schedule and finances and actively pursuing new clients.

When you are running your own show, you are the only person you can depend on. If things aren’t going as well as you planned, it’s your fault. That’s the first tough lesson that I learned, but the concept is simple and the idea is obvious. It really doesn’t matter how artistically skilled you are. If you want to freelance, you have to be able to work some serious managerial magic on a daily basis. If you can’t do that, you will have a difficult time keeping everything together and running smoothly, and more importantly, a hard time keeping your beloved clients around.

I won’t lie. A year ago, I believed I would just remember who owed me what. I made poorly-labeled invoices in InDesign. I was sure I would recall exactly what I had promised in phone conversations with clients. I had a ratty notebook in which I casually jotted down important, project-related notes next to my grocery lists and my super-detailed drawings of the best way to rearrange the furniture in my apartment. Needless to say, when my mind inevitably blanked on a project, I couldn’t find the information I needed to back it up. In fact, I couldn’t remember if I had ever written it down. When I first started, it was easy for me to keep everything in check because there wasn’t a whole lot to worry about. At that time, it didn’t occur to me that when I would become incredibly busy, I’d be lost in a sea of scattered information. I’m sure the transition to full-time freelancing would have been easier if I was prepared with an arsenal of organization strategies.

These days, I use Google Apps religiously. I keep my emails organized, and when I know I’ll have a good deal of correspondence from a particular client, I make them their own tidy email folder. How orderly! I also use Google Apps to keep running to-do lists and manage my ever-evolving schedule.

Another helpful element of my new, well-structured life are time sheets. I whip up nice-looking (if it doesn’t look pretty, I probably won’t use it) blank spreadsheets in Illustrator and print them as I need them. It’s quite handy to have a clean, detailed log of the hours I spent working, what I did and when I did it all in one place. Not to mention, when it’s all filled up, there’s a feeling of accomplishment and awe at the completion of such great feats.

Invoice Machine is another exceptional tool. It’s a lovely online service that simplifies the invoicing process. There is a monthly subscription fee, but it’s well worth it. For me, it has made sending invoices and keeping track of billing a breeze.

There is a whole lot more to the other stuff, like learning everything you can about taxes, writing contracts, quotes and proposals and marketing and self-promotion. I’ve found that by staying as organized as I can helps to keep the administrative monster from eating up all of my time and sanity. If I had prepared myself for all of the other stuff that is as much a part of freelancing as the design part, I would have been a lot better off. And so will you.

I often get a slew of questions from people that have either considered freelancing or don’t know how to start. I hardly mind the inquiries – I myself ask as many people as possible for advice and direction. Hello?! Lessons can be learned, at least partially, by the experiences of other people. I’m pretty sure that before the internet existed, everyone had to learn by trial and error. Imagine!

While I may not be able to offer the same well-seasoned advice as the average, battle-scarred design pro, I have the advantage of being freshly slapped around. You see, time has the convenient effect of smoothing over the rough patches. Reminiscing about early days as a sprightly freelancer may not yield the words of wisdom you need to hear. I’m new enough at this that I remember vividly what it’s like to jump in – head first.

So, I’ve decided to do a series of blog posts devoted to addressing the major issues I struggled with when starting out. Without further ado, Here is:

You need a website. If you don’t have one, make it happen. If you can’t make it happen, then set up a blog where you put up pictures of your work, use a portfolio site (like Coroflot.com), or even Flickr in a worst-case-scenario. As long as you have something to show that will wow the socks off your prospective clients, you’re golden.

When seeking work, I was always told to cold-call the entire city. Well, I don’t believe in cold-calling. Nobody likes to be put on the spot by someone awkwardly reciting a cheesy pitch over the phone. I do believe in cold-emailing. That way, you can say everything you want to say without feeling humiliated. More importantly, you can link to your website so they can see how awesome you are. And there’s no need to make it super-formal. You don’t want to be mistaken for the IRS. I haven’t yet gotten to the point where I have to walk in and sweet talk the local businesses, but if your emails are not working, you best hit the road.

Clients can come in many different forms. If you show a design studio whatchu got – and they like your work, then it’s probable that you will be hired for freelance. If you go on Craigslist and show Mr. Jones how well you can draw a dog holding an iPhone– and he likes your work, then it’s probable that you will be hired for freelance. When you’re just starting out, you have to reach pretty hard for new clients. No one knows you or your work, so you have to “ignite the fire” and get them talking. In my experience, everyone I’ve ever worked with knows at least one other person that needs something designed. Chances are, if you’re doing a stellar job, referral emails will start to trickle in. If your projects are one-time deals and your clients immediately seem to fall off the face of the earth, you probably have to step it up a notch.

Keep in mind that your first few projects won’t be the mind-blowing undertakings that you’ve dreamt about. And that’s perfectly fine. Regardless, do the absolute best work that’s humanly possible, and you will be amazed at how far you can go.

Until next time, slackers!

I just finished illustrating a new sheet of temporary tattoos for this season’s Wine Riot – I’m excited for the mayhem that will inevitably ensue when they get here. I ask myself often – “How the hell did I get a job where I get paid to create temporary tattoos?”  Because that, my friends, is the ultimate paradigm of sickeningly sweet design satisfaction. Not only are they fun to illustrate, but applying them to countless body parts is where I truly feel fulfilled in my life’s work. I. LOVE. TEMPORARY. TATTOOS.

In other news, I’ve created a Twitter page. ‘Bout time, yes, I know, but here I am:
twitter.com/MissHGordon

And I loved it. Even the spiders.

Happy 2010!

Yes, it’s true. I, Holly Gordon, am traveling thousands of miles away, into the depths of Micronesia. To a tiny island – isolated in the North Pacific – hovering vicariously over the Mariana Trench, the very deepest, darkest valley known to the ocean floor.

Okay, so it’s not that treacherous. It’s a US territory located three quarters of the way from Hawaii to the Philippines. The native language is Chamoru, the official language is English and hey! it’s “Where America’s Day Begins!”

From what I’ve learned, Guam is a pretty interesting place. Most of the homes there are made out of cement and rebar, so they – and the occupants inside– survive the violent tropical typhoons. The Jungle in Guam is home to pesky ancient Chamoru spirits – the Taotaomona – who will pinch the hell out of you and leave you covered in painful red welts.

No biggie.

There was quite a bit of destruction on the tiny island during WWII. During the rebuilding process, a creature called the brown tree snake made it’s way over as a stowaway, from Australia or Papua New Guinea. This hungry feller had a heyday, feasting on all the exotic, rare and especially beautiful native birds. The island has been without song ever since.

Guam really is jam-packed with curiosity. Everyone there drives, there’s a university, hospital, breadfruit trees, beautiful beaches, water parks, vampire plants, golf courses, the largest K-Mart in the world, giant African land snails, a WWII tank graveyard, pink sand and lots of barbeques. It’s like a tiny suburbia smack dab in the middle of paradise. I’ve even heard it’s comparably just as gorgeous as Hawaii – except that you have to be super careful of the wild packs of hungry, stray pit bulls.

At least there aren’t as many tourists!

Somehow, I have been churning out work for the past 3 and a half years on a dated iMac that seemed to be suffering from a severe case of Alzheimer’s. I finally upgraded to a gorgeous, shiny and impressive 15.4 inch, aluminum and glass (cool!) MacBook Pro with enough RAM for the entire city of Boston.  The display is as bright and beautiful as the sun – with a sleek and sexy figure to boot.

And the most important perk of all: I am no longer chained to my desk! I AM FREE TO ROAM. I love being able to hang out in the coziest corner of a coffee shop with free wifi and good music.

Right now, I’m at Espresso Royale in Back Bay. Where are your favorite places to work?

You know, it’s weird for us kids these days. We get out of school all revved up and ready for our big break. We’re told by our professors time and time again that we must find a job. Keep sending your resumes. Keep calling. We read stories about the people that inspire us – how “they” did it. Parents call on a daily basis, driven by pure anxiety, with an endless supply of tips on how to get it together.

I have a feeling my generation is going to tap out the pharmacies for anti-anxiety medication at this rate. Student loans are looming, rent needs to be paid, there is a global economic downturn – worst job market in years, and my school is already demanding statistics for my yearly salary. In this fabulous economic climate, we need to get extra creative with what we do and how we do it – a little bravery and innovation wouldn’t hurt. And those are two themes that are not recurring in the recycled suggestions of our predecessors.

My response is to weed out the irrelevant advice. A successful career does not have the same meaning that it used to. For me, a successful career involves the intense satisfaction of supporting myself doing what I love, being able to travel, having the opportunity to teach, inspire others, and to work with people who can match me in enthusiasm and challenge my ideas. Climbing a corporate ladder, one rung at a time, until I’m old and immobile is not included in my business plan.

So as I continually explain myself to others – I do, in fact, have a job – and yes – it is for real – I’m going to keep on working and loving what I do. I’m up to the challenge and I’m excited for what the years ahead have in store.

Most of my summer was spent in a wonderful chaos. It flew by and somehow, in it’s wake, I have some incredible finished projects that I can’t wait to show off! I’ve been working hard – building my own brand and getting comfortable with the thought of freelancing as a professional. I’ve settled into a great new apartment with an environment that really encourages concentration and focus. I’m incredibly thankful for finding that!

Now I’m looking forward to that untapped reserve of energy that the autumn never fails to bring. This is the season that everyone in New England is reminded why they are still here. Something in the air changes, and as always in the mysterious fall, come the unexpected, refreshing twists that make life so inspiring and intriguing.