As with every major life decision that you share with other people, there will be the occasionally welcome opinions about how you should go about it, and whether it’s a good decision to begin with. I think it’s always a good idea to bring up your plans to other people because you never know what you’ll learn about yourself, or about them. And either way it’s usually interesting. But one of the effects of this is the inevitable naysayer. Those who believe, for whatever reason, that whatever you’re about to embark upon will fail for innumerable reasons. And no matter how confident you are, their opinions make you question your decision.

In my case — going from a decade of solid full-time work for large corporations to the life of a freelance designer, there are many things to consider. And it’s not a decision one arrives at overnight, if at all. In fact, there are so many people who would never consider working for themselves that there is a long-held belief that there is more security in working for someone else, than working for yourself. I am here to tell you that it is at least as, if not more risky to work for someone else than it is to work for yourself. Beyond any notion of having more control of your schedule and project destiny, if your income comes from diverse sources, you are *more* secure working for yourself, than if you work for someone else. If you have a single job working for a large company, and that company restructures, or gets bought out, or the recession causes them to cut back, you can lose your job. And there you are. With no source of income. If you have multiple smaller jobs, for multiple people, and one doesn’t work out, you have all of the others.

I’m not saying it’s easy — there’s no falling back on others or blaming someone/something when things go wrong. It’s just you and the quality of your work, and your ability to communicate effectively that keep you afloat. But to me, that’s the *reason* to work for myself. I *like* being invested in what I’m working on. I *like* knowing where it’s going and how it will affect things. I *like* that the buck stops with me. And, I like that I can live wherever I want because my work is location independent….

And out of kindness, many people still tell me how risky it is — how if I move somewhere with fewer jobs because it’s more affordable I better have a back-up plan, and how freelancing without face time is a pipe dream. And yes, it’s risky, but not any more risky than staying where I am and not feeling satisfied with my work. And, yes, living somewhere that doesn’t have tremendous job opportunity will make it more difficult to find a job there if that is important, but if I had to find a job working for someone else, why couldn’t I move again? And, yes, “facetime” can be important, but as we move forward, there are better and better ways of creating that connection with people from afar, and it becomes less and less important for us to be in the same room together, and most of the people I’ve done work for I’ve never met. I’ve noticed a definite gap regarding that thinking — how those whose whole professional career has been during the time with the internet was critical, or those who have embraced the internet economy whole heartedly completely understand. And while it’s not that important to me to help those who don’t understand, it is important to me to not let their thinking make me doubt myself or my goals. Just because not everyone sees the path to get there, doesn’t mean it doesn’t exist.

As my husband and I think ahead to our next move, we’re considering something that hasn’t come up to any great extent for us before: how what we want in our home will be significantly determined by the fact that we will both be working from there. We both regularly work in our current home, me in a rather sunny breakfast room in which we’ve got a desk, and he on our sofa in the living room. But in the long term, that’s very impractical, not only for the health of our eyes and our backs, but also for our marriage. We really each need to have a space where we can keep things however we like to make working more efficient. Even less critical things like the amount of tea we drink while working has meant that we’ve added “instant hot water” to the list of must-haves.

We were just in Portland, Maine — one of the places we’re thinking of relocating when we’re ready to be full-time freelancers later this year. At the beginning of spring (when we were there), it wasn’t as obvious, but during the long stretches of frigid winters they have there we can both imagine that having plenty of space in your house to stave off cabin fever would be critical. But how practical is it to heat a huge house through 6 months of winter? And unless we have solar, how well does the idea of a $400+ heating bill each month factor into our desire to live well with less money? Even with wood fires and the warming aerobic activity of chopping wood.

As of this moment, we’ve decided that we would each like to have our own office space that isn’t shared with something like a dining room, but can serve double-duty as a guest room when necessary. Ideally, these office rooms would be located near both a bathroom and a kitchen, and would have enough space not only for our desks and various peripherals, but also for filing, and clean workspaces on which non-computing projects may take place. They will have good natural light, and plenty of wall space for art and a corkboard on which we can pin whatever’s important. Since neither of us have clients coming to the house, we don’t need a meet & greet public area, but I will need a space in which to do pottery which can be very easily cleaned, and wired with its own circuit for the kiln, which will need to be adequately vented.

In my mind, this means we’ll need a house that is mostly on one floor, with a small out-building in which I can build a pottery studio. We saw lots of spaces like this in Maine, which is promising. Our next stop is Portland, Oregon, where heating bills will be lower, but still a consideration, and it’s more expensive per square foot of space. It’ll be interesting to compare the two after that trip.

There are times when I totally disagree with a client. As in, they give me a direction that I question, then I come up with a solution that I think interprets that direction in a way that reflects good design, and they decide that they simply must have ______. And ______ is usually terrible. It’s a fine line to walk with clients where you want to give them what they really want & hopefully get a great referral or repeat business, but also don’t want to put your name on something you dislike. You can always pick and choose what goes in your portfolio to reflect your work — there is a whole collection of work I did for a vampire romance novelist that I think served its purpose, but isn’t something I want to reflect my skill set and therefore stays safely on my hard drive.

I think it’s a designer’s responsibility to try their best to really get at the goals of a project — and work from there. So, rather than finding a way to include a large illustration of a magnifying glass to designate something as “mysterious” (for example), because that’s the image the client has in their mind’s eye, to interpret “mysterious” in a way that serves the purpose of the project, making sure not to threaten the usability or content clarity of the site, and to create something you’re really proud of.

To get to the point that you really understand the goals of the project, and to help the client understand that what you’re there for is to come up with a design that responds to those goals, and not to draw a digital picture of what they have in their head, you have to establish trust. Trust in your skill set, but also trust as a person. There are too many “designers” out there who charge little money for either templates that include text and images provided to them, or a direct mapping of a client’s direction into a website, without any thought as to who the audience is, what *their* goals are, or really helping the client think through what they’re trying to achieve. Either that, or their goal is to create something where the primary goal is gorgeousness, because it’ll look great in their portfolio and allows them to feel that they’re keeping up with the Joneses. Don’t get me wrong — there’s a time and a place for projects whose sole purpose is to be beautiful, but most call for a great design that is also beautiful.

So, when pitching for a project, make sure the potential client understands your value add — spending time to get to know them, understanding the goals of their project(s), creating a design that is not only beautiful but useful and usable. For you, the designer, your investment in creating trust with the client will allow you to better influence the projects you work on, and have a higher ratio of projects you *want* to put in your portfolio, and hopefully get repeat business and plenty of referrals.

You may or may not have noticed the facelift over at Outbox Online. A while back I had created an online portfolio for myself that was really focused on letting the work speak for itself. So much so that I think I was afraid of having much, if any, visual design associated with the site. In a way, it’s similar to selling your house — you want to keep it as neutral as possible so that potential buyers can see themselves there. In recent memory, I’ve changed my mind about that decision. I really wanted to have a personal aesthetic associated with the site, but allow the work to show the variety of things I can do. Part of what I offer is consistently (hopefully) clean, fresh and unique, and I wanted to capture that in the design of my own site.

In a similar way, it was difficult to design my business cards. Because of an event, they needed to be designed in one evening, but I’m still fairly happy with them. And it’s important that they have a visual relationship to my site, so people who look from one to the other see a relationship between them.

Even one day later, I see things I may want to change about the site, but I’ll sit with it for a week or so before I make any decisions.

When something happens in life, like your kitty getting sick, you just phone into the office and tell your boss you’ve got a family emergency and you’ll be in as soon as you’re through with the vet. Your job will be there on the other side, after you’ve signed off on the iv fluids and x-rays. But when you work for yourself, it’s not so easy. So much of freelancing is availability. How responsive are you when a new client gets in touch? What about your on-going projects? When you’re a one-woman show, it’s hard to find the right balance, especially early on.

I suppose with existing clients it’s easier — you’ve developed a rapport with them already and a level of trust. But when you’re establishing new relationships, especially remotely, it’s hard to know the right way to be unavailable.

When I remember, and know my schedule ahead of time, I can change my outgoing message on my voicemail, or create an auto-response to emails letting people know my availability and when they can expect to hear back from me. But in a world where the expectation of email response is in the minutes, not hours or days, I’m not sure of the answer beyond making sure my iPhone is fully charged.

Last Christmas, my father-in-law passed away in Scotland, and alot of my time leading up to that event was spent waiting for hospitals and doctors, and sleeping odd hours. Because of that, I continued my online freelance work from there — it was good to have something I felt confident about when everything else was seemingly falling to pieces. A client at the time inquired as to why I was in the UK, and after telling her, she was astounded that I was so responsive given the circumstances. In a way, I completely agree that work should have been the last thing on my mind. But in another way, the familiarity of it, and the looking-towards-the-future that it entailed, was a positive thing.

I wouldn’t be doing this if I didn’t really enjoy it, but knowing when to start and stop is a challenge.

Ah, designing for yourself. Even if you follow the same process that you use with clients (ie: setting goals, mapping pages, drawing inspiration, etc..) it is infinitely more difficult than creating something for someone else.

My portfolio site is constantly evolving. Not only as I add new projects to it, but also as I strive to find the balance between enough design to create my own brand, but not so much that others can’t see their own projects executed by me. In some way, just having a good portfolio design in and of itself is enough — if people like what they see, they’ll have more confidence that they’ll like what you create for them. But in another way, you don’t want to pigeonhole yourself into a particular aesthetic.

I know that people hire me because they’re looking for an uncomplicated design, and that thread runs across all of my projects. So, I start with that. I choose colors and fonts that express a friendliness and informality that’s important to me and my process. I try to make the site as easy to navigate as possible, and provide enough examples of recent work that someone can get an idea of my range, but not so many that someone gets lost in them. I give people a way to get in touch with me, and some idea as to what I’m like as a person.

While I continue to be both a full-time user experience designer and a moonlighting freelancer, I consider the goal of the site. It’s not to find another full-time user experience position, so I remove elements that would present me that way. It *is* to create more freelance business, so I highlight projects that I think will help with that goal. When I transition over, I’ll have to reassess given the change in my schedule. Do I need a 1-800 number? What about a business address?

People find me for their projects in a number of ways… sometimes they search the internet for a web designer, other times they see my link on the bottom of one of my project pages, and then there are people who hear about me from someone they know. In certain cases I’ve approached someone I want to work with, generally via email, pointing them to my portfolio and letting them know that if they have a future project they think might suit me, to keep me in mind. In one particular case, they have turned out to be one of my best clients.

One of the things I’ve never done is any sort of advertising, and I don’t know whether it’ll be something I’ll need to do when I’m freelance fulltime. I’ve found a niche with author/book sites, so I could always target literary sites that offer advertising. I’m reluctant do try it at this point, because I’m not sure I could take on any additional clients right now, but that may not always be the case.

Interestingly, especially when people find me themselves, they are all over the map with their understanding of the internet & many times my projects begin with me explaining how to purchase a domain, and “what is a web host anyway.” A great way to build trust with a new client is to spend the time to answer *all* of their questions up front… and to anticipate what they may ask you next. It’s a great opportunity to establish a rapport with someone new, and to help them feel like they made the right choice hiring you. Usually, the time you spend here isn’t billable, so think of it as an investment in your business.

Once the domain and host are organized, I usually begin by building a simple Visio visual sitemap of the site based on conversations with the client. This helps to make sure nothing is overlooked, and that the site is organized so that the client is happy, and it’s easy to navigate. I do this ahead of sending a contract and a 25% deposit invoice. Only once has a prospective client walked off with it and used it on a site they built themselves. I treat it like an addendum to the contract — it defines the scope of the project.

I generally send over the contract, a 25% deposit invoice, and the sitemap together. I also ask the client to send me links to designs that they really like, or really hate. I point them to places like CSS Beauty, Web Creme, Screenalicious & Smashing Magazine to help them out with this, as many times it’s very hard to describe in words what you’re after. Once I receive the signed contract and the deposit in the mail, I start the actual design work.

Usually, I create a visual design mockup in Photoshop. I make sure to keep in mind what will work well in a CSS layout, but not to let that get in the way of the desired effect. I start with a 1024×760 document, put up guides for a 780 pixel wide, centered column, and go from there. Usually, I design fixed-width layouts, and I find these dimensions work really well. Sometimes I’ll create a single mockup, other times, usually when I have less to go on from the client, I’ll create more than one and let them choose. Some clients are happy with it straight away, and others want to get really involved in this part of the process and do a great deal of art direction. I really let the client dictate this part of the process, but to keep things efficient, I make sure to stipulate in my contract that I include up to 5 revisions in the project cost, and beyond that I charge my hourly fee. Speaking of which, usually I charge a per-project fee, and only bill hourly beyond what is defined in the contract & sitemap.

After the client signs off on the visual design, I get to work on the HTML/CSS. If the client’s web server is available, I FTP the files over there. If not, I host them on my own server for the client to review. I usually ask that as much of the content as possible is available before I start in on each page. And if the exact text isn’t ready, to give me an idea of how much I should anticipate. This helps make sure we’re both using our time efficiently.

Once the pages exist and all content is included, the project is finished. This is when I send over the final invoice, update my portfolio (if it’s something I want to include), and make sure my invoicing spreadsheet is up to date.

And that’s the standard process. Of course each client is different, and each project is unique… and I’m constantly evolving this process as I learn.

I started a blog called “Outbox Online” in the year 2000 almost immediately after moving to San Francisco. My plan was never to move to San Francisco, but when the opportunity came up to have a job here, I jumped at the chance, and drove across the country with my houseplants in the back seat. Having just left the UK, and with friends there and all over the east coast of the States, I needed a way to keep in touch, and this new “blog” thing seemed like it might be just the thing.

Since I was starting a career as a designer, I used my then-blog as a playground for new ideas. I changed the design and layout sometimes as often as once a week, and pretty soon other people were asking me to design layouts for them. Then I met Catie. Catie had a greeting card business, and she wanted an online storefront, and she wanted me to design and code it for her. I had never done anything beyond html with a little CSS and javascript, but I jumped into the project and taught myself how to make a shopping cart. Thankfully, there are wonderful (and cheap) outsourcing solutions for that now, as my biggest lesson was that the kind of work involved in creating a shopping cart wasn’t really my cup of tea.

Catie was my first official (wonderful) paid client, and since then I’ve taken on more and more projects, and am working towards doing freelance design fulltime. I still work on Catie’s site, and am thankful to call her a great friend.

Transitioning from the regularity of a well-paid fulltime gig, to the uncertainty and irregularity of a freelance career is a huge undertaking. One that requires lots of planning and preparation, courage, organization, and smarts. This blog will be about that transition (and beyond). Beyond doing various web design projects, I plan to create and market print, ceramic and multimedia art items, and so it will also be about balancing my creativity, and creating a working life.

I’m married to *the* Graeme McMillan, my best friend & the sexiest man in the whole world. We live in San Francisco with our cat, Luna — but to make our freelance life more affordable, we may move to Portland, OR or Portland, ME. Stay tuned.