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.

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.

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.