I was chatting virtually with my friend Britt Raybould about just what it is that she “does” for work; this has been an ongoing three-year conversation since she first introduced herself to me at South by Southwest 2007. I know she’s intelligent, competent, driven, and writes well; I just didn’t know exactly how to frame these desirable qualities in my mind in a “work” context.

In the last exchange we had this morning, she shared with me the fruits of a night’s thinking about the problem, and bing…I finally got it. And at the same time, I had an insight about how I should tackle the challenge of describing myself in a way that felt intuitive. It’s a matter of remembering that the biggest challenge of describing yourself isn’t coming up with the right keywords and categories; it’s being able to paint a picture in people’s minds about how they work with you.

I’ve been spending a lot of time over the past few years figuring out how to describe myself accurately, and I actually enjoy this. I love trying to find the differentiating nuances in my work that also reflect my personality. However, I haven’t spent so much time thinking about how to “paint the picture”, figuring that so long as I kept showing things people would figure out if they liked what I did or not by themselves. It’s a practical implementation of “The Law of Attraction”, the idea that “like attracts like”. It also is a good way to not have to make a decision about what it is that I do in convenient “HIRE ME FOR THIS” form. This is probably because I hate labels and boxes; they feel so limiting, and I that’s why I don’t have a regular “business website” packed with the usual service offerings.

Since I need to start rustling up business for April/May 2009, I can’t put this off too much longer. Thankfully, Britt’s comments to me have kicked me in the butt towards action.

The Standard Approach

As much as I prefer not to be pigeon-holed, I must admit that labels and boxes are effective tools in narrowing down a potential niche of work. I can throw out a few of them quickly–design, writing, interactive, Flash, productivity–and a certain narrowing of understanding occurs. Potential clients actually get an idea if they can use me or not to get certain types of work done. The questions that inevitably arise next are:

• What kind of design/writing/interactive is that?
• Are you good enough to meet my needs?
• And in the best case, will blow away my expectations?
• And will this be a great value for my money?

Back when I worked in more traditional web agencies, my typical reaction to these questions would be to provide the information I thought the prospective client needed to make the decision, using as little boilerplate as possible. By boilerplate, I mean making empty claims on paper. You know, stuff like, “you should hire me because I am excellent and conscientious and devoted to making you look good.” It may be a true sentiment backed by genuine intention, but it lacks substance because experience has also taught us that intention and action do not guarantee satisfaction. In other words, you may get the exact results you paid for, but you might not be happy with what you got. Que sera.

So instead of focusing on these kind of statements or relying on my client list to make indirect claims of excellence, I put the thinking work into the response, provide useful insights, and show examples of past work that are relevant to the problem. A lot of people freak out at this approach, saying that I’m giving away the ideas to a prospect who is likely to turn around and just implement the solution themselves, or even just use it to re-pitch their RFP to get a lower price somewhere else. While this is certainly a possibility, I don’t see how I can lose. In the best case, the prospective client is impressed by my analysis and candor and we start a good working relationship. Or, the prospective client sees that the way I’d implement the problem is how they would do it too, and they’re happy to pay someone to do it right because they don’t have the staff resources to handle it themselves. And if the prospective client is just fishing for free information for the cheapest price under the guise of putting out work for bid, they’ve done you a favor by looking elsewhere because they’ve just shown a lack of business morality that will bite you in the butt later. I’d rather just provide the insight for free, then consider the time well-spent in collecting another datapoint on what people are up to in the business world.

Freelancing is a feast-or-famine lifestyle at times, and since clients are perceived the ones with the power, freelancers is to think in terms of maximizing their exposure to as many clients as possible. Then, the trick is to be as flexible as possible without hurting yourself. This is basic survivalist thinking, which begets what I might call the standard freelancing approach:

• Where do prospective clients look for freelancers? I better make sure I’m with all the other freelancers then, because that’s where the clients will look.
• How do prospective clients find freelancers that do what I do? I know they ask for, so I better list those same things so they find me in keyword searches.
• How do I convince prospective clients to hire me? I need to show them the work I’ve done that is the work they are looking for.

Once you take care of these three questions, the process becomes a game of numbers and luck. If enough people see you, and you stand out in a way that they happen to like, you’ll get chosen. Superb salesmanship and follow-through then come into play, and your reputation will start to grow. It just takes time.

The Personal Approach

I’m not planning pursuing a straight service model, otherwise I’d just be hanging my set of keywords up on various job boards. The skills I have, in other words, are NOT my offering. I’m seeking a certain kind of personal interaction that happens to make use of my skills; this is the expression of my general desire to create more “awesome and inspiring” experiences for myself and people that I like. The logic may sound business-backwards, I know, but wouldn’t it be great if I could make it work? And I know it can work…just go to SXSW Interactive or a Podcamp sometime and see for yourself.

I see my challenge not as “accurately categorize the work”, which is how I would describe the Standard Approach outlined in the previous section. That’s phone-book thinking, guaranteed to put you in competition with everyone else that “does” the same thing. And from a design perspective it’s a big sin, similar to organizing a website based on how the database schema came out, or like writing code documentation based on a list of methods in the API. This is dumb, because there is little sense of what causes what and why, which is essential to creating any kind of meaningful understanding. You just end up with a collection of descriptors that are not connected in any kind of narrative or qualitative sense, which ends up being as frustrating as a bad round of charades. You need to have some kind of story that lays down the foundation, which then helps put you in context to the prospect’s vision of the good life. That’s a great place to be…now you just have to deliver! :-)

So for me, I’d like to reframe the questions in two parts. First, from my perspective:

• What kind of people do I like and respect? Creative, generous, positive people who are trying to do something different and are willing to be a little weird.
• What are my favorite skills that can be made a productive part of their working life? It’s writing, brainstorming, categorizing, explaining, analyzing, and making things make sense to me using whatever supporting media I can dream up. In the past I’d made the mistake of doing things that were not among things I enjoyed doing (straight website development, for example), and the results were disappointing.

And from the client’s personal perspective:

• Are you someone that I’d like to work with? This is a matter of showing enough of myself and my personality that’s relevant to a good mutual working relationship. The various tools and writing I’ve done become the marketing collateral; I’ve just got to make it easier to look through.
• What kind of things can I ask you to help me with? What kind of things can you handle for me? This becomes a statement of what I’m willing and able to do.
• Can I actually envision using your products and services to make my life better in some way? That comes down to composing a picture and telling a story.

The combination of the personal approach with the standard approach creates, for me anyway, a more well-rounded strategy for pursuing new business. You could say what I’m doing is just another way of explaining a certain kind of salesmanship and marketing. The difference, though, is that the interaction satisfies both parties in an authentic fashion: “This is me. You are you. Is there a genuine complement of skills, needs, and collaboration in the making? Let’s find out.”