I’ve been largely struggling with the same issue for most of this year having gone from being a sole freelancer to incorporating and bringing on two full-time employees with a real office space.

I attribute much of the “problem” (and I use the term loosely) to the somewhat personal brand recognition I’ve built for Wishingline over the years, which up until this year, revolved entirely around me. Collectively, we’ve spent much of the year slowly chipping away at that while also drumming up ideas on how to change perceptions with hopefully no detrimental impact. It’s been challenging, and as you said, does it really matter? I wish I knew.

What does your phone answering message say? If it answers “Hi this is Derek Featherstone, President of Further Ahead…” then you are not a freelancer. If it answers with “Hi You’ve reached Derek, I’m not in…” then you’re a freelancer. What’s your title on your business card? If it says “CEO Further Ahead” and others have different titles on Further Ahead business cards, then you’re not a freelancer. My $0.02.

@Scott: Perhaps we are leading parallel (business) lives? Though I think our scenarios might be a little different — your brand as Wishingline has been revolving around you, and that is your company. I think my the brand recognition that I’ve built for myself is just as much about this blog — Box of Chocolates — and not so much about the company, Further Ahead. Something we should sort out, methinks :)

@Carl: aye, there’s the conundrum. The office line voice mail message says the offices of Further Ahead. Of course, that gets forwarded to my mobile, which says you’ve reached the voicemail for Derek Featherstone. So, yes. Both. Sort of. See what I mean? I think you’ve helped me sort at least part of this out… thanks!

Great question, Derek.

The book doesn’t say you are a freelancer, however you certainly have a background which readers will enjoy from the interview. It’s a hard one – I have dozens of staff, yet I often feel like I am working for myself. The truth is, I’m working for my staff, keeping them gainfully employed. :)

I often wonder this too (what I am). But then I figure it doesn’t actually make any difference. Folks hire me. I do good work. End of story ;)

@Miles: I know the book doesn’t say I’m a freelancer, and I definitely acknowledge (and honour) the fact that it is in my past. It was only when I read Russ’s post where he said I was a freelancer that it made me think about it. I know it may seem hard to believe that Russ made me think about something, but it really happened!

@Donna: I don’t think it matters too much, really. I do find I’m becoming more conscious of it as we grow and add more people to the team. I am feeling that perception of us as a company is becoming more important. You are right, though — at the end of the day, the quality of the work we do is what matters most.

You’re not a freelancer? Then what are you in the book for! It was all a con! ;)

@Russ: a con? you mean like the one about you reviewing the book? That would imply you actually read it, and we know that isn’t true, because you can’t read. In fact, I should call you to tell you this as you won’t be able to read it.

What do all these letters mean! I’m confused…

How do you know they are letters?

I have to admit, Russ read the pop-up picture book version, in stores soon. :)

Yes, nothing like “Mile’s pop-up book of freelancing”. Highly recommend it!

Walking in late…

@Miles there is a popup version, I have been ripped off! :(

@Derek Personally I promote “me” as a brand and my business, of late its more about me than the business. As I’m more of a Freelancer with a support crew. But I’m very aware of how and what I market brand I’m building or supporting at what time.

You problem is really the perception that others have of what you are. You are really it seems trying to remold the branding perception from Derek Featherstone Freelancer to Furtherahead. Where Derek Featherstone is not really that much of an important part of the equation. He is just a CEO, working for his staff (as miles said).

It’s just a marketing branding issue. Problem is you have worked hard to build the Featherstone brand that you are now having to flip it all and focus on Furtherahead. Mind you this is all relative to the community segment your are looking at. To the web communities you are “Derek Featherstone” to your client and potential client base you are (or need to be) that guy from “Furtherahead”

Business is a strange thing moving from Freelance to Business your goal becomes to make yourself redundant.

I regard ‘Further Ahead’ as a company.

Scott: Same with Wishingline.

Where there is ‘…insurance, benefits, office space,’ these are more than standard freelancing IMO (especially the benefits part).

Does it really matter? Well, probably not ;)

I agree with Matt, and would toss Bam into that mix as well.

In all cases, though, I’m happy to pay a great deal of attention to the past experiences of Scott, Derek and Miles as freelancers to inform my own development.

And now to actually read Miles’ book …

How about nano- or micro-business? I’m a company of one, but I wear many hats. There’s me the W-2 employee of my LLC, me the president of same LLC, me the member (who receives regular distributions) of same LLC, then there’s me the president of another LLC, who contracts for services with first LLC for “tax reasons”. I work from home and take aggressive tax deductions, including home office/corporate on-site gym deductions and member reimbursements (for home office expenses, mileage, “home security”). Almost all expenses (business and personal) are paid with pre-tax dollars. I consider myself an employee, but an employee who has a lot more freedom (and corporate infrastructure/bookkeeping) than your typical cubicle-dweller. No worries about benefits, salary, performance reviews, relocation, downsizing. The only worry is keeping the project pipeline full (which has proven difficult in light of the current economy). And I have no desire for office space (why would I want to commute further than across the hall or loose my home office deductions?) or employees (a spouse and dogs are enough responsibility). As long as there are agencies and clients who agree to work with me on a corp-to-corp remote basis, I think I have the ideal setup. For me, the issue isn’t what to call myself, but how to find/keep clients who are interested and willing to work with my not-yet-the-norm free agent corp-to-corp remote not-quite-a-freelancer company-of-one arrangement. To recruiters, I’m a person. To most clients, I’m a freelancer. But I think my business would do better if I advertised myself as a company.