Be About It

A few weeks ago a friend asked me for advice about running a freelance business. For years she had run large non-profit organisations, published books of her research and writing, and written op-ed’s for major newspapers like the New York Times. But now it was time for a change, time to go independent.

She wanted to know about practical things like accountants, contracts and presentation, taxes and payroll. All of the things you don’t think about when you have a regular job with a regular pay check.

She also told me that she appreciated that I was really thoughtful about running my own studio. She wanted to talk about the philosophical and ethical questions that come up when choosing clients and thinking about operating a business.

I’m asked questions like this from time to time, and they always elicit two reactions, from both of which much can be learned.

My first reaction reveals my own insecurity. Why is this person who has been a boss, with a title, and a regular pay check, a person at parties can easily recite their title and people will understand exactly what they do, asking me for advice? I’m just some freelancer, I don’t even have a job.

Second, I always feel a bit stumped. I would be lying if I said the path to success as a freelancer was a linear one. There were times when I had no real plan. There were other times when I had a plan, but the outcome of the plan looked nothing like what I set out to do (more about this later).

These reactions beg the question; just exactly how do the people who ask me for advice actually view me? This is a clue into how often we undervalue what it means to work as a freelancer.

If these people thought we were as stupid or mediocre as we thought we were, and if indeed they are as great and impressive as we think they are, then why would they ask us for advice in the first place? It is a real lesson – we’re often selling ourselves short, setting ourselves up for failure and not even giving us the change to reach our full potential and find out what we could do.

It’s also an opportunity to understand what it is we actually do, and how we got here. When in a networking situation, or when you have to fill out the dreaded “occupation” form on linked in or a credit application, it feels like we can pick out of a hat, anything from manager, to art director, pixel monkey, to graphic designer, book editor, even at times psychiatrist to confused or insecure clients.

However in my daily practice these titles doesn’t seem to matter much. My mental capacity is directed at what ever task is at hand. I’m deep in Indesign working on a table of contents and index for a book, or I’m in a presentation helping a client understand why the design choices I made are the best solution for their company, from both a business and aesthetic standpoint. Or I’m working with a developer to figure out how to translate a complex piece of code into something that is easily and instantly understood by a web site visitor.

But on a larger strategic scale, how we present ourselves to the world really does matter. We must have the confidence to tell the story of what we do and why it matters.

Because of our cross-training we are able to bring new perspectives into play. Because we are freelancers, not beholden to a single employer, we enjoy the freedom to tell the big boss his idea isn’t as good as he thinks it is, or to call out someone who is shirking responsibility. We don’t have to deal with the interoffice social repercussions that a person tied to a pay check must.

It’s a sacred position. I started to understand more why my friend asked me not only about practical matters, but about the underlying philosophy . It is after all a life choice – many freelancers don’t realise they perform executive and upper management level decisions everyday. They are clearly perfectly capable, more so than the domain dependent art director or account manager, they just haven’t been given the title that allows them to believe themselves.

An important aspect for me about being freelance is having skin in the game. I learned more about this idea from Nassim Taleb.

I noticed that some graphic designers, often connected to universities and that held permanent teaching positions, who only designed for other designers. They didn’t design for clients. They didn’t have to make money. They didn’t have to survive. This wasn’t the position I was in. I had skin in the game.

This except from Nassim Taleb gives a little insight into what skin in the game is:

“Plumbers, bakers, engineers, and piano tuners are judged by their clients, doctors by their patients (and malpractice insurers), and small town mayors by their constituents. The works of mathematicians, physicists, and hard scientists are judged according to rigorous and unambiguous principles. These are experts, plus or minus a margin of error. Such selection pressures from skin in the game apply to perhaps 99% of the population. But it is hard to tell if macroeconomists, behavioral economists, psychologists, political “scientists” and commentators, and think-tank policymakers are experts. Bureaucrato-academics tend to be judged by other bureaucrats and academics, not by the selection pressure of reality. This judgment by peers only, not survival, can lead to the pestilence of academic citation rings.”

If you have skin in the game, it’s hard to truly fail. At first it might seem counterintuitive – you want total freedom to create whatever you want. The problem is this total freedom often leads to total chaos. Running a business forces you to be disciplined, and to make choices that effectively balance art and design, enabling you to come to solutions that you otherwise never would have thought of.

Of course, you might not succeed in the way that you originally envisioned, but it’s much more likely that you’ll do what it takes, and do it so that your idea of success isn’t simply based on what others expectations of you are. Instead, you’ll do what you need to do because it matters to you. You understand your own parameters for success, and you aren’t basing it on how many likes your project or business is getting in IG.

This is some of the best advice I can give – if you choose to do something, do it because you believe it is important, and that it matters, and then don’t stop doing it until you’ve nailed it.