Taking the Plunge (And Coming Up for Air)

Freelancing can sometimes feel like a roller coaster of emotions, and this post finds me at one of its lowest points. Eight months in, now seems like a good time to consider the ride taken so far, and consolidate some of the lessons learnt.

Since taking the plunge – which increasingly seems like an apt description – in March, I’ve enjoyed a varied range of work and experiences, just as I had hoped. It didn’t take long to land my first project. Working alongside my former colleagues at Clearleft, I pointed a co-operative retailer in the right direction as their online team set about a responsive redesign. Around the same time, I prepared a new talk, which I went on to present at a number of different events around Europe. I then spent much of the summer hunched over my laptop in various coffee shops as I wrote the corresponding article for A List Apart.

I welcomed this opportunity to think more deeply about the work I do, and enjoyed spending time travelling around Europe. Yet since the conclusion of that first project in July, besides a few week-long engagements, I’ve yet to find a project, let alone one I can really get my teeth into. This fallow period has seen plenty of misdirection and introspection, and I’ve come to realise that freelancing is no place for arrogance, naivety or pride.

Foolish mistakes and valuable lessons

While I was working on that first project, I made no attempt to secure any follow-up work. To be fair, I wasn’t sure when it would end – at one point it looked like I may be contracted on it all year – but I could have used this period working in London to attend events and build my network there. When the project did finish, I decided to take a month off to concentrate on my own projects, and again, did so without looking for new clients. Projects don’t just fall into your lap because you have a respectable résumé and a few thousand followers on Twitter, and no amount of retweets can make up for such a colossal lack of business sense.

Of the enquiries I did receive, only a few piqued my interest. Only now have I recognised the need to be explicit about the type of projects I wish to work on. Refusing to work with certain organisations is perfectly principled, but I should be communicating loudly and clearly about where I do wish to invest my time and energy. That said, I could also be more open-minded; all projects offer learning opportunities, and some may even lead to greater rewards.

Following up on the first interesting lead, I thought writing a proposal would be enough to land the job, but I never heard back. Nor did I chase up, because a second lead followed. After a few weeks of back-and-forth, it was decided that the project would be better handled by an agency rather than an individual. After third and fourth leads came to nothing also, I finally realised that chasing one lead at a time is not an effective strategy; nothing is guaranteed until a contract has been signed.

Birth of a salesman

Working for yourself leaves little room for maintaining any dignity. Selling myself is not something that comes naturally, nor does asking for help. The thought of tweeting about my availability, or asking friends and peers for referrals fills me with absolute dread. Doing so feels like an admission of failure, but in fact the opposite is true; I suspect having not done so is precisely why finding work has been difficult.

The good news is, having recognised these character traits, I can now start to adjust them. If finding work means gaining confidence and humility, clarifying my ambitions and being more positive and outgoing, not only will I become a successful freelancer, but a more capable person too.

This entry originally appeared on The Pastry Box Project