Embracing the Pirate Side

For a year I played around with the idea of merging the two sides of me: the designer and the pirate.

The first time it came up was during a business strategy meeting with a friend of mine, Dave. Dave has an awesomely creative mind and I needed an outside perspective on my, then, two-year old business. He asked me a barrage of questions and, after scribbling a few notes, recommended several marketing tactics. The session was almost over when I casually mentioned I was a pirate. “Wait, what?” Dave immediately re-opened his notebook and began scribbling again. He looked up after a few seconds and said, “You absolutely have make this part of your brand!” I promised him I would consider it, even though I mentally shrugged it off as sounding too cheesy.

The catalyst

Fast forward several months and I was in the middle of the Providence Design Catalyst grant program with eleven other business owners. During the fifth workshop my cohorts and I were reviewing my website content. Some of them tried to be kind but others were more honest, “It’s pretty vanilla. Your design work is good but it’s watered down by a generic positioning message and ‘meh’ branding.” They were right. I had recently divulged my pirate side by showing them a picture of me in full kit and several of them urged me to incorporate this side of me into my brand.

But it was clear now, especially after several business strategy workshops, that I had to scuttle my current brand and start over. It was getting increasingly difficult to ignore the call of the pirate. Every time I took a business meeting with someone new and they read in my profile that I was a re-enactor, the topic of pirates dominated the rest of the conversation. There wasn’t a single negative reaction to my alter ego.

So why was I so timid about rebranding myself? The answer was fear. What if people didn’t take me seriously as a designer? What if I couldn’t pull off the rebrand in a convincing way?

I finally decided there’s was nothing to lose. My “coming out” as a pirate/designer would be the night of the Catalyst Showcase, when everyone in the grant program would give a two minute business pitch in front of mentors, workshop instructors, city officials, local artists, and friends. My presentation was the final one of the evening, which only increased my anxiety. No going back now.

The Design Catalyst cohort. “Closeted” pirate on the far left.

Explaining to Mayor Elorza the context of being “fully-cocked.”

Fully cocked

A friend who runs a business incubator reviewed my pitch script and said, “You only need one slide. The pirate slide.” The focus of my pitch was about brand strategy; using a flintlock pistol and the phrase “going off half-cocked” as a metaphor for businesses neglecting their brand strategy. There was a joke at the end of my pitch which credited the Design Catalyst program for giving me the courage to launch my own rebrand and become more “fully-cocked,” as it were. Providence mayor Jorge Elorza had arrived late for the event and only caught the last 20 seconds of my pitch. He approached me afterwards and said, “What is it exactly that you do?” I had the pleasure of explaining to the mayor the context of being “fully-cocked.”

Fully Committed

After the success of my Catalyst presentation came the hard part. Redesigning my website and committing fully to my new brand. I gave myself a deadline of one month and told several friends about my deadline so I couldn’t weasel out of it later.

I recruited my friend Bill to create a video that recreated my “half-cocked” Catalyst pitch; this time in full pirate kit and firing my flintlock pistol (I warned all my neighbors they were going to hear some loud “booms” and hoped they wouldn’t call the cops). You can watch the video from my home page.

My new website launched a couple of weeks ago but I wanted to give myself some time to work out the bugs before making a big announcement (like this post). In hindsight, I’m a little embarrassed it took me a year to screw up the courage to rebrand myself. But now when I’m talking to a client about being more authentic with their brand I can honestly say I understand their anxiety, but I can also honestly say it’s ok to embrace your pirate side.