Leading Creatives and You’re a Sole Proprietor

For ten years now, I’ve had the difficult job, probably my MOST difficult job, of leading a team of creatives.  That team is a team of one.  And, I am the team.  I’m not boasting.  I’m saying it like it is.  In my past, I’ve had the pleasure of working with and leading teams.  I’ve had some successes and a TON of failures in those efforts.  For the past ten years though, I’ve earned a “Leading Creatives” badge and I want to share.

My first task has been to learn what a creative is.  That started with a lesson in what creativity is.  I long thought creativity was all about inspirational moments and butterflies flying around my brain creating vibrant ideas with pixie dust.  Ahh…no!  Creativity is the result of THINKING.  Deep thinking, scientific thinking, computational thinking, social thinking, systems thinking and other labels are fine.  Thinking, and the resulting ideas are the foundation of a creative’s work.  Creatives can’t wait for a moment to be inspired.  Ideas won’t just appear at the wave of a wand.  So, what we do as creatives to ensure ideas CAN happen is my next lesson.

In past jobs, I would spend the majority of my time tracking things that needed to get done.  I had spreadsheets of operational efforts that I would monitor and make notes on.  I would walk around (you know, that Manage by Walking around method) and talk to people.  I would ask how they were and about their work.  I could come back and fill in my sheets.  Tracking was king.  But, over time, tracking became my worst professional enemy.  It filled my days, but was it filling a purpose?  As a sole proprietor, I’ve learned the answer is NO.  We often fool ourselves into thinking being busy operationally equals value.  As a team of one, I can say, being busy means little.  Productivity means nothing if we equate it to keeping up with the influx.  We must get to the point were we are managing, that’s right, managing our creativity to ensure we are moving forward, innovating, ideating, evolving…CREATING.

So, how?  I think of two things to guide my day.

Be Pragmatic & Product Oriented

Being pragmatic as a creative means building an actionable, adaptable plan for everything I do. I use a project management tool for all of my work with clients and personal projects.  Clients expect me to be creative or they wouldn’t hire me.  For my own work, I don’t have much time, so I need to be efficient.  I once heard a quote by an famous author (I forget who).

“I have to be creative Monday through Friday, thank God it happens each of those days at 9:00am.”

I love this quote.  It’s how I feel every day.  I have to be creative, it’s my work.  If I had to wait for inspiration or the butterflies to feel inspired, oh man…I would be in trouble.  Leading creatives means kicking off creative efforts as needed.  “Ok gang, let’s create.”  That statements makes me cringe, but it is real.  Work begins each day and that’s reality.  So, creativity needs to do the same.  In my project tool (monday.com), I have a goal when I start something new.  I capture the first task quickly.  I don’t think about all the task, just one.  I type it in, add an ESD and ECD (earliest start date and earliest completion date) and then I add a few notes.  Typically by then, I start to map related tasks. I don’t worry about dependencies, or order, priority, urgency or any of that at this point.  I just capture tasks that represent relationships to other tasks that support the goal.  If there are three, there are three tasks. If there are ten, I capture ten.  When those thoughts seem complete, I start on task number one.

If I’m doing this work more closely with a client, we do this work together and build a shared understanding of the tasks.  We hold each other accountable for efforts and take ownership of specifics.  When our ideas end at that time, we break and get to work.

In either case, is the plan right?  Well, the definition of a project is “an effort that is new and has not been done before.”  So, yes, the list is right as far as we know.  I trust it.  I use it for all it’s worth.  I obey it and do what it says.  But I am it’s boss.  I change it as needed.  But, I don’t devalue it by ignoring it. I don’t delete items without considerable thought.  I don’t let it limit me or the work.  I add what is needed and consider additions deeply. I keep the creative work in focus and appreciate the power of the PM tool to keep the details out of my head and in clearer view in print.

Being Product Oriented means each day, I produce a product, a complete or incremental version is the goal.  Products are things that are tangible and could be delivered to a customer at some level.  When working with clients, I just think “what can I show them today that is different than yesterday?”  This is where my philosophy of just keeping up with operations isn’t valuable comes from.  Even in the most operationally oriented work, creatives strive to build a product that looks different today than yesterday.  Maybe it’s a report, a dashboard, a narrative about the day’s events.  This is what makes leading creatives hard yet rewarding.  And, as a team of one, playing both roles incredibly complex yet fulfilling.

There’s more to my story than this.  But, I wanted to share the starting point.  Much like my creative effort, my first task was to share the big picture.  With that complete, I can’t wait to hear your thoughts and to build on these ideas.




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