Set yourself free

I was talking to a friend the other day.  I told her about my new job, the one where I am, nominally at least, in charge of developing a whole new practice within an established and growing company.  She was curious.

“How many people work there?”

“240, 250, maybe.”

“Oh, wow. That is so many.”

I laughed.

“Really, it’s just I have been independent so long, that is all I know.  All independents, people who don’t even put on shoes to go to work.  We just live in California, and wear very expensive things and very cheap things, and we are very selfish, and very happy.”

I stopped laughing.

I live in New York.  I like shoes.  I have a collection of them.  But there were words missing from my life: independent, selfish, happy.  My world revolves around a dozen stars, making for a crazy-making orbit of loop-de-loops and figure-8s.  I have a technical boss, an actual boss, and a dozen constantly changing mini-bosses depending on the project I work on.  And then I have clients.  I am not the boss of me.  Even my housekeeper has to chase me down to book appointments.  If it’s something that will be for my benefit or enjoyment, it is always crammed in to an already overloaded schedule, and only adds to the crazy.

My role is defined by all these bosses.  I have limited influence, few privileges, and loads of responsibility.  And in that company of 240, 250 maybe, I am one of three who do this work.  I am also the only one of those three who have ever done this work before.  In essence, I am disproving Donne everyday – this man is an island, but it isn’t bloody Ibiza.

So okay, that’s not their fault.  That’s mine.  I chose to stay on this path – this path of constantly moving away from the roles and responsibilities and tasks that I really enjoy so I can keep moving upward.  But “up” is a poor target – up where? Up with whom?

When my friend said she was happy – and her Facebook photos of herself, her husband, her two kids, on beaches, on boats, on vacation say she is – I took sudden stock of my life.  It was very visual – a solid image in my mind.  Me, at a desk, frustrated and slowly packing on stress-related inches.

I can change this, I thought.  I can be something else.

So I did something on the spur of the moment – I went to Miami, to see Art Basel.  I walked along the beach, my feet in warm sea water in December, and I thought – what do I really want to do?

There were so many things I wanted to do:

• Write a blog about brands that could be a testing ground for chapters in a book.
• Start a strategic consultancy with a focus on creativity and content.
• Develop a model for strategic planning in the entertainment business.
• Invent social network-based games that encourage people to share certain kinds of information with the cloud that can be mined and sold.
• Write a TV script.

These were a few. There are others, and there are permutations of these.  If I focus on one, I will miss the others and ultimately lose interest in the one. My brain likes lots of things to do, lots of problems to solve. And in the end, these problems are all of a piece – I’m interested in how people make decisions and prioritize, and in using that insight to make things.

So this is the list of things I’d like to do – but I’ve already skipped ahead.  Let’s get some clarity about what all this is about.

The Goal: Quit my job and be working as an independent by June 30, 2010.

In this blog, I am going to chronicle each day the steps I take to get to that goal.  Six full months is both an eternity and a fleeting moment.  This is my personal journal, chronicling the steps I’ll take to get from here (working at a desk in a job that is only marginally less soul sucking than my last one) to there (kicking back in my home office, shoes off, doing what I love).

Let’s begin.

The first step was deceptively simple:  It suddenly occurred to me that it was possible.  Once I realized it could be done, I thought – ‘possible’ very quickly turns into ‘too easy’.  When it gets to be too easy, I get distracted, begin to think it’s not worthwhile.

So the second step was deceptively complex:  In order to make it happen, I needed to set a timeline short enough to inspire a healthy dose of panic, but long enough to realistically set aside what one of my friends calls, “Fuck you money” and to hire my replacement at my current job.  Oh, and I decided not to focus on one of the things in my list – I decided instead to focus on all of them.

The next step was to make a list of all the things I’d ever done in my strange little career:

• Designed website navigation systems and wireframes
• Developed and produced a web-based video game for a TV show
• Wrote copy for websites, circulars, brochures, and ads
• Researched and developed the game play for a skydiving video game
• Written creative briefs
• Ideated and developed strategic guidelines for new products, content, ad campaigns, and events for clients spanning software companies, television shows and networks, sporting events, logistics companies, spirits, and consumer packaged goods
• Sat in the writers rooms for two soap operas and helped them develop new modes of storytelling
• Advised a national sporting association on how to position the sport to new fans, as well as how to lay out its Hall of Fame
• Designed and implemented systems for worldwide adaptation and simultaneous launch of advertising campaigns
• Taught people how to think and how to write
• Published a small, non-profit magazine
• Hosted a small, non-profit radio program

There’s more to that list, but it was a good start – it reminded me that I actually have done very interesting things.  Things that go beyond project management and constantly rehashing process and deadlines.  Things, in other words, that do not make up even 20% of my day anymore.  I looked at these things and resolved to do them again.

The final step was another list – and this list was just as revealing.  I wrote down the names of everyone I know who is, in some way, an entrepreneur.

• The owner of the small digital creative boutique
• The owner of the small creative content boutique
• The founder of the photo-sharing and storing start-up
• The founder of the digital advertising agency
• The founder of concert and video production company
• The founder of the video and film production company
• The owner of a small strategic consulting company
• The founder of a data-mining consultancy
• The founder of a marketing and ratings analytics consultancy

And so on. Suddenly I realized that a great many of my friends – the people I’d known the longest and the best – were all doing what I wanted to do: working for themselves, doing what interests them, and making a damn good living at it.  I had the resources – the mentors and advisors – I needed all along.

So I took the fifth step:  I called or emailed all of them to set up appointments – times when we could talk about what they were doing, how they go to this point, what advice they would offer, what things I hadn’t thought about that I should.  Those snippets of advice will be on this blog.  There’s no sense in keeping them secret.

To recap – the path to my emancipation has begun.  I started with 5 simple steps.

1. Realize it’s possible
2. Set aggressive goals
3. Make a list of what you would rather be doing
4. Make a list of people you can turn to for advice, encouragement, and connections
5. Don’t be bashful – call them up or send them an email and ask for their advice.  Better yet, reignite your friendship with them

I strongly suspect that what I’ll need most are sympathetic friends.  And to get friendship you have to give it! Besides, it’s no chore to genuinely reach out to and spend time with the people you like and respect the most – it’s a pleasure. That’s the whole point isn’t it?  To be doing what moves me, with people I enjoy and respect, to make work fun.  And now I have my trajectory – the direction and distance and general idea of the arc this story will follow.  5 easy steps, lads and lassies.  Set yourself free.