"Have you ever jumped out of a plane?"
"What?"
"Ever skydived?"

She shook her back an forth a bit too vigorously.  "No way.  NO. Way."

"You should definitely jump out of a plane.  Once you jump out of a plane and land on the ground alive, you won't have an excuse to be a afraid of fucking ANYTHING."

She has been at her job (one of responsibility and management) for over a decade and has hit that point where her job satisfaction has dipped below her creative impulse.  She’s terrified of quitting and equally terrified of starting a new venture.  Wanting more out of life is the driving force and fear is the roadblock that prevents her from moving in any direction.

It is not an unusual set of circumstances in my experience.

So why would anyone jump out of a plane?  The safety of the ground is so apparent and comforting, yes?  Why go up thousands of feet into the air and then leap from a moving airplane only to plummet to Earth?  What's the fucking point of that?

Our first mental block is in assessing the risk of jumping out of a plane.  The facts are pretty simple.  Far more people are seriously injured riding a bicycle in a major city than are injured skydiving.  Far more people are fatally injured merely owning a gun in a home with a toddler than are killed parachuting from 7,000 feet.  We tend to assess risk based on emotional response rather than quantifiable facts.

Riding a bike doesn't seem scary.  Jumping out of a plane does.

Asking someone out on a date, quitting your job to do something more fulfilling, getting up on a stage to tell a story - all seem scary but the thing we fear isn't injury.  The thing we fear is failure.  Humiliation.  Being wrong.

The first time skydiver has such a tiny possibility of being wrong it's almost silly.  You will wear a chute and harness that has been tested and re-tested and packed and checked.  You will be tethered to an experienced skydiver who will pull the ball if you forget.  That tandem instructor will make sure you land safely.  The worst thing that can happen in the multitude of cases is that you get so overwhelmed you shit your pants or something.  Maybe pass out.  But you probably will not do either of those things.

The second mental block is a fear of change.  The human experience is predicated by a need to control the outcomes.  Risk versus reward and all that.  If I quit my job and go out into the Big Bad World, what are my chances of finding fulfillment somewhere else?  Is the sudden loss of income and connection mitigated by new income, happiness, new connections or will I just be fucked and end up working as a temp for a shitty data processing company or have to walk dogs or do telemarketing to pay my rent?

If you are truly miserable, that change is going to come whether it is your choice or the choice of your employer.  If you hate your gig, it will become apparent. You will cease to be effective.  You will spend more time on Facebook than actually, you know, working.  People will notice.  And you will be shitcanned.  Fearing change is like fearing death.  The inevitability is baked into the human condition so what's the fucking point of being afraid of it?

So why start your own business?  Why forego the stability and comfort of a steady paycheck in a job that is starting to feel like it's stealing the bits of your life that seem to really matter?

Why not jump out of that plane?