I take a lot of risks in my life. I risk financial security, career stability, stability of my heart and mind, and a stability of living situation.

To me, life is messy and unstable.

Whenever I have made decisions based on what is the most stable, I have always reflected on that as a bad decision in hindsight.

For example,  I got a promotion from a Manager position at ABC Family to a Senior Manager position at ABC. Undoubtedly a "good" career move... except that I was miserable in the new job. My new boss and I didn't get along very well, and some of the managerial choices I had to make about my team were against my ethical boundaries.

But I thought I had to stay there because it was the "right" thing to do -- if I couldn't be happy at ABC making six figures per year and managing a team of several kick-ass people, where could I be happy?

I kept reading quotes like, "Wherever you go, there you are," (meaning that you shouldn't try to solve problems by moving), and fiercely believing that I could somehow open up my heart and mind to happiness even as the situations around me were very difficult.

Certainly, there was something wrong with me if I couldn't accept a senior management position at one of the biggest entertainment companies in the world as the best I could do from a career and financial standpoint, right?

Except that I couldn't accept it.

And as soon as I decided I was going to leave no matter what, a position at Oprah opened up for me -- a position that was challenging and fulfilling and enabled me to work with some people I really love.

Nearly three years later, the Oprah job wasn't challenging to me anymore, but I had once again bought into the fear-based refrain that I shouldn't quit my job until I had something else lined up. I had a great paycheck. I had a 401k. I had a career trajectory. I was working on content that I personally supported.

But I wasn't happy in that job.

Some people work to live... their weekends are bright and joyful, and their shitty day-jobs support those weekends. These people come down with cases of the Mondays. They call Wednesday "hump day" because it's the halfway to the weekend. They say things like "TGIF."

I am not like that. I live to work. I love working. I personally identify my self worth with how effective I am at work. So being in a job where I am not empowered to be effective is my version of a personal Hell. I have to personally believe in what I am working on and for.

It's why I wouldn't talk with my friend about his high-powered senior management position for an ad network (even though he really wanted me to).

It's why I am doing freelance work for The Mozilla Developer Network (I'm the voice of MDN on Twitter) and talking with Instagram about an editorial position, even though Russ and I are keeping Outlaw Soaps going.

I follow interesting work and I'm not afraid to jump out of airplanes to chase it down.

Because I trust that the parachute will open if I need it to.

What do you think? Would you trust the parachute to open?

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