The first is that, recently in the WordPress community, I’ve read a few posts from people who have decided to move on from the jobs they’ve had for years to pursue new opportunities. I remember when I negotiated a deal that would allow me to write about WordPress full-time and quit working at the local grocery store.
Although it wasn’t a brand new gig, it was an exciting time as it gave me renewed energy and focus to pour into the site I created. There are only a few times in my life where I’ve participated in potential career paths that seemed exciting and opened the door for new opportunities. I congratulate those who have decided to move on and to embrace the freshness that is their new job.
The second is a question asked by David Bisset on Twitter.
I replied that I’m afraid to answer the question. I think WordPress will be around in some form or fashion 5-10 years from now but will I be writing about it? This is a conversation I’ve been having with myself a lot lately. Is what I do for a living something I want to do for decades or is there a fork in my path where I get to choose a different direction.
The truth is, my current gig is the best I’ve had in my working life. Great medical benefits, vacation policy, paid travel, and a salary I never would have gotten had I stayed at the grocery store. The thought of losing that by losing my job or switching jobs scares me and it scares my wife. My wife thinks that there is no way I can get something better than what I have now. But, I’ve been doing this gig in one fashion or another for a decade and continuing on as if it’s a mundane routine without anything new and refreshing comes at the cost of possibly losing the drive, focus, passion, desire, to continue on.
The other thing that scares me is that I don’t know what I want. I don’t know what I want to do other than what I’m doing. I don’t know what I’m capable of and I sure as hell downplay everything about myself. I don’t know what would make me a happier employee. I’ve been struggling to answer these questions for months.
This is when someone says to me, apply yourself and learn something like PHP, JavaScript or whatever and get some skillsets that make you more valuable or open up more opportunities. Yeah sure, I’ll get right on that.
So the days and nights fly past while I ponder my future and career.
Thoughts and Insanity From Jeff 
I get it man. Really. You’re position is difficult. Also, you’re really, really good at it. Seriously. You’re an excellent journalist and a talented podcast host. This community is lucky to have you. It’s not surprising that you feel this way.
Making some kind of change would be hard. I don’t even know what that would look like. You have the problem of many reasons why you shouldn’t and few obvious ideas for what you’d do instead. So you just keep going.
I don’t have any answers. Walking away from my business was really difficult and took years to finally act on. Your situation is different. I wish you the best though and I’m confident you’ll do really well no matter what you end up doing.
Thanks Kyle.