On Being Good Enough & Belonging

It’s hard to fathom that it’s only been a little over a month since I leapt off the proverbial cliff and quit my job. At the same time, though, my life prior to this momentous change feels as if it were eons ago. Clearly, I’m still in the adjustment phase to my new station in life. Overall, I still feel, in my heart of hearts, that I made the right choice in leaving. And yet, I worry. I have doubts.

I worry about what’s going to happen on this new adventure, long-term. Will I continue to have great success, or will I prove to be a flash-in-the-pan, wannabe freelance technology writer? Will I be able to say even more about accessibility and iOS? Have I typecasted myself as just the “accessibility guy”? Will I ever be able to come up with more solid pitches to The Magazine and Macworld, among others? Do I have an audience, on this site and beyond? Do people really like my work? Are Stephen and Jim going to like me when we meet at WWDC next week? Am I really a good (or great) writer? Stupid shit like that.

My therapist and I talked at length about all these questions during last week’s session. To be honest, I’m fighting my ass off to enjoy every moment of this wild ride, what with all the writing gigs and being invited to Beard Bash. But it’s not easy. I have some deeply-rooted demons that admittedly do a fine job of allowing me to beat myself up, and blunt any pleasure I experience. That’s part of the reason I’ve been in therapy for the last several months. I know this is probably the most insecure, self-indulgent, asinine thing I’ve ever written, and I’m probably certifiably crazy for publishing it, but I’d be lying if I said I wasn’t filled with these questions every day. I’m aware and realistic enough to know that things won’t be easy as a freelancer either, but that’s not the point. The point is, I question, unnecessarily so, whether I belong here, writing words for money.

After having spent a good part of my life being told I wasn’t good enough, I started to believe it. This is just a case of those demons fucking with my mind. But logic and emotion are two different things, and my emotions aren’t aligned with my logic.