What 20 Years in Music Taught Me About Crafting Delicious Copy

How to make your writing sing … even if you can’t carry a tune.

Long before I ever knew I’d spend the bulk of my career twisting phrases to give you warm and fuzzies about software, I spent the bulk of my evenings singing to half-empty bars while mowing down free Jameson shots.

Sure, I played a lot of covers — everything from John Mayer to 2Chainz — but I also did a fair share of writing and workshopping my own material.

Why? Ain’t no cover bands on MTV.

I figured if I played my cards right, one day I could be the opening act for the DJ, who opened for the rapper, who opened for the legacy rock act, who opened for the hot new popstar who opened for Beyonce at Coachella.

Lemme tell you how that went: I finally found steady solo gigs in my 30s, played SXSW a couple of times, dropped an album on my 33rd birthday, and by 36 I was all flamed out. My liver had its number retired in multiple bars across the country, and I moved forward with making my hay behind a desk at one of the world’s ten largest tech conglomerates.

Here’s the thing: I wasn’t half-bad. Grammy winners once opened for me. And, yeah, I was often introduced as “the lyrical miracle” before slogging my way…