There’s a tiny hole on my resume. Now, 20+ years later you need to squint to see it, but it’s still there. I took the gig because I needed the money while in grad school, and, honestly, because maybe the startup could get public before it and the Web 1.0 bubble popped. And that combination of necessity and greed overwhelmed my better judgment.

It was a B2B Enterprise Software shop that really looked more like a dev team trying to turn services revenue into a scalable product. The employee base was a Venn diagram of (a) folks who knew something was off about the place – mostly in its leadership, but wanted to be part of fixing it, (b) grifters and (c) earnest professionals at the beginning of their careers who probably thought this was just what business was like.

When you’re young you hold every job on your resume so tightly – listing the month you started and the month you finished. “No gaps!” was what I recall the career center telling me. As if a seamless path was the dental equivalent of a glorious white smile and a few awkward career transitions became a boxer’s glove punching into your jaw and leaving bloody teeth in your hand, a pitted grin on your face. So I stayed a little longer at the job than I should have. Negative net worth meet negative self worth.

I don’t recall when I first removed the company from my resume. Did a length of time pass after I stepped away? Or did I just feel confident enough in my trajectory a few years later that no one was asking me about a couple month period between graduation and starting at Linden Lab? Reminds me of this tweet:

Regardless, after I became more understanding when interviewing candidates if there was a pause or a decision that didn’t work out the way they wanted. And perhaps they even had to take a step backwards before moving forward. Gap-toothed resumes have their own beautiful stories to tell.