“I find myself thinking it would have potentially been easier to get some sort of company off of the ground instead of dealing with undefined roles, never ending checkboxes on the employer’s side, and unending rejections.”

I left my last job a few years ago. As it often goes, the startup I left to start didn’t take off like it needed to. I chose to depart and search for a design leadership role. It’s been hard. The hardest search of my career by far. I find myself thinking it would have potentially been easier to get some sort of company off of the ground instead of dealing with undefined roles, never ending checkboxes on the employer’s side, and unending rejections. It just seems like the bar in roles seems barely surmountable, but there’s not much flex to give you a chance to show you can do what they want and more.